Siamese,Indian,and Brazilian Rosewoods: A Review on Phytochemistry,Applications,and Pharmacology

Abstract

For the first time, the current review fully provides information on the phytochemicals, applications, and pharmacological aspects relating to 3 Dalbergia species, Siamese Rosewood (Dalbergia cochinchinensis Pierre ex Laness.), Indian Rosewood (D sissoo Roxb.), and Brazilian Rosewood (D nigra (Vell.) Benth.). Based on chromatographic separation, phytochemical studies on these plants have, to date, resulted in the isolation and structural elucidation of 136 secondary metabolites. Among them, flavonoids and simple phenols are major components, whereas terpenoids, quinones, benzofurans, benzophenols, phytosterols, stilbenes, phthalates, xanthones, and lignans have been also detected. Dalbergia rosewoods are heavy and strong, taking an outstanding polish, and are very suitable for furniture. They are also used as natural dyes, raw materials for removing contaminants from water, and might be a rich resource of essential oils, polysaccharides, and active glycosidase enzymes. Dalbergia crude extracts and their secondary metabolites have a wide range of pharmacological actions, such as anti-inflammatory, anti-oxidative, anti-aging, anti-bacterial, anti-nociceptive, anti-diarrheal, anti-pyretic, gastrointestinal, biocontrol activities, but sexual and anti-osteoporosis activities are the most valuable.

Keywords

phytochemistry pharmacology applications flavonoids

Introduction

Traditional herbs with low toxicity and few side effects are always an excellent alternative to expensive pharmaceuticals. Many clinically relevant medications have been discovered as a result of screening natural sources such as microbial fermentation, phytochemical isolation, or pharmacological assay based on plant extract materials.¹

The genus Dalbergia belonging to the subfamily Faboideae of the pea family contains small- to medium-sized trees, shrubs, and lianas.^2–5 This genus is native to the tropical areas of central and southern America, Africa, Madagascar, and especially southern Asia.^2–6 Many Dalbergia species are valuable timber trees, prized for their ornamental and frequently fragrant wood, which is high in aromatic oils. The rosewoods are the most well known, named after the scent of the wood when cut. D cochinchinensis Pierre ex Laness. (Siamese rosewood) is a vulnerable plant distributed in Vietnam, China, Laos, and Thailand.^7–10 D sisoo Roxb., also known as Indian rosewood or Shisham, is a deciduous plant native to India, Pakistan, Bangladesh, Afghanistan, Nepal, Sri Lanka, and Mauritius,^11–14 whereas D nigra (Vell.) Benth. (Brazilian rosewood) is a well-known species in Brazil with the local names “jacaranda da Bahia,” “caviuna,” and “jacaranda preto.”^15,16 Dalbergia rosewoods set a great role in traditional uses, pharmacological developments, and are also used as raw materials for manufactured products.^7–17 For instance, D sissoo heartwood in milk is used to treat fevers, and its bark extract is very suitable for anti-inflammation and blood purification.¹⁷ In addition, D sissoo is among plants utilized most to control termites,¹⁸ and D cochinchinensis seed is rich in glycosidase enzymes with both β-glucosidase and β-fucosidase activities.¹⁹ Regarding phytochemical investigations, flavonoids and simple phenolics predominate in these 3 species, and in other Dalbergia species.^20–23

Although these plants appear in various phytochemical investigations and exhibit remarkably active therapies, a comprehensive review is lacking providing chromatographic separation processes and the uses of the 3 Dalbergia species for drug development. Here, we aim to review the phytochemistry, applications, and pharmaceutical aspects from the 1970s to now. The collective results are mostly based on column chromatographic separation of the compounds and nuclear magnetic resonance (NMR) data for structural elucidation. Electronic resources, including Google Scholar, Web of Science, Sci-Finder, PubMed, Science Direct, and a library search for articles published in peer-reviewed journals, have been used to gather references on the 3 Dalbergia species. “Dalbergia cochinchinensis,” “Dalberiga sisoo,” “Dalbergia nigra,” “phytochemistry,” “application,” and “pharmacology” are the 6 main keywords used to search for publications.

Phytochemistry

Major Components

Flavonoids are the principal bioactive metabolites found in the 3 investigated species, as well as in other Dalbergia species. Herein, compounds 1-99 can be categorized into flavones 1-7, isoflavones 8-33, flavan 34, isoflavans 35-40, isoflaven 41, flavanones 42-55, isoflavanones 56-62, chalcones 63-69, neoflavonoids 70-95, and pterocarpans 96-99 (Table 1 and Figures 1-3).^{7–9,11,12,15,16,20–39} Flavonoids can be found in the leaf, stem, pod, root bark, trunk exudate, and especially in heartwood.

Figure 1.

Flavones and isoflavones from D cochinchinensis, D sissoo, and D nigra.

Figure 2.

Flavan, isoflavans, isoflaven, flavanones, isoflavanones, and chalcones from D cochinchinensis, D sissoo, and D nigra.

Figure 3.

Neoflavonoids and pterocarpans from D cochinchinensis, D sissoo, and D nigra.

Table 1.

Chemical Constituents of D cochinchinensis, D sissoo, and D nigra.

No	Compounds	Methods	References
Flavonoids
Flavones
1	7-Hydroxy-6-methoxyflavone	D cochinchinensis heartwood and D sissoo root bark	^8,9,21,34
2	Kaemferol-3-O-β-D-glucopyranoside	D sissoo leaf	²⁰
3	Kaemferol-3-O-rutinoside	D sissoo leaf	²⁰
4	Norartocarpetin	D sissoo leaf	²⁶
5	Galangin	D cochinchinensis heartwood	^8,9
6	Quercetin 3-β-D-glucopyranoside	D sissoo leaf	²⁰
7	Quercetin-3-O-rutinoside	D sissoo leaf	²⁰
Isoflavones
8	Biochanin A	D cochinchinensis heartwood and D sissoo leaf and root bark	^{20,21,26,30,31}
9	Biochanin A 7-O-glucoside	D sissoo leaf	^20,30
10	Biochanin A 7-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside]	D sissoo leaf	^20,28
11	Biochanin A 7-O-[β-D-apiofuranosyl-(1→5)-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside]	D sissoo leaf	^20,28
12	Calycosin	D cochinchinensis heartwood	³²
13	Caviunin (8)	D nigra heartwood and D sissoo leaf	^15,20
14	Caviunin 7-O-gentiobioside	D sissoo pod	^35,36
15	Caviunin 7-O-β-D-glucopyranoside	D sissoo leaf	²⁰
16	Dalsissooside (Caviunin 7-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside])	D sissoo leaf	^20,30
17	2-(5,7-Dihydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzoquinone	D cochinchinensis heartwood	²⁴
18	5,7-Dihydroxy-2′,3′,4′-trimethoxyisoflavone	D cochinchinensis heartwood	^9,31
19	5-Hydroxy-6,7-dimethoxy-4′-O-(6-O-D-apio-β-D-furanosyl-β-D-glucopyranosyl)isoflavone (7-Methyltectorigenin 4′-O-[β-D-apiofuranosyl- (1→6)-β-D-glucopyranoside])	D nigra leaf and D sissoo stem	^16,28
20	Formononetin	D cochinchinensis heartwood and D sissoo trunk exudate	^9,23,31
21	Genistein	D cochinchinensis heartwood and D sissoo leaf	^20,26,30,31
22	Genistein 8-C-[β-D-glucopyranoside]	D sissoo stem and leaf	^20,28
23	2′-Hydroxyformononetin (Zenognosin B)	D cochinchinensis heartwood and D sissoo trunk exudate	^9,23,31
24	Muningin	D sissoo leaf	²⁶
25	Pratensein	D sissoo leaf	^20,30
26	Prunetin	D sissoo leaf	²⁶
27	Prunetin 4′-O-[β-D-apiofuranosyl- (1→6)-β-D-glucopyranoside]	D sissoo stem	²⁸
28	Prunetin-4′-O-galactoside	D sissoo leaf	²⁶
29	Sissotrin	D sissoo leaf	²⁶
30	Tectorigenin	D sissoo leaf	²⁶
31	Tectorigenin-7-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside]	D sissoo stem	²⁸
32	2′,5,7-Trihydroxy- 4′-methoxyisoflavone	D cochinchinensis heartwood	^9,31
33	7-γ,γ-Dimethylallyloxy-5-hydroxy-4′-methoxyisoflavone	D sissoo root bark	²¹
Flavan
34	6,4′-Dihydroxy-7-methoxyflavan	D cochinchinensis heartwood	^8,34
Isoflavans
35	Dalbergiacochan A	D cochinchinensis heartwood	⁷
36	Dihydrosepiol	D sissoo trunk exudate	²³
37	7-Hydroxy-2′,4′-dimethoxyisoflavan	D cochinchinensis heartwood	³¹
38	Mucronulatol	D cochinchinensis heartwood	^7,8
39	4,7,2′-Trihydroxy-4′-methoxyisoflavanol	D cochinchinensis heartwood	³¹
40	(-)-Vestitol	D sissoo trunk exudate	²³
Isoflaven
41	2′-O-Methylsepiol	D cochinchinensis heartwood	⁷
Flavanones
42	Alpinetin	D cochinchinensis heartwood	⁸
43	3,5-Dihydroxy-7-methoxy-2-phenylchroman-4-one	D cochinchinensis heartwood	³⁸
44	(2S)-6,7-Dihydroxyflavanone	D sissoo trunk exudate	²³
45	7,8-Dihydroxyflavanone	D cochinchinensis heartwood	^8,9
46	Liquiritigenin	D cochinchinensis heartwood	^8,32
47	Naringenin	D cochinchinensis heartwood	^8,9
48	Pinocembrin	D cochinchinensis heartwood and D. sissoo trunk exudate	^8,23
49	Plathymenin	D sissoo trunk exudate	²³
50	(2S)-7-Hydroxyflavanone	D sissoo trunk exudate	²³
51	(2S)-7-Methoxy-4′,6-dihydroxyflavanone	D cochinchinensis heartwood	³²
52	(2S)-4′,6,7-Trihydroxyflavanone	D cochinchinensis heartwood	³²
53	3,5,7-Trihydroxy-2-phenylchroman-4-one	D cochinchinensis heartwood	³⁸
54	3′,5′,5,7 -Tetrahydroxyflavanone	D cochinchinensis heartwood	⁸
55	3′,5′,5,7-Tetrahydroxy-6-C-β-D-glucopyranosylflavanone	D cochinchinensis heartwood	⁸
Isoflavanones
56	Dalcochinin-8′-O-β-D-glucoside	D cochinchinensis seed	³⁷
57	Dehydroamorphigenin	D sissoo root bark	²¹
58	Isodarparvinol B	D cochinchinensis heartwood	³¹
59	Homoferreirin	D cochinchinensis heartwood	³¹
60	3-Hydroxyvestitone	D cochinchinensis heartwood	³¹
61	3′-O-Methylviolanone	D cochinchinensis heartwood	^9,31
62	Sativanone	D cochinchinensis heartwood	³¹
Chalcones
63	Butein	D cochinchinensis heartwood and D sissoo trunk exudate	^8,23
64	2,3-Dimethoxy-4′-γ,γ-dimethylallyloxy-2′-hydroxychalcone (1)	D sissoo root bark	²¹
65	2′,4′-Dimethoxy-4-hydroxychalcone	D cochinchinensis heartwood	³²
66	2′-Hydroxy-4′-methoxychalcone	D sissoo trunk exudate	²³
67	4′-Hydroxy-2′-methoxychalcone	D cochinchinensis heartwood	²²
68	Isoliquiritigenin	D cochinchinensis heartwood and D. sissoo trunk exudate	^8,23
69	4,2′,5′-Trihydroxy-4′-methoxychalcone	D cochinchinensis heartwood	⁸
Neoflavonoids
70	Dalbergenone (S-4-Methoxydalbergione)	D sissoo stem bark and trunk exudate	^23,33
71	Dalbergichromene	D sissoo heartwood, stem and stem bark	^11,29,33
72	Dalbergin	D nigra heartwood and D sissoo heartwood, stem and stem bark	^12,15,29,33
73	Dalbergiphenol	D cochinchinensis heartwood and D sissoo heartwood	^22,29
74	Dalnigrin	D nigra heartwood	¹⁵
75	Dalsissooal	D sissoo heartwood	²⁹
76	1,6-Dihydro-1,6-dihydroxy-4-methoxydalbergione ((+)-5,6-Dihydroxy-2-methoxy-5-(1-phenyl-2-propen-1-yl)-2-cyclohexene-1,4-dione)	D sissoo stem and trunk exudate	^11,23
77	6-Hydroxy-2,7-dimethoxyneoflavene	D cochinchinensis heartwood	³⁴
78	9-Hydroxy-6,7-dimethoxydalberiquinol	D cochinchinensis heartwood	³⁴
79	3′-Hydroxymelanettin	D nigra heartwood	¹⁵
80	Melanettin	D nigra heartwood	¹⁵
81	Melannein	D nigra heartwood	¹⁵
82	Methyldalbergin	D sissoo heartwood and stem bark	^29,33
83	R-Latifolin	D cochinchinensis heartwood	^27,32
84	R-4-Methoxydalbergione	D cochinchinensis heartwood and D sissoo heartwood	^27,29,32
85	R-5-O-Methyllatifolin	D cochinchinensis heartwood	^27,32
86	S-4-Dalbergione	D sissoo trunk exudate	²³
87	S-4′-Hydroxy-4-methoxydalbergione	D sissoo trunk exudate	²³
88	S-4-Methoxydalbergiquinol	D sissoo trunk exudate	²³
89	2-[(1S)-1-Phenyl-2-propenyl]-1,4-benzenediol	D sissoo trunk exudate and stem	^12,23
90	4-[(1S)-1-Phenyl-2-propenyl]-1,3-benzenediol	D sissoo trunk exudate	²³
91	(1S,2S,4S,5S)-2-Methoxy-5-[(1R)-1-phenyl-2-propenyl)]-1,4-cyclohexanediol	D sissoo trunk exudate	²³
92	(2S,4R,5S)-4-Hydroxy-5-methoxy-2-[(1S)-1-phenyl-2-propenyl)]-cyclohexanol	D sissoo trunk exudate	²³
93	(2S,4R,6S)-4-Hydroxy-2-methoxy-6-(1-phenyl-2-propenyl)-cyclohexanone	D sissoo trunk exudate	²³
94	(4S,6S)-4-Hydroxy-3-methoxy-6-(1-phenyl-2-propenyl)-2-cyclohexene-1-one	D sissoo trunk exudate	²³
95	(4S,6S)-4-Hydroxy-6-(1-phenyl-2-propenyl)-2-cyclohexene-1-one	D sissoo trunk exudate	²³
Pterocarpans
96	4-Hydroxymedicarpin	D sissoo trunk exudate	²³
97	(+)-Medicarpin	D cochinchinensis heartwood and D sissoo trunk exudate	^9,23,31,39
98	Melilitocarpan D	D cochinchinensis heartwood	²³
99	(+)-Vesticarpan	D sissoo trunk exudate	²³
Simple phenols
100	Ethyl 4-hydroxybenzoate	D cochinchinensis heartwood	³⁹
101	Ferulaldehyde	D cochinchinensis heartwood	⁴⁰
102	Hydroxyobtustyrene	D sissoo trunk exudate	²³
103	1-(4′-Hydroxy-2′-methoxyphenyl)-3-(3″-hydroxy-4″-methoxyphenyl)propane	D cochinchinensis heartwood	⁴⁰
104	2-(2-Hydroxy-1-methyl- 2-phenylethyl)-4,5-dimethoxyphenol	D cochinchinensis stem	²²
105	5-[3-Hydroxy-1-(2-hydroxyphenyl)-1-propen-1-yl]-2,4-dimethoxyphenol	D cochinchinensis heartwood	³²
106	Sissooic acid	D sissoo leaf	²⁰
107	Isoferulaldehyde	D cochinchinensis heartwood	⁴⁰
108	Methyl 4-hydroxybenzoate	D cochinchinensis heartwood	³⁹
109	Vanillin	D cochinchinensis heartwood	⁴⁰
Terpenoids
Sesquiterpenoids
110	6α-Hydroxycyclonerolidol	D. cochinchinensis heartwood	³⁹
111	4-Epi-cyptomeridiol	D cochinchinensis heartwood	⁴⁰
112	7-Epi-4-eudesmene-1β,11-diol	D cochinchinensis heartwood	⁴⁰
113	Pterocarpol	D cochinchinensis heartwood	^39,40
Triterpenoids
114	β-Amyrin	D sissoo leaf	²⁶
115	Oleanolic acid	D cochinchinensis heartwood	⁴⁰
Quinones
116	2-(3-(4-Hydroxyphenyl)-3-methoxypropyl)-5-methoxycyclohexa-2,5-diene-1,4-dione	D cochinchinensis heartwood	⁹
117	4-Hydroxy-3-methoxy-4-(3-phenyl-2-propenyl)-2-cyclohexene-1-one	D sissoo trunk exudate	²³
118	(-)-4-Hydroxy-2,5-dimethoxy-4-[(2E)-3-phenyl-2-propen-1-yl]-2,5-cyclohexadien-1-one	D sissoo trunk exudate	²³
119	Latinone	D cochinchinensis heartwood and D sissoo heartwood	^22,29
Benzofurans
120	2-[4,5-Dimethoxy-5-(3-phenyl-trans-allyl)cyclohexa-3,6-dien-2-on-1-ylmethyl]-5-hydroxy-6-methoxy-3-phenylbenzofuran	D cochinchinensis stem	²²
121	2-[4,5-Dimethoxy-2-(3-phenyl-trans-allyloxy)benzyl]-5-hydroxy-6-methoxy-3-phenylbenzofuran	D cochinchinensis stem	²²
122	6-Hydroxy-2-(2-hydroxy-4-methoxyphenyl)-benzofuran	D cochinchinensis heartwood	⁹
123	2-(2′-Methoxy-4′-hydroxy)-aryl-3-methyl-6-hydroxybenzofuran	D cochinchinensis heartwood	³⁹
124	Pterolinus B	D cochinchinensis heartwood	³⁹
Benzophenones
125	Cearoin	D cochinchinensis heartwood and D sissoo heartwood and trunk exudate	^23,29,32
126	2,4-Dihydroxy-5-methoxybenzophenone	D cochinchinensis heartwood	⁹
127	2,2′,5-Trihydroxy-4-methoxybenzophenone	D cochinchinensis heartwood	³⁴
Phytosterols
128	β-Sitosterol	D sissoo leaf	²⁶
129	Stigmasterol	D cochinchinensis heartwood and D sissoo leaf	^26,40
Stilbenes
130	3,5-Dimethoxy-4-hydroxy-trans-stilbene	D cochinchinensis heartwood	⁹
131	Pterostilbene	D cochinchinensis heartwood	^39,40
Phthalates
132	Butyl isobutyl phthalate	D cochinchinensis heartwood	³⁹
133	Dibutyl terephthalate	D cochinchinensis heartwood	³⁹
Others
134	2,3-Dimethoxyxanthone	D cochinchinensis heartwood	^8,9
135	Syringaresinol-4″-O-β-D-monoglucoside	D sissoo leaf	²⁰
136	Tritriacontane	D sissoo stem	¹¹

In detail, 7-hydroxy-6-methoxyflavone (1) was observed in both D cochinchinensis heartwood and D sissoo root bark, but galangin (5) was only found in D cochinchinensis heartwood.^8,9,21,34 In the search for osteogenic agents from D sissoo, flavone norartocarpetin (4) and 4 flavone glycosides, kaemferol-3-O-β-D-glucopyranoside (2), kaemferol-3-O-rutinoside (3), quercetin 3-β-D-glucopyranoside (6), and quercetin-3-O-rutinoside (7), were isolated from the EtOH extract of its leaf.^20,26

Regarding isoflavones 8-34, they are present in both free and glycoside forms (Figure 1). Glycosyl units are structurally formed by β-D-glucopyranoside, β-D-galactopyranoside, β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, and β-D-apiofuranosyl-(1→5)-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, and generally substituted at carbons C-7 and C-4′. The free flavone, biochanin A (8), was detected in either the heartwood of D cochinchinensis or the leaf and root bark of D sissoo,^{20,21,26,30,31} while its glycosides 9-11 were only separated from D sissoo leaf.^20,28,30 In particular, biochanin A, 7-O-[β-D-apiofuranosyl-(1→5)-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside] (11), was new to the literature due to its sugar unit. Similarly, caviunin (13) was a known flavone isolated from D nigra heartwood and D sissoo leaf, but its new glycosides, caviunin 7-O-gentiobioside (14) and caviunin 7-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside] (16), were only found in D sissoo pod and leaf, respectively.^15,20,30 D sissoo is thought to be a rich reservoir of isoflavones. For instance, caviunin 7-O-β-D-glucopyranoside (15), genistein (21), genistein 8-C-glucoside (22), muningin (24), pratensein (25), prunetin (26), prunetin-4′-O-galactoside (28), sissotrin (29), and tectorigenin (30) have been successfully separated from its leaf, while formononetin (20) and 2′-hydroxyformononetin (23) are characteristic of its trunk exudate.^20,23,26,30 In addition to known isoflavone glycoside (27), the MeOH extract of D sissoo stem contained a new analog, tectorigenin-7-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside] (31), whereas the prenylated isoflavone, 7-γ,γ-dimethylallyloxy-5-hydroxy-4′-methoxyisoflavone (33), was another new compound detected in its root bark.^21,28 Besides compounds 8, 20, and 23, D cochinchinensis heartwood has further contributed 3 congeners 2-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzoquinone (17), 5,7-dihydroxy-2′,3′,4′-trimethoxyisoflavone (18), and 2′,5,7-trihydroxy-4′-methoxyisoflavone (32).^9,24,31 5-Hydroxy-6,7-dimethoxy-4′-O-(6-O-D-apio-β-D-furanosyl-β-D-glucopyranosyl)isoflavone (19), also known as 7-methyltectorigenin 4′-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside], was a newly reported isoflavone present in D nigra leaf.¹⁶ It was then isolated from D sissoo stem.²⁸

Phytochemical and NMR structural outcomes have further identified the presence of one new flavan, 6,4′-dihydroxy-7-methoxyflavan (34), one new isoflavan, dalbergiacochan A (35), along with 5 known isoflavans, dihydrosepiol (36), 7-hydroxy-2′,4′-dimethoxyisoflavan (37), mucronulatol (38), 4,7,2′-trihydroxy-4′-methoxyisoflavanol (39), and (-)-vestitol (40), and one known, isoflaven 2′-O-methylsepiol (41).^7,8,23,31,34 Among them, compounds 34-35, 37-39, and 41 were purified from the alcoholic extracts of D cochinchinensis heartwood, while compounds 36 and 40 were observed in D sissoo trunk exudate.

In Table 1, a list of 14 flavanones (42-55), following the order of alphabetic name, has been compiled. Dalbergia flavanones have generally been associated with the 2S-configuration, as well as hydroxylation/methoxylation at carbons of rings A and B (Figure 2). D cochinchinensis is rich in flavanones since its heartwood is recorded to contain alpinetin (42), 3,5-dihydroxy-7-methoxy-2-phenylchroman-4-one (43), 7,8-dihydroxyflavanone (45), liquiritigenin (46), naringenin (47), pinocembrin (48), (2S)-7-methoxy-4′,6-dihydroxyflavanone (51), (2S)-4′,6,7-trihydroxyflavanone (52), 3,5,7-trihydroxy-2-phenylchroman-4-one (53), 3′,5′,5,7-tetrahydroxyflavanone (54), and 3′,5′,5,7-tetrahydroxy-6-C-β-D-glucopyranosylflavanone (55).^8,9,32,38 The combination of silica gel chromatographic separation and HPLC tool allowed the isolation of one new flavanone (2S)-6,7-dihydroxyflavanone (44), together with 3 known analogs, pinocembrin (48), plathymenin (49), and (2S)-7-hydroxyflavanone (50).²³

Isoflavanones are also characteristic of these Dalbergia plants. Svasti et al (1999) revealed that the EtOH extract of D cochinchinensis seed contained one new isoflavanone, dalcochinin-8′-O-β-D-glucoside (56).³⁷ Meanwhile, isodarparvinol B (58), homoferreirin (59), 3-hydroxyvestitone (60), 3′-O-methylviolanone (61), and sativanone (62) were among secondary metabolites presented in the heartwood of this species.^9,31 Obviously, dehydroamorphigenin (57), an isoflavanone of D sisoo root bark, is an aglycone of compound 56 (Figure 2).²¹

Seven metabolites, encompassing compounds 63-69, can be classified as flavonoid type chalcones (Table 2 and Figure 2). They were constituents of D cochinchinensis and D sissoo. Butein (63) and isoliquiritigenin (68) have been observed in both D cochinchinensis heartwood and D sissoo trunk exudate.^8,23 2,3-Dimethoxy-4′-γ,γ-dimethylallyloxy-2′-hydroxychalcone (64), a prenylated chalcone, was first isolated from D sissoo root bark.²¹ 2′-Hydroxy-4′-methoxychalcone (66) was extracted from D sissoo trunk exudate, whereas 2′,4′-dimethoxy-4-hydroxychalcone (65), 4′-hydroxy-2′-methoxychalcone (67), and 4,2′,5′-trihydroxy-4′-methoxychalcone (69) were obtained from D cochinchinensis heartwood known as chalcones.^8,23

Table 2.

Pharmacological Activities of D cochinchinensis, D sissoo, and D nigra.

Compounds	Model	Effects	References
Sexual activity
1	In vitro	13.8%/5α-reductase and 29.5%/DHT-receptor inhibition at 50 µg/mL 20.8%/5α-reductase and 30.4%/DHT-receptor inhibition at 100 µg/mL 34.1%/5α-reductase and 25.3%/DHT-receptor inhibition at 200 µg/mL	³⁴
34	In vitro	31.0%/5α-reductase and 44.7%/DHT-receptor inhibition at 50 µg/mL 37.1%/5α-reductase and 49.7%/DHT-receptor inhibition at 100 µg/mL 42.5%/5α-reductase and 49.3%/DHT-receptor inhibition at 200 µg/mL	³⁴
67	In vitro	19.5%/5α-reductase inhibition at 25 µg/mL 20.7%/5α-reductase inhibition at 50 µg/mL 22.8%/5α-reductase inhibition at 100 µg/mL	²²
73	In vitro	8.2%/5α-reductase inhibition at 25 µg/mL 18.9%/5α-reductase inhibition at 50 µg/mL 51.8%/5α-reductase inhibition at 100 µg/mL	²²
77	In vitro	3.0%/5α-reductase and 47.8%/DHT-receptor inhibition at 50 µg/mL 5.1%/5α-reductase and 68.7%/DHT-receptor inhibition at 100 µg/mL 19.5%/5α-reductase and 84.3%/DHT-receptor inhibition at 200 µg/mL	³⁴
78	In vitro	14.1%/5α-reductase and 45.0%/DHT-receptor inhibition at 50 µg/mL 25.3%/5α-reductase and 75.1%/DHT-receptor inhibition at 100 µg/mL 52.6%/5α-reductase and 98.8%/DHT-receptor inhibition at 200 µg/mL	³⁴
119	In vitro	42.8%/5α-reductase inhibition at 25 µg/mL 52.0%/5α-reductase inhibition at 50 µg/mL 65.6%/5α-reductase inhibition at 100 µg/mL	²²
120	In vitro	0.6%/5α-reductase inhibition at 25 µg/mL 3.8%/5α-reductase inhibition at 50 µg/mL 17.0%/5α-reductase inhibition at 100 µg/mL	²²
121	In vitro	11.5%/5α-reductase inhibition at 25 µg/mL 15.9%/5α-reductase inhibition at 50 µg/mL 18.1%/5α-reductase inhibition at 100 µg/mL	²²
127	In vitro	31.0%/5α-reductase and 44.7%/DHT-receptor inhibition at 50 µg/mL 37.1%/5α-reductase and 49.7%/DHT-receptor inhibition at 100 µg/mL 42.5%/5α-reductase and 49.3%/DHT-receptor inhibition at 200 µg/mL	³⁴
70% EtOH extract of D sissoo bark (100 mg/100 g, i.p.)	In vivo	Average weight of 39 g and average uterine weight of 27.6 mg/immature female mice	²⁶
The EtOH extract of D sissoo stem bark (20 mg/mL, p.o.)	In vitro	To immobilize sperm of fertile men aged 25-35 years within 3 minutes	⁵¹
The EtOH extract of D sissoo stem bark (200 mg/kg, p.o.)	In vivo	To decrease the weight of testis and epididymis of mice	⁵¹
The aqueous extract of D sissoo leaf (50 and 100 mg/kg, p.o.)	In vivo	To reduce epididymal sperm motility, and viability and number in serum level of testosterone of mice	⁵²
Anti-Osteoporosis Activity
8 (1.0 pM to 1.0 µM)	In vitro	To increase ALP activity and mineralization	²⁰
9 (1.0 pM to 1.0 µM)	In vitro	To increase ALP activity and mineralization	²⁰
16 (1.0 pM to 1.0 µM)	In vitro	To increase ALP activity and mineralization	²⁰
16 (1 and 5 mg/kg, i.p.)	In vivo	To increase ALP activity and mineralization	²⁰
16 (1.0 µM)	In vitro	To control clinical osteoarthritis symptoms due to interleukin-1β inhibitory effect	³⁰
21 (1.0 pM to 1.0 µM)	In vitro	To increase ALP activity and mineralization	²⁰
25 (1.0 pM to 1.0 µM)	In vitro	To increase ALP activity and mineralization	²⁰
71	In vitro	EC₅₀ = 1.7 µM/ALP increase	²⁹
72	In vitro	EC₅₀ = 1.015 nM/ALP increase	²⁹
72 (1 mg/kg/day, p.o.)	In vivo	To protect trabecular bone loss and reduce bone resorption expression markers TRAP and RANK, but increase osteogenic markers RUNX2, BMP-2, and OPG/RANKL	⁵⁴
73	In vitro	EC₅₀ = 98 µM/ALP increase	²⁹
75	In vitro	EC₅₀ = 6.46 nM/ALP increase	²⁹
75 (5 mg/kg/day, p.o.)	In vivo	To promote trabecular bone micro-architecture indices, biomechanical strength, and bone formation in ovariectomized mice	⁵⁶
82	In vitro	EC₅₀ = 9.1 µM/ALP increase	²⁹
119	In vitro	EC₅₀ = 116 µM/ALP increase	²⁹
EtOH extract of D sissoo leaf (250 and 500 mg/kg, p.o.)	In vivo	To prevent joint cartilage deterioration in subchondral mice bone	³⁰
EtOH extract of D sissoo leaf (250 mg/kg, p.o.)	In vivo	To increase bone volume fraction, trabecular thickness and number, and connective density, reduce trabecular separation, and promote osteogenic genes expressions BMP-2, BMP-4, RunX-2, and COL-1 in mice	⁵⁵
Anti-inflammatory activity
66	In vitro	IC₅₀ = 5.4 µM/NO production inhibition	²³
70	In vitro	IC₅₀ = 38.8 µM/NO production inhibition	²³
76	In vitro	IC₅₀ = 3.19 µM/NO production inhibition	²³
86	In vitro	IC₅₀ = 39.7 µM/NO production inhibition	²³
87	In vitro	IC₅₀ = 11.5 µM/NO production inhibition	²³
118	In vitro	IC₅₀ = 6.22 µM/NO production inhibition	²³
90% EtOH extract of D sissoo leaf (100-300 mg/kg, p.o.)	In vivo	To suppress inflammation of carrageenan, kaolin and nystatin induced paw edema in rats	⁵⁷
90% EtOH extract of D sissoo bark (300-1000 mg/kg, i.p.)	In vivo	To suppress inflammation of carrageenan induced paw edema in rats	¹⁴
MeOH extract of D sissoo bark (100-1000 mg/kg, i.p.)	In vivo	To suppress inflammation of carrageenan induced paw edema in rats	⁵⁸
70% EtOH extract of D sissoo bark (80 mg/100 g, i.p.)	In vivo	Paw thickness of 0.58 cm at 3.0 h and 0.44 cm at 6.0 h/Brewer's yeast induced inflammation in mice	²⁶
Anti-oxidative activity
Aqueous extract of D sissoo stem bark	In vitro	IC₅₀ = 12.23 μg/mL/DPPH^• radical scavenging EC₅₀ = 327.8 μg/mL/FRAP	⁵⁹
The EtOH extract of D sissoo stem bark	In vitro	IC₅₀ = 12.14 μg/mL/DPPH^• radical scavenging EC₅₀ = 754.9 μg/mL/FRAP	⁵⁹
The aqueous extract of D sissoo bark	In vitro	AAI = 2.73/DPPH^• radical scavenging IC₅₀ = 10.02 μg/mL/ABTS⁺^• radical scavenging FRAP = 135.0 mg TE/g dried extract	⁶⁰
Aqueous extract of D sissoo leaf	In vitro	AAI = 1.36/DPPH^• radical scavenging IC₅₀ = 12.95 μg/mL/ABTS⁺^• radical scavenging FRAP = 0.362 mg TE/g dried extract	⁶⁰
Aqueous extract of D sissoo fruit	In vitro	AAI = 0.76/DPPH^• radical scavenging IC₅₀ = 21.30 μg/mL/ABTS⁺^• radical scavenging FRAP = 108.85 mg TE/g dried extract	⁶⁰
Anti-aging activity
Aqueous extract of D sissoo bark	In vitro	SI = 1.89, K_UVB = 3.93, and K_UVA = 3.95	⁶⁰
Aqueous extract of D sissoo leaf	In vitro	SI = 8.69, K_UVB = 2.82, and K_UVA = 1.68	⁶⁰
Aqueous extract of D sissoo fruit	In vitro	SI = 5.97, K_UVB = 2.47, and K_UVA = 1.33	⁶⁰
Anti-bacterial activity
MeOH extract of D nigra leaf	In vitro	IZD = 2 mm/Pseudomonas aeruginosa and Staphylococcus aureus IZD = 3 mm/Bacillus cereus and Escherichia coli	61
MeOH extract of D sisoo fruit	In vitro	MIC = 0.39 mg/mL/Staphylococcus aureus MIC = 0.05 mg/mL/Pseudomonas aeruginosa	62
D sisso bark and D stramonium in cow urine (1:1:2)	In vitro	IZD = 10.63 mm/Staphylococcus aureus SR IZD = 27.53 mm/Staphylococcus aureus CI IZD = 16.98 mm/Streptococcus pnuemonae CI IZD = 9.38 mm/Escherichia coli SR IZD = 7.99 mm/Escherichia coli CI IZD = 9.18 mm/Klebsiella pneumonae IZD = 6.56 mm/Pseudomonas aeruginosa SR IZD = 5.55 mm/Pseudomonas aeruginosa CI	⁶³
Anti-nociceptive activity
EtOH extract of D sissoo bark (1000 mg/kg, p.o.)	In vivo	Mean response time is 29.42 s at 60 min of tail flick model	¹³
MeOH extract of D sissoo leaf (100, 200, and 400 mg/kg, p.o.)	In vivo	Anti-nociceptive activity in mice via cGMP pathway and ATP sensitive K⁺ channel opening and the subsequent efflux of K⁺ ions and membrane repolarization or hyperpolarization	⁶⁵
90% EtOH extract of D sissoo leaf (p.o.)	In vivo	TWN = 32.33 at 100 mg/kg, 31.16 at 300 mg/kg, 26.17 at 1000 mg/kg/acetic acid induced pain in mice	⁶⁴
Anti-diarrheal activity
Decoction of D sissoo leaf (1%-10%)	In vitro	To reduce colonization (adherence and invasion) of E coli B170, E coli E134, and S flexneri in Hep-2 cells	⁶⁶
EtOH extract of D sissoo leaf (p.o.)	In vivo	EI = 24.17/castor oil induced diarrhea/EI = 25.17/MgSO₄ induced diarrhea at 100 mg/kg EI = 18/castor oil induced diarrhea/EI = 21.83/MgSO₄ induced diarrhea at 200 mg/kg EI = 16/castor oil induced diarrhea/EI = 16.83/MgSO₄ induced diarrhea at 400 mg/kg	⁶⁷
Anti-pyretic activity
70% EtOH extract of D sissoo bark (80 mg/100 g, i.p.)	In vivo	To decrease body temperature about 1.0 ^oC for 1-3 h treatment/Brewer's yeast stimulated pyrexia in mice	²⁶
90% EtOH extract of D sissoo leaf (100, 300, and 1000 mg/kg, p.o.)	In vivo	To decrease rectal temperature of mice for 1-6 h treatment/Brewer's yeast stimulated pyrexia in mice	⁶⁴
Gastrointestinal activity
EtOH extract of D sissoo stem bark (200 and 400 mg/kg, p.o.)	In vivo	To reduce ulcer index, TBARSs, H₂O₂, and MPO, but increase enzymatic antioxidants, CAT, SOD, GSH-Px, GST, GSH, and NP-SHs contents in diclofenac induced mice	⁶⁸
Biocontrol activity
EtOH extract of D sissoo fruit and root	In vitro	LC₉₀ < 100 mg/L/Biomphalaria pfeifferi adult	⁶⁹
D sissoo bark powder (2.0 g)	In vitro	85.2% Mortality/Heterotermes indicola	¹⁸
D sissoo sapwood powder (2.0 g)	In vitro	47.61% Mortality/Heterotermes indicola	¹⁸
D sissoo heartwood powder (2.0 g)	In vitro	100% Mortality/Heterotermes indicola	¹⁸
Ethanol-toluene extract (2:1, v/v) of D sissoo heartwood	In vitro	LC₅₀ = 5.54 mg/mL/Heterotermes indicola and 73.3% mortality at 10 mg/mL LC₅₀ = 3.89 mg/mL/Reticulitermes flavipes and 62.7% mortality at 10 mg/mL	⁷¹
Pure oil of D sissoo wood (4 mL/m²)	In vitro	100% Mortality/Anopheles stephensi 90% Mortality/Aedes aegypti 60% Mortality/Culex quinquefasciatus	⁷⁰
Pure oil of D sissoo wood (1 mL)	In vitro	96.1% Protection for 10.3 h/Anopheles culicifacies 100% Protection for 11.0 h/Anopheles annularis 89.7% Protection for 8.0 h/Anopheles subpictus 91.7% Protection for 8.1 h/Culex quinquefasciatus	⁷⁰
Aqueous extract of D sissoo leaf	In vitro	LC₅₀ = 1.58%/Rhipicephalus microplus	⁷²
EtOH extract of D sissoo leaf	In vitro	LC₅₀ = 5.25%/Rhipicephalus microplus	⁷²
Anti-epileptic activity
EtOH extract of D sissoo leaf (500 mg/kg, p.o.)	In vivo	To impede seizure onset against the control pilocarpine	⁷³
DNA protective activity
Aqueous extract of D sissoo fruit (10, 50, and 250 μg)	In vitro	Plasmid DNA protection against H₂O₂ stress	⁶⁰
Aqueous bark extract (50 μg)	In vitro	To form a complex with ct DNA by non-covalent interaction	⁶⁰

Flavonoids derived from D cochinchinensis, D sissoo, and D nigra can be divided into various subgroups. On the basis of structural features, compounds 70-95 have been classified as neoflavonoids (Table 1). The most striking feature is that Dalbergia neoflavonoids are presented in 2 forms: open-ring compounds, such as compound 70, and neoflavens, such as compound 71 (Figure 3). An earlier report by Mukere et al (1971) revealed that the petroleum extract of D sissoo stem bark had a new neoflaven, dalbergichromene (71), and 3 known neoflavonoids, dalbergenone (70), dalbergin (72), and methyldalbergin (82).³³ Some neoflavonoids were observed in D sissoo heartwood such as the new compound dalsissooal (75), and known compound R-4-methoxyldalbergione (84).²⁹ In other studies involving D sissoo, 30 metabolites were isolated and purified from the MeOH extract of its trunk exudate. Among them, 2 new secondary metabolites, (+)-5,6-dihydroxy-2-methoxy-5-(1-phenyl-2-propen-1-yl)-2-cyclohexene-1,4-dione (76) and 2-[(1S)-1-phenyl-2-propenyl]-1,4-benzenediol (89), as well as 9 known analogs 86-88, and 90-95, were structurally elucidated as neoflavonoids. D cochinchinensis heartwood had a new neoflaven, 6-hydroxy-2,7-dimethoxyneoflavene (77), and 2 new open-ring secondary metabolites, 9-hydroxy-6,7-dimethoxydalberiquinol (78) and R-5-O-methyllatifolin (85), as well as 3 known congeners, dalbergiphenol (73), R-latifolin (83), and R-4-methoxyldalbergione (84).^22,27,32,34 The existence of a new metabolite, dalnigrin (74), and 3 known analogs, 3′-hydroxymelanettin (79), melanettin (80), and melannein (81), in the MeOH extract of D nigra heartwood was confirmed by both silica gel chromatographic isolation and LC-UV-HRESIMS analysis.¹⁵

Four pterocarpans are covered in this review, of which 4-hydroxymedicarpin (96) and (+)-vesticarpan (99) appeared in the trunk exudate of D sissoo.²³ Melilotocarpan D (98) has been documented for D cochinchinensis heartwood.²⁵ A bioactive metabolite 97, namely (+)-medicarpin, was reported for both D cochinchinensis heartwood and D sissoo trunk exudate.^9,23,31,39 The isolation of molecule 92 suggested the close relationship between Dalbergia species. This compound has been isolated from the heartwood of various species such as D congestiflora, D odorifera, and D tonkinensis.^5,6,41

Ten compounds (100-109) are assignable to the group of simple phenols (Table 1 and Figure 4).^{20,22,23,32,39,40} D cochinchinensis heartwood is rich in simple phenolics, including ethyl 4-hydroxybenzoate (100), ferulaldehyde (101), 1-(4′-hydroxy-2′-methoxyphenyl)-3-(3″-hydroxy-4″-methoxyphenyl)propane (103), 5-[3-hydroxy-1-(2-hydroxyphenyl)-1-propen-1-yl]-2,4-dimethoxyphenol (105), isoferulaldehyde (107), methyl 4-hydroxybenzoate (108), and vanillin (109).^32,39,40 The application of NMR techniques allowed elucidation of the chemical structure of 2-(2-hydroxy-1-methyl-2-phenylethyl)-4,5-dimethoxyphenol (104), a new phenolic derivative, which precipitated out of the EtOH extract of Vietnamese D cochinchinensis stem.²² Hydroxyobtustyrene (102), a derivative of cinnamyl phenol, has, until now, only been isolated from D sissoo trunk exudate and D odorifera heartwood.^6,23 Fractionation of the EtOH extract of D sissoo leaf resulted in the isolation of the new phenolic compound sissooic acid (106).²⁰ Significantly, the chemical class of this compound is very rare to the genus Dalbergia and could be used as a chemotaxonomic agent to distinguish Dalbergia species.

Figure 4.

Simple phenols and terpenoids from D cochinchinensis and D sissoo.

Minor Components

Apart from flavonoids and phenolics, other chemical classes of compound have been found in D cochinchinensis and D sissoo. Six terpenoids, including 4 sesquiterpenoids (110-113) and 2 triterpenoids (114-115), were separated and purified from these 2 plants (Table 1 and Figure 4). D cochinchinensis heartwood contained 6α-hydroxycyclonerolidol (110), 4-epi-cyptomeridiol (111), 7-epi-4-eudesmene-1β,11-diol (112), pterocarpol (113), and oleanolic acid (115), while β-amyrin (114) belonged to D sissoo leaf.^39,40 It should be noted that sesquiterpenoids 111-113 were isolated from the genus Dalbergia for the first time.

Chromatographic separation of the 70% EtOH extract of D cochinchinensis heartwood led to the separation and determination of a new quinone, 2-(3-(4-hydroxyphenyl)-3-methoxypropyl)-5-methoxycyclohexa-2,5-diene-1,4-dione (116), as a brown waxy solid.⁹ In order to find inflammatory inhibitors, a new quinone, (-)-4-hydroxy-2,5-dimethoxy-4-[(2E)-3-phenyl-2-propen-1-yl]-2,5-cyclohexadien-1-one (118), and the known analog, 4-hydroxy-3-methoxy-4-(3-phenyl-2-propenyl)- 2-cyclohexene-1-one (117), were among metabolites isolated from the MeOH extract of D sissoo trunk exudate.²³ The well-known compound latinone (119) was found in the heartwood of both D cochinchinensis and D sissoo.^22,29

Benzofurans 120-124 are the next chemical class presented for Dalbergia species (Table 1 and Figure 5). However, they were only found in D cochinchinensis. 2-[4,5-Dimethoxy-5-(3-phenyl-trans-allyl)cyclohexa-3,6-dien-2-on-1-ylmethyl]-5-hydroxy-6-methoxy-3-phenylbenzofuran (120) and 2-[4,5-dimethoxy-2-(3-phenyl-trans-allyloxy)benzyl]-5-hydroxy-6-methoxy-3-phenylbenzofuran (121) were characteristic of the stem, while 6-hydroxy-2-(2-hydroxy-4-methoxyphenyl)-benzofuran (122), 2-(2′-methoxy-4′-hydroxy)-aryl-3-methyl-6-hydroxybenzofuran (123), and pterolinus B (124) were found in the heartwood.^9,22,39 Among these isolates, compound 120 was previously undescribed compound.

Figure 5.

Quinones, benzofurans, benzophenones, phytosterols, stilbenes, phthalates, and other types from D cochinchinensis and D sissoo.

Three compounds, 125-127, which might be assigned as benzophenones (Table 1 and Figure 5), were detected in D cochinchinensis heartwood.^9,32,34 Cearoin (125) has been further observed in D sissoo heartwood and trunk exudate, as well as 2,2′,5-trihydroxy-4-methoxybenzophenone (127), which was a new natural compound.^23,29,34 Phytochemical research has also shown the appearance of other chemical classes, including 2 phytosterols, β-sitosterol (128) and stigmasterol (129), 2 stilbenes 3,5-dimethoxy-4-hydroxy-trans-stilbene (130) and pterostilbene (131), 2 phthalates, butyl isobutyl phthalate (132) and dibutyl terephthalate (133), 1 xanthone 2,3-dimethoxyxanthone (134), 1 lignan glucoside, syringaresinol-4″-O-β-D-monoglucoside (135), and 1 alkane tritriacontane (136) (Table 1 and Figure 5). Phytosterols 128-129 were found in D cochinchinensis and D sissoo.^26,40 Stilbenes 130-131, phthalates 132-133, and xanthone 134 have only been found to date in D cochinchinensis heartwood.^8,9,39,40 Lignan 135 and alkane 136 have been reported in the leaf and stem of D sissoo, respectively.^11,20

GC-MS Identification and Other Products

Siamese and Indian rosewoods were also used as raw materials in phytochemical studies using GC-MS (gas chromatography-mass spectrometry). A recent GC-MS analysis revealed that the petroleum extract of D cochinchinensis dried heartwood contained 2,6-dimethoxyphenyl 3-phenylpropanoate (43.8%), 1,1-diphenyl-2-propanol (10.3%), naringenin (8.8%), [2-hydroxy-4-(2-hydroxyethoxy)phenyl]phenyl-methanone (5.6%), triphenylmethane (5.2%), and 5-methoxy-6-[1-[4-methoxyphenyl]ethyl]-1,3-benzodioxole (3.1%).³⁸ The benzene-ethanol (1:2, v/v) extract of D cochinchinensis heartwood was associated with the presence of 6-iodo-2-methylquinazolin-4(3H)-one (54.43%), 4-cyclohexanedicarboxylic acid, 2,5-dioxo-diethyl ester (15.9%), 1-(3-aminopropyl)-azacyclotridecan-2-one (4.0%), naringenin (3.9%), and liquiritigenin (2.8%).⁴² GC × GC-MS study of the volatile components of D cochinchinensis heartwood showed that aldehydes and ketones such as benzaldehyde, cinnamaldehyde, 4-chromanone, acetophenone, and 1-(2-hydroxyphenyl)ethanone are the main components.⁴³ Fatty acids are the major constituents of the oils of D sissoo fresh pod, some of which reached significant amounts, such as linoleic acid (22.3%), oleic acid (10.2%), palmitic acid (10.1%), behenic acid (9.3%), lauric acid (5.7%), myristic acid (4.9%), palmitoleic acid (2.2%), and stearic acid (2.9%).⁴⁴

Srisomsap et al (1996) successfully isolated and purified a glycosidase enzyme with both β-glucosidase and β-fucosidase activities from the seed of D cochinchinensis by ammonium sulfate fractionation, focusing-isoelectric preparation, and Sephadex G-150 column chromatography.¹⁹ The β-glucosidase showed a high effect in hydrolyzing isoflavonoid glycosides to increase free isoflavones in soybean products.⁴⁵ The enzyme was also able to catalyze the break in the bond between aglycone and glycone of dalcochinin-8′-O-β-D-glucoside (56), better than cassava stem linamarase, almond β-glucosidase, and mustard seed myrosinase enzymes.³⁷

D cochinchinensis heartwood extracts, as natural dyes, have been effective in the staining of wood veneers with anti-UV capacity.¹⁰ In the same manner, the meta-mordant technique for wool dyeing using D sissoo leaf dye and mordant ferrous sulfate caused the highest shade depth value of 17.⁴⁶ D sissoo SSD₆₇₃ (sawdust charred at 673 K) has potential for removal of phenol from contaminated water, with a maximal adsorption capacity of 344.83 mg phenol/g SSD₆₇₃ at 45 °C.⁴⁷

Mucilaginous polysaccharide derived from D sissoo leaf exhibited many potential pharmacological uses, thereby elucidating the structure and ratio of monosaccharides in the polysaccharide to help highlight the structure-activity relationship. Chemical engineering studies conducted by Rana et al showed that D sissoo leaf contained about 14.0% of a pure polysaccharide (molecule weight of 1.5 × 10⁵ Da, 15.7% of glucuronic acid).^48–50 Monosaccharides in this saccharide were α-L-rhamnose, β-D-glucuronic acid, β-D-galactose, and β-D-glucose in 1:1:2:2.33 molar ratio, as well as these units linked to each other by 1→2, 1→3, and 1→4 linkages.^48–50

Pharmacological Activities

Table 2 outlines the pharmacological results using the 3 Dalbergia plant extracts and their isolated compounds, comprising sexual,^{22,26,34,51–53} anti-osteoporosis,^{20,29,30,54–56} anti-inflammatory,^{14,23,26,57,58} anti-oxidative,^59,60 anti-aging,⁶⁰ anti-bacterial,^61–63 anti-nociceptive,^13,64,65 anti-diarrheal,^66,67 anti-pyretic,^26,64 gastrointestinal,⁶⁸ biocontrol,^18,69–72 and other activities.^60,73

Sexual Activity

Testosterone has been known for a long time as a crucial hormone in driving male sexual function. It is completely converted to 5α-dihydrotestosterone (DHT) by 5α-reductase. The DHT-receptor complex, which causes diseases, is formed when DHT binds to an androgen receptor.³⁴ Five phytochemicals derived from D cochinchinensis, flavone (1), flavan (34), neoflavonoids (77-78), and benzophenone (127), exhibited inhibition of 5α-reductase and DHT-receptor binding at concentrations ranging from 50 to 200 µg/mL (Table 2).³⁴ Shirota et al also reported that other D cochinchinensis metabolites (67, 73, 104, 119, 120, and 121) at concentrations of 25-100 µg/mL possessed inhibitory percentages of 0.6%-52.0% against 5α-reductase, as compared with those of the positive control glycyrrhetinic acid (31.7%-87.1%).²² Chalcone 67 and quinone 119 showed better activity than neoflavonoid 73, and benzofurans 120-121 (Table 2).²² The 70% EtOH extract of D sissoo bark (100 mg/100 g) showed estrogenic activity, maintaining an unchanged bodyweight of 39 g for immature female mice, but increasing the average uterine weight to 27.6 mg, as compared with that of the non-treated group (20 mg).²⁶

In an anti-spermatogenic assay, the EtOH extract of D sissoo stem bark (20 mg/mL) caused immobilization of sperm of fertile men aged 25 to 35 years within 3 min.⁵¹ This extract, at a concentration of 200 mg/kg, also decreased the weight of testis and epididymis of Swiss male albino mice in an in vivo anti-spermatogenic model.⁵¹ D sissoo aqueous leaf extract at doses of 50 and 100 mg/kg significantly reduced epididymal sperm motility, viability and number during 35 days.⁵² The anti-spermatogenic mechanism involved decreased StAR protein, P450scc enzyme expression, and 3β and 17β-hydroxysteroid dehydrogenase (HSD) enzyme activity, and induced oxidative stresses in the testis of Park male mice, and increased germ cell apoptosis and caspase-3 expression (Figure 6).⁵³

Figure 6.

The plausible mechanism of action of D sissoo aqueous leaf extract on spermatogenic suppression in Parke male mice.

Anti-Osteoporosis Activity

Osteoporosis is mainly caused by low bone and micro-architectural deterioration of the trabecular and cortical bone.^{20,29,30,54–56} Naturally occurring flavonoids without adverse effects are now potential dietary agents to decrease the risk of this disease.⁶ Five isoflavones (8, 9, 16, 21, and 25), at doses ranging from 1.0 pM to 1.0 µM, showed in vitro osteogenic activity by increasing alkaline phosphatase (ALP) activity and mineralization.²⁰ The capacity to increase the ALP number of the tested neoflavonoids 71-73, 75, and 82, and phenol 116 is followed by a visible order of 72 (EC₅₀ 1.01 nM) > 75 (EC₅₀ 6.46 nM) > 71 (EC₅₀ 1.7 µM) > 82 (EC₅₀ 9.1 µM) > 73 (EC₅₀ 98 µM) > 119 (EC₅₀ 116 µM).²⁹ A new isoflavone glycoside, dalsissooside (16), at doses of 1 and 5 mg/kg, i.p., increased the ALP number in an in vivo model, but failed at the higher dose of 10 mg/kg.²⁰ Compound 16 controlled the clinical osteoarthritis symptoms due to its interleukin-1β inhibitory effect at a concentration of 1.0 µM.³⁰ Oral administration of dalbergin (72) at a dose of 1.0 mg/kg/day protected against trabecular bone loss in cancellous bone in distal tibial metaphyseal fractures and lumbar vertebra regions of ovariectomized mice.⁵⁴ This compound also reduced bone resorption expression markers TRAP and RANK, but increased osteogenic markers RUNX2, BMP-2, and OPG/RANKL.⁵⁴ The neoflavonoid, dalsissooal, (75) (5 mg/kg/day, p.o.) induced significant effects to protect against bone loss in post-menopausal osteoporosis in ovariectomized mice.⁵⁶ Dalsissooal (75) promoted trabecular bone, micro-architecture parameters, biomechanical strength, and bone formation (osteoblast gene expression increase/osteoclastic gene expression decrease).⁵⁶

The EtOH extract of D sissoo leaf (250 and 500 mg/kg, p.o.) prevented joint cartilage damage and deterioration in subchondral mice bone in vivo, while at a dose of 250 mg/kg remarkably increased bone volume fraction, trabecular thickness and number, and connective density, reduced trabecular separation, and promoted osteogenic genes expression of BMP-2, BMP-4, RunX-2, and COL-1.^30,55

Anti-Inflammatory Activity

In an anti-inflammatory assay against NO (nitric oxide) production in LPS (lipopolysaccharide) stimulated J774.1 macrophage cells, the IC₅₀ values were found to run in the consistent order of neoflavonoid 76 (IC₅₀ 3.19 µM) > chalcone 66 (IC₅₀ 5.4 µM) > quinone 118 (IC₅₀ 6.22 µM) > neoflavonoid 87 (IC₅₀ 11.5 µM) > the positive control L-NMMA (IC₅₀ 32.0 µM), neoflavonoid 70 (IC₅₀ 38.8 µM) > neoflavonoid 86 (IC₅₀ 39.7 µM).²³ Comparison of the 3 open ring neoflavonoids 70 and 86-87 showed that a 4′-OH group increased activity, but 4-OMe had a little effect on NO production (Figure 2).

The 90% EtOH extract of D sissoo leaf was safe for mice at a dose of 10.125 g/kg, p.o., and demonstrated remarkably suppression of carrageenan, kaolin, and nystatin induced paw edema at doses of 100-300 mg/kg.⁵⁷ Similarly, the 90% EtOH extract of D sissoo bark (safe dose 3000 mg/kg, p.o.) at a concentration of 1000 mg/kg had a more potent anti-inflammation effect than doses of 300 and 500 mg/kg against carrageenan stimulated paw edema in rats.¹⁴ In the same model, the MeOH extract of D sissoo root at a dose of 1000 mg/kg was better than that at doses of 100 and 500 mg/kg.⁵⁸

Injection of Brewer's yeast (Saccharomyces cerevisiae) leads to lethargy, fever, and anorexia because it causes the release of pro-inflammatory cytokines in the brain and blood.⁶ The 70% EtOH extract of D sissoo bark (80 mg/100 g) helped to reduce paw thickness by up to 0.58 and 0.44 cm after injection of Brewer's yeast in mice at 3.0 and 6.0 h post treatment, as compared with those of the non-treated group (0.72 and 0.68 cm).²⁶

Anti-Oxidant and Anti-Aging Activities

The DPPH^• (2,2-diphenyl-1-picrylhydrazyl) radical scavenging activity of the aqueous extract of D sissoo stem bark was comparable with the positive control gallic acid (IC₅₀ = 12.14 μg/mL), and better than that of the MeOH extract (IC₅₀ = 12.14 μg/mL).⁵⁹ It was further observed that the aqueous extract, with an EC₅₀ value of 327.8 μg/mL in the FRAP (ferric reducing antioxidative power) assay, is less than that of the MeOH extract (EC₅₀ = 754.9 μg/mL).⁵⁹

The aqueous extract of D sissoo bark, with better antioxidant activity index (AAI), IC₅₀, and FRAP values, has greater antioxidant activity than the aqueous extracts of either the leaf or fruit in the DPPH^• and ABTS^•+(2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) radical scavenging, and FRAP assays (Table 2).⁶⁰ The bark aqueous extract showed the best AAI of 2.73 in the DPPH^• assay, the best IC₅₀ value of 10.02 μg/mL in the ABTS⁺^• assay, and the best FRAP value of 135.0 mg TE (trolox equivalent)/g dry extract.⁶⁰

For anti-aging activity, the SI values (selectivity index = IC₅₀ for mouse melanoma B16 skin cancer cells/IC₅₀ for non-cancerous HaCaT skin cells) run in the order of aqueous extract of D sissoo leaf (SI = 8.69) > the fruit aqueous extract (SI = 5.79) > the bark aqueous extract (SI = 1.89) > the positive control paclitaxel (SI = 1.33).⁶⁰ It is safe to conclude that D sissoo aqueous extracts show cytotoxicity toward B16 cells. Furthermore, the absorption coefficients K_UV−B _{(300 nm)} and K_{UV−A (365 nm)} of the aqueous bark extract are always better than those of the aqueous extracts of the leaf and fruit (Table 2).⁶⁰

Anti-Bacterial Activity

The MeOH extract of D nigra leaf induced an inhibitory zone diameter (IZD) of 2 mm against Pseudomonas aeruginosa and Staphylococcus aureus, and an IZD value of 3 mm against Bacillus cereus and Escherichia coli.⁶¹ The MeOH extract of D sisoo fruit inhibited the growth of S aureus and P aeruginosa with minimum inhibitory concentration values of 0.386 and 0.05 mg/mL, respectively.⁶² A herbal drug formulation containing D sisso bark (100 g) and Datura stramonium (100 g) in cow urine (200 mL) inhibited the growth of S aureus SR, S aureus CI, Streptococcus pnuemonae CI, E coli SR, E coli CI, Klebsiella pneumonae, P aeruginosa SR, and P aeruginosa CI with IZD values of 5.55 to 27.53 mm, as compared with those of the positive control, chloramphenicol (IZD = 11.23-21.33 mm).⁶³

Anti-Nociceptive Activity

Anti-nociceptive action is involved in blocking the detection of a painful stimulus by sensory neurons. In the tail-flick model, the EtOH extract of D sissoo bark at a dose of 1000 mg/kg reduced the pain at 1 h (mean response time 29.42 s, compared to 30.85 s of the positive control aspirin), but the doses of 300 and 500 mg/kg failed to do so.¹³ The MeOH extract of D sissoo leaf at doses of 100, 200, and 400 mg/kg showed anti-nociceptive activity in both heat and chemical stimulated pain models such as hot plate and acetic acid-induced nociception in mice via the cGMP pathway and ATP sensitive K⁺ channel opening and the subsequent efflux of K⁺ ions and membrane depolarization or hyperpolarization.⁶⁵ The 90% EtOH extract of D sissoo leaf, at doses of 100, 300, and 1000 mg/kg, p.o., showed analgesic activity since the writhing number (TWN) caused by acetic acid induced pain in mice decreased from 32.33 to 26.17/per 20 min.⁶⁴

Anti-Diarrheal Activity

In traditional uses of the Indian community, D sissoo parts are the best selection to treat infectious diarrhea. The decoction of D sissoo leaf (1%-10%) reduced colonization (adherence and invasion) of E coli B170, E coli E134, and S flexneri in Hep-2 cells.⁶⁶ The EtOH extract of D sissoo leaf has an LD₅₀ value of more than 2000 mg/kg for mice, p.o.⁶⁷ In the models of castor oil and MgSO₄ induced diarrheal disease (Table 2), a dose increase from 1000 to 4000 mg/kg was responsible for a decrease in the EI (evacuation index), as compared with the non-treated group (EI > 56.83).⁶⁷ This increase in dose also promoted the reduction of peristalsis activity of barium sulfate milk and charcoal meal in mice.⁶⁷

Anti-Pyretic and Gastrointestinal Activities

The 70% EtOH extract of D sissoo bark (80 mg/100 g, i.p.) also reduced the body temperature of mice by about 1.0 °C for 1-3 h treatment in the Brewer's yeast stimulated pyrexia model.²⁶ The 90% EtOH extract of D sissoo leaf, at doses of 100, 300, and 1000 mg/kg, p.o., produced a slight decrease in rectal temperature of mice after 1-6 h treatment.⁶⁴

Oral administration of the EtOH extract of D sissoo stem bark (200 and 400 mg/kg) resulted in a gastrointestinal protective effect.⁶⁸ This was evidenced by the extract remarkably reducing the ulcer index, TBARSs (thiobarbituric acid reactive substances), H₂O₂, and MPO (myeloperoxidase) activity in the gastric mucosa of the ulcerated mice, but increasing the contents of the enzymatic antioxidants CAT (catalase), SOD (superoxide dismutase), GSH-Px (glutathione peroxidase), GST (glutathione-S-transferase), GSH (reduced glutathione), and NP-SHs (nonprotein sulfhydryls) in the gastric mucosa of diclofenac-induced mice.⁶⁸

Biocontrol Activity

The EtOH extract of D sissoo fruit and root gave an LC₉₀ value of less than 100 mg/L for molluscicidal activity against Biomphalaria pfeifferi adult, with additional toxicity toward its 0-24 h-old egg masses.⁶⁹ The bark, sapwood, and heartwood (2.0 g powder, each) of this plant also caused respective mortality rates of 85.2%, 47.61%, and 100% to Heterotermes indicola termite within 6 days.¹⁸ In another report, the ethanol-toluene extract (2:1, v/v) of D sissoo heartwood controlled H indicola and Reticulitermes flavipes, with respective LC₅₀ values of 5.54 and 3.89 mg/mL, and induced the respective highest mortalities of 73.3% and 62.7% at the concentration of 10 mg/mL.⁷¹ The pure oil of D sissoo wood at a dose of 4 mL/m² produced death percentages of 100%, 90%, and 60% to Anopheles stephensi, Aedes aegypti, and Culex quinquefasciatus immature mosquitoes within 24 h of treatment.⁷⁰ Additionally, as shown in Table 2, its protective effect against mosquito bites during 8 to 11 h was comparable with the commercial product mylol oil (93.8%).⁷⁰ The aqueous extract of D sissoo leaf, with an LC₅₀ value of 1.58%, showed acaricidal activity against Rhipicephalus microplus tick, better than that of its EtOH extract (LC₅₀ = 5.25%).⁷²

Other Activities

Another point is that, in Pakistan, parts of D sissoo are used for the treatment of epilepsy. A pharmacological study conducted by Majeed et al revealed that the alcoholic extracts of bark and leaf have non-toxic and non-mutagenic effects.⁷³ From in vivo experimental results, both of these 2 extracts also reduced seizure intensity, and convulsive duration when pilocarpine was used to induce seizures in albino Wistar rats.⁷³ Especially, at the dose of 500 mg/kg, p.o., D sissoo leaf extract impeded seizure onset against the control pilocarpine.⁷³

The aqueous extract of D sissoo fruit (10, 50, and 250 μg) showed plasmid DNA protection against H₂O₂ stress, whereas the aqueous bark extract (50 μg) had non-covalent interaction with ct DNA complex [λ_max at 210 nm (the aqueous bark extract, only) shifted to 220 nm (the aqueous bark extract-ct DNA complex].⁶⁰

Conclusion

For the first time, the current review gives an insight into the phytochemistry, applications, and pharmacological aspects relating to 3 well-known Dalbergia species, Siamese rosewood, Indian rosewood, and Brazilian rosewood. The studies focus on 2 main species, D cochinchinensis and D sissoo. More than 130 secondary metabolites have been completely isolated and structurally elucidated, to date. Dalbergia constituents appear in a wide variety of chemical classes, such as simple phenols, sesquiterpenoids, benzofurans, and benzophenones, but phenolics, especially flavonoids, are major compounds. Flavonoids 1-99 derived from 3 Dalbergia species are classified into 9 main backbones, comprising flavones, isoflavones, flavans, isoflavans, isoflaven, flavanones, isoflavanones, chalcones, and neoflavonoids. Some of the isolated compounds were new to the literature, eg, isoflavone dalsissooside (16), and isoflavan dalbergiacochan A (35). Both Dalbergia crude plant extracts and their isolated compounds act as bioactive agents in many in vitro and in vivo pharmacological examinations. The neoflavonoid dalsissooal (75), at a dose of 5 mg/kg/day, p.o., produced significant effects to protect bone loss in post-menopausal osteoporosis in ovariectomized mice. The anti-spermatogenic mechanism of D sissoo aqueous leaf extract (50 and 100 mg/kg) is caused by decreasing StAR protein and P450scc enzyme expression and 3β and 17β-HSD enzyme activity in Park male mice. Besides pharmacological properties, rosewoods and other Dalbergia species have also drawn much interest due to their uses as sources of essential oil, for furniture, dye, water treatment, and biocontrol products. It is desirable to obtain more phytochemical, clinical and mechanical results.

Footnotes

Abbreviations

Declaration of Conflicting Interests

The authors declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

Funding

The authors received no financial support for the research, authorship, and/or publication of this article.

ORCID iD

Ninh The Son

References

Linh

NTT

Son

. Genus Tupistra: a comprehensive review of phytochemistry and pharmacological activity. Nat Prod Commun. 2022;17(1):1‐20. doi: 10.1177/1934578X221074851

Son

Oda

Hayashi

, et al. Antimicrobial activity of the constituents of Dalbergia tonkinensis and structural-bioactive highlights. Nat Prod Commun. 2018;13(2):157‐161. doi: 10.1177/1934578X1801300212

Son

Harada

Cuong

Fukuyama

. Two new carboxyethylflavanones from the heartwood of Dalbergia tonkinensis and their antimicrobial activities. Nat Prod Commun. 2017;12(11):1721‐1723. doi: 10.1177/1934578X1701201115

Son

Suenaga

Matsunaga

, et al. Serine protease inhibitors and activators from Dalbergia tonkinensis species. J Nat Med. 2020;48(1):257‐263. doi:10.1007/s11418-019-01347-y

Son

Yamamoto

Fukuyama

. Chemotaxonomic aspects of the constituents of the plant Dalbergia tonkinensis. Biochem Syst Ecol. 2018;78:98‐101. doi:10.1016/j.bse.2018.04.009

The

. A review on the medicinal plant Dalbergia odorifera species: phytochemistry and biological activity. Evid Based Complementary Altern Med. 2017;2017:ID 7142370. doi: 10.1155/2017/7142370

Zhong

Chen

Qiu

Liu

. A new isoflavan from the heartwood of Dalbergia cochinchinensis. Nat Prod Commun. 2021;16(10):1‐4. doi: 10.1177/1934578X211049673

Liu

Wen

Shao

Zhang

Huang

Zhang

. Flavonoids from heartwood of Dalbergia cochinchinensis. Chin Herb Med. 2016;8(1):89‐93. doi:10.1016/S1674-6384(16)60014-X

Liu

Shao

, et al. A new chalcone from heartwood of Dalbergia cochinchinensis. Chem Nat Compd. 2016;52(3):405‐408. doi:10.1007/s10600-016-1659-7

10.

Zhu

Sheng

Chen

, et al. Staining of wood veneers with anti-UV property using the natural dye extracted from Dalbergia cochinchinensis. J Clean Prod. 2021;284:124770. doi:10.1016/j.jclepro.2020.124770

11.

Devi

Singh

Promila . Isolation and characterization of chemical constituents from Dalbergia sisoo Roxb. Stem. Int J Chem Stud. 2017;5(6):1504‐1506

12.

Devi

Singh

Promila . Phytochemical and pharmacological profiling of Dalbergia sissoo Roxb. Stem. J Pharmacogn Phytochem. 2017;6(6):2483‐2486.

13.

Asif

Kumar

. Phytochemical investigation and evaluation of antinociceptive activity of ethanolic extract of Dalbergia sissoo (Roxb.) bark. J Nat Sc Biol Med. 2011;2(1):76‐79. doi:10.4103/0976-9668.82315

14.

Asif

Kumar

. Anti-inflammatory activity of ethanolic extract of Dalbergia sissoo (Roxb.) bark. Malays J Pharm Sci. 2009;7(1):39‐50.

15.

Kite

Green

PWC

Veithc

Groves

Gasson

Simmonds

MSJ

. Dalnigrin, a neoflavonoid marker for identification of Brazilian rosewood (Dalbergia nigra) in CITES enforcement. Phytochemistry. 2010;71(10):1122‐1131. doi:10.1016/j.phytochem.2010.04.011

16.

Mathias

Vieira

IJC

Braz-Filho

Rodrigues-Filho

. A new isoflavone glycoside from Dalbergia nigra. J Nat Prod. 1998;61(9):1158‐1161. doi:10.1021/np9800598

17.

Al-Snafi

. Chemical constituents and pharmacological effects of Dalbergia sissoo – a review. IOSR J Pharm. 2017;7(2):59‐71.

18.

Qureshi

Ali

Athar

Ullah

. Protozoidal activities of Eucalyptus cammeldulensis, Dalbergia sissoo and Acacia arabica woods and their different parts on the entozoic flagellates of Heterotermes indicola and Coptotermes heimi. Afr J Biotechnol. 2012;11(57):12094‐12102. doi: 10.5897/AJB12.375

19.

Srisomsap

Svasti

Surarit

, et al. Isolation and characterization of an enzyme with β-glucosidase and β-fucosidase activities from Dalbergia cochinchinensis Pierre. J Biochem. 1996;119(3):585‐590. doi:10.1093/oxfordjournals.jbchem.a021282

20.

Dixit

Chillara

Khedgikar

, et al. Constituents of Dalbergia sissoo Roxb. Leaves with osteogenic activity. Bioorg Med Chem Lett. 2012;22(2):890‐897. doi:10.1016/j.bmcl.2011.12.036

21.

Reddy

RVN

Reddy

Khalivulla

, et al. O-Prenylated flavonoids from Dalbergia sissoo. Phytochem Lett. 2008;1(1):23‐26. doi:10.1016/j.phytol.2007.11.001

22.

Shirota

Pathak

Sekita

, et al. Phenolic constituents from Dalbergia cochinchinensis. J Nat Prod. 2003;66(8):1128‐1131. doi:10.1021/np0300683

23.

Shrestha

Amano

Narukawa

Takeda

. Nitric oxide production inhibitory activity of flavonoids contained in trunk exudates of Dalbergia sissoo. J Nat Prod. 2008;71(1):98‐101. doi:10.1021/np070478h

24.

Aree

Tip-pyang

Seesukphronrarak

Chaichit

. 2-(5,7-Dihydroxy-4-oxo-4H-chromen-3-yl)-5-methoxy-1,4-benzoquinone (isoflavonequinone). Acta Cryst. 2003;E59(3):o363‐o365. doi: 10.1107/S1600536803003684

25.

Aree

Tip-pyang

Paramapojn

. Chaichit N. 3,9–dimethoxy-6a,11a-dihydro-6H-benzo[4,5]furo[3,2-c]chromene-4,10-diol monohydrate. Acta Cryst. 2003;E59(3):o381‐o383. doi: 10.1107/S1600536803004227

26.

Sarg

Ateya

Abdel-Ghani

Badr

Shams

. Phytochemical and pharmacological studies of Dalbergia sissoo growing in Egypt. Pharm Biol. 1999;37(1):54‐62. doi:10.1076/phbi.37.1.54.6310

27.

Donnelly

DMX

Nangle

Prendergast

Osullivan

. Dalbergia species-V*, isolation of R-5-O-methyllatifolin from Dalbergia cochinchinensis Pierre. Phytochemistry. 1968;7(4):647‐649. doi:10.1016/S0031-9422(00)88241-2

28.

Farag

Ahmed

Terashima

Takaya

Niwa

. Isoflavonoid glycosides from Dalbergia sissoo. Phytochemistry. 2001;57(8):1263‐1268. doi:10.1016/S0031-9422(01)00195-9

29.

Kumar

Kushwaha

Khedgikar

, et al. Neoflavonoids as potential osteogenic agents from Dalbergia sissoo heartwood. Bioorg Med Chem Lett. 2014;24(12):2664‐2668. doi:10.1016/j.bmcl.2014.04.056

30.

Kothari

Tripathi

Girme

, et al. Caviunin glycoside (CAFG) from Dalbergia sissoo attenuates osteoarthritis by modulating chondrogenic and matrix regulating proteins. J Ethnopharmacol. 2022;282:114315. doi:10.1016/j.jep.2021.114315

31.

Liu

Wen

Zhang

, et al. Chemical constituents of isoflavonoids from Dalbergia cochinchinensis. J Chin Med Mater. 2015;46(19):2851‐2855.

32.

Masanori

Akira

Yutaka

, et al. Anti-androgen active constituents from Dalbergia cochinchinensis PIERRE. Nat Med. 1996;59(6):408‐412.

33.

Mukerjee

Saroja

Seshadri

. Dalberichromene, A new neoflavonoid from stem bark and heartwood of Dalbergia sissoo. Tetrahedron. 1971;27(4):799‐803. doi:10.1016/S0040-4020(01)92474-3

34.

Pathak

Shirota

Sekita

, et al. Antiandrogenic phenolic constituents from Dalbergia cochinchinensis. Phytochemistry. 1997;46(7):1219‐1223. doi:10.1016/S0031-9422(97)80015-5

35.

Sharma

Chibber

Chawla

. Caviunin 7-O-gentiobioside from Dalbergia sissoo pods. Phytochemistry. 1979;18(7):1253. doi:10.1016/0031-9422(79)80160-0

36.

Sharma

Chibber

Chawla

. Isocaviunin 7-O-gentiobioside, a new isoflavone glycoside from Dalbergia sissoo. Phytochemistry. 1980;9(4):715. doi:10.1016/0031-9422(80)87054-3

37.

Svastia

Srisomsapa

Techasakula

Surarit

. Dalcochinin-8′-O-β-D-glucoside and its β-glucosidase enzyme from Dalbergia cochinchinensis. Phytochemistry. 1999;50(5):739‐743. doi:10.1016/S0031-9422(98)00552-4

38.

Zhang

Wang

Guo

Huang

Wang

. Study on the characteristic components of distinguishing Dalbergia cochinchinensis from the other three similar Dalbergia species. For Prod J. 2021;71:336‐341.

39.

Liu

Wen

, et al. Chemical constituents from Dalbergia cochinchinensis. J Chin Med Mater. 2015;38:1868‐1871.

40.

Zhong

Huang

Zhou

Zhu

Qiu

. Chemical constituents from the heartwood of Dalbergia cochinchinensis. Nat Prod Res Dev. 2013;25:1515‐1518.

41.

Martínez-Sotres

López-Albarrán

Cruz-de-León

, et al. Medicarpin, an antifungal compound identified in hexane extract of Dalbergia congestiflora Pittier heartwood. Int Biodeterior Biodegr. 2012;69:38‐40. doi:10.1016/j.ibiod.2011.11.016

42.

Jiang

Liu

Yang

. The effects of drying methods on extract of Dalbergia cochinchinensis Pierre. Eur J Wood Prod. 2016;74(5):663‐669. doi:10.1007/s00107-016-1041-2

43.

Xiang

Chen

Zhao

, et al. Analysis of volatile components in Dalbergia cochinchinensis Pierre by a comprehensive two-dimensional gas chromatography with mass spectrometry method using a solid-state modulator. J Sep Sci. 2018;41(23):4315‐4322. doi:10.1002/jssc.201800636

44.

Ali

Rizwani

Rasheed

, et al. Chemical analysis of Dalbergia sissoo (Roxb.) pod oil by (GC-MS) GC-FID and evaluation of antioxidant potential. Pak J Pharm Sci. 2019;32(5):2175‐2181.

45.

Chuankhayan

Rimlumduan

Svasti

Cairns

JRK

. Hydrolysis of soybean isoflavonoid glycosides by Dalbergia β-glucosidases. J Agric Food Chem. 2007;55(6):2407‐2412. doi:10.1021/jf062885p

46.

Nawaz

Rehman

Hussain

Safdar

Iqbal

. Dyeing of wool with Dalbergia sissoo as an eco-friendly substituent of conventional hazardous synthetic dye. J Nat Fibers. 2021:1‐14. https://doi.org/10.1080/15440478.2021.1993480

47.

Mubarik

Saeed

Mehmood

Iqbal

. Phenol adsorption by charred sawdust of sheesham (Indian rosewood; Dalbergia sissoo) from single, binary and ternary contaminated solutions. J Taiwan Inst Chem Eng. 2012;43(6):926‐933. doi:10.1016/j.jtice.2012.07.003

48.

Rana

Kumar

Soni

. Structure of the oligosaccharide isolated from Dalbergia sissoo Roxb. Leaf polysaccharide. Carbohydr Polym. 2009;78(3):520‐525. doi:10.1016/j.carbpol.2009.05.014

49.

Rana

Kumar

Soni

. Structural characterization of an acidic polysaccharide from Dalbergia sissoo Roxb. Leaves. Carbohydr Polym. 2012;90(1):243‐250. doi:10.1016/j.carbpol.2012.05.031

50.

Rana

Das

Gogoi

Kumar

. Multifunctional properties of polysaccharides from Dalbergia sissoo, Tectona grandis and Mimosa diplotricha. Carbohydr Polym. 2014;102:341‐350. doi:10.1016/j.carbpol.2013.11.035

51.

Vasudeva

Vats

. Anti-spermatogenic activity of ethanol extract of Dalbergia sisoo Roxb. Stem bark. J Acupunct Meridian Stud. 2011;4(2):116‐122. doi:10.1016/S2005-2901(11)60017-4

52.

Verma

Singh

. Dalbergia sissoo Roxb. On spermatogenesis and fertility in male mice. Eur J Contracept Reprod Health Care. 2014;19(6):475‐486. doi:10.3109/13625187.2014.945165

53.

Verma

Singh

. An insight into the possible mechanisms of antispermatogenic action of Dalbergia sissoo in male mice. Andrologia. 2018;50(3):e12917. doi:10.1111/and.12917

54.

Choudhary

Kushwaha

Gautam

, et al. Fast and long acting neoflavonoids dalbergin isolated from Dalbergia sissoo heartwood is osteoprotective in overiectomized model of osteoporosis: Osteoprotective effect of dalbergin. Biomed Pharmacother. 2016;83:942‐957. doi:10.1016/j.biopha.2016.08.010

55.

Khedgikar

Kushwaha

Ahmad

, et al. Ethanolic extract of Dalbergia sissoo promotes rapid regeneration of cortical bone in drill-hole defect model of rat. Biomed Pharmacother. 2017;86:16‐22. doi:10.1016/j.biopha.2016.11.140

56.

Kushwaha

Khedgikar

Ahmad

, et al. A neoflavonoid dalsissooal isolated from heartwood of Dalbergia sissoo Roxb. Has bone forming effects in mice model for osteoporosis. Eur J Pharmacol. 2016;78:65‐74. doi:10.1016/j.ejphar.2016.06.003

57.

Hajare

Chandra

Sharma

Tandan

Lal

Telang

. Anti-inflammatory activity of Dalbergia sissoo leaves. Fitoterpia. 2001;200(72):131‐139.

58.

Kumar

Kumud

. Anti-inflammatory activity of root of Dalbergia sissoo (Roxb) in carrageenan-induced paw edema in rats. Phcog J. 2010;2(11):427‐430. doi:10.1016/S0975-3575(10)80026-4

59.

Roy

Laskar

Ismail

Kumari

Ghosh

Begum

. A detailed study on the antioxidant activity of the stem bark of Dalbergia sissoo Roxb., an Indian medicinal plant. Food Chem. 2011;26(3):1115‐1121. doi:10.1016/j.foodchem.2010.11.143

60.

Yasmeen

Gupta

. Cosmeceutical and anticancer potential of aqueous extracts of Dalbergia sissoo Roxb. Aerial parts. J Herb Med. 2021;29:100456. doi:10.1016/j.hermed.2021.100456

61.

Almeida Alves

TMD

Fonseca Silva

Brandao

Mesquita Grandi

Fatima

Smania

. Biological screening of Brazilian medicinal plants. Mem Inst Oswaldo Cruz. 2000;85(3):367‐373.

62.

Prasad

Nandi

Arora

Pandey

. In vitro evaluation of antibacterial properties of Moringa oleifera, Dalbergia sissoo and Alstonia sholaris. J Biol Agric Healthc. 2014;4(15):54‐62.

63.

Yadav

Jain

, et al. Antimicrobial property of herbal preparation containing Dalbergia sissoo and Datura stramonium with cow urine against pathogenic bacteria. Int J Immunopathol Pharm. 2008;21(4):1013‐1020. doi:10.1177/039463200802100427

64.

Hajare

Chandra

Tandan

Sarma

Lal

Telang

. Analgesic and antipyretic activities of Dalbergia sissoo leaves. Indian J Pharmcol. 2000;32(6):357‐360.

65.

Mannan

Khatun

Khan

MFH

. Antinociceptive effect of methanol extract of Dalbergia sissoo leaves in mice. BMC Complement Altern Med. 2017;17(1):72. doi:10.1186/s12906-017-1565-y

66.

Brijesha

Daswania

Tetalib

Antiaa

Birdi

. Studies on Dalbergia sissoo (Roxb.) leaves: possible mechanism(s) of action in infectious diarrhea. Indian J Pharmacol. 2006;38(2):1201–1124.

67.

Chandra

Sachan

Pal

. Protective effect of Dalbergia sissoo Roxb. Ex DC. (family: fabaceae) leaves against experimentally induced diarrhea and peristalsis in mice. Toxicol Ind Health. 2015;31(12):1229‐1235. doi:10.1177/0748233713491815

68.

Khan

. Gastroprotective potential of Dalbergia sissoo Roxb. Stem bark against diclofenac induced gastric damage in rats. Osong Public Health Res Perspect. 2013;4(5):271‐277. doi:10.1016/j.phrp.2013.09.006

69.

Adenusi

Odaibo

. Laboratory assessment of molluscicidal activity of crude aqueous and ethanolic extracts of Dalbergia sissoo plant against Biomphalaria pfeifferi. Travel Med Infect Dis. 2008;6(4):219‐227. doi:10.1016/j.tmaid.2007.12.004

70.

Ansari

Razdan

Tandon

Vasudevan

. Larvicidal and repellent actions of Dalbergia sissoo Roxb. (F. Leguminosae) oil against mosquitoes. Bioresour Technol. 2000;73(3):207‐211. doi:10.1016/S0960-8524(99)00180-7

71.

Hassan

Mankowshi

Kirker

Ahmed

Haq

MMU

. Antitermitic activities of Shisham (Dalbergia sissoo Roxb.) heartwood extractives against two termite species. Int Res Group Wood Protection. 2016;1:1‐16.

72.

Singh

Vemu

Prerna

Singh

Dumka

Sharma

. Acaricidal activity of leaf extracts of Dalbergia sissoo Roxb. (Fabaceae) against synthetic pyrethroid resistant Rhipicephalus (Boophilus) microplus. Res Vet Sci. 2016;106:1‐6. doi:10.1016/j.rvsc.2016.03.002

73.

Majeed

Munir

Rashid

Zubair

. Antimicrobial, cytotoxicity, mutagenicity and anti-epileptic potential of ethanol extracts of a multipurpose medicinal plant Dalbergia sissoo. Biocatal Agric Biotechnol. 2019;19:101155. doi:10.1016/j.bcab.2019.101155