New amide alkaloids from Piper longum fruits

doi:10.1007/s13659-013-0073-0

Natural Products and Bioprospecting ›› 2013, Vol. 3 ›› Issue (6): 277-281.DOI: 10.1007/s13659-013-0073-0

• Regular Article • Previous Articles Next Articles

New amide alkaloids from Piper longum fruits

Jun YANG^a, Yao SU^a,b, Ji-Feng LUO^a, Wei GU^a, Hong-Mei NIU^a, Yan LI^c, Yue-Hu WANG^a, Chun-Lin LONG^a,d

a Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b College of Resources and Environmental Sciences, Hebei Agricultural University, Hebei 071000, China;
c State Key Laboratory of Phytochemisty and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
d College of Life and Environmental Sciences, Minzu University of China, Beijing 100081, China

Received:2013-09-15 Revised:2013-11-12 Online:2018-02-11 Published:2013-12-24
Supported by:
This work was funded by the Natural Science Foundation of Yunnan Province, China (No. 2011FZ205), the National Natural Science Foundation of China (Nos. 31070288, 31161140345), the Ministry of Education of China through its 111 and 985 projects (Nos. B08044, MUC98506-01000101 & MUC985-9), and the Japan Society for the Promotion of Science (No. JSPS/AP/109080).

New amide alkaloids from Piper longum fruits

Jun YANG^a, Yao SU^a,b, Ji-Feng LUO^a, Wei GU^a, Hong-Mei NIU^a, Yan LI^c, Yue-Hu WANG^a, Chun-Lin LONG^a,d

a Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b College of Resources and Environmental Sciences, Hebei Agricultural University, Hebei 071000, China;
c State Key Laboratory of Phytochemisty and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
d College of Life and Environmental Sciences, Minzu University of China, Beijing 100081, China

通讯作者: Yue-Hu WANG,E-mail:wangyuehu@mail.kib.ac.cn;Chun-Lin LONG,E-mail:long@mail.kib.ac.cn
基金资助:
This work was funded by the Natural Science Foundation of Yunnan Province, China (No. 2011FZ205), the National Natural Science Foundation of China (Nos. 31070288, 31161140345), the Ministry of Education of China through its 111 and 985 projects (Nos. B08044, MUC98506-01000101 & MUC985-9), and the Japan Society for the Promotion of Science (No. JSPS/AP/109080).

Abstract

Abstract: 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.

Key words: Piperaceae, Piper longum, amide alkaloids, piperlongumamides, piperchabamide B, cytotoxicity

摘要： 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.

关键词: Piperaceae, Piper longum, amide alkaloids, piperlongumamides, piperchabamide B, cytotoxicity

Jun YANG, Yao SU, Ji-Feng LUO, Wei GU, Hong-Mei NIU, Yan LI, Yue-Hu WANG, Chun-Lin LONG. New amide alkaloids from Piper longum fruits[J]. Natural Products and Bioprospecting, 2013, 3(6): 277-281.

Jun YANG, Yao SU, Ji-Feng LUO, Wei GU, Hong-Mei NIU, Yan LI, Yue-Hu WANG, Chun-Lin LONG. New amide alkaloids from Piper longum fruits[J]. 应用天然产物, 2013, 3(6): 277-281.

References

[1] 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.
[2] 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.
[3] Jiang, Z. Y.; Liu, W. F.; Huang, C. G.; Huang, X. Z. Fitoterapia 2013, 84, 222-226.
[4] 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.
[5] Ghosal, S.; Deb, A.; Mishra, P.; Vishwakarma, R. Planta Med. 2012, 78, 906-908.
[6] Mishra, P.; Sinha, S.; Guru, S.; Bhushan, S. K.; Vishwakarma, R. A.; Ghosal, S. J. Asian Nat. Prod. Res. 2011, 13, 143-148.
[7] Madhu, S. K.; Vijayan, V. A.; Shaukath, A. K. Asian Pac. J. Tropical Med. 2011, 4, 112-116.
[8] 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.
[9] Huang, H. Z.; Morgan, C. M.; Asolkar, R. N.; Koivunen, M. E.; Marrone, P. G. J. Agric. Food Chem. 2010, 58, 9994-10000.
[10] 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.
[11] Jin, Z.; Borjihan, G.; Zhao, R.; Sun, Z.; Hammond, G. B.; Hammond, T. Phytother. Res. 2009, 23, 1194-1196.
[12] 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.
[13] 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.
[14] Iwashita, M.; Oka, N.; Ohkubo, S.; Saito, M.; Nakahata, N. Eur. J. Pharmacol. 2007, 570, 38-42.
[15] 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.
[16] 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.
[17] Shoji, N.; Umeyama, A.; Saito, N.; Takemoto, T.; Kajiwara, A.; Ohizumi, Y. J. Pharm. Sci. 1986, 75, 1188-1189.
[18] 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.
[19] Kumar, S.; Arya, P.; Mukherjee, C.; Singh, B. K.; Singh, N.; Parmar, V. S.; Prasad, A. K.; Ghosh, B. Biochem. 2005, 44, 15944-15952.
[20] 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.
[21] 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.
[22] 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.
[23] Olsen, R. A.; Spessard, G. O. J. Agric. Food Chem. 1981, 29, 942-944.
[24] Hashimoto, K.; Yaoi, T.; Koshiba, H.; Yoshida, T.; Maoka, T.; Fujiwara, Y.; Yamamoto, Y.; Mori, K. Food Sci. Technol. Int. 1996, 2, 24-29.
[25] 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.
[26] Yasuda, I.; Takeya, K.; Itokawa, H. Chem. Pharm. Bull. 1981, 29, 564-566.
[27] Abad Martínez, M. J.; Benito, P. B. Stud. Nat. Prod. Chem. 2005, 30, 393-418.
[28] Morikawa, T.; Matsuda, H.; Yamaguchi, I.; Pongpiriyadacha, Y.; Yoshikawa, M. Planta Med. 2004, 70, 152-159.
[29] Shakhmaev, R. N.; Ishbaeva, A. U.; Zorin, V. V. Russ. J. Org. Chem. 2012, 48, 908-913.
[30] Yang, X.; Yuan, D. D.; Jiang, X. J.; Xi, Z. J. J. Peking Univ. (Health Sci.). 2013, 45, 221-226.
[31] 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.

New amide alkaloids from Piper longum fruits

New amide alkaloids from Piper longum fruits

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Pengkun Li, Qin Li, Aimin Fu, Yang Xiao, Chunmei Chen, Hucheng Zhu, Changxing Qi, Wei Wei, Yuan Zhou, Yonghui Zhang. Emestrin-type epipolythiodioxopiperazines from Aspergillus nidulans with cytotoxic activities by regulating PI3K/AKT and mitochondrial apoptotic pathways [J]. Natural Products and Bioprospecting, 2025, 15(2): 17-17.
[2]	Dong-Yang Wang, Ming-Xing Li, Yan-Chao Xu, Peng Fu, Wei-Ming Zhu, Li-Ping Wang. Dibohemamines I-O from Streptomyces sp. GZWMJZ-662, an endophytic actinomycete from the medicinal and edible plant Houttuynia cordata Thunb. [J]. Natural Products and Bioprospecting, 2025, 15(1): 9-9.
[3]	Yue-Mei Chen, Nan-Kai Cao, Si-Si Zhu, Meng Ding, Hai-Zhen Liang, Ming-Bo Zhao, Ke-Wu Zeng, Peng-Fei Tu, Yong Jiang. Euchrestifolines A-O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia [J]. Natural Products and Bioprospecting, 2025, 15(1): 5-5.
[4]	Alica Fischle, Mika Lutsch, Florian Hübner, Linda Sch?ker-Hübner, Lina Schürmann, Finn K. Hansen, Svetlana A. Kalinina. Micro-scale screening of genetically modified Fusarium fujikuroi strain extends the apicidin family [J]. Natural Products and Bioprospecting, 2024, 14(6): 51-51.
[5]	Qi-Xiu Hai, Kun Hu, Su-Ping Chen, Yang-Yang Fu, Xiao-Nian Li, Han-Dong Sun, Hong-Ping He, Pema-Tenzin Puno. Silvaticusins A-D: ent-kaurane diterpenoids and a cyclobutane-containing ent-kaurane dimer from Isodon silvaticus [J]. Natural Products and Bioprospecting, 2024, 14(5): 45-45.
[6]	Shuyuan Mo, Ziming Zhao, Zi Ye, Zhihong Huang, Yaxin Zhang, Wanqi Yang, Jianping Wang, Zhengxi Hu, Yonghui Zhang. New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti [J]. Natural Products and Bioprospecting, 2023, 13(3): 17-17.
[7]	Li Hou, Cui-Xuan Mei, Chun-Mao Yuan, Gui-Hua Tang, Duo-Zhi Chen, Qing Zhao, Hong-Ping He, Ming-Ming Cao, Xiao-Jiang Hao. Five new limonoids isolated from Walsura robusta [J]. Natural Products and Bioprospecting, 2023, 13(2): 7-7.
[8]	Ya-Li Hu, Xing-Ren Li, Gang Xu. Carascynol A, a hybrid of caryophyllane-type terpenoid and a C₆ unit degraded by polyprenylated acylphloroglucinols from Hypericum ascyron [J]. Natural Products and Bioprospecting, 2022, 12(6): 38-38.
[9]	Xin Zhang, Yun-Bao Ma, Xiao-Feng He, Tian-Ze Li, Chang-An Geng, Li-Hua Su, Shuang Tang, Zhen Gao, Ji-Jun Chen. Artemyrianosins A–J, cytotoxic germacrane-type sesquiterpene lactones from Artemisia myriantha [J]. Natural Products and Bioprospecting, 2022, 12(3): 16-16.
[10]	Natividad Herrera Cano, Sebastian A. Andujar, Cristina Theoduloz, Daniel A. Wunderlin, Ana N. Santiago, Guillermo Schmeda-Hirschmann, Ricardo D. Enriz, Gabriela E. Feresin. Arylated analogues of cypronazole: fungicidal effect and activity on human fibroblasts. Docking analysis and molecular dynamics simulations [J]. Natural Products and Bioprospecting, 2022, 12(2): 9-9.
[11]	Ruo-Song Zhang, Yang-Yang Liu, Pei-Feng Zhu, Qiong Jin, Zhi Dai, Xiao-Dong Luo. Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity [J]. Natural Products and Bioprospecting, 2021, 11(6): 651-658.
[12]	Patrick O. Sakyi, Richard K. Amewu, Robert N. O. A. Devine, Emahi Ismaila, Whelton A. Miller, Samuel K. Kwofie. The Search for Putative Hits in Combating Leishmaniasis: The Contributions of Natural Products Over the Last Decade [J]. Natural Products and Bioprospecting, 2021, 11(5): 489-544.
[13]	Chen Shi, Yue-Ling Peng, Juan He, Zheng-Hui Li, Ji-Kai Liu, Tao Feng. Structures, Chemical Conversions, and Cytotoxicity of Tricholopardins C and D, Two Tricholoma Triterpenoids from the Wild Mushroom Tricholoma pardinum [J]. Natural Products and Bioprospecting, 2021, 11(2): 235-241.
[14]	Yi Chen, Song-Wei Li, Fang-Zhou Yin, Min Yang, Xia-Juan Huan, Ze-Hong Miao, Xiao-Ming Wang, Yue-Wei Guo. Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus [J]. Natural Products and Bioprospecting, 2021, 11(1): 73-79.
[15]	Mohammad Sanad Abu-Darwish, Célia Cabral, Zulfigar Ali, Mei Wang, Shabana I. Khan, Melissa R. Jacob, Surendra K. Jain, Babu L. Tekwani, Fazila Zulfiqar, Ikhlas A. Khan, Hatem Taifour, Lígia Salgueiro, Thomas Efferth. Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities [J]. Natural Products and Bioprospecting, 2020, 10(5): 307-316.