Phytochemical Composition and Bioactivities of Essential Oils from Rhizomes of Homalomena pendula and Homalomena cochinchinensis

Abstract

In this study, we investigated the chemical composition and potential biological properties of essential oils extracted from the rhizomes of two Homalomena species, H. pendula (Blume) Bakh.f. and H. cochinchinensis Engl. Using GC–MS analysis, we found that H. pendula essential oil contains 59 components while H. cochinchinensis essential oil contains 58. Both essential oils were rich in oxygenated monoterpenes, with linalool and terpinen-4-ol being the most prevalent compounds. Additionally, H. cochinchinensis essential oil exhibited moderate anti-inflammatory activity with an IC₅₀ value of 170.81 ± 11.44 µg/mL, whereas H. pendula essential oil showed moderate activity against acetylcholinesterase (AChE) with an IC₅₀ value of 130.65 ± 1.27 µg/mL. This study is the first to report the chemical composition and biological effects of H. pendula essential oil, as well as the anti-inflammatory effects of H. cochinchinensis essential oil.

Keywords

anti-inflammatory anti-acetylcholinesterase essential oil

Introduction

Homalomena, a diverse and extensive genus of tropical plants in the Araceae family, contains over 150 species, the greatest diversity of which is located in the perhumid climate of Southeast Asia.¹ These plants are known for their ornamental value, attractive foliage, and medicinal properties. They are important not only for their cultural and ecological value but also for their potential use in traditional medicine. For centuries, Homalomena species have been used in traditional medicine for ailments such as stomach disorders, fever, pain, inflammation, and infections.² H. occulta is used to treat rheumatism and stomach pain, as well as to stimulate digestion, whereas H. pendula can suppress cough and reduce pain. In addition, in China, H. pendula rhizomes are used to treat high fevers, cough, influenza, and joint pain.³ Essential oils have also received considerable attention for their potential therapeutic effects; several Homalomena species have been investigated in this context, including H. aromatica, H. cochinchinensis, H. occulta, H. pierreana, H. pineodora, H. sagittifolia,⁴ and H. josefii.⁵ These studies have revealed that Homalomena essential oils contain abundant terpenoids, phenolic compounds, and fatty acids, compounds known for health benefits such as antibacterial,^5-7 antifungal,⁸ and antioxidant⁵ properties.

Despite the promising therapeutic potential of Homalomena essential oils, little is known about the essential oils of H. pendula and H. cochinchinensis, which are rare species in Vietnam. Recently, Van et al. reported the chemical composition and antibacterial activities of H. cochinchinensis essential oil.⁷ However, the chemical composition and bioactivities of H. pendula essential oil have not been published. Investigating the phytochemical composition and biological activity of these essential oils is crucial for validating their traditional uses and exploring their potential therapeutic applications.

In the current study, we report the phytochemical compositions of the essential oils of H. pendula and H. cochinchinensis rhizomes. In addition, their anti-inflammatory and anti-cholinesterase activities are described. By exploring the potential therapeutic applications of these Homalomena species, this study may contribute to the development of natural and effective remedies for various ailments. Understanding the chemical constituents and biological activities of Homalomena essential oils may also lead to the discovery of novel therapeutic agents for treating human diseases.

Results and Discussion

Extraction and Profiling

The proportion of essential oil extracted from H. pendula and H. cochinchinensis rhizomes was 0.15% (v/w) and 0.20% (v/w), respectively, calculated on a fresh weight basis. Table 1 displays the chemical compositions of these essential oils as determined by GC–MS analysis.

Table 1.

Components of Essential Oil from Rhizomes of H. pendula and H. cochinchinensis.

No	RT		Compounds^a	Type	RI^b	RI^c	Content (%)
No	RT		Compounds^a	Type	RI^b	RI^c	H. pendula	H. cochinchinensis
1	6.48		α-Thujene	HM	924	925	0.2	–
2	6.71		α-Pinene	HM	932	932	0.4	0.2
3	8.00		Sabinene	HM	969	972	6.2	1.0
4	8.11		β-Pinene	HM	974	975	–	0.4
5	8.60		Myrcene	HM	988	990	1.9	0.7
6	9.10		α-Phellandrene	HM	1002	1005	0.6	–
7	9.32		δ-3-Carene	HM	1008	1010	5.1	0.5
8	9.56		α-Terpinene	HM	1014	1016	1.1	0.3
9	9.86		m-Cymene	HM	1022^#	1023	0.5	0.6
10	9.86		p-Cymene	HM	1024^#	1023	0.6	–
11	10.04		Limonene	HM	1024	1028	–	0.8
12	10.05		Sylvestrene	HM	1025	1028	3.3	–
13	10.13		1,8-Cineole	OM	1026	1030	4.5	0.6
14	10.81		E-β-Ocimene	HM	1044	1047	0.3	0.2
15	11.24		γ-Terpinene	HM	1054	1058	1.7	0.7
16	11.82		cis-Linalool oxide (furanoid)	OM	1067	1072	0.4	1.9
17	12.49		trans-Linalool oxide (furanoid)	OM	1084	1088	–	2.0
18	12.47		Terpinolene	HM	1086	1088	1.4	–
19	13.35		Linalool	OM	1095	1109	31.6	56.3
20	13.98		cis-p-Menth-2-en-1-ol	OM	1118	1123	–	0.3
21	13.94		dehydro-Sabina ketone	O	1117	1122	0.3	–
22	14.27		allo-Ocimene	OM	1128	1130	–	0.1
23	14.73		trans-p-Menth-2-en-1-ol	OM	1136	1140	–	0.2
24	14.85		Isopulegol	OM	1145	1143	–	0.1
25	15.21		Thujanol	OM	1149	1151	–	0.1
26	15.54		Sabina ketone	OM	1154	1158	–	0.1
27	15.62		p-Mentha-1,5-dien-8-ol	OM	1166	1160	1.0	0.1
28	16.02		cis-Linalool oxide (pyranoid)	OM	1170	1169	–	0.2
29	16.26		trans-Linalool oxide (pyranoid)	OM	1173	1175	–	0.3
30	16.42		Terpinen-4-ol	OM	1174	1178	4.0	5.2
31	16.58		m-Cymen-8-ol	OM	1176	1182	0.5	0.2
32	16.58		p-Cymen-8-ol	OM	1179	1182	–	0.2
33	16.78		Cryptone	O	1183	1187	0.4	0.2
34	16.99		α-Terpineol	OM	1186	1191	2.2	2.0
35	17.17		cis-Piperitol	OM	1195	1195	0.1	–
36	17.73		trans-Piperitol	OM	1207	1208	–	0.1
37	17.72		cis-Sabinene hydrate acetate	O	1219	1208	0.2	–
38	18.64		Nerol	OM	1227	1229	0.2	0.4
39	19.20		Neral	OM	1235	1241	0.2	–
40	19.66		Car-3-en-2-one	O	1244	1252	0.1	–
41	19.82		Geraniol	OM	1249	1255	0.3	1.4
42	20.51		Geranial	OM	1264	1271	0.3	–
43	21.39		p-Cymen-7-ol	OM	1289	1291	–	0.1
44	23.43		δ-Elemene	HS	1335	1338	0.4	0.1
45	24.60		Neryl acetate	O	1359	1365	–	0.3
46	25.43		Geranyl acetate	O	1379	1384	0.2	0.6
47	25.79		β-Elemene	HS	1389	1393	0.4	0.6
48	26.93		(E)-Caryophyllene	HS	1417	1420	0.7	0.3
49	27.50		γ-Elemene	HS	1434	1434	0.1	–
50	28.34		α-Humulene	HS	1452	1454	0.7	0.4
51	28.64		allo-Aromadendrene	HS	1458	1462	0.2	0.1
52	29.15		Dauca-5,8-diene	HS	1471	1474	0.2	–
53	29.29		γ-Muurolene	HS	1478	1477	0.4	0.1
54	29.90		trans-Muurola-4(14),5-diene	HS	1493	1492	0.2	–
55	30.12		Curzerene	HS	1499	1498	1.7	–
56	30.10		Bicyclogermacrene	HS	1500	1497	–	0.1
57	30.26		α-Muurolene	HS	1500	1501	1.0	0.4
58	30.81		γ-Cadinene	HS	1513	1515	1.2	0.3
59	31.19		δ-Cadinene	HS	1522	1525	3.9	1.6
60	31.52		trans-Cadina-1,4-diene	HS	1533	1534	0.1	–
61	31.73		α-Cadinene	HS	1537	1539	0.3	0.1
62	32.18		Elemol	OS	1548	1550	0.2	–
63	32.75		(E)-Nerolidol	OS	1561	1565	0.2	0.6
64	33.30		Spathulenol	OS	1577	1579	1.2	–
65	33.53		Caryophyllene oxide	OS	1582	1585	0.4	0.8
66	34.08		Guaiol	OS	1600	1599	0.3	–
67	34.30		Ledol	OS	1602	1604	0.3	0.4
68	34.53		Humulene epoxide II	OS	1608	1611	–	0.7
69	35.26		1,10-di-epi-Cubenol	OS	1618	1630	–	0.2
70	35.23		1-epi-Cubenol	OS	1627	1630	0.4	–
71	35.62		β-Acorenol	OS	1636	1640	–	0.2
72	35.78		epi-α-Muurolol	OS	1640	1644	–	2.1
73	35.94		α-Muurolol	OS	1644	1648	–	0.4
74	35.79		Cubenol	OS	1645	1645	3.5	–
75	36.08		β-Eudesmol	OS	1649	1653	0.1	–
76	36.28		α-Cadinol	OS	1652	1657	–	3.7
77	36.30		Valerianol	OS	1656	1659	5.6	–
78	36.70		Allohimachalol	OS	1661	1669	0.2	–
79	37.57		Eudesm-7(11)-en-4-ol	OS	1700	1692	–	3.4
80	38.02		Amorpha-4,9-dien-2-ol	OS	1700	1705	0.4	0.6
81	38.62		(3E)-Butylidene phthalide	O	1718	1722	0.3	–
82	39.25		Oplopanone	OS	1739	1739	–	0.2
83	39.24		Cedr-8(15)-en-9-α-ol acetate	O	1741	1739	0.2	–
84	42.18		Khusinol acetate	O	1823	1823	–	0.1
		Hydrocarbon monoterpenes (HM)					23.3	5.4
		Oxygenated monoterpenes (OM)					45.3	71.9
		Hydrocarbon sesquiterpenes (HS)					11.5	4.1
		Oxygenated sesquiterpenes (OS)					12.8	13.3
		Others (O)					1.7	1.2
		Total					94.6	95.9

Elution order on Equity-5 column.

Retention indices taken from Ref.⁹

Retention indices on Equity-5 column.

Retention indices taken from Ref.¹⁰

–, not identified.

This analysis (Supplementary Figures S1 and S2) revealed that the essential oils extracted from H. pendula and H. cochinchinensis rhizomes are dominated by oxygenated monoterpenes (45.3% and 71.9%, respectively). Notably, H. pendula essential oil contains substantial amounts of hydrocarbon monoterpenes (23.3%) and hydrocarbon sesquiterpenes (11.5%), whereas these types of compounds occur in low concentrations in H. cochinchinensis essential oil. The two major components found in both essential oils are linalool (31.6% and 56.3% in H. pendula and H. cochinchinensis, respectively) and terpinen-4-ol (4.0% and 5.2% in H. pendula and H. cochinchinensis, respectively). Interestingly, these compounds have also been reported as major constituents of other Homalomena essential oils. In particular, the essential oil extracted from H. aromatica rhizomes was composed of 62.5% linalool and 7.08% terpinen-4-ol,⁸ whereas the oil extracted from its roots contained 58.3% linalool and 16.7% terpinen-4-ol.¹¹ Linalool was also the most abundant compound in the essential oils extracted from H. occulta (36.9%)¹² and H. sagittifolia (61.9%) rhizomes.¹³ Thus, it is reasonable to consider linalool a “marker” of Homalomena essential oils.

The chemical composition of H. cochinchinensis rhizome essential oil reported herein is generally consistent with that reported in the literature⁷ in terms of primary components and major classes of volatile compounds. In particular, two independent studies of H. cochinchinensis rhizome essential oil detected a large proportion of oxygenated monoterpenes (71.9% and 76.5%, respectively), linalool (56.3% and 57.4%, respectively), and terpinen-4-ol (5.2% and 10.6%, respectively). Interestingly, the H. cochinchinensis rhizome essential oil used in the present study was obtained from Dong Nai province; its hydrocarbon monoterpene and oxygenated sesquiterpene contents were very different from those of essential oil from Binh Phuoc province (5.4% vs 13.1% and 13.3% vs 6.3%, respectively).⁷ These differences may be due to differences in species distributions, sample collection times, and analytical and identification methods.

Furthermore, we compared the chemical composition of H. cochinchinensis rhizome essential oil with that of essential oil from the aerial parts of the plant.⁷ This comparison revealed substantial differences in the prevalence of the primary components. Specifically, Van et al.⁷ reported that myrcene (41.1%), sabinene (8.2%), and d-limonene (9.1%) are the main constituents in the essential oil from the aerial parts of H. cochinchinensis; however, these compounds were only minor components of our H. cochinchinensis rhizome essential oil (0.7%, 1.0%, and 0.8%, respectively).

Finally, we note that this report is the first to characterize the chemical composition of H. pendula rhizome essential oil. In addition to its primary components, linalool and terpinen-4-ol, this essential oil also contained a number of highly prevalent compounds including sabinene (6.2%), valerianol (5.6%), δ-3-carene (5.1%), 1,8-cineole (4.5%), δ-cadinene (3.9%), and cubenol (3.5%).

Anti-Inflammatory Activity and Anti-Acetylcholinesterase Activity

The anti-inflammatory and acetylcholinesterase (AChE) activities of H. cochinchinensis and H. pendula rhizome essential oils are presented in Table 2.

Table 2.

In Vitro Anti-Inflammatory and Anti-Acetylcholinesterase Activity of Essential Oil from Rhizomes of H. pendula and H. cochinchinensis.

Essential oil	Anti-inflammatory activity	Anti-acetylcholinesterase activity
Essential oil	IC₅₀ (µg/mL)	IC₅₀ (µg/mL)
H. pendula	NA	130.65 ± 1.27
H. cochinchinensis	170.81 ± 11.44	NA
Berberine		0.77 ± 0.14
l-NMMA	8.90 ± 0.48

NA: not available.

The H. cochinchinensis essential oil showed moderate nitric oxide inhibitory capacity with an IC₅₀ value of 170.81 ± 11.44 µg/mL. In addition, an MTT assay revealed that cell viability was 93.14% when treated with a concentration of 200 µg/mL. This finding implies that this essential oil did not elicit any significant cytotoxicity. l-NMMA was used as a positive control; it was stable under the conditions of this experiment. The anti-inflammatory activity of H. cochinchinensis may be attributed to its high linalool¹⁴ and terpinen-4-ol¹⁵ content, as well as the presence of other monoterpenes such as geraniol, trans-linalool oxide, cis-linalool oxide, and sabinene. Many studies have shown that monoterpenes have potential for treating inflammatory diseases.¹⁶ Herein, our results show that H. cochinchinensis essential oil can be considered a natural resource for anti-inflammatory applications.

The AChE-inhibitory activities of the two essential oils were determined using a microplate assay. H. pendula essential oil elicited moderate AChE-inhibitory activity (IC₅₀ = 130.65 ± 1.27 µg/mL). Our study is the first to show that H. pendula essential oil exhibits anti-AChE activity. This anti-cholinesterase activity may result from the high monoterpene content (α-pinene, δ-3-carene, and 1,8-cineole) observed in this study.^17,18 Monoterpenoids can be either competitive or non-competitive cholinesterase inhibitors; given their lipophilicity, migration into and throughout membranous structures such as the blood–brain barrier may promote their AChE-inhibitory activities on its hydrophobic sites.¹⁹ The AChE-inhibitory activity of H. pendula essential oil extract may also be explained by its high hydrocarbon sesquiterpene (11.5%) and oxygenated sesquiterpene (12.8%) content. Sesquiterpenes are lipophilic terpenes with a wide range of pharmacological properties, including AChE-inhibitory activity. In the literature, multiple sesquiterpenes have been shown to play crucial roles in improving cholinergic transmission by inhibiting AChE.²⁰ However, whether or not the three major sesquiterpene constituents of H. pendula oil—valerianol, δ-cadinene, and cubenol—can inhibit AChE activity is unknown. However, other studies contend that essential oils in which these components predominate have anti-AChE effects.²¹ Hence, our findings indicate that these compounds in their purified forms should be investigated for their inhibitory effects.

Conclusion

This study is the first to report the biological activities and chemical composition of volatile compounds in H. pendula rhizome essential oil. Oxygenated monoterpenes predominated in rhizome essential oils from both H. pendula and H. cochinchinensis. Linalool, followed by terpinen-4-ol, were additional major compounds in both essential oils. Furthermore, we observed for the first time that H. cochinchinensis essential oil exhibits moderate anti-inflammatory activity and that H. pendula essential oil possesses anti-AChE activity. These bioactivity data indicate that these species should be examined further in future studies.

Materials and Methods

Plant Materials

The rhizomes of H. pendula were collected from Lam Dong Province, Vietnam (geographical coordinates: 11°25′25.3″N; 108°03′28.9″E) in January 2021 (Supplementary Figure S3). The plant was authenticated by Dr Chinh Tien Vu (Vietnam National Museum of Nature, VAST, Vietnam). The rhizomes of H. cochinchinensis were collected from Dong Nai Province, Vietnam (geographical coordinates: 11°22′51.1″N; 107°03′46.3″E) in May 2022 (Supplementary Figure S4). The plant was authenticated by Dr Anh Tuan Le (Mientrung Institute for Scientific Research, Vietnam National Museum of Nature, VAST, Vietnam). Voucher specimens (TNK-LD-01, TNK-DN-02) have been deposited at the Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, Vietnam.

Distillation of the Essential Oils

The essential oils from H. pendula and H. cochinchinensis rhizomes were obtained by hydro-distillation. From 1 kg of each Homalomena rhizome, we obtained 1.5 mL of H. pendula essential oil and 2.0 mL of H. cochinchinensis essential oil. The essential oils were dried over anhydrous sodium sulfate to remove the remaining water and then the essential oils were kept under refrigeration until further experiments. The obtained essential oil was used to analyze chemical composition and evaluate biological activities. The essential oil yields were determined: H = V_EO/m × 100%, where V_EO is the volume of the extracted essential oil (mL) and m is the initial rhizomes biomass (g).

Gas Chromatography–Mass Spectrometry (GC–MS) Analysis

The chemical composition of the volatile compounds was identified using gas chromatography coupled with mass spectrometry (GC–MS). The GC–MS analyses were performed using a Shimadzu GCMS-QP2010 Plus system (Kyoto, Japan) with an Equity-5 capillary column (30 m × 0.25 mm, 0.25 m film thickness), and a mass spectrometer (MSD QP2010 Plus). The essential oil (1 mg) was diluted in a 1:100 ratio with dichloromethane, and 1 µL was used for analysis. The oven temperature was set at 60°C (2 minutes hold) and then programmed from 240°C at a rate 3°C/min (10 min hold) and increasing to 280°C at a rate of 5°C/min (40 minutes hold). The carrier gas was helium at a flow rate of 1.5 mL/min. Mass detector conditions were set up as follows: interface temperature 280°C and mass acquisition range 40–500. Splitless injection mode was used to inject the samples. The constituents were identified by matching their mass spectra to Wiley 7 and National Institute of Standards and Technology (NIST 11) library. In addition, a standard solution of C₈–C₃₈ alkanes was used to obtain the retention index of compounds and comparing them with literature values.⁹ The relative amounts of individual components were calculated based on the peak area in GC–MS chromatogram without correction.

Anti-Inflammatory Assay

The inhibitory activity of essential oils against the production of nitrogen monoxide (NO) induced by lipopolysaccharide in RAW 264.7 cells was assessed. Nitrite concentration, a marker for the presence of NO in the culture medium, was measured using the Griess reaction. The detailed protocols for the evaluation were previously described in our reports.^22,23

Acetylcholinesterase Inhibition Assay

The evaluation of essential oils for their AChE inhibitory activity was conducted using 96-well microtiter plates. The assay method was based on Ellman's method²⁴ with slight modification. The detailed protocols are presented in our previous publication.²⁵

Supplemental Material

sj-docx-1-npx-10.1177_1934578X231175263 - Supplemental material for Phytochemical Composition and Bioactivities of Essential Oils from Rhizomes of Homalomena pendula and Homalomena cochinchinensis

Supplemental material, sj-docx-1-npx-10.1177_1934578X231175263 for Phytochemical Composition and Bioactivities of Essential Oils from Rhizomes of Homalomena pendula and Homalomena cochinchinensis by Linh Thuy Khanh Nguyen, Tuan Quoc Doan and Phu Quynh Dinh Nguyen, Chau Bao Hoai Nguyen, Linh Thuy Thi Tran, Thi Van Anh Tran, Hoai Thi Nguyen, Duc Viet Ho in Natural Product Communications

Footnotes

Acknowledgements

This research was supported by Hue University (ID No. DHH2022-04-165), Vingroup Innovation Foundation (Nguyen Khanh Thuy Linh was funded by the Master, PhD Scholarship Programme of Vingroup Innovation Foundation (VINIF), code VINIF.2022.TS163). The authors also acknowledge the partial support of Hue University under the Core Research Program, Grant No. NCM.DHH.2023.02.

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

Not applicable, because this article does not contain any studies with human or animal subjects.

Funding

The author(s) disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: This work was supported by Hue University (ID No. DHH2022-04-165), Vingroup Innovation Foundation (Nguyen Khanh Thuy Linh was funded by the Master, PhD Scholarship Programme of Vingroup Innovation Foundation (VINIF), code VINIF.2022.TS163). The authors also acknowledge the partial support of Hue University under the Core Research Program, Grant No. NCM.DHH.2023.02.

Informed Consent

Not applicable, because this article does not contain any studies with human or animal subjects.

Trial Registration

Not applicable, because this article does not contain any clinical trials.

ORCID iDs

Duc Viet Ho

Linh Thuy Thi Tran

Linh Thuy Khanh Nguyen

Supplemental Material

Supplemental material for this article is available online.

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