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Unexpected Irregular Monoterpene “Yomogi Alcohol” in the Volatiles of the Lathyrus L

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Unexpected Irregular Monoterpene “Yomogi Alcohol” in the Volatiles of the Lathyrus L Journal of Oleo Science Copyright ©2016 by Japan Oil Chemists’ Society doi : 10.5650/jos.ess15165 J. Oleo Sci. 65, (3) 241-249 (2016) Unexpected Irregular Monoterpene “Yomogi Alcohol” in the Volatiles of the Lathyrus L. species (Leguminosae) of Cyprus Kaan Polatoğlu1＊ , Seniha Arsal2, Betül Demirci3 and Kemal Hüsnü Can Başer3, 4 1 İstanbul Kemerburgaz University, Faculty of Pharmacy, Department of Analytical Chemistry, 34217 İstanbul, TURKEY 2 Near East University, Faculty of Pharmacy, Department of Analytical Chemistry, 10 Mersin/Nicosia, TURKEY 3 Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, 26470 Eskişehir, TURKEY 4 King Saud University, College of Science, Department of Botany and Microbiology, Riyadh, SAUDI ARABIA Abstract: Lathyrus species including L. ochrus and L. sativus are known for their food, feed and horticultural uses. Despite their widespread uses and cultivation, there is limited information on their chemistry. Previously, only the essential oil composition of L. rotundifolius, L. vernus and volatiles of L. odoratus have been reported. In the present research, volatiles of seven Lathyrus L. species, namely, L. aphaca, L. ochrus, L. cicera, L. sativus, L. gorgonei, L. saxatilis and L. blepharicarpos var. cyprius were analyzed by SPME GC-MS for the first time. Plant materials were collected from five different locations in Cyprus (February-March 2012). The main components of L. aphaca volatiles from four locations were yomogi alcohol 26.1-16.5%, camphor 21.6-10.1%, tetradecane 14.3-0%; L. cicera from five locations were yomogi alcohol 20.3-3.0%, camphor 18.7-2.0%; L. gorgonei from two locations were yomogi alcohol 24.5- 13.1%, camphor 17.1-9.0% and L. sativus was yomogi alcohol 11.4%, camphor 9.0%. Yomogi alcohol was not present as the major compound in L. ochrus (2-methyl butanoic acid 7.2%), L. saxatilis (hexanal 7.7%) and L. blepharicarpos var. cyprius ((Z)-3-hexenal 8.6%) volatiles. The volatiles of the Lathyrus species were also compared with each other quantitative and qualitatively using AHC analysis to find out differences among the species. The irregular monoterpene yomogi alcohol is reported from the Lathyrus and the Leguminosae family for the first time. The existence of yomogi alcohol in Lathyrus volatiles points out that the irregular monoterpenes are not restricted solely to Asteraceae family. Key words: Leguminosae, Lathyrus, volatiles, yomogi alcohol, SPME, chemotypes 1 Introduction L. ochrus L.（Aerial parts oil phytol 49.39％ and hexadeca- Lathyrus L. species of Fabaceae are well known with noic acid 20.64％）and volatile composition of three differ- their food, livestock feed and horticultural uses as well as ent cultivars of L. odoratus（（ E）-β-ocimene 46.5-22.9％, for the notorious“ Lathyrism” illness caused by the over linalool 26.2-16.6％, nerol 10.1-3.3％,（ Z）-β-ocimene 7.3- consumption of the Lathyrus species that contains the 2.3％, geraniol 6.5-4.5％）3－6）. Non-volatile secondary me- special amino acid of this genus“ oxally di amino propionic tabolites reported from Lathyrus species include new fla- acid”1）. This genus is represented with nine species in vonoids, flavonols, chalcones, pterocarpans, saponins as Cyprus. Lathyrus ochrus（L.）DC.（Luvana）and L. sativus well as known sterols7－14）. Additionally new primary me- L. are cultivated for edible and livestock feed uses2）. Previ- tabolites were also reported from Lathyrus species that ously there are only a couple of investigations on the vola- include amino acids α-N-oxalyl-L-α, β-diaminopropionic tiles or essential oil composition of the Lathyrus species. acid（α-ODAP）, β-N-oxalyl-L-α, β-diaminopropionic acid These include essential oil composition of L. rotundifolius （β-ODAP）and carbohydrate L-bornesitol15, 16）. Willd.（Germacrene D 50.4％; germacrene B 18.7％; Previously, very little information related to the volatile γ-elemene 9.5％）, L. vernus L.（Flower and stem oils re- composition of the Lathyrus species existed in the litera- spectively palmitic acid 34.2 - 35.3％, 1-octen-3-ol 49.8％）, ture and no report was present on L. ochrus and L. ＊Correspondence to: Dr. Kaan POLATOĞLU, İstanbul Kemerburgaz University, Faculty of Pharmacy, Department of Analytical Chemistry, 34217 İstanbul, TURKEY E-mail: [email protected] / [email protected] Accepted December 16, 2015 (received for review July 10, 2015) Journal of Oleo Science ISSN 1345-8957 print / ISSN 1347-3352 online http://www.jstage.jst.go.jp/browse/jos/ http://mc.manusriptcentral.com/jjocs 241 K. Polatoğlu, S. Arsal and B. Demirci et al. sativus cultivated as food products. Prior to this study we ferent locations（Yeniceköy, Kalavaç, Kaleburnu, Haspolat, have investigated essential oil composition of L. ochrus Güzelyurt）in Cyprus. Voucher specimens have been depos- which we have reported to have the main components of ited at the Herbarium in the Near East University, Cyprus. the oil as diterpenes and alkanes. However to our surprise Plant materials were identified by Dr. Kaan Polatoglu and we have not identified any monoterpene and sesquiterpene Dr. Salih Gucel. The collection dates and locations of the type compounds5）. Previous reports indicated that essential plant materials used in the research and their voucher oils of other Lathyrus species contained monoterpenes specimen numbers were given in Table 1. and sesquiterpenes. In our present study, we attempted to identify the volatile composition of the Lathyrus species of 2.2 Isolation of the Volatiles Cyprus as a part of our phytochemical composition and bio- Aerial parts of the fresh plant material（0.5 g）were logical activity screening of this genus. Here, we report on placed in a 10 mL vial and sealed with parafilm. Headspace the volatile composition of seven species including L. solid phase micro extraction（Headspace SPME）was used aphaca L., L. ochrus（L.）DC., L. cicera L., L. sativus L., L. for the isolation of the volatiles. A manual SPME injector gorgonei Parl., L. saxatilis（Vent.）Vis. and L. blephari- （Supelco, Ballafonte, PA, USA）that have a fibre coated carpos Boiss. var. cyprius Meikle. Volatiles of these with a layer of polydimethylsiloxane/divinylbenzene（65 µm species were obtained by solid phase micro extraction - PDMS/DVB-blue）was used for the adsorption of the vola- method and analysed by gas chromatography – mass spec- tiles. Prior to the analysis of adsorbed volatiles on the fiber trometry. Comparison of the volatile composition of the in- a blank run was initiated with the fiber to make sure it does vestigated Lathyrus species was performed using agglom- not contain any contamination. After the blank run the erative hierarchical cluster analysis in order to provide fiber was inserted into the vial through the parafilm and similarity/dissimilarity of the volatile secondary metabolite exposed to the plant volatiles for 15 min at 50℃. The profiles of the mentioned species. To the best of our SPME injector than inserted immediately to the injection knowledge, their chemical compositions are reported for port manually for desorption of the plant volatiles for GC/ the first time. MS analysis. 2.3 Analysis of the Volatiles The volatiles were analyzed by GC-MS using a Hewlett 2 Materials and Methods Packard GCD system. An HP-Innowax FSC column（60 m× 2.1 Plant Materials 0.25 mm, 0.25 µm film thickness）and helium as carrier gas Plant materials were collected during the flowering （0.8 mL/min）. The oven temperature was programmed to period between 11 February – 13 April 2012 from five dif- 60℃ for 10 min and raised to 220℃ at a rate of 4℃/min. Table 1 Collection locations and voucher specimen numbers of the plant materials used in the research. Plant Species Collection Location Collection Date Altitude Herbarium No. Lathyrus aphaca Yeniceköy 11.02.2012 79 m 6795 Kalavaç 19.02.2012 179 m 6798 Karpaz – Kaleburnu Köyü Location I 17.03.2012 24 m 6810 Karpaz – Kaleburnu Köyü Location II 17.03.2012 81 m 6814 Lathyrus blepharicarpus var. cyprius Karpaz – Kaleburnu Köyü Location I 09.03.2012 24 m 6808 Lathyrus cicera Haspolat – Location I 25.02.2012 267 m 6800 Haspolat – Location II 04.03.2012 267 m 6802 Kalavaç 04.03.2012 179 m 6804 Karpaz – Kaleburnu Köyü Location I 09.03.2012 24 m 6807 Karpaz – Kaleburnu Köyü Location II 17.03.2012 81 m 6811 Lathyrus gorgonei Haspolat – Location I 25.02.2012 267 m 6799 Karpaz – Kaleburnu Köyü Location I 09.03.2012 24 m 6806 Karpaz – Kaleburnu Köyü Location I 17.03.2012 24 m 6809 Lathyrus ochrus Güzelyurt 18.03.2012 － 6772 Lathyrus sativus Karpaz – Kaleburnu Köyü Location II 13.04.2012 81 m 6817 Lathyrus saxatalis Karpaz – Kaleburnu Köyü Location II 17.03.2012 81 m 6813 242 J. Oleo Sci. 65, (3) 241-249 (2016) Unexpected Irregular Monoterpene “Yomogi Alcohol” in the Volatiles of the Lathyrus L. species (Leguminosae) of Cyprus The temperature kept constant at 220℃ for 10 min and to observe a similar volatile profile as explained by these then raised to 240℃ at a rate of 1℃/min. The injector tem- reports. However high composition of irregular monoter- perature was set at 250℃. Splitless injection mode was pene yomogi alcohol and cyclic monoterpene camphor was employed. Mass spectra were recorded at 70 eV with the present in most of the volatiles. Volatile composition of mass range m/z 35 to 450. The relative percentage of the Lathyrus aphaca from four different locations produced components of the volatiles were calculated from the inte- three different groups that were separated from each other gration of the peaks obtained from GC-MS analysis. The at 0.28 dissimilarity level in AHC analysis. According to the results of the analysis are given in Table 2.
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