Total synthesis of chiricanine A, arahypin-1, trans -arachidin-2, trans -arachidin-3, and arahypin-5 from peanut seeds

Journal of Natural Products

Volumn 74, Issue 4, 2011, Pages 644-649

  Park, Byung Ho ^a   Lee, Hee Jin ^a   Lee, Yong Rok ^a  

^a Yeungnam University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 BIS METHOXYMETHOXY 2 (1 HYDROXY 3 METHYLBUTYL)STILBENE; 3,5 BIS METHOXYMETHOXY 2 (3 METHYLBUT 2 ENYL) 4 TRIISOPROPYLSILYLOXYSTILBENE; 3,5 BIS METHOXYMETHOXY 2 (3 METHYLBUT 2 ENYL)STILBENE; 3,5 BIS METHOXYMETHOXY 4' TRIISOPROPYLSILYLOXYSTILBENE; 3,5 BIS METHOXYMETHOXYSTILBENE; 3,5 DIHYDROXY 2 (3 METHYLBUT 2 ENYL) 4' TRIISOPROPYLSILYLOXYSTILBENE; 3,5 DIHYDROXY 4' TRIISOPROPYLSILYLOXYSTILBENE; 3,5 DIMETHOXYBENZALDEHYDE; ARACHIDIN 2; ARACHIDIN 3; ARAHYPIN 1; ARAHYPIN 5; BENZALDEHYDE; CHIRICANINE A; PINOSYLVIN; PLANT MEDICINAL PRODUCT; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DEMETHYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HORNER WADSWORTH EMMONS REACTION; NONHUMAN; PEANUT; PLANT SEED; PRENYLATION; STRUCTURE ANALYSIS; SYNTHESIS;

ARACHIS HYPOGAEA; HEMITERPENES; MOLECULAR STRUCTURE; SEEDS; STEREOISOMERISM; STILBENES;

ARACHIS HYPOGAEA;

EID: 79955459631     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np100696f     Document Type: Article

References (48)

1. Paxton, J. D. In Mycotoxins and Phytoalexins; Sharma, R. P.; Salunkhe, D. K., Eds.; CRC Press: Boca Raton, FL, 1991; pp 485 - 499.
2. Subba Rao, P. V.; Strange, R. N. In Handbook of Phytoalexin Metabolism and Action; Daniel, M.; Pukayastha, R. P., Eds.; Dekker: New York, 1995; pp 199 - 227.
3. Cole, R. J.; Cox, R. H. Handbook of Toxic Fungal Metabolites; Academic Press: New York, 1981; p 937.
4. Sobolev, V. S.; Guo, B. Z.; Holbrook, C. C.; Lynch, R. E. J. Agric. Food Chem. 2007, 55, 2195-2200
5. Dorner, J. W.; Cole, R. J.; Sanders, T. H.; Blankenship, P. D. Mycopathhologia 1989, 105, 117-128
6. Athar, M.; Back, J. H.; Tang, X.; Kim, K. H.; Kopelovich, L.; Bickers, D. R.; Kim, A. L. Toxicol. Appl. Pharmacol. 2007, 3, 274-283
7. de la Lastra, C. A.; Villegas, I. Mol. Nutr. Food Res. 2005, 49, 405-430
8. King, R. E.; Bomser, J. A; Min, D. B. Compr. Rev. Food Sci. Food Saf. 2006, 5, 65-67
9. Sobolev, V.; Neff, S. A.; Glœr, J. B. J. Agric. Food Chem. 2009, 57, 62-68
10. Sobolev, V. J. Agric. Food Chem. 2008, 56, 1949-1954
11. Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W.; Fong, H. H.; Farnsworth, N. R.; Kinghorn, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Science 1977, 275, 218-220
12. Howitz, K. T.; Bitterman, K. J.; Cohen, H. Y.; Lamming, D. W.; Siva Lavu, S.; Wood, J. G.; Zipkin, R. E.; Chung, P.; Kisielewski, A.; Zhang, L.-L.; Scherer, B.; Sinclair, D. A. Nature 2003, 425, 191-196
13. Aggarwal, B. B.; Bhardwaj, A.; Aggarwal, R. S.; Swwram, N. P.; Shishodia, S.; Takada, Y. Anticancer Res. 2004, 24, 2783-2840
14. Stivala, L. A.; Savio, M.; Carofoli, F.; Perucca, P.; Bianchi, L.; Maga, G.; Forti, L.; Pagnoni, U. M.; Albini, A.; Prosperi, E. J. Biol. Chem. 2001, 276, 22586-22594
15. Bhat, K. P.; Pezzuto, J. M. Ann. N. Y. Acad. Sci. 2001, 957, 210-229
16. Huang, L. M.; Chen, J. K.; Huang, S. S.; Lee, R. S.; Su, M. J. Cardiovasc. Rev. 2000, 47, 549-555
17. Fremont, L.; Belguendouz, L.; Delpal, S. Life Sci. 1999, 64, 2511-2521
18. Fremont, L. Life Sci. 2000, 66, 663-673
19. Carbo, N.; Costelli, P.; Baccino, F. M.; Lopez-Soriano, F. J.; Argiles, J. M. Biochem. Biophys. Res. Commun. 1999, 254, 739-743
20. Ioset, J.-R.; Marston, A.; Gupta, M. P.; Hostettmann, K. J. Nat. Prod. 2001, 64, 710-715
21. Gorham, J.; Tori, M.; Asakawa, Y. The Biochemistry of the Stilbenoids; Chapman & Hall: London, 1995; pp 128 - 133.
22. He, S.; Wu, B.; Pan, Y.; Jiang, L. J. Org. Chem. 2008, 73, 5233-5241
23. Ito, T.; Tanaka, T.; Linuma, M.; Iliya, I.; Nakaya, K.; Ali, Z.; Takahashi, Y.; Sawa, R.; Shirataki, Y.; Murata, J.; Dardaedi, D. Tetrahedron 2003, 59, 5347-5363
24. Sotheeswaran, S.; Pasupathy, V. Phytochemistry 1993, 32, 1083-1092
25. Seo, E.-K.; Chai, H.; Constant, H. L.; Santisul, T.; Reutrakul, V.; Beecher, C. W. W.; Farnsworth, N. R.; Cordell, G. A.; Pezzuto, J. M.; Kinghorn, A. D. J. Org. Chem. 1999, 64, 6976-6983
26. Dai, J.-R.; Hallockm, Y. F.; Cardellina, J. H., II.; Boyd, M. R. J. Nat. Prod. 1998, 61, 351-353
27. Ali, M. A.; Kondo, K.; Tsuda, Y. Chem. Pharm. Bull. 1992, 40, 1130-1136
28. Boonlaksiri, C.; Onnanant, W.; Kongsaeree, P.; Kittakoop, M.; Tanticharœn, Y.; Thebtaranonth, Y. Phytochemistry 2000, 54, 415-417
29. Matsuda, H.; Morikawa, T.; Toguchida, I.; Park, J. Y.; Harima, S.; Yoshikawa, M. Bioorg. Med. Chem. 2001, 9, 41-50
30. Fang, J.; Lu, M.; Chen, J.; Zhu, H.; Yang, L.; Wu, L.; Liu, J. Chem. - Eur. J. 2002, 8, 4191-4198
31. Zheng, J. B.; Ramirez, V. D. Biochem. Biophys. Res. Commun. 1999, 261, 499-503
32. Orsini, F.; Pelizzoni, F.; Verotta, L.; Aburjai, T. J. Nat. Prod. 1977, 60, 1082-1087
33. Aburjai, T. A. Phytochemistry 2000, 55, 407-410
34. Yang, L. M.; Lin, S. J.; Hsu, F. L.; Yang, T. H. Bioorg. Med. Chem. Lett. 2002, 12, 1013-1015
35. Wang, X.; Heredia, A.; Song, H.; Zhang, Z.; Yu., B.; Davis, C.; Redfield, R. J. Pharm. Sci. 2004, 93, 2448-2457
36. Likhitwitayawuid, K.; Sritularak, B.; Benchanak, K.; Lipipun, V.; Mathew, J.; Schinazi, R. F. Nat. Prod. Res. 2005, 19, 177-182
37. Thakkar, K.; Geahlen, R. L.; Cushman, M. J. Med. Chem. 1993, 36, 2950-2955
38. Huang, K. S.; Lin, M.; Yu, L. N.; Kong, M. Tetrahedron 2000, 56, 1321-1329
39. Uenobe, F.; Nakamura, S.; Miyazawa, M. Mutat. Res. 1997, 373, 197-200
40. Bokel, M.; Diyasena, C.; Gunatilaka, A. A. L.; Kraus, W.; Sotheeswaran, S. Phytochemistry 1988, 27, 377-380
41. Oshima, Y.; Namao, K.; Kamijou, A.; Matsuoka, S.; Nakano, M.; Terao, K.; Ohizumi, Y. Experimentia 1995, 51, 63-66
42. Condori, J.; Sivakumar, G.; Hubstenberger, J.; Dolan, M. C.; Sobolev, V. S.; Medina-Bolivar, F. Plant Physiol. Biochem. 2010, 48, 310-318
43. Botta, B.; Delle Monache, G.; Menendez, P.; Boffi, A. Trends Pharmacol. Sci. 2005, 26, 606-608
44. Heide, L. Curr. Opin. Chem. Biol. 2009, 13, 171-179
45. Xia, L.; Lee, Y. R. Synlett 2008, 1643-1646
46. Lee, H. J.; Lee, Y. R.; Kim, S. H. Helv. Chim. Acta 2009, 92, 1404-1412
47. Park, B. H.; Lee, Y. R.; Lyoo, W. S. Synthesis 2009, 2146-2150
48. Chakrapani, L.; Jung, E. M.; Lee, Y. R. Helv. Chim. Acta 2010, 93, 829-836