The steam volatile oil from the aerial parts of Hyptis suaveolens has been examined by combined

GC-MS. Of the 70 components detected, 38 have been identified accounting for approximately 86%

of the oil. ( β Caryophyllene was present to 41% and 1,8-cincole, terpinen-4-o 1, ex-bergamotene, sabinene

and ex -copaene were the other major components. This oil appears to be chemically distinct from the

one reported from H. suaveolens collected in South America

Brophy, Joseph

Din, Laily

Samsudin, Mohd Wahid

Toia, Robert F.

Zakaria, Zuriati

ABSTRAK Minyak pati hasil persulingan wap dari bahagian atas tumbuhan Hyptis suaveolens telah dikafi dengan gabungan KG -SJ. Daripada 70 komponen yang dikesan, 38 komponen yang membentuk kirakira 86% daripada fumlah minyak tersebut telah dicamkan. $-Kariofilena wufud dalam fumlah 41% dan komponen utama yang lain ialah l,8~sineol, terpinen-4-ol, a-bergamotena, sabinena dan &lt;x-kopaena. Kandungan kimia minyak ini berbeza daripada yang dilaporkan untuk minyak H. suaveolens dariAmerika Selatan ABSTRACT The steam volatile oil from the aerial parts of Hyptis suaveolens has been examined by combined GC-MS. Of the 70 components detected, 38 have been identified accounting for approximately 86% of the oil fi-Caryophyllene was present to 41% and l,8&lt;incole t terpinen-4-o 1, a-bergamotene, sabinene and a -copaene were the other major components. This oil appears to be chemically distinct from the one reported from H. suaveolens collected in South America

Laily Bin Din

Zuriati Zakaria

Mohd Wahid Samsudin

Joseph Brophy

Robert F Toia

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Composition of the steam volatile oil from Hyptis suaveolens Poit.

Universiti Putra Malaysia Institutional Repository

Pertanika 11(2), 239-242 (1988)Composition of the Steam Volatile Oil from Hyptissuaveolens PoitLAlLY BIN DIN, ZURIATI ZAKARIA and MOHD WAHID SAMSUDINDepartment ofChemistry, Universiti Kebangsaan Malaysia,43600 UKM BANGI, Malaysia.andJOSEPH BROPHY and ROBERT F. TOIASchool ofChemistry, University ofNew Sou,th WalesP. O. Box 1, Kensington, NSW 2033, Australia.Key words: Hyptis suoveokns; essential oil; (j. caryophyllene.ABSTRAKMinyak pati hasil persulingan wap dari bahagian atas tumbuhan Hyptis suaveolens telah dikajidengan gabungan KG - SJ. Daripada 70 komponen yang dikesan, 38 komponen yang membentuk kira-kira 86% daripada jumlah minyak tersebut teiah dicamkan. (>Kariojilena wujud dalam jumiah 41% da",komponen utama yang lain ialah 1,8-sineol, terpinen-4-o1, ex - bergamotena, sabinena dan ex - kopaena.Kandungan kimia minyak ini berbeza daripada yang dilaporkan untuk minyak H. suaveolens dari AmerikaSelatanABSTRACTThe steam volatile oil from the aerial parts of Hyptis suaveolens has been examined by combinedGC-MS. Of the 70 components detected, 38 have been identified accounting for approximately 86%of the oil. (>Caryophyllene was present to 41% and 1,8-cincole, terpinen-4-o 1, ex-bergamotene, sabineneand ex -copaene were the other major components. This oil appears to be chemically distinct from theone reported from H. suaveolens collected in South America.INTRODUCTIONHyptis suaveolens, Poit (Labiatae) occurs widelythroughout Peninsular Malaysia, especially in thesandy areas resulting from tin-mining operations.Although the plant is commonly regarded as aweed, it fmds extensive use in traditional folkmedicine practices with a variety of effects attri-buted to it (Burkill, 1966). For example, a decoc-tion of leaves is used to stimulate muscle contrac-tion and the crushed leaves are used for fever andheadache. The plant is also reported to be aneffective treatment for catarrh, as a stimulant forthe secretion of milk and useful as a poulticingagent for skin. In addition, the leaves have beenused for food flavouring and as an adulterant forpatchouli oil.H. suaveolens has been the subject of someprevious chemical work. In the past efforts havebeen directed towards the non-volatile compo-nents, and a number of di- and triterpenoids(Manchand et ai, 1973, 1974; Misra et al. 1983)and steroids (Saluja et al. 1981) have been identi-fied. Some work has also appeared on the essen-tial oil from this species, largely on plant materialcollected from South America. However, substan-tial differences in composition have been noted.As part of our continuing interest in thechemotaxonomy of the medicinally importantflora of the Malayan peninsula we present resultsobtained from the examination of the essentialoil extracted from this species.LAlLY BIN DIN, ZURIATI ZAKARIA AND MOHO WAHID SAMSUDINMATERIALS AND METHODSH. suaveolens (Labiateae) was collected from BatuGajah in Perak on the west coast of PeninsularMalaysia. A voucher specimen has been depositedat the Hebrarium in the Department of Botany atUniversiti Kebangsaan Malaysia.A sample of the air dried aerial parts of theplant (500g) was steam distilled in an all·glassDean and Stark apparatus modified to give lowerphase return, to give a mobile pale yellow oil(l.9g, 0.38%, R1 = 1.4895 at 290 C, p =0.9732 at290 C, a= -1.45~.The oil was examined by GC·MS using aShimadzu GC6-AMP gas chromatograph fittedwith an FFAP·coated SCOT column (85m x 0.5mm) coupled to an AEI MS12 mass spectrometerthrough an all glass straight split. Helium was usedas the carrier gas. The gas chromatograph was pro-grammed from 650 to 2300 at 30 per minute withthe m.s. operating at 70 eV and with an ion sourcetemperature of 1700 . Spectra were acquired andprocessed by a V.G. Digispec Display data systemwhich produced standard bar graphs. Identifica-tions were made by g.l.c. analysis with either co-injection with authentic materials or by GC-MSanalysis. Mass spectra were compared directlywith those from authentic materials or frompublished data (Stanhagen et al., 1974; Hellerand Milne, 1978, 1980, 1983).RESULTS AND DISCUSSIONSteam distillation of the aerial portion of H. sua-veolens gave a pale yellow oil with a pungent smell17in 0.38% yield. Analysis of the oil by capillary GCresolved it into 70 components of which 38 wereidentified by GC-MS (Table 1 and Figure 1). Inaddition, one trace component was tentativelyassigned as linalool oxide. One component, 13 -caryophyllene, predominated in the oil, andaccounted for 41.1% of the total. This result wasin contrast to previously published works for theoil of South American grown plants where 1,8-cineol was reported to be the major component(30.4%) in one instance (Luz et al., 1983) andfenchone (42.3%) in another (Flores etal., 1970).In the latter report, published prior to theadvent of capillary GC columns, five componentswere identified (camphene 0.8%, 'Y - terpinene5.1%, (3 - pinene '3.2%, limonene 13.5%, and fen-chone trace) and five other monoterpenes, elevensesquiterpenes and three diterpenes were detectedbut could be not assigned. In the more recent ofthe two reports, 24 components were identifiedaccounting for approximately 78% of the oil, in-cluding 13 . caryophyllene (l0.4%) and 'Y - elemene(13.6%) (Luz et al., 1983). It is also interesting tonote that the earliest report on this oil was fromplant material collected in the Philippines andoccurrence of menthol was noted (Bacon, 1909);this component, however, has not been detectedin any of the more recent investigations.From comparison of the various results, theMalaysian and South American oils seem quitedistinct. Whereas sesqui- and monoterpenes ac-count for 93% of the Malaysian oil, they are onlypresent to approximately 78% in the SouthAmerican variety; the difference being accountedfor by an increase in the percentage of volatile,II"240Fig. 1: Gas CMomatogram of volatile oil from Hyptis suaveolens PoitPERTANIKA VOL. II NO.2, 1988COMPOSITION OF STEAM VOLATILE OIL FROM H. SUAVEOLENS POITTABLE IComposition of the essential oil from H. lUaveolenaPeakNo.l.2.3.4.5.6.7.8.9.10.ll.12.13.14.15.16.17.18.19.20.2l.22.23.24.25.26.27.28.29.30.31.32.33.34.35.Assignmenta- pinenecamphene(3- pinenesabinenemyrcenea- phellandrenea- terpinenelimonene1,8 - cineole'Y- terpinenep- cymeneterpinolenelinalooloxidefenchonea- p - dimethylstyreneoct-1-ene-3-o1C10H180a- cubebenea- copaenebenzaldehyde(3- bourboneneC15H24ClOH180a- cubebeneClOH180fencholterpinen-'k>1a- bergamotene(3- caryophylleneC15H24C15 H24alIoaromadendrene(3- farneseneC15 H24humulene%1.0tr1.64.9tr1.20.60.77.91.21.10.2trtrtr0.5tr0.23.9tr0.5trtr0.1tr0.84.34.641.1trtr0.5trtr2.5PeakNo.36.37.38.39.40.41.42.43.44.45.46.47.48.49.50.51.52.53.54.55.56.57.58.59.60.61.62.63.64.65.66.67.68.69.70.Assignmenta- terpineolC15H24borneolgermacrene DC15H24(3 - selinenea- selinene5- cadinenecada - 1,4 - dieneC15H260calamaneneC15 H260calacoreneC15H240C15 H260C15 H240caryophyllene oxideC15 H260C15 H260C15H260C15H260C15H240C15H260C15H260C20H320C15H260C15 H260C15H260C15H260C15H260C20H32C20H32C20H32C20H32C20H32%tr0.10.10.90.22.01.11.50.1trtrtrtrtr0.10.12.4tr0.10.10.1tr0.5tr0.30.40.50.5trtrtr5.21.70.20.2but unidentified diterpenes. In addition, only atrace amount of fenchone occurs in the Malay-sian grown plant and this is not compensated forin terms of an increase in fenchol. The patternof monoterpenoids also appears different, withsabinene, I,S-cineole, a-copaene and terpinen-4-01 dominating in the Malaysian variety anda-pinene, I,S-cineole, terpinolene and camphorin the latter. It is possible, therefore, that the plantmay occur as distinct chemotypes, as had beennoted for various Australian Melaleuca species.PERTANIKA VOL. II NO.2, 1988 241LAlLY BIN DIN, ZURIATl ZAKARIA AND MOHO WAHID SAMSUDINACKNOWLEDGEMENTSWe thank the Network for the Chemistry ofBiologically Important Natural Products forsupport and Mohd Nor Ibrahim for his assistance.REFERENCESBACON, R.F. (1909): Philippine Terpenes and Essen-tial Oil (III). Philipp. J. Set. (A), 4: 93.BURKILL, I.H. (1966): A Dictionary of the EconomicProducts of the Malay Peninsula, Vol. II, Ministryof Agriculture' and Cooperative, Kuala Lumpur,Malaysia.FLORES, S.E. and J.D. Medina (1970): Note on Compo·sition of oil H. 8UQveo1ens (Labiatae) Acta. Cient.Venez., 21: 161.HELLER, S.R. and G.W.A. Milne (1978, 1980, 1983):EPH/NIH Mass Spectral Data Base, U.S. Govern-ment Printing Office, Washington D.C.LUZ, A.I.R., M.G.B., ZOGHBI, L.S. RAMOS, J.G.S.MAlA, and M.L. Da SILVA (1984): EssentialOils of Some Amazonian Labiatae, 1. GenusHyptis,J. Nat. Prod., 47: 745.MANCHAND, P.S., J.D. WHITE, H. WRIGHT, and J.CLARDY (1973): Chemical Constituents ofTropical Plants. Part IV, J. Amer. Soc., 95:2705.MANCHAND, P.S., J.D. WHITE, J. FAYOS, and J.CLARDY (1974): Structures of Suaveolic Acidand Suaveolol, J. Org. Chern. 39: 2306.MISRA, T.N., R.S. SINGH, and J. UPADHAY (1983):Triterpenoids from H. lUaveolenl roots, Phyta-~hemi,try 22: 2557.SALUJA, A.K., D.O. SANTANI, and J.D. SINGH, (1981): Indian Drugs, !t9: 84.STANHAGEN, E., S. ABRAHAMSON, and F.W. McLaf-ferty, (1974): Registry of Mass Spectral Data,Wiley, New York.(Received 11 November, 1987)242 PERTANlKA VOL. 11 NO.2, 1988

Composition of the Steam Volatile Oil from Hyptis

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Composition of the Steam Volatile Oil from Hyptis suaveolens Poit

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