Characterization of Chemical Constituents of Luffa operculata(Cucurbitaceae)


A mixture of new ceramides (1, 2, 3, 4 and 5) together with a binary mixture of ceramides with long chain alkyl (6 and 7), triterpenoid (10) and steroids (11 and 12) have been isolated from bark of the fruits and of the stems of Luffa operculata (Cucurbitaceae). The structures were elucidated by comprehensive spectro- scopic analysis including 1H and 13C NMR, DEPT (distortionless enhancement by polarization transfer), COSY (correlated spectroscopy), HMQC (heteronuclear multiple quantum coherence), HMBC (heteronu- clear multiple bond connectivity), IR (infrared), HR-ESI-MS (electrospray ionization-high resolution mass spectra) and LR-MS (low resolution electron ionization mass spectra) experiments. All the ceramides are reported for the first time in Cucurbitaceae and this is the first report of the rare triterpene 10 isolated from Luffa operculata. The ceramides 6 and 7 showed a high acetylcholine esterase inhibitory effect.

Share and Cite:

C. Feitosa, R. Silva, R. Braz-Filho, J. Menezes, S. Siqueira and F. Monte, "Characterization of Chemical Constituents of Luffa operculata(Cucurbitaceae)," American Journal of Analytical Chemistry, Vol. 2 No. 8, 2011, pp. 989-995. doi: 10.4236/ajac.2011.28116.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] R. Braga, “Plantas do Nordeste Especialmente do Ceará,” 5th Edition, Funda??o Guimar?es Duque, Mossoró-RN, 2001.
[2] F. J. Q. Monte, S. M. A. Papa, C. R. Sousa and R. Braz-Filho, “Cucurbitacins of Luffa operculata: Isolation and Complete 1H and 13C Chemical Shifts Assignment,” Revista Latinoamericana de Química, Vol. 31, No. 3, 2003, pp. 89-99.
[3] M. H. Oueslati, Z. Mighri, H. B. Jannet and P. M. Abreu, “New Ceramides from Rantherium suaveolens,” Lipids, Vol. 40, No. 10, 2005, pp. 1075-1079. doi:10.1007/s11745-005-1472-3
[4] Viegas Junior, V. S. Bolzani and M. Furian, “Produtos Naturais Como Canditatos a Fármacos úteis no Trata- mento do Mal de Alzheimer,” Química Nova, Vol. 27, No. 4, 2004, pp. 655-660. doi:10.1590/S0100-40422004000400021
[5] I. K. Rhee, M. V. Meent, K. Ingkaninan and R. Verpoorte, “Screening for Acetylcholinesterase Inhibitors from Amaryllidaceae Using Silica Gel Thin-Layer Chromatogramphy in Combination with Bioactivity Staining,” Journal of Chromatography, Vol. 915, No. 1, 2001, pp. 217-223. doi:10.1016/S0021-9673(01)00624-0
[6] F. Cateni, J. Zilic, G. Falsone, G. Scialino and E. Banfi, “New Cerebrosides from Euphorbia peplis, L.: Antim- icrobial Activity Evaluation,” Bioorganic & Medicinal Chemistry Letters, Vol. 13, No. 24, 2003, pp. 4345-4350. doi:10.1016/j.bmcl.2003.09.044
[7] M. L. Veras, “Estudo Químico e Farmacológico de Acnistus arborescens L. Schlecht e Physalis angulata L.,” Thesis, Programa de Química, DQOI, Universidade Federal do Ceará, Fortaleza, 2006.
[8] A. I. V. Maia, M. L. Veras, R. Braz-Filho, N. P. Lopes, E. R. Silveira and O. D. L. Pessoa, “New Ceramides from Acnistus arborescens,” Journal of Brazilian Chemical Society, Vol. 21, No. 5, 2010, pp. 867-871. doi:10.1590/S0103-50532010000500014
[9] F. Ramos, Y. Takaishi, K. Kawazoe, C. Osorio, C. Duque, R. Acu?a, Y. Fujimoto, M. Sato, M. Okamoto, T. Oshi- kawa and S. U. Ahmed, “Immunosuppressive Diace- tylenes, Ceramides and Cerebrosides from Hydrocotyle leucocephala,” Phytochemistry, Vol. 67, No. 11, 2006, pp. 1143-1150. doi:10.1016/j.phytochem.2006.03.004
[10] L. P. Sandjo, P. Hannewald, M. Yemloul, G. Kirsch and B. T. Ngadjui, “ Triumfettamide and Triumfettoside Ic, Two Ceramides and Other Secondary Metabolites from the Stems of Wild Triumfetta cordifolia A. Rich. (Tili- aceae),” Helvetica Chimica Acta, Vol. 91, No. 7, 2008, pp. 1326-1335. doi:10.1002/hlca.200890144
[11] C. F. S. Christophe, F. S. Kouam, S. F. Kouam, M. P. P. Herve, I. K. Simo, B. T. Ngadjui, I. R. Green and K. Krohn, “Benjaminamide: A New Ceramide and Other Com- pounds from the Twigs of Ficus benjamina (Moraceae),” Biochemical Systematics and Ecology, Vol. 36, No. 3, 2008, pp. 238-243. doi:10.1016/j.bse.2007.08.014
[12] F. Khallouki, W. E. Hull and R. W. Owen, “Characterization of a Rare Triterpenoid and Minor Phenolic Compounds in the Root Bark of Anisophyllea dichostyla R. Br.,” Food and Chemical Toxicolgy, Vol. 47, No. 8, 2009, pp. 2007-2012. doi:10.1016/j.fct.2009.05.018
[13] C. Honda, K. Suwa, S. Takeyama and W. Kamisako, “Relative Population of S-Form and F-Form Conformers of Bryonolic Acid and Its Derivates in Equilibrium in CDCl3 Solutions,” Chemical & Pharmaceutical Bulletin, Vol. 50, No. 4, 2002, pp. 467-474. doi:10.1248/cpb.50.467
[14] N. Jahan, W. Ahmed and A. Malik, “New Steroidal Gly- cosides from Mimusops elengi,” Journal of Natural Pro- ducts, Vol. 58, No. 8, 1995, pp. 1244-1247. doi:10.1021/np50122a014
[15] W. Y. Kang and X. J. Xu, “Structure of a New Xanthone from Securidaca inappendicuata,” Chemistry of Natural Compounds, Vol. 44, No. 4, 2008, pp. 432-434. doi:10.1007/s10600-008-9089-9

Copyright © 2023 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.