Cytotoxic vobasine, tacaman, and corynanthe-tryptamine bisindole alkaloids from Tabernaemontana and structure revision of tronoharine

Journal of Natural Products

Volumn 77, Issue 11, 2014, Pages 2504-2512

  Sim, Dawn Su Yin ^a   Chong, Kam Weng ^a   Nge, Choy Eng ^a   Low, Yun Yee ^a   Sim, Kae Shin ^b   Kam, Toh Seok ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

[No Author keywords available]

Indexed keywords

16 EPIVOBASENAL; 16 EPIVOBASINE; AIPINISINE; CYTOTOXIC AGENT; DREAGAMINE; INDOLE ALKALOID; TABERNAEMONTANINE; TACAMAN; TACAMINE; TACAMONINE; TRONOHARINE; UNCLASSIFIED DRUG; VINCRISTINE; VOBASENAL; VOBASIDINE A; VOBASIDINE B; VOBASIDINE C; VOBASIDINE D; VOBASINE; ANTINEOPLASTIC AGENT; CORYNANTHE; INDOLE DERIVATIVE; TRYPTAMINE; TRYPTAMINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DENSITY FUNCTIONAL THEORY; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HUMAN; HUMAN CELL; IN VITRO STUDY; KB CELL LINE; MOUTH SQUAMOUS CELL CARCINOMA; PROTON NUCLEAR MAGNETIC RESONANCE; TABERNAEMONTANA; X RAY DIFFRACTION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG SCREENING; ISOLATION AND PURIFICATION; MALAYSIA; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

CORYNANTHE; TABERNAEMONTANA;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLE ALKALOIDS; INDOLES; MALAYSIA; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANTS, MEDICINAL; TABERNAEMONTANA; TRYPTAMINES;

EID: 84913534503     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np500589u     Document Type: Article

References (24)

1. Leeuwenberg, A. J. M. Tabernaemontana: The Old World Species; Royal Botanic Gardens: Kew, U.K., 1991.
2. Van Beek, T. A.; Verpoorte, R.; Svendsen, A. B.; Leeuwenberg, A. J. M.; Bisset, N. G. J. Ethnopharmacol. 1984, 10, 1-156
3. Danieli, B.; Palmisano, G. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1986; Vol. 27, pp 1-130.
4. Kam, T. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Amsterdam, 1999; Vol. 14, pp 285-435.
5. Kam, T. S.; Choo, Y. M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: Amsterdam, 2006; Vol. 63, pp 181-337.
6. Nge, C. E.; Gan, C. Y.; Low, Y. Y.; Thomas, N. F.; Kam, T. S. Org. Lett. 2013, 15, 4774-4777
7. Lim, K. H.; Etoh, T.; Hayashi, M.; Komiyama, K.; Kam, T. S. Tetrahedron Lett. 2009, 50, 752-754
8. Kam, T. S.; Pang, H. Y.; Choo, Y. M.; Komiyama, K. Chem. Biodiversity 2004, 1, 646-656
9. Kam, T. S.; Pang, P. H.; Lim, T. M. Org. Biomol. Chem. 2003, 1, 1292-1297
10. Kam, T. S.; Sim, K. M.; Lim, T. M. Tetrahedron Lett. 2001, 42, 4721-4723
11. Kam, T. S.; Sim, K. M.; Lim, T. M. Tetrahedron Lett. 2000, 41, 2733-2736
12. Kam, T. S.; Sim, K. M.; Lim, T. M. Tetrahedron Lett. 1999, 40, 5409-5412
13. Sangster, A. W.; Stuart, K. L. Chem. Rev. 1965, 65, 69-130
14. Ahond, A.; Bui, A. M.; Potier, P.; Hagaman, E. W.; Wenkert, E. J. Org. Chem. 1976, 41, 1878-1879
15. Van Beek, T. A.; Lankhorst, P. P.; Verpoorte, R.; Baerheim Svendsen, A. Tetrahedron Lett. 1982, 23, 4827-4830
16. Van Beek, T. A.; Verpoorte, R.; Baerheim Svendsen, A. Tetrahedron 1984, 40, 737-748
17. Lim, K. H.; Sim, K. M.; Tan, G. H.; Kam, T. S. Phytochemistry 2009, 70, 1182-1186
18. Azoug, M.; Loukaci, A.; Richard, B.; Nuzillard, J. M.; Moreti, C.; Zeches-Hanrot, M.; Le Men-Olivier, L. Phytochemistry 1995, 39, 1223-1228
19. Angenot, L. Plant Med. Phytother. 1978, 12, 123-129
20. Lerchner, A.; Carreira, E. M. J. Am. Chem. Soc. 2002, 124, 14826-14827
21. Wenkert, E.; Bindra, J. S.; Chang, C. J.; Cochran, D. W.; Schell, F. M. Acc. Chem. Res. 1974, 7, 46-51
22. Brown, R. T. In Indoles: The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; Wiley-Interscience: New York, 1983; Part 4, pp 85-93.
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, M. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision C.01; Gaussian Inc.: Wallingford, CT, 2010.
24. Lim, S. H.; Low, Y. Y.; Sinniah, S. K.; Yong, K. T.; Sim, K. S.; Kam, T. S. Phytochemistry 2014, 98, 204-215