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Abstract

Meistera tomrey, Zingiberaceae is a species native to Indochina. The present study reports the chemical compositions of essential oils extracted from the pseudostem and leaves of M tomrey. The results of the gas chromatography-mass spectrometry (GC/MS) analysis revealed varying compositions of specific compounds in both the pseudostem and leaves. In the pseudostem, β-pinene accounted for 14.2% and 1,8-cineole for 13.5%. As for the leaves, β-pinene comprised 6.6% and 1,8-cineole 16.7%. α-Pinene represented 6.9% in the pseudostem and 4.6% in the leaves, while borneol contributed 4.6% in the pseudostem and 4.2% in the leaves. Additionally, (E)-caryophyllene constituted 3.6% in the pseudostem and 4.4% in the leaves, and (E)-nerolidol 3.5% in the pseudostem and 7.6% in the leaves. This is the first report on the chemical compositions of essential oil from M tomrey.

Keywords

Zingiberaceae essential oil monoterpenes sesquiterpenes

Introduction

In Vietnam, the ginger family is represented by 21 genera and about 100 species.¹ Several reports exist on the chemical compositions of essential oils from Zingiberaceae.^2–7 Meistera Giseke, Zingiberaceae, is a genus native to tropical and subtropical Asia to North Queensland. The genus was previously classified as being synonymous with the genus Amomum Roxb.^2,8 There are 44 species of Meistera, of which 12 have been recorded in Vietnam. These are M aculeata, M caudata, M celsa, M sudae, M chinensis, M cristatissima, M elephantorum, M gagnepainii, M koenigii, M muricarpa, M tormey, and M vespertilio.^1,9 Information is scanty on the chemical characterization and pharmacological evaluation of extracts from Mesitera species. Phytochemical screening showed that M chinensis fruit extracts contained saponins, terpenoids, steroids, alkaloids, phenolics, tannins, and flavonoids.³ The extracts exhibited antioxidant activity by scavenging DPPH radicals in a dose-dependent pattern with an IC₅₀ of 47.62 ± 2.93. The results of the analysis of variance on antibacterial and antifungal properties showed that there was a significant difference (p = .00 < .05) against fungal and bacterial growth.³

Meistera tomrey (Gagnep.) Škorničk & M. F. Newman is a rhizomatous geophyte and grows primarily in the wet tropical biome. The native range of this species is Indo-China.¹⁰ It is known in Vietnamese as Sa nhan tomre and is found mainly in Lâm Đông forest reserve. There is no record of the phytochemical composition and biological potential of M. tomrey. Previous research has highlighted the chemical compositions of essential oils from several other Meistera species. For example, β-pinene (27.4%), α-pinene (21.2%), limonene (12.1%), and myrcene (8.6%) were the characteristic components of M sudae leaf essential oil.⁴ The leaf essential oil of M caudata contained 27.61% of α-pinene, 21.29% of β-pinene, and 8.62% of camphene while the figures for the rhizome essential oil were 10.37%, 9.69%, and 12.1%, respectively.⁵ A recent finding identified β-pinene (30.8%), and α-pinene (23.8%) as the principal compounds of the leaf oil of M caudata, while bicyclogermacrene (13.3%), camphene (10.7%), and 1,8-cineole (7.7%) were significant compounds of the rhizome essential oil.¹¹ The main compounds of the leaf oil of M cristatissima were α-pinene (19.8%), caryophyllene oxide (9.8%), and (E)-nerolidol (7.3%), whereas spathulenol (14.6%), bornyl acetate (7.4%), caryophyllene oxide (7.1%), cubeban-11-ol (6.5%), and humulene epoxide II (5.3%) were the abundant compounds of the rhizome oil.¹² The leaf oil of M sudae exhibited strong antimicrobial activity, with the same minimum inhibitory concentration (MIC) value of 25 µg/mL against the 2 Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, and the yeast Saccharomyces cerevisiae.⁴ This good antimicrobial result was attributed to the role of the major components such as α-pinene, β-pinene, and limonene present in the essential oil.⁴ The essential oils from M caudata were also shown to exhibit strong antimicrobial activities against several pathogenic bacterial and fungal strains with MIC values ranging from 8 to 128 μg/mL. The essential oil displayed the most potent activity against Enterococcus faecalis with a MIC value of 8 μg/mL.⁶ The leaf oil of M caudata possessed a MIC value of 256 µg/mL against 2 Gram-positive bacteria, B subtilis and S aureus, and the yeast Sacharomyces cerevisiae, and a MIC value of 128 µg/mL against the fungus Fusarium oxysporum. Meanwhile, M caudata rhizome oil was moderately active against the fungus Aspergillus niger and yeast S cerevisiae, with a MIC value of 128 µg/mL. This oil also inhibited the Gram-positive bacterium B subtilis and Gram-negative bacterium Escherichia coli with a MIC value of 256 µg/mL.¹¹ The leaf oil of M cristatissima showed greater antimicrobial activity than the rhizome oil against E faecalis, B subtilis, and C albicans with MIC values of 20.45, 29.45, and 18.45 μg/mL, respectively.¹²

In the current study, we report the chemical compositions of the essential oils from the pseudostem and leaves of M tomrey from Vietnam. This is part of ongoing research activities aimed at the determination of chemical constituents and biological actions of essential oils of Zingiberaceae species from Vietnam.^6,7,12

Results and Discussion

The yields of the essential oils were 0.33% for the pseudostem and 0.28% for the leaves (Table 1). Overall, 75 different constituents, mostly terpenes, were identified in both essential oils. A total of 60 compounds accounting for 89.3% of the total oil content were identified in the pseudostem essential oil of M tomrey. The essential oil was pale-yellow-colored. The oil was characterized by oxygenated monoterpenes (29.7%), monoterpene hydrocarbons (23.8%), oxygenated sesquiterpenes (21.9%), and sesquiterpene hydrocarbons (10.4%). The compounds occurring in higher quantity were β-pinene (14.2%), 1,8-cineole (13.5%), α-pinene (6.9%), borneol (4.6%), (E)-caryophyllene (3.6%), and (E)-nerolidol (3.5%). There was also a significant amount of linalool (4.1%), α-eudesmol (3.1%), β-eudesmol (2.4%), and guaiol (2.6%), among others.

Table 1.

Chemical Constituents of Essential Oils From the Pseudostem and Leaves of M tomrey.

Sr. no	RT (min)	Compounds^a	RI^b	RI^c	Concentration (%)
Sr. no	RT (min)	Compounds^a	RI^b	RI^c	Pseudostem	Leaves
1	6.77	α-Pinene	932	929	6.9	4.6
2	7.19	Camphene	946	943	1.6	1.4
3	8.30	β-Pinene	976	978	14.2	6.6
4	8.62	6-Methyl-5-hepten-2-one	981	988	0.3	0.3
5	9.58	α-Terpinene	1014	1015	0.2	–
6	9.90	β-Phellandrene	1025	1023	0.1	–
7	10.32	1,8-Cineole	1026	1034	13.5	16.7
8	11.26	γ-Terpinene	1054	1057	0.5	0.6
9	11.85	cis-Linalool oxide	1067	1072	–	1.2
10	12.48	Terpinolene	1086	1088	0.3	0.3
11	12.63	2-Nonanone	1087	1091	0.4	–
12	13.08	Linalool	1095	1102	4.1	3.8
13	13.18	n-Nonanal	1100	1104	0.3	–
14	13.91	dehydro-Sabina ketone	1117	1121	0.2	–
15	14.11	α-Campholenal	1122	1126	0.2	–
16	14.88	trans-Pinocarveol	1135	1143	–	0.2
17	14.92	Camphor	1141	1144	1.9	2.0
18	15.71	Pinocarvone	1160	1162	0.4	0.3
19	16.00	Borneol	1165	1168	4.6	4.2
20	16.28	cis-Pinocamphone	1172	1175	1.2	0.5
21	16.43	Terpinen-4-ol	1174	1178	1.4	1.3
22	16.61	(3Z)-Hexenyl butanoate	1184	1182	0.1	–
23	17.04	α-Terpineol	1186	1192	1.2	1.0
24	17.27	Myrtenol	1194	1198	1.9	3.5
25	18.75	cis-Carveol	1226	1231	0.3	0.5
26	19.26	cis -Myrtanol	1250	1242	0.4	–
27	19.33	neo-iso-Dihydro carveol	1226	1244	–	0.4
28	19.55	Piperitone	1248	1249	–	0.3
29	19.87	Geraniol	1249	1256	–	0.3
30	20.65	Perilla aldehyde	1269	1274	0.2	–
31	20.75	(2Z)-Hexenyl valerate	1282	1276	0.1	0.4
32	21.21	endo-Fenchyl acetate	1283	1286	1.3	–
33	21.26	Isobornyl acetate	1283	1287	–	1.4
34	22.92	Myrtenyl acetate	1324	1326	0.4	0.2
35	24.02	Butyl butyryl lactate	1353	1351	0.5	2.2
36	24.54	cis -Carvyl acetate	1365	1363	0.2	–
37	25.10	α-Copaene	1374	1376	0.5	–
38	25.10	(2E)-Octenol butanoate	1386	1376	–	2.5
39	25.46	(Z)-β-Damascone	1386	1385	0.1	–
40	25.80	β-Elemene	1389	1393	0.9	0.5
41	27.03	(E)-Caryophyllene	1417	1422	3.7	4.4
42	27.29	Dihydro-β-ionone	1434	1429	–	0.2
43	27.51	γ-Elemene	1434	1434	0.2	–
44	27.73	Aromadendrene	1439	1439	0.3	0.4
45	28.35	α-Humulene	1452	1454	0.9	1.3
46	28.64	(E)-Ethyl cinnamate	1465	1461	0.3	–
47	29.29	Valencene	1469	1477	0.4	0.5
48	29.46	γ-Muurolene	1478	1481	0.2	–
49	29.48	α-Amorphene	1483	1482	–	0.2
50	29.71	β-Selinene	1489	1487	1.2	1.2
51	29.93	δ-Selinene	1492	1493	–	0.2
52	30.07	α-Selinene	1498	1496	1.0	1.0
53	30.54	trans-β-Guaiene	1502	1508	0.2	–
54	30.81	γ-Cadinene	1513	1515	0.4	0.2
55	31.19	δ-Cadinene	1522	1524	0.5	0.5
56	32.86	(E)-Nerolidol	1561	1567	3.5	7.6
57	33.35	Spathulenol	1577	1579	0.4	–
58	33.54	Caryophyllene oxide	1582	1585	1.0	1.8
59	33.90	Globulol	1590	1594	0.8	0.5
60	34.20	Guaiol	1600	1601	2.6	1.5
61	34.54	Rosifoliol	1600	1610	0.3	–
62	35.44	γ-Eudesmol	1635	1635	1.2	0.8
63	35.69	Hinesol	1640	1641	0.2	0.2
64	35.80	epi-α-Muurolol	1642	1644	0.4	0.2
65	36.16	β-Eudesmol	1649	1654	2.4	1.7
66	36.30	α-Eudesmol	1661	1658	3.1	1.8
67	36.78	Bulnesol	1670	1671	1.6	0.7
68	36.89	14-Hydroxy-9-epi-(E)-caryophyllene	1670	1674	–	0.2
69	37.63	Acorenone	1692	1693	–	0.9
70	37.75	Eudesm-7(11)-en-4-ol	1700	1697	0.1	0.1
71	38.57	(E)-Nerolidyl acetate	1716	1720	–	0.3
72	38.67	(2Z,6E)-Farnesol	1722	1722	0.1	–
73	45.40	(5E,9E)-Farnesyl acetone	1913	1918	–	0.6
74	47.00	Hexadecanoic acid	1959	1968	1.9	0.9
75	62.23	n-Pentacosane	2500	2498	–	0.2
Monoterpene hydrocarbons					23.8	13.2
Oxygenated monoterpenes					29.7	34.6
Sesquiterpene hydrocarbons					10.4	10.3
Oxygenated sesquiterpenes					21.9	22.7
Fatty acids					1.9	1.1
Nonterpenes					1.6	5.4
Total					89.3	87.3

Abbreviations: RT, retention time; RIs, retention indices.

Elution order on Equity-5 capillary column.

Retention indices on Equity-5 capillary column.

Literature retention index taken from Adams.¹⁴

– Not identified.

The 55 constituents of the leaf essential oil were comprised of oxygenated monoterpenes (34.6%), oxygenated sesquiterpenes (22.8%), monoterpene hydrocarbons (13.2%), and sesquiterpene hydrocarbons (10.3%). The pale-yellow-colored essential oil sample had 5.4% of fatty acids and 1.1% of nonterpene compounds. The total oil content was 87.3%. The main constituents of the essential oil include β-pinene (6.6%), 1,8-cineole (16.7%), α-pinene (4.6%), borneol (4.2%), (E)-caryophyllene (4.4%), and (E)-nerolidol (7.6%). The minor compounds present in the essential oil were linalool (3.8%), myrtenol (3.5%), (2E)-octenol butanoate (2.5%), and butyl butyryl lactate (2.2%).

Of the 76 identified constituents in the 2 oils, 39 were common to both. However, quantitative variations were observed among the main and minor compounds of the essential oils. For example, for the major compounds, the amount of α-pinene was 6.9% and 4.6%, respectively, for both the pseudostem and leaves oil samples. The β-pinene contents were 14.2% and 6.6%, respectively, while 13.5% and 16.7% of 1,8-cineole were present, respectively. (E)-Nerolidol was identified in larger quantities in the leaf essential oil (7.6% and. 3.5%). The pseudostem oil sample contained an appreciably higher content of hexadecanoic acid (1.9%) than the leaf oil (0.9%). However, n-pentacosane was present only in the leaf oil sample.

There are instances of particular compounds where both the leaf and pseudostem oil samples contained nearly or equal quantitative amounts. These can be seen in Table 1, where α-selinene represented 1% in both oil samples, whereas δ-cadinene formed 0.49% (pseudostem oil) and 0.47% (leaf oil). In addition, hinesol was present in 0.20% of the pseudostem oil and 0.21% of the leaf oil. Other examples in which both the leaves and pseudostem oil samples contained nearly or equal quantitative amounts of particular compounds could be found in γ-terpinene, pinocarvone, aromadendrene, and eudesm-7(11)-en-4-ol (Table 1).

The chemical composition of essential oils of the pseudostem and leaves of M tomrey was compared with available data on essential oil constituents of other Meistera species. The presence of α-pinene and β-pinene in M tomrey is noteworthy. These 2 compounds feature prominently in the essential oil of Meistera species and the 2 are among the significant constituents of the leaf of M sudae,⁷ M caudata,^8,9 and M cristatissima,¹⁰ as well as the rhizomes of M caudata.⁸ However, some compounds, such as camphene, β-elemene, α-selinene, and β-selinene in M caudata, occurred in lower quantities in M tomrey. Also, the essential oils of M tomrey contained a lower amount of caryophyllene oxide and spathulenol when compared with M cristatissima.¹⁰ More importantly, myrcene and limonene found in the essential oils of M sudae⁷ and δ-3-carene⁸ and bicyclogermacrene⁹ identified in M caudata were conspicuously absent in M tomrey. More data are required to substantiate the importance of α-pinene and β-pinene as chemotaxonomic markers of Meistera essential oils from Vietnam.

Conclusions

For the first time, the chemical compositions of essential oils from M tormey were reported. Monoterpenes and sesquiterpenes were the main classes of compounds identified in the essential oils of the pseudostem and leaves of M tormey. In addition, monoterpenes constituted the main compounds of the essential oils. These are β-pinene (14.2%), 1,8-cineole (13.5%), and α-pinene (6.9%) from the pseudostem oil sample; as well as β-pinene (6.6%), 1,8-cineole (16.7%), α-pinene (4.6%), and borneol (4.2%) in the leaf essential oil. Notably, within the leaf essential oil, (E)-nerolidol (7.6%) emerged as the most prominent sesquiterpene.

Materials and Methods

Plant Materials

The fresh leaves and pseudostem (1.0 and 1.0 kg) of M tomrey were collected from Bao Lam district, Lam Dong province (GPS: 11°42'52.8"N 107°38'27.3"E) in April 2022. The plant samples were identified by Mr Nguyen Danh Duc and Dr Le Tuan Anh, Vietnam National Museum of Nature. A voucher specimen (MT-D49) was deposited at the Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, Vietnam.

Hydrodistillation of the Essential Oils

To prepare for hydrodistillation, we followed the methods established in previous studies.^6,12 The fresh pseudostem and leaf samples of M tomrey were shredded separately.

For the pseudostem and leaves, fresh material (1.0 kg each) was subjected to hydrodistillation using a Clevenger-type apparatus. The pulverized sample of each plant was divided into 3 equal parts to enable the distillation of essential oils 3 times. Each of the samples was packed separately inside a 2-L flask. The samples were submerged completely inside the flask with enough distilled water (1.2-L), and then connected to the Clevenger-type apparatus. The essential oils were allowed to distill for 3 h after the whole apparatus had been connected to a heating mantle maintained at normal pressure according to Vietnamese Pharmacopoeia.¹³ On completion, the hydrodistilled essential oils were collected, dried with sodium sulfate, and stored in a refrigerator at 4 °C. The experiments were repeated 3 times. The yield (%) of the essential oils was calculated separately by dividing the mass (g) of the essential oil by the mass (g) of the pulverized pseudostem and leaves of M tomrey, as described previously.^6,12

Analysis of the Essential Oils

The chemical composition of the essential oil was analyzed using the GCMS-QP2010 Plus system, manufactured by Shimadzu in Kyoto, Japan. The system was equipped with an Equity-5 capillary column measuring 30 m in length and 0.25 mm in diameter, coated with a 0.25-µm film thickness, and coupled with a mass spectrometer (MSD QP2010 Plus) for GC/MS analysis. To carry out the analysis, each of the essential oils was first diluted with n-hexane at a ratio of 1:100. Thereafter, 1 μL of each of the diluted oil was introduced separately into the GC/MS column. Helium was used as the carrier gas at a flow rate of 1.5 mL/min, while the injector and interface temperatures were set at 280 °C. The column temperature was programmed to increase from 60 °C (2 min hold) to 240 °C at a rate of 3 °C/min (10 min hold), followed by an increase to 280 °C at a rate of 5 °C/min (40 min hold). The samples were injected in splitless mode. The mass spectrometer was set to an ionization voltage of 70 eV and an acquisition scan mass range of 45 to 500 (m/z) at a sampling rate of 1.0 scan/s.

Identification of Terpenes and Nonterpene Compounds of the Essential Oils

The constituents’ retention indices (RIs) were established by co-injecting a reference homologous series of n-alkanes (C₈-C₃₈) under the same conditions. The identification of components was carried out by comparing their RI values with those reported by Adams,¹⁴ and further identification was performed by comparing their mass spectra with those stored in the GC/MS database from NIST 11¹⁵ and WILEY seventh. Quantification was done by using the relative peak area percentage. See Supplemental Material for further information.

Supplemental Material

sj-docx-1-npx-10.1177_1934578X231186019 - Supplemental material for Chemical Composition of Essential Oils From the Pseudostem and Leaves of Meistera tomrey Growing in Vietnam

Supplemental material, sj-docx-1-npx-10.1177_1934578X231186019 for Chemical Composition of Essential Oils From the Pseudostem and Leaves of Meistera tomrey Growing in Vietnam by Tuan Quoc Doan, Duc Danh Nguyen, Hoai Thi Nguyen and Isiaka Ajani Ogunwande in Natural Product Communications

Footnotes

Acknowledgments

This research was supported by Hue University (no. DHH2022-04-177).

Authors’ Contributions

The research idea was provided by DQ Tuan and NT Hoai. Extraction and analysis were carried out by DQ Tuan. Reading and revising the manuscript were undertaken by DQ Tuan, ND Duc, NT Hoai, and IA Ogunwande.

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.

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 the This research was funded by Hue University (grant no. DHH2022-04-177).

Ethical Approval

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

Statement of Human and Animal Rights

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

Informed Consent

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

Trial Registration

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

ORCID iDs

Hoai Thi Nguyen

Supplemental Material

Supplemental material for this article is available online.

References

Binh

. Flora of Vietnam, Zingiberaceae, vol. 21. Natural Science and Technology Publishing House, Ha Noi; 2017.

Lamxay

Newman

. A revision of Amomum (Zingiberaceae) in Cambodia, Laos and Vietnam. Edinburgh J Bot. 2012;69(1):99–206.

Musdalipah

Karmilah

Selfyana

, et al. Meistera chinensis fruit properties: chemical compound, antioxidant, antimicrobial, and antifungal activity. IOP Conf Ser. 2021;755:012014.

Huong

Son

Sam

, et al. Chemical compositions and antimicrobial activity of essential oils from the leaves of 4 Vietnamese Zingiberaceae species. Nat Prod Commun. 2022;17(12):1–6.

Hieu

Giang

Huyen

, et al. Chemical examination and antimicrobial activity of essential oils from the leaves and rhizomes of Meistera caudata Šída f. & Škorničk. (Zingiberaceae). J Biol Active Prod Nature. 2023;13(1):68–75.

Tuan

Dien

Pham

, et al. Chemical composition of essential oil from the rhizomes and leaves of Newmania sontraensis H.Ð.Trân, Luu & Škornick (Zingiberaceae) from Vietnam. J Essent Oil Bearing Plants. 2021;24(6):1260–1268.

Tuan

Dien

Tran

, et al. Chemical composition of essential oil from the Zingiber monophyllum (Zingiberaceae) from Vietnam. J Essent Oil Bearing Plants. 2022;25(5):987–993.

Boer

Newman

Poulsen

, et al. Convergent morphology in Alpiniaea (Zingiberaceae): recircumscribing Amomum as a morphyletic genus. Taxon. 2018;67(1):6–36.

Rafaël

Eimear

Nicholas

, et al. The world checklist of vascular plants, a continuously updated resource for exploring global plant diversity. Sci Data. 2021;8(215):1–10.

10.

Kaewsri

. Amomum tomrey gagnep. (Zingiberaceae), a new record for Thailand. Thai For Bull (Bot). 2012;40(1):17–19.

11.

Huong

Son

Sam

, et al. Essential oils of the ginger plants Meistera caudata and Conamomum vietnamense: chemical compositions, antimicrobial, and mosquito larvicidal activities. Z Naturforsch C J Biosci. 2023;78(5-6):89–94. Doi: 10.1515/znc.2022.0244

12.

Viet

Sam

Huong

, et al. Antimicrobial activities and compositions of essential oils from the leaves and rhizomes of Meistera cristatissima (N.S.Lý & Škorničk.) Škorničk. from Vietnam. Chem Nat Compds. 2023;59(2):396–399.

13.

Vietnamese Pharmacopoeia. Medical Publishing House. Ministry of Health, 2017.

14.

Adams

. Identification of essential oil components by gas chromatography/mass spectrometry. 4th edition. Allured Publishing Corporation; 2017.

15.

NIST. 2011. Chemistry WebBook. Data from NIST Standard Reference Database 69. (http://www.nist.gov/).

Supplementary Material

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