Jean-Claude Chalchat a & Jacques Lamy b a Laboratoire de Chimie des Huiles Essentielles, Ecole. Nyons, France Published online: 09 Dec 2011.

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1 This aricle was downloaded by: [Ams/Girona*barri Lib] On: 14 Ocober 2014, A: 01:08 Publisher: Taylor & Francis Informa Ld Regisered in England and Wales Regisered Number: Regisered office: Morimer House, Morimer Sree, London W1T 3JH, UK Journal of Essenial Oil Research Publicaion deails, including insrucions for auhors and subscripion informaion: hp:// Chemical Composiion of he Essenial Oil Isolaed from Wild Canip Nepea caaria L. cv. ciriodora from he Drôme Region of France Jean-Claude Chalcha a & Jacques Lamy b a Laboraoire de Chimie des Huiles Essenielles, Ecole Naionale Supérieure de Chimie e Universié Blaise Pascal de Clermon-Fd, 63177, Aubière Cedex, France b Chambre d'agriculure de la Drôme, Roue de Veneroles, Nyons, France Published online: 09 Dec To cie his aricle: Jean-Claude Chalcha & Jacques Lamy (1997) Chemical Composiion of he Essenial Oil Isolaed from Wild Canip Nepea caaria L. cv. ciriodora from he Drôme Region of France, Journal of Essenial Oil Research, 9:5, , DOI: 180/ To link o his aricle: hp://dx.doi.org/180/ PLEASE SCROLL DOWN FOR ARTICLE Taylor & Francis makes every effor o ensure he accuracy of all he informaion (he Conen ) conained in he publicaions on our plaform. However, Taylor & Francis, our agens, and our licensors make no represenaions or warranies whasoever as o he accuracy, compleeness, or suiabiliy for any purpose of he Conen. Any opinions and views expressed in his publicaion are he opinions and views of he auhors, and are no he views of or endorsed by Taylor & Francis. The accuracy of he Conen should no be relied upon and should be independenly verified wih primary sources of informaion. Taylor and Francis shall no be liable for any losses, acions, claims, proceedings, demands, coss, expenses, damages, and oher liabiliies whasoever or howsoever caused arising direcly or indirecly in connecion wih, in relaion o or arising ou of he use of he Conen.

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3 J. Essen. Oil Rex, 9, (Sep/Oc 1997) RESEARCH REPORT Chemical Composiion of he Essenial Oil Isolaed from Wild Canip Nepea caaria L. cv. ciriodora from he Dr6me Region of France Downloaded by [Ams/Girona*barri Lib] a 01:08 14 Ocober 2014 Inroducion jean-cla~de chalchar Laboraofre de Chfmfe des Hufles Esenielles Ecole Naionale Supdrfeure de Ch fmie e Unfversie Blaise Pascal de Clermon-Fd Aubih Cedex, France Jacques Lamy Chambre d Agrculure de la Dr6me, Roue de Veneroles, Nyons, France Absrac Nepea caaria L. cv. cirfodora growing wild in he Dr6me region of France was brough ino culivaion. Oils produced from culivaed plans harvesed hroughou he growing season were analyzed by GC and GC/MS. Alhough 42 componens were idenifed, he oil composiion did no depend on he ime of harvesing or sorage of he plan maerial prior o disillaion. The oil was found o comprise mainly of cironellol ( %), nerol ( %), geraniol ( %) and geranial( m). The highes oil yield was found o be a he ime of full flowering. Key Word Index Nepea caara L. cv. cirfodora, Labiaae, essenial oil composiion, cironellol, cironellyl aceae, geranial, nerol, geraniol. The genus Nepea is represened by eiher annual or perennial herbs or shrubs mos ofen found in emperae Eurasia and Norh Africa. Though no naive o Norh America, hree species have been found (1): Nepea caaria L., including he garden escape cv. cirfodora, N. grandfflora Bieb. and N. racemosa Lam. (Syn. N. musnil Spreng. ex Henckel). Six oher species (2) are in collecions, in a Souhern Onario experimenal garden [Nepea disans Royle, N. nepeella L., N. nuda L. ssp. nuda (syn. N. pannonica L.) and N. podosachys Benh.], and in an experimenal garden in Norh Carolina (N. nmsa Royle ex Benh. and N. eydea Webb. e Benh.). N. cuam, usually called canip, is naive o Europe and Asia bu is well-acclimaized in Norh America where i occurs in abundance near he Grea Lakes. Is essenial oil (2-7) is characerized by he presence of erpenes and isomers of nepealacone, he mos abundan of which can accoun for 99% of he oal (2-7). An oil from N. caarfa cv. cfriodora (someimes incorrecly named Nepea cfrlodora) Address for correspondence Received: Febnra y 1996 Rded: Sepember 19% /97/ $04.00/ Allured Publishing Cop.

4 Table 1. Chemical composiion of essenial 011 No. Year of hanes Bach Name Downloaded by [Ams/Girona*barri Lib] a 01:08 14 Ocober a-pinene a-thujene a-pinene Sabinene Myrcene Lirnonene 1,&Cineole y-terpinene (E)-P-Ocirnene p-cymene Terpinolene 6-Mehyl-5-hepen-2-one rans-rose oxide cis-rose oxide Phoociral B Phoociral A Perillene Arernisia keone Nerol oxide cis,cis-phoociral Cironella1 rans,rans-phoociral Linalool Linalyl aceae p-caryophyllene Geranyl formae Cironellyl formae a-hurnulene Neral lsoborneol Neryl aceae Piperione Mehyl chavicol Geranial p-menh-3-en-9-01 Cironellol Nerol Geraniol 2-Phenylehyl hexanoae iso-caryophyllene oxide Caryophyllene oxide Hurnulene oxide Correc isomer no given

5 of Nepea caaria cv. ciridom oil Downloaded by [Ams/Girona*barri Lib] a 01:08 14 Ocober OO

6 ~ 530 Downloaded by [Ams/Girona*barri Lib] a 01:08 14 Ocober 2014 Figure 1. Chromaogram of Nepeu cuurfu L. cv. cirlodoru oil Table 11. Physical and chemical consans of essenial oils of Nepera caaria cv. cirriodora Year Bach n dg Table 111. Oil yields obained from Nepea caaria cv. cirriodora harvesed a differen saaes of maurlv. Toal oil Yield Harves Disillaion Mass obained of oil Vegeaive sage Bach dae Dae disilled (kg) (ml) (mukg) Buds Flowers Faded flowers 1 Jul 19, '89 Jul ' Jul 19, '89 Jul " Jul24, '89 Jul Jul28, '89 Jul Aug2,'89 Aug **' Aug 2, '89 Aug Aug16,'89 Aug end of flowering 8 Jun 28, '91 Jun Jul 14, '91 Jul "' Jul 14, '91 Jul **' Jul 14, '91 Aug *** Jull4, '91 Aug 'Very green plans; "Yellow plans; "'Dry disilled baches

7 NEPBTA arm 531 which was analyzed by Regnier (3), was found o comprise mainly of cironellol, geraniol, neral and geranial wih nepealacones making up a mos abou 10% of he mixure. In 1980, Zamureenko (13) found he same componens in oil from he former Sovie Union, bu no nepealacone was deermined. In 1981, Dmiriev e al. deermined he variaions in oil accumulaion and chemical composiion during he growh cycle and sorage of he harvesed canip plans ha hey referred o as N. cuuriu var. cfriodoru Balb. (14). N. cuuriu cv. cirfodoru grows wild in he Dr6me region of France. The resuls of iniial work on wild plans have induced local herb growers o culivae his species and develop pilo-scale indusrial producion of he oil. We repor here he firs analyical resuls obained in 1989 and 1991 of he oil composiion carried ou on culivaed plans ransplaned from he wild. Downloaded by [Ams/Girona*barri Lib] a 01:08 14 Ocober 2014 Experimenal Plan maerid. N. cuuriu cv. ciriodoru was harvesed in July 1989 and 1991 in he Dr6me region when he plans were in full flower. Excep for baches 12, 13, 14 and 15, which were produced from dried plan maerial harvesed on 14 July 1991 and disilled 31 July, 21 and 28 Augus and 3 Sepember, all oher oils were isolaed from fresly harvesed plan maerial. Oil isolaion was performed by seam disillaion (2-lire/h) on a sainless seel experimenal pilo apparaus fied wih wo 10-lire vessels cusom buil a he laboraories of he Chamber of Agriculure a Nyons, France. Pilo ess were carried ou on culivaed plan maerial disilled in a 2000-lire indusrial sill a he farm. Amdyss: Physical and chemical characerisics of he oils such as refracive index, densiy and opical roaion, were deermined by sandard mehods. Analysis by GC was carried ou on a DELSI 121C chromaograph fied wih a 25 m x 0.25 mm CP Wax 52CB capillary column wih emperaure programming from 50 C (5 min) o 220 C a 2"C/min. Injecor and deecor emperaures were se a 240 C and 255 C and he spli raio was 1/60. GC/MS coupling was achieved using a SIGMA 300 chromaograph coupled o an HP 5970 mass specromeer fied wih a 50 m x 0.3 mm CP Wax column which was emperaure programmed from 60"-240 C a 2"C/min. Ionizaion volage was 70 ev. Componens were idenified by comparison of mass specra wih hose repored in he lieraure (191, calculaion of reenion indices and also comparing hem wih our own as well as published daa, and by he co-injecion wih sandard compounds. Resuls and Discussion Fory-five componens were idenified in he oil (Table I, Figure 1). The oil of canip sudied, which was similar o ha described elsewhere (3,14,15-17), was composed mosly of cironellal, neral, geranial, cironellol, nerol and geraniol (85 o 95%). In addiion, small amouns of oher oxygenaed monoerpenes were also idenified. Monoerpenes were also presen, while P-caryophyllene and a-humulene ogeher wih heir oxides were he only sesquierpenes found. This may be explained by he variaion of chemical composiion during he hydrodisillaion (18). I was surprising o us ha no nepealacone were found in he oils produced. As a resul, we believe ha his is a disinguishing feaure of his culivar of N. cuuriu. As can be seen from Table I he chemical composiion of he oil of N. cuuria cv. ciriodoru varies lile during is life cycle (baches 1 o 7). I is apparenly no affeced by drying he plan maerial before disillaion, or by sorage before disillaion (baches 13 o 15). Also, large scale disillaion (baches 16 and 17) yielded an oil similar o ha obained from lab-prepared oils. Given he consisen chemical composiion, i is our belief ha producion could be opimized by choosing he ime of harves ha afforded he highes yield (mid-augus). Yields were much lower if plans were harvesed earlier in he season (July) (baches 8, 11 and 12) (Table 11). The physical and chemical characerisics (refracive index, densiy and opical roaion) of he baches analyzed were remarkably sable and did no vary wih ime of producion (Table 111).

8 532 c W.CHATANDLAMY Downloaded by [Ams/Girona*barri Lib] a 01:08 14 Ocober 2014 The specific chemical composiion of his oil gives i a poenially useful olfacive profile. Is consisen physical and chemical characerisics are no appreciably influenced by producion condiions, which remain o be opimized. These feaures make i a poenial complemen or replacemen for melissa (Melissa off{cnalis> and venreine cironnee (Verbena ciriodora> oils, Aloysiu riphylla (L Heri.) Brion (syn. A. cirlodoru Palau) oils used in perfumery and flavorings. References 1. B. M. Lawrence, Essenial oils, pp 76-79, Allured Publ. Cop, Carol Sream, IL (1981). 2. B. M. Lawrence, Essenial ofls, pp , Allured Publ. Corp., Carol Sream, IL (1992) I. G. Kapelev, Inroducion and culivaion of new species of essenial-ofl-bearingplans. Maslo-Zhir. Prom-s, 8, (1982) F. E. Regnier, E. J. Eisenbraun and G. R. Waller, Nepealacones and Epinepealacone of Nepea caaria L. Phyochemisry, 6, (1967); F. E. Regnier, E. J. EisenbraunandG. R. Waller, Sudiesonbecompion of be essenial ofls of bree Nepea species. Phyochemisry, 6, (1967). D. L. Nelson, Mebylcyclopenanemonoepnes ofnepea caaria andacindfapolygama. PhD hesis, Purdue Universiy (1968). S. D. Sasry, W. R. Springsube and G. R. Waller, Idenflcafon of 5,9-debydmnepealacone, a new monoerpene from Nepea caaria. Phyochemisry, 11, (1972). S. M. McElvain, R. D. Brigh and P. R. Johnson, Consiuens of he volaile oil of canip. I. Nepealic acid, nepealacone and relaed compounds. J. Amer. Chem. Soc., 63, (1941). S. M. McElvain, P. M. Walers and R. D. Brigh, Consiuens of be volaile oil of canip. LI. Tbe neuml componens of Nepealic anbydride. J. Amer. Chem. SOC., 64, (1942). F. Bellesia, R. Grandi, U. M. Pagnoni, A. Pinei and R. Trave, Biosynbesis ofnepealacone in Nepea caaria. Phyochemisry, 23, (1984). A. 0. Tucker and S. S. Tucker, Canip and he Canip Response. Economic Boany,, 42, (1988). K. Sakurai, K. Ikeda and K. Mori, Boh (4aS, 74 7aR)-(+)-Nepealacone and is anipode are powerful amcanls for cals. Agric. Biol. Chem., 52, (1988). A. Velasco-Negueruela, M. Maa Rico, P. Bermejo Benio and M. J. Perez-Alonso, Composicion de los aceies esenciales de nepea nepeellasubsp. amgonensis, Nepea coerulea subsp. coerulea y Nepea caaria. Giom. Bo. Ial., 122, (1988). S. S. Mishurova and Sh. R. Mamedova, Morphological cbaracerisics and essenial oil composiion of Nepea caaria L. Izv. Akad. Nauk Az. SSR, Ser. Biol. Nauk, 3, (1989). V. A. Zamureenko, N. A. Klyuev, M. G. Mumladze, L. B. Dmiriev and I. I. Grandberg, Idenificaion of componens of Nepea caaria varciriodora Bulb. essenial oil. Izv. Timiryazevsk. S-kh. Akad., 5, (1980). L. B. Dmiriev, M. G. Mumladze, G. A. Esvandzhiva, I. I. Grandgerg and I. 2. Yakubashvili, Dynamics of be accumulaion and cornposiion of be essenfal of1 of canip (Nepea caaria war. cirlodora Bulb.) during vegeaion and sorage of raw maerial. Izv. Timiryazevsk. S-kh. Akad., 3, (1981). G. Tiel, H. Wagner and R. Bos, Cbemfcal composiion ofmelissa oil. Plana Med., 46(2), (1982). I. I. Lyashch and S. I. Vasil kevich, Cbaicalcomposifon ofspfceplansandbeirfnf&ons. Vessi Akad. Navuk BSSR, Ser. Biyal. Navuk, 3, (1987). C. Bourrel, F. Perineau, G. Michel and J. M. Bessiere, Canfp (Nepea caaria L.) essenfal oil: Analysis of cbemical consiuens, baceriosaic and fungisakpmperies. J. Essen. Oil Res., 5, (1993). F. W. McIaffery and D. B. Sauffer, Tbe WilqAV3SRegisry ofmass SpecrralDaa. Vol. 1, Wiley and Sons, New York (1988).