Antiausterity agents from Uvaria dac and their preferential cytotoxic activity against human pancreatic cancer cell lines in a nutrient-deprived condition

Journal of Natural Products

Volumn 75, Issue 6, 2012, Pages 1177-1183

  Awale, Suresh ^a   Ueda, Jun Ya ^a   Athikomkulchai, Sirivan ^b   Abdelhamed, Sherif ^a   Yokoyama, Satoru ^a   Saiki, Ikuo ^a   Miyatake, Ryuta ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b SRINAKHARINWIROT UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE; DICHLOROMETHANE; GRANDIFLORACIN; UNCLASSIFIED DRUG; UVARIDACANE A; UVARIDACANE B; UVARIDACOL A; UVARIDACOL B; UVARIDACOL C; UVARIDACOL D; UVARIDAPOXIDE A; ANTINEOPLASTIC AGENT; BRIDGED COMPOUND;

ANNONACEAE; ARTICLE; CANCER CELL CULTURE; CELL STRAIN KLM 1; CELL STRAIN MIA PACA 2; CELL STRAIN PANC 1; CELL STRAIN PSN 1; CIRCULAR DICHROISM; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; NUTRITIONAL DEFICIENCY; PANCREAS CANCER; STEREOCHEMISTRY; TUMOR MICROENVIRONMENT; UVARIA DAC; X RAY CRYSTALLOGRAPHY; CHEMISTRY; DRUG SCREENING; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; PANCREAS TUMOR; THAILAND; UVARIA;

AGOUTI PACA; UVARIA;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BRIDGED COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXENES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PANCREATIC NEOPLASMS; THAILAND; UVARIA;

EID: 84866465067     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np300295h     Document Type: Article

References (32)

1. Zhou, G. X.; Zhou, L. E.; Chen, R. Y.; Yu, D. Q. J. Nat. Prod. 1999, 62, 261-264.
2. Zhou, G. X.; Chen, R. Y.; Yu, D. Q. J. Asian Nat. Prod. Res. 1999, 1, 227-238.
3. Hufford, C. D.; Lasswell, W. L., Jr. J. Org. Chem. 1976, 41, 1297-1298.
4. Lasswell, W. L., Jr.; Hufford, C. D. J. Org. Chem. 1977, 42, 1295-1302.
5. Chantrapromma, K.; Rat, A. P. Y.; Karalai, C.; Lojanapiwatana, V.; Seechamnanturakit, V. Phytochemistry 2000, 53, 511-513.
6. Muhammad, I.; Waterman, P. G. J. Nat. Prod. 1988, 51, 719-724.
7. Cole, J. R.; Torrance, S. J.; Wiedhopf, R. M.; Arora, S. K.; Bates, R. B. J. Org. Chem. 1976, 41, 1852-1855.
8. Dai, Y.; Harinantenaina, L.; Brodie, P. J.; Callmander, M. W.; Randrianaivo, R.; Rakotonandrasana, S.; Rakotobe, E.; Rasamison, V. E.; Shen, Y.; Tendyke, K.; Suh, E. M.; Kingston, D. G. I. J. Nat. Prod. 2012, 75, 479-483.
9. Asha, K. N.; Chowdhury, R.; Hasan, C. M.; Rashid, M. A. Fitoterapia 2003, 74, 159-163.
10. Nkunya, M. H.; Weenen, H.; Bray, D. H.; Mgani, Q. A.; Mwasumbi, L. B. Planta Med. 1991, 57, 341-343.
11. Hufford, C. D.; Lasswell, W. L., Jr. Lloydia 1978, 41, 156-160.
12. Awale, S.; Lu, J.; Kalauni, S. K.; Kurashima, Y.; Tezuka, Y.; Kadota, S.; Esumi, H. Cancer Res. 2006, 66, 1751-1757.
13. Awale, S.; Nakashima, E. M.; Kalauni, S. K.; Tezuka, Y.; Kurashima, Y.; Lu, J.; Esumi, H.; Kadota, S. Bioorg. Med. Chem. Lett. 2006, 16, 581-583.
14. Awale, S.; Miyamoto, T.; Linn, T. Z.; Li, F.; Win, N. N.; Tezuka, Y.; Esumi, H.; Kadota, S. J. Nat. Prod. 2009, 72, 1631-1636.
15. Awale, S.; Linn, T. Z.; Li, F.; Tezuka, Y.; Myint, A.; Tomida, A.; Yamori, T.; Esumi, H.; Kadota, S. Phytother. Res. 2011, 25, 1770-1775.
16. Awale, S.; Li, F.; Onozuka, H.; Esumi, H.; Tezuka, Y.; Kadota, S. Bioorg. Med. Chem. 2008, 16, 181-189.
17. Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. Chem. Pharm. Bull. 2008, 56, 491-496.
18. Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. Bioorg. Med. Chem. Lett. 2008, 18, 4688-4691.
19. Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. Bioorg. Med. Chem. 2008, 16, 8653-8660.
20. Win, N. N.; Awale, S.; Esumi, H.; Tezuka, Y.; Kadota, S. J. Nat. Prod. 2007, 70, 1582-1587.
21. Zhang, C. R.; Yang, S. P.; Liao, S. G.; Wu, Y.; Yue, J. M. Helv. Chim. Acta 2006, 89, 1408-1416.
22. Harada, N.; Nakanishi, K.; Berova, N. In Comprehensive Chiroptical Spectroscopy; Berova, N., Polavarapu, P. L., Nakanishi, K., Woody, R. W., Eds.; John Wiley & Sons, Inc.: New York, 2012; p 115.
23. Liao, Y. H.; Xu, L. Z.; Yang, S. L.; Dai, J.; Zhen, Y. S.; Zhu, M.; Sun, N. J. Phytochemistry 1997, 45, 729-732.
24. Palframan, M. J.; Kociok-Köhn, G.; Lewis, S. E. Org. Lett. 2011, 13, 3150-3153.
25. Lasswell, W. L., Jr.; Hufford, C. D. Phytochemistry 1977, 16, 1439-1441.
26. Compound 6 was not tested due to the small amount isolated.
27. Lu, J.; Kunimoto, S.; Yamazaki, Y.; Kaminishi, M.; Esumi, H. Cancer Sci. 2004, 95, 547-552.
28. Ghaneh, P.; Kawesha, A.; Evans, J. D.; Neoptolemos, J. P. J. Hepatobiliary Pancreat. Surg. 2002, 9, 1-11.
29. Izuishi, K.; Kato, K.; Ogura, T.; Kinoshita, T.; Esumi, H. Cancer Res. 2000, 60, 6201-6207.
30. Eltawil, K. M.; Renfrew, P. D.; Molinari, M. J. Hepatobiliary Pancreat. Surg. 2012, 14, 260-268.
31. Flack, H. D. Acta Crystallogr. A 1983, 39, 876-881.
32. Sheldrick, G. M. Acta Crystallogr. A 2007, 64, 112-122.