Sage Journals: Discover world-class research

Abstract

Three new glycosides, derriacuminosides A-C (1-3), were isolated from the stems of Derris elliptica (Wall.) Benth. Their chemical structures were determined by interpretations of HRESIMS and NMR spectra. The anti-inflammatory activity of compounds 1-3 were evaluated by inhibiting NO production in LPS activated RAW264.7 cells. Compounds 1-3 potentially inhibited NO production with IC₅₀ values of 26.54 ± 3.08, 26.35 ± 1.37, and 49.71 ± 2.93 µM, respectively, compared to the positive control, L-NMMA (IC₅₀ 35.56 ± 2.98 µM).

Keywords

Leguminosae acuminose derivative derriacuminoside nitric oxide inhibitor

Introduction

Derris elliptica is a climbing shrub belonging to the Leguminosae family. It is widely grown or cultivated in subtropical and tropical regions. The roots of D elliptica have long been used for poisoning fish and plant pests.^1-3 In traditional medicines, D elliptica is used to treat sickness of breasts, toothache, bleeding, and stomachache.⁴ Up to date, several phytochemical studies have been reported on the roots and aerial parts of D elliptica. Flavonoids in several subgroups, such as flavone, isoflavone, pterocarpan, cumaronochromone, and especially rotenoid, were identified as major components of this plant.^5-8 These types of compounds have been shown to have potential cytotoxic and anti-inflammatory activities.^9,10 The roots of D elliptica contain rotenoids, such as rotenone, deguelin, and tephrosin, which are toxic ingredients responsibility for the plant's insecticidal property.^5,7 Other phenolic compounds, including flavone, isoflavone, pterocarpan, and cumaronochromone, have been revealed from the aerial parts of this plant.⁸ However, there have been no continuous phytochemical studies on this plant for the past decade. In our program to find natural anti-inflammatory agents, the water extract of D elliptica stems showed potential NO inhibitory activity, which was selected for chemical investigation. Herein, we report the identification of 3 new glycosides and their inhibitory activity on NO production in LPS activated RAW264.7 cells.

Results and Discussion

The stems of D elliptica were extracted with methanol. The methanol extract was suspended in water and successively partitioned with dichloromethane and ethyl acetate. The water-soluble extract was fractionated by column chromatography, and purified by semi-preparative HPLC to obtain compounds 1-3 (Figure 1).

Figure 1.

Structures of compounds 1-3 isolated from the stems of D elliptica.

Compound 1 was isolated as a white amorphous powder. Its molecular formula, C₃₁H₄₄O₁₃, was determined by high-resolution electron spray ionization mass spectrometry (HRESIMS), showing quasi-molecular ion peaks at m/z 623.2699 [M - H]⁻ (calcd. for [C₃₁H₄₃O₁₃]⁻, 623.2709) and m/z 659.2485 [M + Cl]⁻ (calcd. for [C₃₁H₄₄O₁₃Cl]⁻, 659.2476). The ¹H NMR spectrum of 1 revealed 4 aromatic protons in an AA′BB′ coupled system [δ_H 7.91 (2H, d, J = 8.0 Hz) and 6.83 (2H, d, J = 8.0 Hz)], one olefinic proton [δ_H 5.77 (1H, s)], 2 anomeric protons [δ_H 4.28 (1H, d, J = 7.5 Hz) and δ_H 5.04 (1H, d, J = 2.0 Hz)], 3 oxygenated methylene groups [δ_H 4.34 (2H, s), 4.04 and 3.86 (each 1H, d, J = 9.5 Hz), 3.98 (1H, dd, J = 11.5 and 2.0 Hz) and 3.58 (1H, dd, J = 11.5 and 5.5 Hz)], and 4 methine groups [δ_H 2.00, 1.04, 0.96 (each 3H, s), and 1.14 (3H, d, J = 7.0 Hz)]. The ¹³C NMR spectrum of 1 contained signals assigning for 31 carbons and recognized by the HSQC spectrum including 7 non-protonated carbons, 14 methine groups, 6 methylene groups, and 4 methyl groups. The signals of the AA′BB′ coupled protons together with the HMBC correlations between H-2‴ (δ_H 7.91)/H-6‴ (δ_H 7.91) and C-4‴ (δ_C 163.8)/ C-7‴ (δ_C 167.8) indicated the presence of a p-hydroxybenzoyl group (Figure 2). Two anomeric protons [δ_H 4.28 and 5.04] suggested the presence of 2 sugar units. Additionally, the presence of an apiofuranosyl moiety was determined by a deshielded signal of an anomeric carbon (δ_C 110.7), a tertiary oxygenated carbon (δ_C 79.0, C-3″), and 4 oxygenated methylene protons (δ_H 4.04 and 3.86, H₂-4″; δ_H 4.34, H₂-5″). The presence of a glucopyranosyl moiety was confirmed by axial-trans coupled protons (J = 7.5-9.0 Hz) in their carbinol protons (H-1′ to H-5′). The HMBC correlation between Api H-1″ (δ_H 5.04) and Glc C-6′ (δ_C 68.8) indicated an apiofuranosyl-(1→6)-glucopyranosyl disaccharide (acuminose) moiety. Moreover, carbon chemical shifts, values of the coupling constants, and multiplicity of the anomeric signals agreed with the β-glucopyranosyl (J = 7.5 Hz) and β-apiofuranosyl (J = 2.0 Hz) linkages, as previously described.¹¹ The HMBC correlation between Api H₂-5″ (δ_H 4.34) and carbonyl carbon C-7‴ (δ_C 167.8) confirmed anester linkage between p-hydroxybenzoyl and Api C-5″. The remaining 13 carbon signals were assigned to a megastigmane backbone containing an α,β-unsaturated ketone functional group (showing 3 deshielded carbons at δ_C 202.5, 170.2, 125.4). Of these, the ketone functional group at C-3 and the double bond at C-4/C-5 were demonstrated by HMBC correlations between H₃-13 (δ_H 2.00) and C-4 (δ_C 125.4)/ C-5 (δ_C 170.2)/ C-6 (δ_C 52.4), H₃-11 (δ_H 1.04)/ H₃-12 (δ_H 0.96) and C-2 (δ_C 48.1), H₂-2 (δ_H 2.42 and 1.96) and C-3 (δ_C 202.5). The doublet signals of methyl protons (H₃-10, δ_H 1.14) and HMBC correlation between H₃-10 and C-9 (δ_C 76.0)/ C-8 (δ_C 37.7) suggested the presence of an oxygenated group at C-9. Furthermore, HMBC correlation between Glc H-1′ (δ_H 4.28) and C-9 (δ_C 76.0) indicated the sugar moiety linked to C-9 of the megastigmane moiety. The absolute configuration of 1 was elucidated by analysis of its ECD spectrum, ¹³C-NMR spectral data, and acid hydrolysis. Particularly, the ECD spectrum of 1 showed positive Cotton effects at 337 nm ( + 0.85 mdeg) and 239 nm ( + 3.65 mdeg) indicating a 6R-configuration, as previously reported.¹² On the other hand, carbon chemical shift values of C-9 (δ_C 76.0), C-10 (δ_C 20.2), and Glc C-1′ (δ_C 102.5) demonstrated a 9R configuration, which was identical to that of byzantionoside B (9R: δ_C−9 75.7, δ_C−10 19.9, and δ_C−1′ 102.3), but significantly different from blumenol C glucoside (9S: δ_C−9 77.7, δ_C−10 22.0, and δ_C−1′ 104.1).¹² Finally, acid hydrolysis of 1 obtained D-glucose and D-apiose, which were confirmed by HPLC analysis of their thiocarbamoylthiazolidine derivatives by comparison with authentic sugars.^13,14 Consequently, the structure of 1 was established and named derriacuminoside A (Supplemental Figures S1-S7).

Figure 2.

Key HMBC (H→C) and COSY (H⁃H) correlations of 1-3.

Compounds 2 and 3 were obtained as white amorphous powders. The molecular formula of 2 was determined as C₂₅H₃₀O₁₂ by HRESIMS ions at m/z 521.1640 [M - H]⁻ (calcd. for [C₂₅H₂₉O₁₂]⁻, 521.1664) and 557.1414 [M + Cl]⁻ (calcd. for [C₂₅H₃₀O₁₂Cl]⁻, 557.1431). Meanwhile, the molecular formula of 3 was determined as C₂₃H₃₄O₁₂ by HRESIMS ions at m/z 501.1954 [M - H]⁻ (calcd. for [C₂₃H₃₃O₁₂]⁻, 501.1978) and 537.1725 [M + Cl]⁻ (calcd. for [C₂₃H₃₄O₁₂Cl]⁻, 537.1744). The ¹H and ¹³C NMR spectral data of 2 and 3 were identical to those of 1 by signals corresponding to an acuminose disaccharide moiety and a p-hydroxybenzoyl group (Table 1). Differences between them were signals of the aglycone moiety. The aglycone moiety of 2 was determined to be an O-benzyl group showing 5 aromatic protons [δ_H 7.39 (2H, dd, J = 8.5 and 1.5 Hz), 7.30 (2H, dd, J = 8.5 and 1.5 Hz), 7.26 (1H, t, J = 8.5 Hz)] and an oxymethylene group [δ_H 4.86 and 4.63 (each 1H, d, J = 11.5 Hz), δ_C 71.8]. The HMBC correlations between the oxymethylene protons H₂-7 (δ_H 4.86 and 4.63) and C-1 (δ_C 138.9)/C-2 (δ_C 129.2)/C-6 (δ_C 129.2) further confirmed the presence of the O-benzyl group. The HMBC correlation between Glc H-1′ (δ_H 4.34) and C-7 (δ_C 71.8) indicated the linkage between the O-benzyl group and the sugar moiety in 2. On the other hand, the aglycone moiety of 3 was an α-methylbutoxy group showing 5 saturated carbons (δ_C 76.1, 36.3, 27.1, 16.9, and 11.6). The HMBC correlations from H₃-4 (δ_H 0.88) to C-3 (δ_C 27.1)/C-2 (δ_C 36.3), and H₃-5 (δ_H 0.91) to C-3/C-2/C-1 (δ_C 76.1) additionally confirmed the α-methylbutoxy group. The HMBC correlations from Glc H-1′ (δ_H 4.22) to C-1 (δ_C 76.1) also indicated a linkage between the α-methylbutoxy group and the sugar moiety in 3. However, due to a lack of significant evidence, the absolute configuration of the α-methylbutoxy group is still undetermined. Later, the presence of D-glucose and D-apiose in both 2 and 3 were also confirmed by acid hydrolysis, HPLC analysis of the thiocarbamoylthiazolidine products, and comparison with authentic sugars.^13,14 Thus, the structures of 2 and 3 were established and named as derriacuminosides B and C, respectively (Supplemental Figures S8-S18).

Table 1.

¹H NMR and ¹³C NMR Spectroscopic Data for Compounds 1-3 in CD₃OD.

No.	1		2		3
No.	δ _C ^a	δ_H^b (mult., J in Hz)	δ _C ^a	δ_H^b (mult., J in Hz)	δ _C ^a	δ_H^b (mult., J in Hz)
1	37.3	-	138.9	-	76.1	3.73 (dd, 11.5, 6.0) 3.28 (dd, 11.5, 6.0)
2	48.1	2.42 (d, 17.5) 1.96 (d, 17.5)	129.2	7.39 (dd, 8.5, 1.5)	36.3	1.64 (m)
3	202.5	-	129.3	7.30 (dd, 8.5, 1.5)	27.1	1.47 (m) 1.13 (m)
4	125.4	5.77 (s)	128.7	7.26 (t, 8.5)	11.6	0.88 (t, 6.5)
5	170.2	-	129.3	7.30 (dd, 8.5, 1.5)	16.9	0.91 (d, 6.5)
6	52.4	1.90 (m)	129.2	7.39 (dd, 8.5, 1.5)
7	26.9	1.43 (m)/1.92 (m)	71.8	4.63 (d, 11.5) 4.86 (d, 11.5)
8	37.7	1.55 (m)
9	76.0	3.76 (m)
10	20.2	1.14 (d, 7.0)
11	27.5	1.04 (s)
12	29.0	0.96 (s)
13	25.0	2.00 (s)
1′	102.5	4.28 (d, 7.5)	103.3	4.34 (d, 8.0)	104.7	4.22 (d, 8.0)
2′	75.0	3.14 (dd, 9.0, 7.5)	75.0	3.27 (dd, 9.0, 8.0)	75.2	3.20 (dd, 9.0, 8.0)
3′	78.1	3.33 (t, 9.0)	78.1	3.35 (t, 9.0)	78.2	3.35 (t, 9.0)
4′	71.9	3.23 (t, 9.0)	71.8	3.29 (t, 9.0)	71.8	3.29 (t, 9.0)
5′	76.9	3.40 (m)	77.0	3.43 (m)	76.8	3.42 (m)
6′	68.8	3.98 (dd, 11.5, 2.0) 3.58 (11.5, 5.5)	68.7	4.06 (dd, 11.5, 2.0) 3.66 (dd, 11.5, 5.5)	68.6	4.02 (dd, 11.5, 2.0) 3.64 (11.5, 5.5)
1″	110.7	5.04 (d, 2.0)	110.8	5.10 (d, 2.0)	110.7	5.07 (d, 2.0)
2″	78.4	3.96 (d, 2.0)	78.6	4.05 (d, 2.0)	78.5	4.01 (d, 2.0)
3″	79.0	-	79.1	-	79.1	-
4″	75.1	4.04 (d, 9.5) 3.86 (d, 9.5)	75.1	3.91 (d, 10.0) 4.12 (d, 10.0)	75.1	4.11 (d, 9.5) 3.90 (d, 9.5)
5″	67.7	4.34 (s)	67.6	4.38 (s)	67.6	4.36 (s)
1‴	121.9	-	121.9	-	122.0	-
2‴	133.0	7.91 (d, 8.0)	133.0	7.93 (d, 8.5)	133.0	7.94 (d, 8.0)
3‴	116.3	6.83 (d, 8.0)	116.3	6.83 (d, 8.5)	116.2	6.86 (d, 8.0)
4‴	163.8	-	163.8	-	163.7	-
5‴	116.3	6.83 (d, 8.0)	116.3	6.83 (d, 8.5)	116.2	6.86 (d, 8.0)
6‴	133.0	7.91 (d, 8.0)	133.0	7.93 (d, 8.5)	133.0	7.94 (d, 8.0)
7‴	167.8	-		-	167.9	-

Measured at ^a125 MHz and ^b500 MHz.

The water-soluble extract of D elliptica (100 µg/mL) was screened for NO inhibitory activity and showed an inhibitory percentage of 70.8 ± 3.5%. Thus, compounds 1-3 were evaluated for their anti-inflammatory activity by inhibition of NO production in LPS activated RAW264.7 cells. At the highest concentration of 100 µM, compounds 1-3 did not significantly affect the growth of cells (cell viability of 98.2%, 97.9%, and 98.6%, respectively). Therefore, the NO inhibitory properties of the compounds were evaluated at diluted concentrations ranging from 0.8 to 100 µM. The NO assay was based on Griess reaction, as previously described.^14,15 Compounds 1-3 inhibited NO production with IC₅₀ values of 26.54 ± 3.08, 26.35 ± 1.37, and 49.71 ± 2.93 µM, respectively, compared to the positive control N^G-methyl-L-arginine acetate salt (L-NMMA), which had an IC₅₀ value of 35.56 ± 2.98 µM. Therefore, compounds 1-3 could be active anti-inflammatory constituents and partly responsible for the anti-inflammatory property of D elliptica.

Material and Methods

General Experimental Procedures

Optical rotation was recorded on a JASCO P-2000. HRESIMS were obtained on an AGILENT 6530 Accurate Mass Q-TOF, and NMR spectra on a BRUKER Avance III spectrometer. Semi-preparative HPLC was performed on an AGILENT 1260 Infinity II system using a YMC J′sphere ODS-H80 column (20 mm × 250 mm, 4 µm) and isocratic mobile phase at a flow rate of 3.0 mL. Thin layer chromatography (TLC) was carried out on pre-coated plates (silica gel 60 F₂₅₄ or RP-18 F_254S), and column chromatography (CC) using either silica gel, reversed phase (RP-18), or diaion HP-20 resins.

Plant Material

Fresh samples of Derris elliptica (Wall.) Benth. were collected in October 2020 at the Me Linh station for biodiversity, Vinh Phuc, Vietnam, and identified by Dr Nguyen The Cuong at the Institute of Ecology and Biological Resources, VAST. A voucher specimen (code: NCCT-P105) is kept at the Institute of Marine Biochemistry, VAST.

Extraction and Isolation

The stems of D elliptica were dried at 60 °C and pulverized to fine powder. The powdered material (15 kg) was ultrasonically extracted with methanol at room temperature, 3 times (10 L of methanol and 30 min each time), to give the methanol extract. The methanol extract (450 g) was then mixed with 3 L of water and successively extracted with dichloromethane and ethyl acetate to give dichloromethane, ethyl acetate, and water-soluble fractions. The water soluble fraction was separated by diaion HP-20 CC eluting with methanol/water (1/3, 1/1, 1/0, v/v) to yield 3 fractions, W1-W3. Fraction W1 was chromatographed on a silica gel column, eluting with dichloromethane/acetone (2/1, v/v) to give 5 fractions, W1A-W1E. Fraction W1A was repeatedly chromatographed on a silica gel column, eluting with dichloromethane/ethyl acetate (1/1, v/v) to give 2 fractions, W1A1 and W1A2. Fraction W1A1 was purified by semi-preparative HPLC using acetonitrile/water (3/7, v/v) to give compound 3 (12 mg, t_R 43.7 min). Fraction W1A2 was purified by semi-preparative HPLC using methanol and water (6/4, v/v) to give compound 1 (17 mg, t_R 29.3 min). Fraction W1B was chromatographed on reversed phase C-18 column, eluting with methanol/water (1/1, v/v) to give 3 fractions, W1B1-W1B3. Fraction W1B2 was purified by semi-preparative HPLC using acetonitrile/water (3/7, v/v) to give compound 2 (15 mg, t_R 26.2 min).

Derriacuminoside A (1)

White amorphous powder, $[α]_{D}^{25}$ : + 71 (c 0.1, MeOH); UV (MeOH): λ_max (logε) 253 (4.1) nm; IR (KBr): ν_max 3402, 2991, 1694, 1668, 1597, 1191 cm⁻¹; HRESIMS m/z 623.2699 [M - H]⁻ (calcd. for [C₃₁H₄₃O₁₃]⁻, 623.2709) and m/z 659.2485 [M + Cl]⁻ (calcd. for [C₃₁H₄₄O₁₃Cl]⁻, 659.2476); ¹H NMR (CD₃OD, 500 MHz), and ¹³C NMR (CD₃OD, 125 MHz) data are given in Table 1.

Derriacuminoside B (2)

White amorphous powder, $[α]_{D}^{25}$ : + 54 (c 0.1, MeOH); UV (MeOH): λ_max (logε) 260 (3.7) nm; IR (KBr): ν_max 3398, 2989, 1697, 1602, 1195 cm⁻¹; HRESIMS m/z 521.1640 [M - H]⁻ (calcd. for [C₂₅H₂₉O₁₂]⁻, 521.1664) and m/z 557.1414 [M + Cl]⁻ (calcd. for [C₂₅H₃₀O₁₂Cl]⁻, 557.1431); ¹H NMR (CD₃OD, 500 MHz), and ¹³C NMR (CD₃OD, 125 MHz) data given in Table 1.

Derriacuminoside C (3)

White amorphous powder, $[α]_{D}^{25}$ : + 47 (c 0.1, MeOH); UV (MeOH): λ_max (logε) 284 (3.0) nm; IR (KBr): ν_max 3404, 2987, 2969, 1698, 1596, 1201 cm⁻¹; HRESIMS m/z 501.1954 [M - H]⁻ (calcd. for [C₂₃H₃₃O₁₂]⁻, 501.1978) and m/z 537.1725 [M + Cl]⁻ (calcd. for [C₂₃H₃₄O₁₂Cl]⁻, 537.1744); ¹H NMR (CD₃OD, 500 MHz), and ¹³C NMR (CD₃OD, 125 MHz) data given in Table 1.

Acid Hydrolysis and Confirmation of Sugar Residue

Compounds 1-3 (each 2.0 mg) were dissolved in 1.0 mL acid solution (1.0 N HCl in dioxane/H₂O (1/1, v/v)] and heated at 80 °C in a water bath for 3 h. After that, solvent was removed using N₂ gas. After addition of 1.0 mL of water, the solution was extracted twice with chloroform (1.0 mL each). The water portion was neutralized by Amberlite IRA400 resin and then dried in vacuo. The residue was re-dissolved in 100 µL pyridine containing 1.0 mg of L-cysteine methyl ester hydrochloride and heated at 60 °C for 1 h. After that, 100 µL pyridine containing 1.0 mg of o-tolyl isothiocyanate was added to the reaction mixture and continuously heated at 60 °C for an additional 1 h. Thiocarbamoyl-thiazolidine products were analyzed by an Agilent infinity II 1290 HPLC system using a Zorbax extend C18 rapid resolution column (2.1 × 50 mm, 1.8 micron), a flow rate of 300 µL/min of ACN/water (20% ACN in volume), and an UV detector at 250 nm. Peaks at 14.6 and 24.7 min were confirmed to be D-glucose and D-apiose derivatives, respectively, by comparison of their retention times with those of authentic D-glucose and D-apiose derivatives prepared in the same manner.

Nitric Oxide Assay

RAW 264.7 cells were cultured in DMEM containing L-glutamine (2 mM), HEPES (10 mM), sodium pyruvate (1 mM), and fetal bovine serum (10%). The cells (2 × 10⁵ cells/well) were incubated in humidified atmosphere (95% air and 5% CO₂) at 37 °C. After 24 h incubation, to each well was added either compounds (0.8-100 µM/mL) or vehicle, followed by LPS (1 μg/mL) in the next 2 h. The cells were then incubated for an additional 24 h. After that, cell viability was measured by MTT assay and the amount of NO production in the cell medium was determined by Griess reaction. Culture medium (100 μL) was mixed with an equal volume of Griess reagent and incubated at room temperature for 10 min. Absorbance was measured at 540 nm on a microplate reader. Nitrite concentration as an indicator of NO production was determined using a standard curve, which was built by NaNO₂ serial diluted solutions. Experiments were performed in triplicate. IC₅₀ values were generated by TableCurve 2Dv4 software.

Conclusions

From the stems of D elliptica 3 new glycosides were isolated, characterized, and named derriacuminosides A-C (1-3). Compounds 1 and 2 inhibited NO production in LPS activated RAW264.7 cells with IC₅₀ values of 26.54 ± 3.08 and 26.35 ± 1.37 µM, respectively, which are smaller than that of compound 3 (IC₅₀ = 49.71 ± 2.93 µM) and the positive control, N^G-methyl-L-arginine acetate salt (IC₅₀ = 35.56 ± 2.98 µM).

Supplemental Material

sj-docx-1-npx-10.1177_1934578X221126299 - Supplemental material for Three New Glycosides From the Stems of Derris elliptica

Supplemental material, sj-docx-1-npx-10.1177_1934578X221126299 for Three New Glycosides From the Stems of Derris elliptica by Bui Thi Thu Trang, Nguyen Xuan Nhiem, Nguyen Thi Huong, Nguyen Thi Thanh Mai, Nguyen Tuan Anh and Phan Van Kiem in Natural Product Communications

Footnotes

List of Abbreviations

Authors’ contributions

Research idea: NX Nhiem, PV Kiem. Isolation and bioassay: BTT Trang, NT Huong, NT Anh. Structure elucidation and writing: BTT Trang, NTT Mai, NX Nhiem, PV Kiem.

Declaration of Conflicting Interests

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

Ethical Approval

Our institution does not require ethical approval for reporting individual cases or case series.

Funding

The author(s) disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: This research is funded by Graduate University of Science and Technology under grant number GUST.STS.ĐT2020-HH12.

ORCID iD

Phan Van Kiem

Statement of Human and Animal Rights

This article does not contain any studies with human or animal subjects.

Statement of Informed Consent

There are no human subjects in this article and informed consent is not applicable.

Supplemental Material

Supplemental material for this article is available online.

References

Harper

. Active principles of leguminous fish-poison plants. II. The isolation of l-elliptone from Derris elliptica. J Chem Soc. 1939:1099-1105. doi:10.1039/jr9390001099

Worsley

RRLG

Nutman

. Biochemical studies of Derris and Mundulea. I. Histology of rotenone in Derris elliptica. Ann Appl Biol. 1937;24:696-702. doi:10.1111/j.1744-7348.1937.tb05050.x

Wiwattanapatapee

Sae-Yun

Petcharat

Ovatlarnporn

Itharat

. Development and evaluation of granule and emulsifiable concentrate formulations containing Derris elliptica extract for crop pest control. J Agric Food Chem. 2009;57(23):11234-11241. doi:10.1021/jf901862z

Khan

Omoloso

Barewai

. Antimicrobial activity of the Derris elliptica, Derris indica and Derris trifoliata extractives. Fitoterapia. 2006;77(4):327-330. doi:10.1016/j.fitote.2006.03.007

Ahmed

Shireen

Rashid

Mahmud ul

. A further rotenoid from Derris elliptica. Planta Med. 1989;55(2):207-208. doi:10.1055/s-2006-961936

Liang

. Novel N-containing rotenoid and seco-rotenoid from the root of Derris elliptica. J Asian Nat Prod Res. 2009;11(1):58-62. doi:10.1080/10286020802514002

Liang

Zhao

. Two new rotenoids from the root of Derris elliptica. Chin Chem Lett. 2008;19(10):1218-1220. doi:10.1016/j.cclet.2008.06.014

Song

Zhang

Chen

Liu

. Chemical constituents of the aerial part of Derris elliptica. Fitoterapia. 2012;83(4):732-736. doi:10.1016/j.fitote.2012.02.015

Ito

Murata

Tan

Kaneda

Furukawa

Itoigawa

. Rotenoid derivatives from Derris trifoliata with nitric oxide production inhibitory activity. Nat Prod Commun. 2012;7(11):1479-1482. doi:10.1177/1934578X1200701117

10.

Chokchaichamnankit

Kongjinda

Khunnawutmanotham

Chimnoi

Pisutcharoenpong

Techasakul

. Prenylated flavonoids from the leaves of Derris malaccensis and their cytotoxicity. Nat Prod Commun. 2011;6(8):1934578X1100600813. doi:10.1177/1934578X1100600813

11.

Dini

Carlo Tenore

Dini

. Phenolic constituents of kancolla seeds. Food Chem. 2004;84(2):163-168. doi:10.1016/S0308-8146(03)00185-7

12.

Matsunami

Otsuka

Takeda

. Structural revisions of blumenol C glucoside and byzantionoside B. Chem Pharm Bull. 2010;58(3):438-441. doi:10.1248/cpb.58.438

13.

Tanaka

Nakashima

Ueda

Tomii

Kouno

. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem Pharm Bull. 2007;55(6):899-901. doi:10.1248/cpb.55.899

14.

Tai

Anh

NTH

Cuc

, et al. Three new constituents from the parasitic plant Balanophora laxiflora. Nat Prod Commun. 2019;14(5):1934578X19849959. doi:10.1177/1934578X19849959

15.

Chinh

Tham

Giang

PTT

, et al. New nitric oxide inhibitory p-coumaroyl flavone glycosides from Fissistigma bicolor. Phytochem Lett. 2021;44:169-172. doi:10.1016/j.phytol.2021.06.019

Supplementary Material

Please find the following supplemental material available below.

For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.

For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.

0.00 MB

1.45 MB