[en] A secoiridoid aglycone with atypical skeleton, named fagraldehyde (1), together with several known secoiridoids (gentiopicroside (2), sweroside (3) and swertiamarin (4)) were isolated from the bark and leaves of Fagraea fragrans collected in Cambodia. The conformations of 1 were evaluated on the basis of molecular modeling and NOESY correlations. A hypothetical biogenesis of fagraldehyde was proposed to explain the unusual skeleton. Compound 1 was weakly active in vitro against Plasmodium falciparum.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Jonville, Marie ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Capel, Marie; ULg - Université de Liège
Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Angenot, Luc ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Dive, Georges ; Université de Liège - ULiège > Centre d'ingénierie des protéines
Faure, Robert; Université Paul Cézanne
Azas, Nadine; Université de la Méditerranée > Pharmacie > Parasitologie
Ollivier, Evelyne; Université de la Méditerranée > Pharmacie > Pharmacognosie
Language :
English
Title :
Fagraldehyde, a Secoiridoid Isolated from Fagraea fragrans
Publication date :
November 2008
Journal title :
Journal of Natural Products
ISSN :
0163-3864
eISSN :
1520-6025
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Douk, P. Contribution à l'Etude des Plantes Médicinales du Cambodge. Ph.D. Thesis, Paris, 1966; p 264.
Krishnan, M. K. S. The Useful Plants of India; Publication and Information Directorate: New Delhi, 1992; p 918.
Pételot,A. Les Plantes Médicinales du Cambodge, du Laos et du Vietnam; I.D.E.O.: Saigon, 1952; p 1346.
Perry, L. M. Medicinal Plants of East and Southeast Asia; MIT Press: Cambridge, 1980; p 620.
Hout, S.; Chea, A.; Bun, S. S.; Elias, R.; Gasquet, M.; Timon-David, P.; Balansard, G.; Azas, N. J. Ethnopharmacol. 2006, 107, 12-18.
Wan, A. S. C.; Chow, Y. L. J. Pharm. Pharmacol. 1964, 16, 484-486.
Natarajan, P. N.; Wan, A. S. C.; Zaman, V. Planta Med. 1974, 25, 258-260.
Jensen, S. R.; Schripsema, J. Chemotaxonomy and Pharmacology of Gentianaceae. In Gentianaceae: Systematics and Natural History; Struwe, L., Albert, V. A., Eds.; Cambridge University Press: Cambridge, 2002; pp 573-631.
Boros, C. A.; Stermitz, F. R. J. Nat. Prod. 1991, 54, 1173-1246.
Van der Sluis, W. G.; van der Nat, J. M.; Spek, A. L.; Ikeshiro, Y.; Labadie, R. P. Planta Med. 1983, 49, 211-215.
Ishiguro, K.; Yamaki, M.; Takagi, S. Planta Med. 1983, 49, 208-210.
Msonthi, J. D.; Galeffi, C.; Nicoletti, M.; Messana, I.; Marini-Bettolo, G. B. Phytochemistry 1985, 24, 771-772.
Dive, G.; Dehareng, D.; Ghuysen, J. M. Theor. Chim. Acta 1993, 85, 409-421.
Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
Jensen, S. R.; Franzyk, H.; Wallander, E. Phytochemistry 2002, 60, 213-231.
Sampaio-Santos, M. I.; Kaplan, M. A. C. J. Braz. Chem. Soc. 2001, 12, 144-153.
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H. ; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; CioslowskiJ.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
Frédérich, M.; Jacquier, M. J.; Thepenier, P.; De Mol, P.; Tits, M.; Philippe, G.; Delaude, C.; Angenot, L.; Zeches-Hanrot, M. J. Nat. Prod. 2002, 65, 1381-1386.
Kenmogne, M.; Prost, E.; Harakat, D.; Jacquier, M. J.; Frédérich, M.; Sondengam, L. B.; Zeches, M.; Waffo-Teguo, P. Phytochemistry 2006, 67, 433-438.