Journal of Essential Oil Research

ISSN: 1041-2905 (Print) 2163-8152 (Online) Journal homepage: http://www.tandfonline.com/loi/tjeo20

Constituents of the Leaf and Flower Oils of

Agastache rugosa (Fisch. et Mey) O. Kuntze from
Vietnam

Nguyêñ Xuân Dũng , Luu Dàm Cu , Nguyêñ Huy Thái , Lã Dình Mõi , Lê Van
Hac & Piet A. Leclercq

To cite this article: Nguyêñ Xuân Dũng , Luu Dàm Cu , Nguyêñ Huy Thái , Lã Dình Mõi , Lê Van
Hac & Piet A. Leclercq (1996) Constituents of the Leaf and Flower Oils of Agastache rugosa
(Fisch. et Mey) O. Kuntze from Vietnam, Journal of Essential Oil Research, 8:2, 135-138, DOI:
10.1080/10412905.1996.9700580

To link to this article: http://dx.doi.org/10.1080/10412905.1996.9700580

Published online: 09 Dec 2011.

Submit your article to this journal

Article views: 8

View related articles

Citing articles: 2 View citing articles

Full Terms & Conditions of access and use can be found at

http://www.tandfonline.com/action/journalInformation?journalCode=tjeo20

Download by: [University of Exeter] Date: 12 October 2016, At: 04:01

RESEARCH REPORT 1.Essent. Oil Res., 8,135-138 (Mar/Apr 1996)

Constituents of the Leaf and Flower Oils

of Agastache mgosa (Fisch. et Mey)
0. Kuntze from Vietnam

Nguy6ii X u h Dfing’
Centerfor Education and Development of Chromatography, EDC Vietnam
3 Giai Phhnng Street, Hai Bh District, 10000 Hanoi, Vietnam

Luu D h Cu, Nguy6ii Huy Th5, Lsi Dinh M6i

Institute of Ecology and Natural Resources
Nghia D6, Tii LGm, Hanoi, Vietnam

Li2 Van Hac

Vinh Teachers Training College, Ngh.2 An, Vietnam

Piet A. Leclercq’
Laboratoy of lnstrumentd Andy&, Department of Chemical Engineering
Eindhoven University of Technology, PO Box 513
5600 M B Eindhoven, The Netherlands

Received: May 1995

ABSTRACT The volatile leaf and flower oils from Agastache rugosa (Fisch. et Mey) 0.Kuntze
were analyzed by GC and GC/MS and found to contain more than 40 mono- and sesquiterpenes,
of which about 30 constituents have been identified. The oils are characterized by a high
proportion of methyl chavicol(92.0% and 75.9% in the leaf and flower oils, respectively).

KEY WORD INDEX Agastache rugosa, Labiatae, essential oil composition, methyl chavicol.

1NTRODUCTION:Agastache rugosa (Fisch.et Mey) 0.Kuntzeis one ofthe speciesofthe genus

Agastache (Labiatae),occurring in many places in tropical and subtropical areas. This aromatic
plant is used throughout the year as a flavoring agent and as folk medicine against fever, headache,
cold, stomach pain, etc. (1).In view of the potential for commercializationof this plant we studied
the composition of the leaf and flower oils. The chemical composition of the various parts of
A. rugosa (“catnipgiant hyssop”)has been investigated extensively (2-21).The aerial parts of this
plant have been shown to contain acacetin, tilianin, agastachoside,isoagastachoside,linarin and
agastachin (2,3).The first three compounds were also isolated from the roots, which additionally
contained maslinic and oleanolic acid, daucosterol, p-sitosterol and dehydroagastol (4). The
presence of the triterpenes 3-0-acetyloleanolicaldehyde (4,5),erythrodiol-3-O-acetate ( 5 ) ,3-0-
acetyloleanolic acid (6), and of the diterpenes agastenol, dehydroagastol, agastanone, and
methylagastanol(7,8)in the roots has been reported as well. Flavonoids from the leaves,stems and

‘Addresses for correspondence

1041-2905/96/0002-0135$04.~/0-@1996Allured PublishingCOT. 135

136 JOURNAL OF ESSENTIAL OIL RESEARCH

inflorescences of eight Agustache species have been charactertized, and the flavonoid profile of
Asian and western North American A. rugosa species was reported to be identical (9). The foliage
oil contained 1.5-5.0% free alcohols, while the seed oil had a high linolenic acid content (10).
Linolenic, palmitic, lauric, linoleic and 11more fatty acids were detected in the leaves, stems and
flowers of “bangah,”the South Korean variety of A. rugosa (11).These plant materials were also
analyzed on their protein, lipid, sugar, amino acid, and mineral contents (11).Rosmarinic acid was
present in a fairly large amount in the leaves of Japanese A. rugosa and other Labiatae plants (12).

More relevant to the present study is the literature on the analyisis of giant hyssop oils (13-21).
Fujita and Fujita reported that the oils from fresh and dried plants contained 83.5-92.2% of
methyl eugenol as major compound (13-16). Other identified components included methyl
chavicol (1.5-6.3%) and safrole (0.1-0.4%), together with small amounts of a-and P-pinene,
limonene, p-cymene, 3-octanone, 3-octano1, (Z)-P,y-hexenol,1-octen-3-01,linalool, P-elemene,
P-caryophyllene, a-humulene and 6-cadinene (13,14). The same authors earlier reported the
presence of 0.5% of sesquiterpene hydrocarbons in A. rugosa oil, mainly consisting of
P-caryophyllene and small amounts of a-ylangene, p-elemene, P-humulene, p-famesene,
y-cadinene and calamenene (15). The similarity of the oils from A. rugosa and Mosla
methylchauicoZ~erahas been reported (16).

Contrary to these reports ( 13-16)and in more recent publications, all other authors found methyl
chavicol (estragole)to be the major constituent ofA. rugosa (17-21).The volatile part of the plant
was reported to contain more than 90% of methyl chavicol, while minor constituents were
anisaldehyde and p-methoxycinnamaldehye(18).A total of 32 components were identified in the
leaf, stem and flower oils from the South Korean variety (19).The major flavor componentswere
methyl chavicol,limonene, caryophyllene,eugenol and anethol. The concentrationof these flavor
components was highest in the flower oil.

Charles et al. reported the presence of methyl chavicol(46-95%)in the leaf and flower oils (20),
and also among the volatiles in the headspace of inflorescences and leaves (21). Additional oil
constituents, in concentrations of about I%, included P-bourbonene, bornyl acetate, y-cadinene,
a-cadinol, 6-cadinene, a-camphene, P-caryophyllene, damascenone, p-ionone, isomenthone,
limonene, linalool, methyl eugenol, myrcene, (Z)-P-ocimene, 7-octen-4-01, pulegone and
spathulenol. The flower and leaf oils of A. rugosa and A. foeniculum (anise hyssop) had similar
compositions, while the oils from A. nepetoihs (Korean mint) were quite different (20).

EXPERIMENTAL. Pkant Muterial-Cultivated plants were harvested, in 1993 during the

flowering stage, in the botanical garden of the Institute of Ecology and Natural Resources, Hanoi,
Vietnam. A voucher specimen has been deposited in the herbarium of this institute.

Zeolation of the Essential Oil-The oils were prepared by steam distillation of fresh plant
materials in a glass apparatus for 6 h. The oil yields were 0.52% and 0.83% from the leaves and
flowers, respectively.

GC-A Hewlett Packard 5890 Series I1 gas chromatograph equipped with a FID detector and a
HP-1 fused silica column (25 m x 0.32 mm, 0.25 pm film thickness) was used. The samples,
dissolved in hexane, were injected in the splitless mode. Injector and detector temperatures were
mained at 250°C. The column temperature was programmed from 60°C (after 2 min) to 220°C at
4O/min and the final temperature was held for 20 min. Peak areas and retention times were
measured by electronic integration. The relative amounts of individual components are based on
the peak areas obtained, without FID response factor correction.

GCMS-Analyses were carried out on a Hewlett-Packard 5970A mass selective detector (MSD),
directly coupled to a HP 57904 gas chromatograph. A 26 m x 0.22 mm column, coated with 0.13
pm of CP-Sil5CB was employed, using helium as carrier gas. The oven temperature program was
 JOURNAL OF ESSENTIAL OIL RESEARCH 137

Table 1. Percentage composition of the leaf and flower oils

of Agastache rugosa (Fisch. et Mey) 0. Kuntze from Vietnam

Compounda Leaf Flower

a-pinene t
1-octen-3-01 t t
3-octanone t 0.1
3-octanol t t
p-cymene t 0.1

1&cineole t 0.2
limonene 0.7 0.9
linalool t 0.4
1-octen-3-yl acetate 0.1 t
camphor t t

menthone 0.2 1.7

isomenthone 0.1 0.8
rosefuran epoxide t t
menthol 0.4 5.5
methyl chavicol 92.0 75.9

Carvone 0.4 2.2

piperitone t
menthyl acetate t 0.6
dihydrocawyl acetate t 0.5
B-bourbonene t 0.2

j3-caryophyllene t 0.5
a-humulene t 2.4
ycadinene t t
2-methoxycinnamaldehyde 0.6 0.6
(2)-nerolidol t 0.6

carophyllene oxide 0.2

ij-cadinol 0.3
a-cadinol 0.3
other compounds 4.7 5.7

a compounds are listed in the order of elution

t = trace (~0.1%)

60°C (3min), then 5'C/min to 250°C (30 min). Other conditions were the same as described
under GC.

Component Identifwation-The constituents of the oil were identified by matching their 70 eV

mass spectra and Kovats indices with reference libraries (22-27).Co-elution GC with reference
compounds was used for confirmation of some of the compound identifications.

RESULTS AND DISCUSSION:The chemical composition of the leaf and flower oils from
A. rugosa is presented in Table I. From the more than 40 leaf and floweroil constituentsseparated
by GC, 30 components have been identified by G m S , representing about 95% of the oils.The
marked fragrance and aroma of these oils is due to the high content of oxygenated compounds, of
which methyl chavicol is the major one (92.0% and 75.9% in the leafand flower oils,respectively).
These results show that A. mgosa species from Vietnam may be used as a promising source of
methyl chavicol for use in the cosmetics and perfumery industry.
138 JOURNAL OF ESSENTIAL OIL RESEARCH

REFERENCES

1. DB Tgt h i , Medicinal Plants and Prescriptionsfrom Vietnam. Science and Technology Publisher, Hanoi,
Vietnam (1988).
2. 0.I. Zakharova,A. M. Zakharov and V. I. Glyzin, F l a d of Agastacherugosa. Khim. Prir. Soedin.,(5),642-
646 (1979).
3. H. Itokawa, K. Suto and K. Takeya, Structures of isoagastacho& and agastachin, new glucosylflaoones
isolated f m Agastache rugosa. Chem. Pharm. Bull., 29,1777-1779 (1981).
4. Z. M. Zou and P. Z. Cong, Chemicalwnstituentsfimn the roots of Agastacherugosa. Yaowe Zuebao, 26,906-
910 (1991).
5. D. S. Han, Triterpenmfrom the root of Agastache rugosa. Saengyak Hakhoechi, 18,50-53 (1987).
6. D. S. Han and S. J. Byon, Triterpmesf m the root of Agastache rugosa (11).Saengyak Hakhoechi, 19,97-98
(1988).
7. D. S. Han, Y. C. Kim, S. E. Kim, H. S. Ju and S. J. Byon, Studies on the diterpene constituent of the root of
Agastache rugosa 0. Kuntze. Saengyak Hakhoechi, 18,99-102 (1987).
8. H. K. Lee, S. J. Byon, S. E. Oh, J. I. Kim, Y. H. Kim and C. 0. Lee, Dterpenoids from the roots of Agastache
rugosa and their cytotmic actimtias. Saengyak Hakhoechi, 25,319-327 (1994).
9. J. E. Vogelmann, Fkzvanoids of Agastache section Agastache. Biochem. Syst. Ecol., 12,363-366’(1984).
10. A. M. Zakharov, V. S. Dolya, 0. I. Zakhamw, A. S. Bespalow and N. V. Litxinova, Essential and glyceridic oil
ofAg&ache rugosa. Khim. Prir. Soedin., (3),448-450 (1988).
11. B. Ahn and C. B. Yang. Chemkalmposition of bangha (Agastacherugosa 0.Kuntze) herb. Han’guk Slkp’um
Kwahakhoechi, 23,375-378 (1991).
12. T. Okuda, T. Hatano, I. Agata and S. Nishibe, The components of tannic activities in Labiatae plants. I.
Rosmarinic a c i d f m Labiataeplants in Japan. Yakugaku Zasshi, 106,1108-1111(1986).
13. S. Fujita and Y. Fujita, Essential oils of the plantsfi-oomvarious territories.XXXIII. Essential oil of Agastache
rugosa. 6. Yakugaku Zasshi, 93,1679-1681 (1973).
14. S. Fujita and Y. Fujita, Essential dls of the plantsfi-oomvarious territories.XXXIII. Essential oil of Agastache
rugosa. 6. Osaka Kogyo Gijutsu Shikensho Kiho, 25,221-223 (1974).
15. S. Fujita and Y. Fujita, Miscellaneous contributionsto the essential oils ofplantsf m v a r i o u s territories.XXIX,
Essential oil of Agastache rugosa. 5. Yakugaku Zasshi, 92,908-909 (1972).
16. S. Fujita and Y. Fujita, Essential oils ofthe plantsf m various territories. XXXIX.Comparativebiochemistry
of the essential oil of Mosla methylchavicol$era. Yakugaku Zasshi, 95,475-477 (1975).
17. S.H.Shm,H.K.KimandH. J.Chi,Pl;oductionofgianthyssopoililplanttissueclllture. SaengyakHakhoechi,
22,91-94 (1991).
18. P. Weyerstahl, H. Marschall and E. Manteuffel, Volatile constituentsof Agastache rugosa. J. Essent. Oil Res.,
4,585-587 (1992).
19. B. Ahn and C.B. Yang, Volatileflavw mponents of bangha (Agmtache mgosa 0. Kuntze) herb. Han’guk
S w u m Kwahakhmchi, 23,582-586 (1991).
20. D. J. Charles,J. E. Simon and M. P. Widrlechner, Characterization of the essential oil of Agastache species.
J. Agric. Food Chem., 39,1946-1949 (1991).
21 L. A. Wilson, N. P. Senechal and M. P. Widrlechner, Headspace analysis of the volatile oils of Agastache.
I

J. Agric. Food Chem., 40,1362-1366 (1992).

22 Y. Masada,AnolysisofEssentialOilsby Gar ChromatographyandMmsSpectrometry.Wdey, NewYork(l967)
23. P. SandraandC.Bicchi,CapiUa?lGasChranatographyinEssentialOilAnalysis. Hiithig,Heidelberg,Germany
(1987).
24. L. M. Libbey,AParaa!uxdatabmefwGC/MSdataoncomponentsofessential&andotherwlat~. J. Essent.
Oil Res., 3,193-194 (1991).
25. D. Henneberg, B. Weimann and W. Joppek, Libmy Search System MASS-LIB, version 5.3, Max-Planck-
Institut fiir Kohlenforschung, Miilheim a.d. Ruhr, Germany (1989).Using this software,the following
databasesweresearched:
(a) F. W. McLafferty, Wiley/NBS Registry ofMass Spectral Data. 4th ed., Wiley, New York (1988);
(b)D. Henneberg, B. Weimann and W. Joppek, MPI Library ofMass Spectral Data. Max-Planck-
Institut fiir Kohlenforschung, Mulheim a.d. Ruhr, Germany (1980);
(c) M. C. ten Noever de Brauw, J. Bouwman, A. C. Tas and G. F. L a Vos, Compilatiofi ofMass
Spectra of Vokde Compoundr in Food. TNO-CIVOInstitutes, Zeist, The Netherlands (1988).
26. F. W. McLafferty and D. B. Stauffer, Mass spectrometry library search system BenchTop/PBM, version
3.0. Palisade Co., Newfield, New York (1993).Using BenchTopPBM, the following database was searched:
F. W. McLafferty and D. B. Stauffer, The Wiley/NBS Registy of Mass Spectral Data. 5th ed., Waey
and Sons, New York (1991).
27. National Institute of Standards and Technology,PC Version of the NIH/EPA/NIH Mass Spectral Database,
Version 4.5. US. Department of Commerce, Gaithersburg, MD, USA (1994).