Cytotoxic C35 terpenoid cryptotrione from the bark of cryptomeria japonica

Organic Letters

Volumn 12, Issue 12, 2010, Pages 2786-2789

  Chen, Cheng Chi ^a   Wu, Jyh Horng ^f   Yang, Ning Sun ^b   Chang, Jang Yang ^c,d   Kuo, Ching Chuan ^c   Wang, Sheng Yang ^f   Kuo, Yueh Hsiung ^a,b,e  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b AGRICULTURAL BIOTECHNOLOGY RESEARCH CENTER   (Taiwan)

^c NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

^d TRI SERVICE GENERAL HOSPITAL   (Taiwan)

^e CHINA MEDICAL UNIVERSITY   (Taiwan)

^f NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CRYPTOTRIONE; ETOPOSIDE; TERPENE;

ARTICLE; BARK; CELL STRAIN KB; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; HUMAN; IC 50; ISOLATION AND PURIFICATION; JAPANESE CEDAR; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE; TAIWAN;

ANTINEOPLASTIC AGENTS; CRYPTOMERIA; DRUG SCREENING ASSAYS, ANTITUMOR; ETOPOSIDE; HUMANS; INHIBITORY CONCENTRATION 50; KB CELLS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT BARK; PLANTS, MEDICINAL; TAIWAN; TERPENES;

EID: 77953564925     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1009027     Document Type: Article

References (30)

1. Gan, W. S. Manual of Medicine Plants in Taiwan; National Research Institute of Chinese Medicine: Taipei, Taiwan, 1958; Vol. 1, pp 54 - 55.
2. Shieh, M.; Iizuka, Y.; Matsubara, Y. Agric. Biol. Chem. 1981, 45, 1493-1495
3. Nagahama, S.; Tazaki, M. Mokuzai Gakkaishi 1993, 39, 1077-1083
4. Nagahama, S.; Tazaki, M.; Sanetika, T.; Nishimura, K.; Tajima, M. Mokuzai Gakkaishi 1996, 42, 1121-1126
5. Nagahama, S.; Tazaki, M.; Nomura, H.; Nishimura, K.; Tajima, M.; Iwasita, Y. Mokuzai Gakkaishi 1996, 42, 1127-1133
6. Nagahama, S.; Tazaki, M.; Sanetika, T.; Nishimura, K.; Tajima, M. Mokuzai Gakkaishi 1998, 44, 282-286
7. Morita, S.; Yatagai, M.; Fujita, S. Mokuzai Gakkaishi 1995, 41, 938-944
8. Narita, H.; Yatagai, M.; Ohira, T. J. Essent. Oil Res. 2006, 18, 68-70
9. Shimizu, M.; Tsuji, H.; Shogawa, H.; Fukumura, H.; Tanaami, S.; Hayashi, T.; Arisawa, M.; Morita, N. Chem. Pharm. Bull. 1988, 36, 3967-3973
10. Nagahama, S.; Tazaki, M.; Kobayashi, H.; Sumimoto, M. Phytochemistry 1993, 33, 879-882
11. Su, W. C.; Fang, J. M.; Cheng, Y. S. Phytochemistry 1993, 34, 779-782
12. Su, W. C.; Fang, J. M.; Cheng, Y. S. Phytochemistry 1994, 35, 1279-1284
13. Su, W. C.; Fang, J. M.; Cheng, Y. S. Phytochemistry 1994, 37, 1109-1114
14. Su, W. C.; Fang, J. M.; Cheng, Y. S. Phytochemistry 1995, 39, 603-607
15. Su, W. C.; Fang, J. M.; Cheng, Y. S. Phytochemistry 1996, 41, 255-261
16. Su, W. C.; Fang, J. M.; Cheng, Y. S. Tetrahedron Lett. 1995, 36, 5367-5370
17. Chen, X. H.; Kim, C. S.; Kashiwagi, T.; Tebayashi, S. I.; Horiike, M. Biosci. Biotechnol. Biochem. 2001, 65, 1434-1437
18. Morisawa, J.; Kim, C. S.; Kashiwagi, T.; Tebayashi, S. I.; Horiike, M. Biosci. Biotechnol. Biochem. 2002, 66, 2424-2428
19. Arihara, S.; Umeyama, A.; Bando, S.; Imoto, S.; Ono, M.; Tani, M.; Yoshikawa, K. Chem. Pharm. Bull. 2004, 52, 354-358
20. Shibuya, T. Phytochemistry 1992, 31, 4289-4294
21. Kofujita, H.; Fujino, Y.; Sasaki, T.; Hasebe, M.; Ota, M.; Suzuki, K. Mokuzai Gakkaishi 2001, 47, 479-486
22. Yu, J. Q.; Komada, H. Plant Epidemic Prevent. 1995, 49, 388-390
23. Yu, J. Q.; Komada, H.; Yamamoto, M.; Terada, T.; Matsui, Y. J. Hortic. Sci. 1997, 72, 989-996
24. Kofujita, H.; Ota, M.; Takahashi, K.; Kawai, Y.; Hayashi, Y. Phytochemistry 2002, 61, 895-898
25. Yoshikawa, K.; Suzuki, K.; Umeyama, A.; Arihara, S. Chem. Pharm. Bull. 2006, 54, 574-578
26. Yoshikawa, K.; Tanaka, T.; Umeyama, A.; Arihara, S. Chem. Pharm. Bull. 2006, 54, 315-319
27. 3) δ 18.6 (C-2), 19.3 (C-20), 19.5 (C-6), 20.0 (C-13′), 20.4 (C-12′), 20.5 (C-16), 20.8 (C-17), 22.0 (C-19), 23.9 (C-8′), 24.3 (C-1′), 25.5 (C-6′), 29.0 (C-15), 26.9 (C-2′), 29.9 (C-14′), 31.3 (C-11′, -3′), 32.0 (C-5′), 33.3 (C-4), 36.6 (C-1), 33.8 (C-18), 38.7 (C-10), 41.6 (C-3), 42.1 (C-9′), 46.6 (C-7′), 50.7 (C-5), 58.3 (C-4′), 123.6 (C-9), 136.2 (C-13), 144.5 (C-8), 144.8 (C-11), 149.0 (C-14), 152.0 (C-7), 182.5 (C-12), 205.1 (C-15′), 209.0 (C-10′).
28. Dellar, J. E.; Cole, M. D.; Waterman, P. G. Phytochemistry 1996, 41, 735-738
29. Finlay, G. J.; Baguley, B. C.; Wilson, W. R. Anal. Biochem. 1984, 139, 272-277
30. X-ray data have been included in Supporting Information.