New amide alkaloids from Piper longum fruits

Natural Products and Bioprospecting - Tập 3 - Trang 277-281 - 2013
Jun Yang1, Yao Su1,2, Ji-Feng Luo1, Wei Gu1, Hong-Mei Niu1, Yan Li3, Yue-Hu Wang1, Chun-Lin Long1,4
1Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
2College of Resources and Environmental Sciences, Hebei Agricultural University, Hebei, China
3State Key Laboratory of Phytochemisty and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
4College of Life and Environmental Sciences, Minzu University of China, Beijing, China

Tóm tắt

Three new amide alkaloids piperlongumamides A-C (1–3), together with 12 known ones (4–15), were isolated from the fruits of Piper longum. The structures of the new isolates were determined using spectroscopic data analyses. Cytotoxic activity of these amides against HL-60 (human leukemia), A-549 (human lung cancer), MCF-7 (human breast cancer), SMMC-7721 (human liver cancer) and SW480 (human rectal cancer) cell lines were evaluated. Piperchabamide B (11) exhibited weak inhibitory activity against HL-60 (IC50 = 21.32 μM ), A-549 (IC50 = 23.82 μM ) and MCF-7 (IC50 = 16.58 μM ) cell lines.

Tài liệu tham khảo

Editorial Board of ‘Zhonghua Bencao’, State Administration of Traditional Chinese Medicine of the People’s Republic of China, Zhonghua Bencao; Shanghai Scientific and Technical Publishing House: Shanghai, 1999, Vol. 3, p. 434. Jiang, Z. Y.; Liu, W. F.; Zhang, X. M.; Luo, J.; Ma, Y. B.; Chen, J. J. Bioorg. Med. Chem. Lett. 2013, 23, 2123–2127. Jiang, Z. Y.; Liu, W. F.; Huang, C. G.; Huang, X. Z. Fitoterapia2013, 84, 222–226. Lee, W.; Kim, K. Y.; Yu, S.N.; Kim, S. H.; Chun, S. S.; Ji, J. H.; Yu, H. S.; Ahn, S. C. Biochem. Biophys. Res. Commun. 2013, 430, 406–412. Ghosal, S.; Deb, A.; Mishra, P.; Vishwakarma, R. Planta Med. 2012, 78, 906–908. Mishra, P.; Sinha, S.; Guru, S.; Bhushan, S. K.; Vishwakarma, R. A.; Ghosal, S. J. Asian Nat. Prod. Res. 2011, 13, 143–148. Madhu, S. K.; Vijayan, V. A.; Shaukath, A. K. Asian Pac. J. Tropical Med. 2011, 4, 112–116. Yang, Y. C.; Lee, S. G.; Lee, H. K.; Kim, M. K.; Lee, S. H.; Lee, H. S. J. Agric. Food Chem. 2002, 50, 3765–3767. Huang, H. Z.; Morgan, C. M.; Asolkar, R. N.; Koivunen, M. E.; Marrone, P. G. J. Agric. Food Chem. 2010, 58, 9994–10000. Lee, S. W.; Kim, M. S.; Park, M. H.; Park, S. J.; Lee, W. S.; Chang, J. S.; Rho, M. C. Bull. Korean Chem. Soc. 2010, 31, 921–924. Jin, Z.; Borjihan, G.; Zhao, R.; Sun, Z.; Hammond, G. B.; Hammond, T. Phytother. Res. 2009, 23, 1194–1196. Lee, S. W.; Rho, M. C.; Park, H. R.; Choi, J. H.; Kang, J. Y.; Lee, J. W.; Kim, K.; Lee, H. S.; Kim, Y. K. J. Agric. Food Chem. 2006, 54, 9759–9763. Lee, S. W.; Kim, Y. K.; Kim, K.; Lee, H. S.; Choi, J. H.; Lee, W. S.; Jun, C. D.; Park, J. H.; Lee, J. M.; Rho, M. C. Bioorg. Med. Chem. Lett. 2008, 18, 4544–4546. Iwashita, M.; Oka, N.; Ohkubo, S.; Saito, M.; Nakahata, N. Eur. J. Pharmacol. 2007, 570, 38–42. Lee, S. W.; Rho, M. C.; Nam, J. Y.; Lim, E. H.; Kwon, O. E.; Kim, Y. H.; Lee, H. S.; Kim, Y. K. Planta Med. 2004, 70, 678–679. Lee, S. E.; Park, B. S.; Kim, M. K.; Choi, W. S.; Kim, H. T.; Cho, K. Y.; Lee, S. G.; Lee, H. S. Crop Prot. 2001, 20, 523–528. Shoji, N.; Umeyama, A.; Saito, N.; Takemoto, T.; Kajiwara, A.; Ohizumi, Y. J. Pharm. Sci. 1986, 75, 1188–1189. Ohno, O.; Watabe, T.; Nakamura, K.; Kawagoshi, M.; Uotsu, N.; Chiba, T.; Yamada, M.; Yamaguchi, K.; Yamada, K.; Miyamoto, K. Biosci. Biotechnol. Biochem. 2010, 74, 1504–1506. Kumar, S.; Arya, P.; Mukherjee, C.; Singh, B. K.; Singh, N.; Parmar, V. S.; Prasad, A. K.; Ghosh, B. Biochem. 2005, 44, 15944–15952. Liu, H. X.; Chen, K.; Sun, Q. Y.; Yang, F. M.; Hu, G. W.; Wang, Y. H.; Long, C. L. J. Nat. Prod. 2013, 76, 732–736. Tang, G. H.; Chen, D. M.; Qiu, B. Y.; Sheng, L.; Wang, Y. H.; Hu, G. W.; Zhao, F. W.; Ma, L. J.; Wang, H.; Huang, Q. Q.; Xu, J. J.; Long, C. L.; Li, J. J. Nat. Prod. 2011, 74, 45–49. Yang, S. X.; Sun, Q. Y.; Yang, F. M.; Hu, G. W.; Luo, J. F.; Wang, Y. H.; Long, C. L. Planta Med. 2013, 79, 693–696. Olsen, R. A.; Spessard, G. O. J. Agric. Food Chem. 1981, 29, 942–944. Hashimoto, K.; Yaoi, T.; Koshiba, H.; Yoshida, T.; Maoka, T.; Fujiwara, Y.; Yamamoto, Y.; Mori, K. Food Sci. Technol. Int. 1996, 2, 24–29. Lee, S. A.; Hwang, J. S.; Han, X. H.; Lee, C.; Lee, M. H.; Choe, S. G.; Hong, S. S.; Lee, D.; Lee, M. K.; Hwang, B. Y. Arch. Pharmacal Res. 2008, 31, 679–683. Yasuda, I.; Takeya, K.; Itokawa, H. Chem. Pharm. Bull. 1981, 29, 564–566. Abad Martínez, M. J.; Benito, P. B. Stud. Nat. Prod. Chem. 2005, 30, 393–418. Morikawa, T.; Matsuda, H.; Yamaguchi, I.; Pongpiriyadacha, Y.; Yoshikawa, M. Planta Med. 2004, 70, 152–159. Shakhmaev, R. N.; Ishbaeva, A. U.; Zorin, V. V. Russ. J. Org. Chem. 2012, 48, 908–913. Yang, X.; Yuan, D. D.; Jiang, X. J.; Xi, Z. J. J. Peking Univ. (Health Sci.). 2013, 45, 221–226. Ghafar, S. A. A.; Ismail, M.; Yazan, L. S.; Fakurazi, S.; Ismail, N.; Chan, K. W.; Tahir, P. M. Evid-Based Complement. Altern. Med. 2013, 2013, 1–8.