Chemical investigation on the cultures of the fungus Xylaria carpophila

doi:10.1007/s13659-011-0011-y

应用天然产物 ›› 2011, Vol. 1 ›› Issue (2): 75-80.DOI: 10.1007/s13659-011-0011-y

• Regular Article • 上一篇下一篇

Chemical investigation on the cultures of the fungus Xylaria carpophila

Xia YIN^a,b, Tao FENG^a, Zheng-Hui LI^a, Jia SU^a, Yan LI^a, Ning-Hua TAN^a, Ji-Kai LIU^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b Graduate University of Chinese Academy of Sciences, Beijing 100039, China

收稿日期:2011-08-05 修回日期:2011-09-20 出版日期:2011-04-24 发布日期:2017-11-24
通讯作者: Ji-Kai LIU,E-mail:jkliu@mail.kib.ac.cn
基金资助:
This project was supported by the National Basic Research Program of China(973 Program, 2009CB522300), the National Natural Sciences Foundation of China(30830113), and MOST(2009ZX09501-029).

Chemical investigation on the cultures of the fungus Xylaria carpophila

Xia YIN^a,b, Tao FENG^a, Zheng-Hui LI^a, Jia SU^a, Yan LI^a, Ning-Hua TAN^a, Ji-Kai LIU^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b Graduate University of Chinese Academy of Sciences, Beijing 100039, China

Received:2011-08-05 Revised:2011-09-20 Online:2011-04-24 Published:2017-11-24
Supported by:
This project was supported by the National Basic Research Program of China(973 Program, 2009CB522300), the National Natural Sciences Foundation of China(30830113), and MOST(2009ZX09501-029).

摘要/Abstract

摘要： A chemical investigation on the cultures of Xylaria carpophila led to the isolation of one known cyclopeptide cyclo(Nmethyl-_L-Phe-_L-Pro-_L-Leu-_D-Ile-_L-Val)(1), five new sesquiterpenes, named as xylcarpins A-E(2-6), and another known compound(7). The structures were determined by extensive NMR and MS spectroscopic analysis. The absolute configuration of 1 was established by use of Marfey's method and ROESY spectroscopic data. All compounds were tested for their cytotoxicities against five human cancer cell lines. Compound 7 showed week inhibitory activity.

关键词: Xylaria carpophila, sesquiterpenes, cyclopeptide, cytotoxicity

Abstract: A chemical investigation on the cultures of Xylaria carpophila led to the isolation of one known cyclopeptide cyclo(Nmethyl-_L-Phe-_L-Pro-_L-Leu-_D-Ile-_L-Val)(1), five new sesquiterpenes, named as xylcarpins A-E(2-6), and another known compound(7). The structures were determined by extensive NMR and MS spectroscopic analysis. The absolute configuration of 1 was established by use of Marfey's method and ROESY spectroscopic data. All compounds were tested for their cytotoxicities against five human cancer cell lines. Compound 7 showed week inhibitory activity.

Key words: Xylaria carpophila, sesquiterpenes, cyclopeptide, cytotoxicity

Xia YIN, Tao FENG, Zheng-Hui LI, Jia SU, Yan LI, Ning-Hua TAN, Ji-Kai LIU. Chemical investigation on the cultures of the fungus Xylaria carpophila[J]. 应用天然产物, 2011, 1(2): 75-80.

Xia YIN, Tao FENG, Zheng-Hui LI, Jia SU, Yan LI, Ning-Hua TAN, Ji-Kai LIU. Chemical investigation on the cultures of the fungus Xylaria carpophila[J]. Natural Products and Bioprospecting, 2011, 1(2): 75-80.

参考文献

[1] Shiono, Y.; Motoki, S.; Koseki, T.; Murayama, T.; Tojima, M.; Kimura, K. I. Phytochemistry 2009, 70, 935-939.
[2] Isaka, M.; Yangchum, A.; Auncharoen, P.; Srichomthong, K.; Srikitikulchai, P. J. Nat. Prod. 2011, 74, 300-302.
[3] Quang, D. N.; Bach, D. D. Nat. Prod. Res. 2008, 22, 901-906.
[4] Rukachaisirikul, V.; Khamthong, N.; Sukpondma, Y.; Pakawatchai, C.; Phongpaichit, S.; Sakayaroj, J.; Kirtikara, K. Chem. Pharm. Bull. 2009, 57, 1409-1411.
[5] Quang, D. N.; Bach, D. D.; Hashimoto, T.; Asakawa, Y. Nat. Prod. Res. 2006, 20, 317-321.
[6] Deyrup, S. T.; Gloer, J. B.; O'Donnell, K.; Wicklow, D. T. J. Nat. Prod. 2007, 70, 378-382.
[7] Abate, D.; Abraham, W. R.; Meyer, H. Phytochemistry 1997, 44, 1443-1448.
[8] McDonald, L. A.; Barbieri, L. R.; Bernan, V. S.; Janso, J.; Lassota, P.; Carter, G. T. J. Nat. Prod. 2004, 67, 1565-1567.
[9] Pongcharoen, W.; Rukachaisirikul, V.; Isaka, M.; Sriklung, K. Chem. Pharm. Bull. 2007, 55, 1647-1648.
[10] Boonphong, S.; Kittakoop, P.; Isaka, M.; Pittayakhajonwut, D.;Tanticharoen, M.; Thebtaranonth, Y. J. Nat. Prod. 2001, 64, 965-967.
[11] Pongcharoen, W.; Rukachaisirikul, V.; Phongpaichit, S.; Kuhn, T.; Pelzing, M.; Sakayaroj, J.; Taylor Walter, C. Phytochemistry 2008, 69, 1900-1902.
[12] Pittayakhajonwut, P.; Suvannakad, R.; Thienhirun, S.; Prabpai, S.; Kongsaeree, P.; Tanticharoen, M. Tetrahedron Lett. 2005, 46, 1341-1344.
[13] Tansuwan, S.; Pornpakakul, S.; Roengsumran, S.; Petsom, A.; Muangsin, N.; Sihanonta, P.; Chaichit, N. J. Nat. Prod. 2007, 70, 1620-1623.
[14] Singh, S. B.; Zink, D.; Polishook, J.; Valentino, D.; Shafiee, A.; Silverman, K.; Felock, P.; Teran, A.; Vilella, D.; Hazuda, D. J.; Lingham, R. B. Tetrahedron Lett. 1999, 40, 8775-8779.
[15] Shiono, Y.; Murayama, T.; Takahashi, K.; Okada, K.; Katohda, S.; Tkeda, M. Biosci. Biotechnol. Biochem. 2005, 69, 287-292.
[16] Wu, W. D.; Dai, H. Q.; Bao, L.; Ren, B.; Lu, J. C.; Luo, Y. M.; Guo, L. D.; Zhang, L. X.; Liu, H. W. J. Nat. Prod. 2011, 74, 1303-1308.
[17] (a) Sakamaki, H.; Kitanaka, S.; Chai, W.; Hayashida, Y.; Takagi, Y.; Horiuchi, C. A. J. Nat. Prod. 2001, 64, 630-631. (b) Kawai, T.; Ooi, T.; Kusumi, T. Chem. Pharm. Bull. 2003, 51, 291-294. (c) Hnawia, E.; Menut, C.; Agrebi, A.; Cabalion, P. Biochem. Syst. Ecol. 2009, 36, 859-866.
[18] Marco, J. A.; Juan, F. S. C.; Vicente, G. L.; Natalia, B. Phytochemistry 1997, 45, 755-763.
[19] Mosmann, T. J. Immunol. Methods 1983, 65, 55-63.
[20] Lang, G.; Blunt, W. B.; Cummings, N. J.; Cole, A. L. J.; Munro, M. H. G. J. Nat. Prod. 2005, 68, 1303-1305.
[21] Reed, L. J.; Muench, H. Am. J. Hyg. 1938, 27, 493-497.

Chemical investigation on the cultures of the fungus Xylaria carpophila

Chemical investigation on the cultures of the fungus Xylaria carpophila

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 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]. 应用天然产物, 2021, 11(5): 489-544.
[13]	Yi-Jie Zhai, Jian-Nan Li, Yu-Qi Gao, Lin-Lin Gao, Da-Cheng Wang, Wen-Bo Han, Jin-Ming Gao. Structurally Diverse Sesquiterpenoids with Anti-neuroinflammatory Activity from the Endolichenic Fungus Cryptomarasmius aucubae[J]. 应用天然产物, 2021, 11(3): 325-332.
[14]	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]. 应用天然产物, 2021, 11(2): 235-241.
[15]	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]. 应用天然产物, 2021, 11(1): 73-79.