Diterpenoids of the Cassane Type from Caesalpinia decapetala

作者: Yuben Qiao , Qianqian Xu , Zhengxi Hu , Xiao-Nian Li , Ming Xiang

DOI: 10.1021/ACS.JNATPROD.6B00910

关键词: CaesalpiniaIc50 valuesChemistryCircular dichroismPancreatic cancer cellStereochemistryChemical constituents

摘要: Eighteen compounds, including eight new cassane-type furanoditerpenoids, 3β-hydroxyphanginin H (1), 3β-acetoxyphanginin (2), 7β-acetoxyphanginin (3), 7β-hydroxyphanginin (4), 4-epi-3β-hydroxycaesalpinilinn (5), 4-epi-3β-acetoxycaesalpinilinn (6), 20-acetoxytaepeenin D (7), and tomocin E (8), along with 10 known compounds (9–18) were isolated from the roots of Caesalpinia decapetala. Compounds 1–13 C. decapetala for first time. The their absolute configurations determined by extensive spectroscopic analysis, single-crystal X-ray diffraction, electronic circular dichroism calculations. 1, 4, 5, 7, 11 exhibited inhibitory activities against SW1990 human pancreatic cancer cell line IC50 values ranging 2.9 to 8.9 μM.

参考文章(40)
Qiong ZHANG, Xue-Ting LIU, Jing-Yu LIANG, Zhi-Da MIN, Chemical Constituents from the Stems of Caesalpinia decapetala Chinese Journal of Natural Medicines. ,vol. 6, pp. 168- 172 ,(2008) , 10.1016/S1875-5364(09)60015-7
George M. Sheldrick, Thomas R. Schneider, SHELXL: high-resolution refinement. Methods in Enzymology. ,vol. 277, pp. 319- 343 ,(1997) , 10.1016/S0076-6879(97)77018-6
Daniel Torres Mendoza, Luis D. Ureña González, Eduardo Ortega-Barría, Todd L. Capson, Luis Cubilla Rios, Five new cassane diterpenes from Myrospermum frutescens with activity against Trypanosoma cruzi. Journal of Natural Products. ,vol. 66, pp. 928- 932 ,(2003) , 10.1021/NP030010O
Jiming Wu, Gang Chen, Xiaotong Xu, Xiaoling Huo, Shilong Wu, Zhaohua Wu, Huiyuan Gao, Seven new cassane furanoditerpenes from the seeds of Caesalpinia minax. Fitoterapia. ,vol. 92, pp. 168- 176 ,(2014) , 10.1016/J.FITOTE.2013.11.002
Orapun Yodsaoue, Sarot Cheenpracha, Chatchanok Karalai, Chanita Ponglimanont, Suchada Chantrapromma, Hoong-Kun Fun, Akkharawit Kanjana-Opas, Phanginin A-K, diterpenoids from the seeds of Caesalpinia sappan Linn. Phytochemistry. ,vol. 69, pp. 1242- 1249 ,(2008) , 10.1016/J.PHYTOCHEM.2007.11.013
Hucheng Zhu, Chunmei Chen, Jing Yang, Xiao-Nian Li, Junjun Liu, Bin Sun, Sheng-Xiong Huang, Dongyan Li, Guangmin Yao, Zengwei Luo, Yan Li, Jinwen Zhang, Yongbo Xue, Yonghui Zhang, Bioactive Acylphloroglucinols with Adamantyl Skeleton from Hypericum Sampsonii Organic Letters. ,vol. 16, pp. 6322- 6325 ,(2014) , 10.1021/OL5030579
Ren-Wang Jiang, Shuang-Cheng Ma, Paul Pui-Hay But, Thomas C. W. Mak, New antiviral cassane furanoditerpenes from Caesalpinia minax. Journal of Natural Products. ,vol. 64, pp. 1266- 1272 ,(2001) , 10.1021/NP010174+
Young J. Hong, Dean J. Tantillo, Formation of Beyerene, Kaurene, Trachylobane, and Atiserene Diterpenes by Rearrangements That Avoid Secondary Carbocations Journal of the American Chemical Society. ,vol. 132, pp. 5375- 5386 ,(2010) , 10.1021/JA9084786
Ranjani Maurya, Makthala Ravi, Snehlata Singh, Prem P. Yadav, A review on cassane and norcassane diterpenes and their pharmacological studies. Fitoterapia. ,vol. 83, pp. 272- 280 ,(2012) , 10.1016/J.FITOTE.2011.12.007
Ya-Zhou Wang, Chun-Ping Tang, Chang-Qiang Ke, Hans-Christoph Weiss, Ernst-Rudolf Gesing, Yang Ye, Diterpenoids from the pericarp of Platycladus orientalis Phytochemistry. ,vol. 69, pp. 518- 526 ,(2008) , 10.1016/J.PHYTOCHEM.2007.07.023