The chemical composition of the leaves’ oil of Artabotrys vinhensis Ast. (family: Annonaceae) from Vietnam

Keywords: Artabotrys vinhensis Ast, Annonaceae, essential oil composition, neral, geranial, -caryophyllene.

Introduction

The genus Artabotrys of the family Annonaceae is a paleotropical genus compose of one hundred species of climbers and scandent shrubs distribute mainly in the tropical zone and the subtropical areas, especially Africa and Asia [1], of which only the widespread Asia. Some Asian species of the Annonaceae are economically important as sources of the edible fruit and aromatic oils. Little is known about the potential uses or chemistry of the species of Artabotrys [2, 3, 5, 7].

The flowers of A. hexapetalus (L.f.) Bhand. from the Indian subcontinent are used to make a stimulant tea [4] and are also apparently useful in the treatment of choler [6]. Four Artabotrys species from China has long been used among the ordinary people as medicinal plant which  have antipyretro, antidotal, antiphlogistic and analgesic effects and are often used for malaria [3].

Analysis of the essential oils of A. adoratissimus fruits and leaves from South India have found move than 80 compounds, in which sesquiterpenes as a-caryophyllene (14.7% - 17.3%), a-copanene (6.4-9.3%), (E)-nerolidol, d-cadinene (4.2% - 7.3%), caryophyllene oxide (3.2% - 16.8%), (E,E)-a-farnesene (5.8-7.4%) and t-cadinol (2.9% - 3.29%) are main components, some monoterpenes and hexane derivatives were found also [8]. The steam-distilled oil from the bark of Artabotrys lastourvillensis from Gabon. All seventeen components identified were sesquiterpenoids of which cyperene (25.9%) and cyperenone (11.1%) [9]. The essential oils extracted from five Artabotrys species, Annonaceae (A. insignis, A pierreanus, A. rufus, A. thomsoni and A. venustus) [10]. The main components of each oil have been identified. Among them, two compounds seem to have a chemotaxonomic significance: cyperenone and 1,5-epoxysalvial-4(14)-ene. Pleasant flower smelling essential oil of Artabotrys hexapetalus from Vietnam, twenty-six components of the oil including sesquiterpene hydrocarbons (33.3% of the oil) and oxygenated sesquiterpenoids (47.7%) were identified β-caryophyllene (11.4%) and caryophyllene oxide (31.5%) were identified as the major components of the oil [13]. The primary study of the chemical composition of the Artabotrys hexapetalus flower in Ninh Binh province. The main compounds in this essential oil were caryophyllene oxide (36.19%); β-caryophyllene (7.87%); α-copaene (10.78%); β-asarone (6.12%) [11]. Up to date only 15 Artabotrys species have been recoded in Vietnam. To the best of our knowledge  the leaf oil of Artabotrys vinhensis Ast has never been previously analyzed  has 4 species edemic in Vietnam [12].

Experimental

1. Source- Artabotrys vinhensis Ast (Annonaceae), is a clember to 7 – 10 m long, growing in Vietnam. The leaves of Artabotrys vinhensis Ast were collected in April 2007, in Quynh Luu district, Nghe An province and identified by Assoc. Prof. Dr. Vu Xuan Phuong of Institute of Ecology and Biological Resources. A voucher specimen (DD110) was deposited at the Herbarium of the Institute of Ecology and Biological Resources, Vietnamese Academy of Science and Technology and  Vinh University.

Fresh leaves were shredded and their oil were obtained by steam distillation for 3 h at normal pressure, according to the Vietnamese Pharmacopoeia [14]. The yield of the fresh leaf oil was 0.1%. 

2. GC- About 15mg of oil, which was dried with anhydrous sodium sulfate, was dissolved in 1ml of n-hexane (for spectroscopy or chromatography).
GC analysis was performed on an Agilent Technologies HP 6890 Plus Gas chromatograph equipped with a FID and fitted with HP-5MS column (L = 30 m, ID = 0.25 mm, film thickness = 0.25 mm). The analytical conditions were: carrier gas H2, injector temperature (PTV) 250^oC, detector temperature 260^oC, temperature programmed 60^o (2 min hold) to 220^o (10 min hold) at 4^oC/min.

3. GC/MS- An Agilent Technologies HP 6890 N Plus Chromatograph was fitted with a fused silica capillary col. HP-5MS column (L = 30 m, ID = 0.25 mm, film thickness = 0.25 mm). The condition of use were the same as described above with He as carrier gas, and interface with a mass spectrometer HP 5973 MSD (70 eV). The temperature was programmed as reported above. Component identification was carried out by comparing MS data with those reported in Library Willey on Chemstation HP, and in some cases substances identified from oils known composition and also with standard substances [15 - 20].

Results and discussion

The  oil yield  of fresh leaf was 0.1% after 3 h of distillation. The average oil composition in Table 1., in which the identified compounds are given, representing about 96,98% of the oil. The main components were α-pinene (16.67%), myrcene (15.40%), germacrene D (14.41%), benzyl benzoate (8.81%), β-pinene (7.48%), β-caryophyllene (7.47%) and germacrene B (5.02%).

Table 1:  Chemical composition of the essential oil of  Artabotrys vinhensis  from Vietnam

No	Compounds	KI	% FID
1.	α-pinene	939	16.67
2.	camphene	953	0.07
3.	sabinene	976	0.55
4.	β-pinene	980	7.64
5.	β-myrcene	990	2.41
6.	limonene	1032	15.40
7.	(Z)-β-ocimene	1042	0.05
8.	(E)-β-ocimene	1053	0.59
9.	g-terpinene	1061	0.05
10.	α-terpinolene	1090	0.06
11.	linalool	1100	0.66
12.	nonanal	1102	0.06
13.	geijerene	1143	0.06
14.	isomenthone	1167	0.10
15.	l-menthone	1171	0.42
16.	p-anisyl alcohol	1281	0.31
17.	bicycloelemene	1327	0.28
18.	α-cubebene	1351	0.27
19.	α-ylangene	1375	0.03
20.	α-copaene	1376	1.24
21.	β-bourbonene	1388	0.34
22.	β-cubebene	1388	0.22
23.	β-elemene	1391	1.47
24.	trans-α-bergamotene	1413	0.14
25.	β-caryophyllene	1419	7.47
26.	α-bergamotene	1435	0.73
27.	α-humulene	1454	2.66
28.	germacrene D	1485	14.47
29.	α-amorphene	1485	1.13
No	Compounds	KI	% FID
30.	(+)-epi-bicyclosesquiphellandrene	1489	0.44
31.	β-selinene	1490	0.09
32.	cadina-1,4-diene	1496	0.13
33.	α-muurolene	1500	0.04
34.	cis-z-α-bisabolene epoxide	1515	0.37
35.	endo-1-bourbonanol	1520	0.25
36.	d-cadinene	1525	2.18
37.	nerolidol	1563	0.08
38.	germacrene B	1576	5.02
39.	spathulenol	1578	0.15
40.	caryophyllene oxide	1583	0.68
41.	salvial-(14)-en-1none	1595	1.03
42.	guaiol	1601	0.29
43.	(Z)-β-asarone	1617	0.17
44.	t-muurolol	1645	0.64
45.	α-cadinol	1654	1.06
46.	benzyl benzoate	1760	8.81

Acknowledgements

The Authors wish to thank Assoc. Prof. Dr. Vu Xuan Phuong, Institute of Ecology and Biological Resources, Vietnamese Academy of Science and Technology, for confirmation of the plant identity.

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Do Ngoc Dai, Tran Minh Hoi
Institute of Ecology and Biological Resources, Viet Nam Academy of Science and Technology, Ha Noi.
Tran Dinh Thang
Faculty of Chemistry, Vinh University, 182- Le Duan, Vinh, Vietnam
Nguyen Xuan Dung
Faculty of Chemistry, College of Natural Science, Hanoi National University, 19-Le Thanh Tong, Hanoi, Vietnam
(Science and Technology Journal, No (48): 2A/2010)