Sains Malaysiana 46(9)(2017): 1581–1586

http://dx.doi.org/10.17576/jsm-2017-4609-29

 

A New Cyclopentylidene and Other Chemical Constituents from Malaysian Crotalaria pallida

(Siklopentilidena Baru dan Juzuk Kimia Lain daripada Crotalaria pallida Malaysia)

 

 

SITI RABEAH FADZIL, ANN-CHEE YAP & YEUN-MUN CHOO*

Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Federal Territory

Malaysia

Received: 9 January 2017/Accepted: 18 March 2017

 

ABSTRACT

Crotalaria pallida Aiton is an herbaceous legume from the family Fabaceae. In the present study, one new cyclopentyliene, crotolidene (1) and seven known compounds, i.e. hydroxydihydrobovolide (2), octacosane (3), trans-phytyl palmitate (4), linoleic acid (5), methyl oleate (6), ethyl palmitate (7), and palmitic acid (8) were isolated from the C. pallida collected from Perak, Malaysia. These compounds were isolated and characterized using extensive chromatographic and spectroscopic methods.

 

Keywords: Crotalaria pallida; crotolidene; cyclopentylidene; spectroscopic analysis; (3E,5Z)-5-(4-hydroxy-2,2-dimethylcyclopentylidene)hex-3-en-2-one

 

ABSTRAK

Crotalaria pallida Aiton merupakan legum herba daripada famili Fabaceae. Satu siklopentilidena baru, crotolidine (1) dan tujuh sebatian lain, iaitu hidroksidihidrobovolide (2), octacosana (3), trans-phytil palmitat (4), asid linoleik (5), metil oleat (6), etil palmitat (7) dan asid palmitik (8) telah diasingkan daripada C. pallida dari Perak, Malaysia. Sebatian ini diasing dan dicirikan menggunakan kaedah kromatografi dan spektroskopi.

 

Kata kunci: Analisis spektroskopi; Crotalaria pallida; crotolidene; siklopentilidena; (3E,5Z)-5-(4-hidroksi-2,2-dimetilsiklopentilidene)heks-3-en-2-on

REFERENCES

Abdullah, A.S. 1990. Poisonous Plants of Malaysia. Kuala Lumpur: Tropical Press.

Asand, M., Urixm, A.H. & Ahmad, V.U. 1991. Diterpene fatty acid ester from Leucas nutans. J. Nat Prod. 54(5): 1444-1446.

Chong, K.Y., Tan, H.T.W. & Corlett, R.T. 2009. A Checklist of the Total Vascular Plant Flora of Singapore: Native, Naturalised and Cultivated Species. Singapore: Raffles Museum of Biodiversity Research, National University of Singapore.

Farida Hanum, I. & Vander Maesen, L.J.G. 1997. Plant Resources of South-East Asia No.11. Auxiliary Plants. Leiden: Backhuys Publisher.

Farnsworth, N.R., Wagner, H., Hoerhammer, L., Hoerhammer, H.P. & Fong, H.H.S. 1968. Euphorbia esula. I. Preliminary phytochemical and biological evaluation. J. Pharm. Sc. 57(6): 933-939.

Gunstone, F.D. 2007. 13C-NMR Spectroscopy of Fatty Acids and Derivatives. The AOCS Lipid Library. http://lipidlibrary.aocs. org/nmr/nmrmono/index.html.

Gunstone, F.D. & Jacobsberg, F.R. 1972. Fatty acids, part 36 the synthesis, silver ion chromatographic, and NMR spectroscopic properties of the nine 9,12-diunsaturated n-C18 acids. Chem. Phy. Lipids. 9(2): 112-122.

Joshi, H., Joshi, A.B., Sati, H., Gururaja, M.P., Shetty, P.R., Subrahmanyam, E.V.S. & Satyanaryana, D. 2009. Fatty acids from Memecylon umbellatum (Burm.). Asian J. Research Chem. 2(2): 178-180.

Koshino, H., Yoshihara, T., Sakamura, S., Shimanuki, T., Sato, T. & Tajimi, A. 1989. Novel C-ll epoxy fatty acid from stromata of epichloe typhina on phleum pretense. Agric. Biol. Chem. 53(9): 2527-2528.

Lawrie, W., McLean, J. & Younes, M.E.G. 1968. Constituents of the seeds of Heracleum sphondylium. Phytochemistry 7(11): 2065-2066.

Miranda-Vilela, A.L. & Grisolia, C.K. 2009. Characterization of the major nutritional components of Caryocar brasiliense fruit pulp by NMR spectroscopy. Quim. Nova. 32(9): 2310- 2313.

Rajkumar, S. & Jebanesan, A. 2004. Mosquitocidal activities of octacosane from Moschosma polystachyum Linn. (lamiaceae). J. Ethnopharmacology 90: 87-89.

Rakoff, H., Weisleder, D. & Emken, E.A. 1979. 13C-Nuclear magnetic resonance of mono- and dihydroxy saturated and unsaturated fatty methyl esters. Lipids 14(1): 81-83.

Sigma-Aldrich. 1H NMR of Octacosane. 17 March 2017. Retrived from http://www.sigmaaldrich.com/catalog/product/aldrich/ o504?lang=en&region=MY

Speight, R.J., Rourke, J.P., Wong, A., Barrow, N.S., Ellis, P.R., Bishop, P.T. & Smith, M.E. 2011. 1H and 13C solution- and solid-state NMR investigation into wax products from the Fischer-Tropsch process. Solid State Nuclear Magnetic Resonance 39: 58-64.

Williams, M.C. & Molyneux, R.J. 1987. Occurrence, concentration, and toxicity of pyrrolizidine alkaloids in crotalaria seeds. Weed Science 35(4): 476-481.

Wu, J., Tsujimori, M., Hirai, H. & Kawagishi, H. 2011. Novel compounds from the mycelia and fruiting bodies of Climacodon septentrionalis. Biosci. Biotechnol., Biochem. 75(4): 783-785.

Yuan, W., Cheng, A., Fu, W., Zhao, M., Li, X., Cai, Y., Dong, J., Huang, K., Gustafson, K.R. & Yan, P. 2016. Structurally diverse metabolites from the soft coral Sinularia verruca collected in the South China Sea. J. Nat Prod. 79(4): 1124- 1131.

 

 

*Corresponding author; email: ymchoo@um.edu.my