A New Polyoxygenated Seco-cyclohexene Derivative from Artabotrys pilosus

doi:10.6023/cjoc201505007

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (9): 1981-1984.DOI: 10.6023/cjoc201505007 Previous Articles Next Articles

Notes

毛叶鹰爪花中一个新颖的裂环多氧取代环己烯类化合物

刘艳萍^a, 黄丽刚^a, 汪晓翠^a, 文成全^a, 许莎莎^a, 宋小平^a, 韩长日^a, 陈光英^a,b, 付艳辉^a

a 海南师范大学热带药用植物化学教育部重点实验室海口 571158;
b 海南师范大学化学与化工学院海口 571158

收稿日期:2015-05-05 修回日期:2015-05-25 发布日期:2015-05-29
通讯作者: 陈光英, 付艳辉 E-mail:chgying123@163.com;fuyanhui80@163.com
基金资助:
国家自然科学基金(Nos. 31360069, 21302181)、海南省自然科学基金(No. 214027)、国际科技合作与交流专项(No. 2014DFA40850)、海南省应用技术研发与示范推广专项(No. ZDXM2015063)、海南省高校科研(No. HNKY2014-41)和国家大学生创新训练计划(Nos. 201411658031, 3010151053)资助项目.

A New Polyoxygenated Seco-cyclohexene Derivative from Artabotrys pilosus

Liu Yanping^a, Huang Ligang^a, Wang Xiaocui^a, Wen Chenquan^a, Xu Shasha^a, Song Xiaoping^a, Han Changri^a, Chen Guangying^a,b, Fu Yanhui^a

a Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158;
b College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158

Received:2015-05-05 Revised:2015-05-25 Published:2015-05-29
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 31360069, 21162009), the Natural Science Foundation of Hainan Province (No. 214027), the International S&T Cooperation Program of China (No. 2014DFA40850), the Major Technology Project of Hainan (No. ZDXM2015063), the Scientific Research Project of Hainan Colleges and Universities (No. HNKY2014-41) and the National Undergraduate Innovation Training Programs (Nos. 201411658031, 3010151053).

1. A New Polyoxygenated Seco-cyclohexene Derivative from Artabotrys pilosus.PDF(1258KB)

Abstract

A new polyoxygenated seco-cyclohexene derivative, artapilosol A (1), together with two known polyoxygenated seco-cyclohexene derivatives, microcarpin A (2) and uvarisubol B (3), was isolated from the stems and leaves of Artabotrys pilosus. Their structures were established on the basis of extensive spectral data. This is the first report that polyoxygenated seco-cyclohexene derivatives were isolated from the genus Artabotrys. Cytotoxicities of compounds 1~3 were tested against five cancer cell lines (HL-60, A549, SMMC-7721, MCF-7 and SW480). Results showed that compounds 1~3 exhibited significant inhibitory effects with IC₅₀ values comparable to those of cisplatin.

Key words: Artabotrys, Artabotrys pilosus, artapilosol A, cytotoxicity

Cite this article

Liu Yanping, Huang Ligang, Wang Xiaocui, Wen Chenquan, Xu Shasha, Song Xiaoping, Han Changri, Chen Guangying, Fu Yanhui. A New Polyoxygenated Seco-cyclohexene Derivative from Artabotrys pilosus[J]. Chin. J. Org. Chem., 2015, 35(9): 1981-1984.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Flora Reipublicae Popularis Sinicae Editorial Board Flora Reipublicae Popularis Sinicae, Vol. 30, Science Press, Beijing, 1979, p. 121 (in Chinese). (中国科学院中国植物志编委会, 中国植物志, 30卷, 科学出版社, 北京, 1979, p. 121.)
[2] Zhou, Q.; Fu, Y. H.; Li, X. B.; Chen, G. Y.; Wu, S. Y.; Song, X. P.; Liu, Y. P.; Han, C. R. Phytochem. Lett. 2015, 11, 296.
[3] Sichaem, J.; Ruksilp, T.; Worawalai, W.; Siripong, P.; Khumkratok, S.; Tip-pyang, S. Fitoterapia 2011, 82, 422.
[4] Hsieh, T. J.; Chang, F. R.; Chia, Y. C.; Chen, C. Y.; Lin, H. C.; Chiu, H. F.; Wu, Y. C. J. Nat. Prod. 2001, 64, 1157.
[5] Hsieh, T. J.; Chen, C. Y.; Kuo, R. Y.; Chang, F. R.; Wu, Y. C. J. Nat. Prod. 1999, 62, 1192.
[6] Gupta, C.; Prasad, S.; Sahai, M.; Asai, T.; Hara, N.; Fujimoto, Y. Helv. Chim. Acta 2010, 93, 1925.
[7] Zhang, L.; Zhou, W. S.; Xu, X. X. J. Chem. Soc., Chem. Commun. 1988, 523.
[8] Liang, X. T.; Yu, D. Q.; Wu, W. L.; Deng, H. C. Acta Chim. Sinica 1979, 37, 215 (in Chinese). (梁晓天, 于德泉, 吴伟良, 邓槐春, 化学学报, 1979, 37, 215.)
[9] Wong, H. F.; Brown, G. D. Phytochemistry 2002, 59, 99.
[10] Li, T. M.; Yu, J. G. Chin. Chem. Lett. 1997, 8, 43.
[11] Singh, A. P.; Sahai, M. Planta Med. 1996, 62, 192.
[12] Chen, Z.; Liu, Y. L.; Xu, Q. M.; Liu, J. Y.; Duan, H. Q.; Yang, S. L. J. Asian Nat. Prod. Res. 2013, 15, 53.
[13] Zhang, C. R.; Wu, Y.; Yue, J. M. Chin. J. Nat. Med. 2010, 8, 84.
[14] Wang, S.; Chen, R. Y.; Yu, S. S.; Yu, D. Q. J. Asian Nat. Prod. Res. 2003, 5, 17.
[15] Lu, Y. P.; Mu, Q.; Zheng, H. L.; Li, C. M. Chin. Chem. Lett. 1995, 6, 775.
[16] Li, X. D.; Miao, F. P.; Ji, N. Y. Molecules 2011, 16, 8646.
[17] Funel, C.; Berrue, F.; Roussakis, C.; Fernandez, R. R.; Amade, P. J. Nat. Prod. 2004, 67, 491.
[18] Mosmann, T. J. Immunol. Methods 1983, 65, 55.
[19] Reed, L. J.; Muench, H. Am. J. Hyg. 1938, 27, 493.

毛叶鹰爪花中一个新颖的裂环多氧取代环己烯类化合物

A New Polyoxygenated Seco-cyclohexene Derivative from Artabotrys pilosus

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Lei Li, Congcong Zhu, Quangang Zhu, Zhongjian Chen, Xike Gao. Design, Synthesis and Bioactivity Evaluation of Guaiazulene Derivatives with Antioxidant and Anti-inflammatory Activities [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2906-2913.
[2]	Mingqiong Li, Huibin Huang, Yuchan Chen, Saini Li, Zhaoming Liu, Yanlin Wang, Weimin Zhang, Xiaoxia Gao. Polyketides from the Deep-Sea-Derived Fungus Talaromyces indigoticus FS688 and Their Cytotoxicites [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2975-2980.
[3]	Qi Lu, Feixia Ye, Xiaotong Sun, Jianquan Weng, Qian Yu, Dexuan Hu. Design and Synthesis of Novel Nature-Inspired Stilbene Analogues as Potential Topoisomerase 1 Inhibitors [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3321-3329.
[4]	Caiyun Hu, Saini Li, Yuchan Chen, Xiaoxia Gao, Zhaoming Liu, Weimin Zhang. Polyketides from the Deep-Sea-Derived FungusDiaporthe phaseolorum FS459 [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1591-1598.
[5]	Hongtao Li, Fei Xie, Yue Sun, Meng Wang, Jingyuan Chen, Hao Zhou, Zhongtao Ding. A New Protoilludane Sesquiterpene Aryl Ester from Armillaria sp. YUD17010 [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4493-4497.
[6]	Li Fangyao, Huang Lin, Zhou Xiaoqun, Li Qian, Ma Xianli, Duan Wengui, Wang Xiu. Synthesis and Cytotoxicity Evaluation of Dehydroabietic Acid Derivatives Bearing Nitrate Moiety [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2845-2854.
[7]	Zhang Jie, Chen Yuchan, Liu Zhaoming, Guo Bohong, Gao Xiaoxia, Liu Hongxin, Zhang Weimin. Cytotoxic Secondary Metabolites from a Sea-Derived Fungal Strain of Hypoxylon rubiginosum FS521 [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1367-1371.
[8]	Wang Zengbo, Tian Cheng, Liu Qingqing, Zhang Wei, Pan Chengxue, Su Guifa. Study on the Synthesis of Benzophenanthridine Analogues via the Cyclization Reaction of Aryl-enamine Ester and Their Cytotoxicity [J]. Chin. J. Org. Chem., 2019, 39(7): 1962-1969.
[9]	Liu Hongxin, Li Haohua, Chen Yuchan, Tan Haibo, Zhang Weimin. Cytotoxic Secondary Metabolites from an Endophytic Fungal Strain of Phomopsis phyllanthicola [J]. Chin. J. Org. Chem., 2019, 39(5): 1475-1478.
[10]	Liu Haishan, Zhu Guoliang, Zhao Shuige, Fu Peng, Zhu Weiming. Bioactive Natural Products from the Marine Sponge-Derived Nocardiopsis dassonvillei OUCMDZ-4534 [J]. Chin. J. Org. Chem., 2019, 39(2): 507-514.
[11]	Song Yongbin, Li Dan, Yang Yihui, Ji Hongrui, Liu Bo. Synthesis and Cytotoxicity of Dinaphtho [2, 1-b: 1', 2'-d]furan Derivatives [J]. Chin. J. Org. Chem., 2018, 38(6): 1516-1524.
[12]	He Jie, Cao Yong, Yuan Qiang. Preparation and Photocytotoxicity in vitro of Oridonin-porphyrinchitosan Microspheres [J]. Chin. J. Org. Chem., 2017, 37(3): 759-766.
[13]	Wang Cong, Wang Liping, Fan Jie, Sun Kunlai, Zhu Weiming. Cytotoxic Compounds from the DeepSea Sediment-Derived Streptomyces malaysiensis OUCMDZ-2167 [J]. Chin. J. Org. Chem., 2017, 37(3): 658-666.
[14]	Chen Lingling, Zhu Tonghan, Zhu Guoliang, Liu Yunlong, Wang Cong, Piyachaturawat Pawinee, Chairoungdua Arthit, Zhu Weiming. Bioactive Natural Products from the Marine-Derived Penicillium brevicompactum OUCMDZ-4920 [J]. Chin. J. Org. Chem., 2017, 37(10): 2752-2762.
[15]	Zhang Pingzhu, Wei Xiao, Liu Huan, Wang Qiwei, Ma Chen, Rong Ruixue, Li Xiaoliu. Synthesis and Cytotoxicity of Azasugar Modified Anthraquinone Derivatives [J]. Chin. J. Org. Chem., 2016, 36(8): 1921-1925.