Two pyranocoumarins from the seeds of Calophyllum polyanthum

Journal of Natural Products

Volumn 67, Issue 9, 2004, Pages 1598-1600

  Ma, Chun Hui ^a,b   Chen, Bin ^a   Qi, Hua Yi ^a   Li, Bo Gang ^a   Zhang, Guo Lin ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3,4,5 DIHYDROXY 4 METHOXYBENZOIC ACID; 3,5 DIMETHOXYBENZOIC ACID; 5,7,3',4' TETRAHYDROXYISOFLAVONE; ALCOHOL; CALANOLIDE E2; CALOPHYLLUM POLYANTHUM EXTRACT; CALOPOLYANOLIDE A; CALOPOLYANOLIDE B; CALOPOLYANOLIDE C; CALOPOLYANOLIDE D; PLANT EXTRACT; PROTOCATECHUIC ACID; PYRANOCOUMARIN DERIVATIVE; UNCLASSIFIED DRUG; URSOLIC ACID;

ANTIVIRAL ACTIVITY; ARTICLE; CALOPHYLLUM POLYANTHUM; CONTROLLED STUDY; DIASTEREOISOMER; DRUG ISOLATION; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MEDICINAL PLANT; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PLANT SEED; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

CALOPHYLLUM; CHINA; COUMARINS; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PLANTS, MEDICINAL; PYRANOCOUMARINS; SEEDS; STEREOISOMERISM;

CALOPHYLLUM; HUMAN HERPESVIRUS 1; HUMAN HERPESVIRUS 2; SIMPLEXVIRUS;

EID: 4644371064     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0499158     Document Type: Article

References (22)

1. Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae Edita. Flora Reipublicae Popularis Sinicae; Science Press: Beijing. 1990; Vol. 50 (2), pp 82-86.
2. Ito, C.; Itoigawa, M.; Mishina, Y.; Filho, V. C.; Enjo, F.; Tokuda, H.; Nishino, H.; Furukawa, H. J. Nat. Prod. 2003, 66, 368-371.
3. Guilet, D.; Helesbeux, J.-J.; Seraphin, D.; Sevenet, T.; Richomme, P.; Bruneton, J. J. Nat. Prod. 2001, 64, 563-568.
4. Guilet, D.; Seraphin, D.; Rondeau, D.; Richomme, P.; Bruneton, J. Phytochemistry 2001, 58, 571-575.
5. Cao, S. G.; Sim, K. Y.; Pereira, J.; Goh, S. H. Phytochemistry 1998, 47, 773-777.
6. Gustafson, K. R.; Bokesch, H. R.; Fuller, R. W.; Cardellina, J. H., II; Kadushin, M. R.; Soejarto, D. D.; Boyd, M. R. Tetrahedron Lett. 1994, 35, 5821-5824.
7. Dharmaratne, H. R. W.; Sotheeswaran, S.; Balasubramaniam, S.; Waight, E. R. Phytochemistry 1985, 24, 1553-1556.
8. Ito, C.; Itoigawa, M.; Mishina, Y.; Filho, V. C.; Mukainaka, T.; Tokuda, H.; Nishino, H.; Furukawa, H. J. Nat. Prod. 2002, 65, 267-272.
9. Morel, C.; Seraphin, D.; Oger, J.-M.; Litaudon, M.; Sevenet, T.; Richomme, P.; Bruneton, J. J. Nat. Prod. 2000, 63, 1471-1474.
10. Ranjith H.; Dharmaratne, W.; Nishanthi, W. M.; Wijesinghe, M. Phytochemistry 1997, 46, 1293-1295.
11. Iinuma, M.; Tosa, H.; Toriyama, N.; Tanaka, T.; Ito, T.; Chelladurai, V. Phytochemistry 1996, 43, 681-685.
12. Iinuma, M.; Tosa, H.; Tanaka, T.; Yonemori, S. Phytochemistry 1995, 38, 725-728.
13. Kashman, Y.; Gustafason, K. R.; Fuller, R. W.; Cardellina, J. H., II; McMahon, J. B.; Currens, M. J.; Buckheit, B. W., Jr.; Hughes, S. H.; Gragg, G. M.; Boyd, M. R. J. Med. Chem. 1992, 35, 2735-2743.
14. Patil, A. D.; Freyer, A. J.; Eggleston, D. S.; Haltiwanger, R. C.; Bean, M. F.; Tayor, P. B.; Caranfa, M. J.; Breen, A. L.; Bartus, H. R.; Johnson, R. K.; Hertzberg, R. P.; Westley, J. W. J. Med. Chem. 1993, 36, 4131-4138.
15. Chen, J. J.; Xu, M.; Luo, S. D.; Wang, H. Y.; Xu, J. C. Yunnan Zhiwu Yanjiu 2001, 23, 521-526.
16. The chemical shift of the OH group at δ 12.31 also suggests that it is intramolecularly hydrogen bonded to a carbonyl.
17. Mckee, T. C.; Fuller, R. W.; Covington, C. D.; Cardellina, J. H., II Gulakowski, R. J.; Krepps, B. L.; McMahon, J. B.; Boyd, M. R. J. Nat. Prod. 1996, 59, 754-758.
18. Van Heerden, F. R.; Brandt, E. V.; Roux, D. G. J. Chem. Soc., Perkin Trans 1 1980, 2463-2469.
19. Anhut, S.; Zinsmeister, H. D.; Mues, R.; Barz, W.; Mackenbrock, K.; Köster, J.; Markham, K. R. Phytochemistry 1984, 23, 1073-1075.
20. Crystallographic data (including structure factors) for compound 1 reported in this paper have been deposited with the Cambridge Crystallographic Data Center (deposition number CCDC230762). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44-0-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk]
21. Sheldrick, G. M. SHELXS.97, Manual of Programs for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1990.
22. Mahmoud, H.; Vladimir, I.; Jacov, T.; Shoshana, M. A. J. Biochem. Biophys. Methods 2002, 50, 189-200.