Journal of Natural Medicines

, Volume 60, Issue 3, pp 248–250 | Cite as

Chemical constituents of the essential oil from the bark of Cinnamomum illicioides A. Chev. from Vietnam

  • Phan Minh Giang
  • Wilfried A. König
  • Phan Tong Son
Note

Abstract

The chemical constituents of the hydrodistilled essential oil from the bark of Cinnamomum illicioides A. Chev., Lauraceae, from Vietnam, have been studied by GC and GC–MS. Seventeen monoterpenoids, eugenol, and thirty-six sesquiterpenoids, accounting for 25, 41.2, and 27.9% of the oil, respectively, were identified. Terpinen-4-ol (10.4%), eugenol (41.2%), and δ-cadinene (5.6%) are the major components of the oil.

Keywords

Cinnamomum illicioides Lauraceae Eugenol Terpinen-4-ol δ-Cadinene GC GC–MS 

Introduction

The tree Cinnamomum illicioides A. Chev. (Lauraceae), commonly known in Vietnam as Gu huong, is up to 30 m tall and 1–1.5 m in diameter. The plant grows in forested valleys or in dense forest approximately 800 m above sea level in Hainan, Guangxi (China), and Northern Vietnam. Cinnamomum camphora, C. balansae, C. burmannii, C. aromaticum, C. cassia, C. caryophyllus, C. iners, C. loureirii, C. obtusifolium, C. parthenoxylon, C. simmondii, C. tetragonum, and C. zeylanicum, which are known to produce essential oils, are used in Vietnamese traditional medicine [1]. The odor of C. illicioides is reported to be similar to that of C. camphora L. Nees. et Eberm. (syn. Laurus camphora L.); the tree is, therefore, a very interesting target for research. Although investigation of the chemical constituents of other Cinnamomum species, for example C. cassia, C. zeylanicum, or C. osmophloeum, and correlation of these with their antibacterial and antifungal activity has been extensively undertaken [2, 3, 4], there is no report of the chemical constituents of C. illicioides essential oil. Our study revealed that hydrodistillation of the dried bark of C. illicioides furnished a large amount of essential oil (1.36% yield based on the dry material). Chemical study of this essential oil has revealed the presence of constituents which, by correlation with those of previously investigated Cinnamomum oils, will help us to examine the economic value of the oil as a natural flavoring and/or antibacterial and antifungal agent. This paper reports the analysis of the chemical constituents of the essential oil from the dried bark of C. illicioides.

Results and discussion

Fifty-four components of the essential oil from the dried bark of C. illicioides, representing 94.1% of the oil, were identified in this study. Seventeen monoterpenoids, eugenol, and thirty-six sesquiterpenoids accounting for 25, 41.2, and 27.9% of the oil, respectively, are listed in Table 1. The oil is rich in eugenol (41.2%) and terpinen-4-ol (10.4%), which can be used as chemical markers of the oil. δ-Cadinene (5.6%), α-copaene (4.1%), (E)-β-caryophyllene (3.0%), and α-cadinol (1.6%) are the most abundant sesquiterpenoid components. A gas chromatogram obtained from the essential oil is shown in Fig. 1. Previous studies classified two samples of C. cassia and C. zeylanicum bark oils from Taiwan into cinnamaldehyde–coumarin [2] and cinnamaldehyde–eugenol types [3], respectively, on the basis of the main constituents of the oils. The bark oil of C. illicioides from Vietnam could therefore be classified as the eugenol–terpinen-4-ol type.
Table 1

Constituents of the essential oil from the dried bark of Cinnamomum illicioides

No.a

Compound

Content (%)b

1

α-Thujene

0.1

2

α-Pinene

1.9

3

Camphene

0.5

4

β-Pinene

0.9

5

Myrcene

0.3

6

α-Terpinene

0.4

7

p-Cymene

1.1

8

1,8-Cineol

2.6

9

γ-Terpinene

0.5

10

Terpinolene

0.2

11

cis-p-Menthen-2-en-1-ol

tr.c

12

Pinocarvone

0.1

13

Borneol

2.7

14

Terpinen-4-ol

10.4

15

α-Terpineol

3.3

16

Bornyl acetate

tr.

17

Carvacrol

tr.

18

Eugenol

41.2

19

α-Cubebene

1.4

20

α-Copaene

4.1

21

β-Elemene

0.5

22

cis-α-Bergamotene

tr.

23

(E)-β-Caryophyllene

3.0

24

trans-α-Bergamotene

tr.

25

Guaia-6,9-diene

0.2

26

Aromadendrene

tr.

27

H,10αH-Guaia-1(5),6-diene

0.2

28

α-Humulene

0.8

29

allo-Aromadendrene

0.2

30

H,10βH-Cadina-1(6),4-diene

0.8

31

5-epi-Aristolochene

0.3

32

β-Neoclovene

0.1

33

γ-Humulene

0.2

34

Eremophyla-1(10),7-diene

0.3

35

α-Muurolene

0.7

36

(E,E)-α-Farnesene

0.1

37

γ-Cadinene

0.4

38

Calamenene

0.8

39

δ-Cadinene

5.6

40

Zonarene

tr.

41

Cadina-1,4-diene

0.6

42

α-Calacorene

0.2

43

Elemol

0.2

44

Spathulenol

0.3

45

Globulol

0.2

46

α-Guaiol

1.1

47

1-epi-Cubenol

1.2

48

T-Muurolol

1.0

49

Amorph-4-en-7-ol

1.0

50

α-Cadinol

1.6

51

Eudesm-4(15)-en-7-ol

tr.

52

7-epi-α-Eudesmol

tr.

53

Bulnesol

0.7

54

Cadalene

0.1

aNumbering refers to Fig. 1

bRelative percentages of components were calculated using the GC CPSil-5-CB column

cTrace constituent (≤0.05%)

Fig. 1

Gas chromatogram obtained from the essential oil of Cinnamomum illicioides of Vietnam

Experimental

Plant material and oil preparation

The dried bark of C. illicioides A. Chev. (Lauraceae) was collected in Province Thai Nguyen, Vietnam. The plant was identified by Dr Nguyen Hoanh Coi, a botanical taxonomist of the Military Institute of Pharmaceutical Research and Control, Hanoi, Vietnam, in September 2001, and a voucher specimen (HCTN CI 9-01) is deposited in the Laboratory of Chemistry of Natural Products, Faculty of Chemistry, Vietnam National University, Hanoi, Vietnam. The bark was ground to powder and hydrodistillation of the material for 8 h produced an oil in 1.36% yield.

Gas chromatography (GC)

An Orion Micromat 412 instrument equipped with two fused-silica capillary columns (25 m×0.25 mm i.d., film thickness 0.15 μm), coated with CPSil-5-CB and CPSil-19-CB, split injection, and flame ionization detection, was used. Injector and detector temperatures were at 200 and 250°C. The oven temperature was programmed from 50 to 230°C at 3° min−1. The carrier gas was H2 at 1.2 mL min−1.

Gas chromatography–mass spectrometry (GC–MS)

A Hewlett–Packard HP 5890 gas chromatograph coupled to a VG Analytical 70-250S mass spectrometer was used. The GC was fitted with a fused-silica capillary column coated with CPSil-5-CB (25 m×0.25 mm i.d., film thickness 0.15 μm). The GC operating conditions were identical with those described above except that helium was used as carrier gas. The MS operating conditions were: ionization potential 70 eV and ion source temperature 230°C.

Identification of the components

The oil was analyzed by dual GC on a non-polar CPSil-5-CB capillary column and on a more polar CPSil-19-CB capillary column of identical dimensions. GC–MS was performed with a CPSil-5-CB column. Compounds were identified by comparison of retention indices and mass spectra with those of authentic samples, obtained under identical experimental conditions, and use of a computer-supported spectral library (MassFinder 2.3) [5, 6].

Notes

Acknowledgment

The authors are grateful to the VolkswagenStiftung (Partnerschaftsvorhaben “Untersuchung ätherischer Öle Vietnams”) for financial support of this work.

References

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    Hu TW, Lin YT, Ho CK (1985) Natural variation of chemical components of the leaf oil of Cinnamomum osmophloeum Kaneh. Bulletin of Taiwan Forestry Research Industry, New Series 78:18Google Scholar
  3. 3.
    Ross MSF (1976) Analysis of cinnamon oils by high-pressure liquid chromatography. J Chromatogr 118:273–275CrossRefGoogle Scholar
  4. 4.
    Chang ST, Chen PF, Chang SC (2001) Antibacterial activity of leaf essential oils and their constituents from Cinnamomum osmophloeum. J Ethnopharmacol 77:123–127CrossRefPubMedGoogle Scholar
  5. 5.
    Joulain D, König WA (1998) The atlas of spectral data of sesquiterpene hydrocarbons. E.B.-Verlag, HamburgGoogle Scholar
  6. 6.
    Hochmuth DH, König WA, Joulain D (2003) MassFinder 2.3, Software & Data Bank, Hamburg. Available at: http://www.massfinder.com

Copyright information

© The Japanese Society of Pharmacognosy and Springer 2006

Authors and Affiliations

  • Phan Minh Giang
    • 1
  • Wilfried A. König
    • 2
  • Phan Tong Son
    • 1
  1. 1.Faculty of Chemistry, College of Natural ScienceVietnam National UniversityHanoiVietnam
  2. 2.Institut für Organische ChemieUniversität HamburgHamburgGermany

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