中国化学快报(英文版)2024,Vol.35Issue(3) :415-418.DOI:10.1016/j.cclet.2023.108206

Rearranged 19-nor-7,8-seco-labdane diterpenoids and Diels-Alder cycloadducts from the Chinese liverwort Pallavicinia ambigua:Structural elucidation,photoinduced rearrangement,and cytotoxic activity

Chunyang Zhang Yuelan Li Zhaojun Chu Shuangzhi Yuan Yanan Qiao Jiaozhen Zhang Lin Li Yueqing Zhang Ruifeng Tian Yajie Tang Hongxiang Lou
中国化学快报(英文版)2024,Vol.35Issue(3) :415-418.DOI:10.1016/j.cclet.2023.108206

Rearranged 19-nor-7,8-seco-labdane diterpenoids and Diels-Alder cycloadducts from the Chinese liverwort Pallavicinia ambigua:Structural elucidation,photoinduced rearrangement,and cytotoxic activity

Chunyang Zhang 1Yuelan Li 2Zhaojun Chu 1Shuangzhi Yuan 1Yanan Qiao 1Jiaozhen Zhang 1Lin Li 1Yueqing Zhang 1Ruifeng Tian 1Yajie Tang 2Hongxiang Lou1
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作者信息

  • 1. Department of Natural Products Chemistry,Key Lab of Chemical Biology(MOE),School of Pharmaceutical Sciences,Shandong University,Ji'nan 250012,China
  • 2. State Key Laboratory of Microbial Technology,Shandong University,Qingdao 266237,China
  • 折叠

Abstract

Two distinctive rearranged 19-nor-7,8-seco-labdane diterpenoids(1 and 2)with a novel tetracyclo[5.2.1.02,5.04,10]decane skeleton,a derivative of the open tetrahydrofuran ring(7),three dimeric compounds(8-10),and four revised homologs(3-6)were obtained from Chinese liverwort Pallavicinia ambigua.Their structures were identified via combined analysis of their spectroscopic data,single-crystal X-ray diffraction patterns,and ECD calculations.The light-driven conversion of compound 5 to compounds 1-4 demonstrated that photochemically induced postmodification involved in biosyn-thesis is an important way to diversify natural structures.A preliminary cytotoxicity assay revealed that compound 5 showed significant inhibition in the human prostate cancer(PC-3)cell line via an apoptotic pathway.

Key words

Liverwort/Pallavicinia ambigua/19-nor-7,8-seco-Labdan diterpenoid/Photoinduced rearrangement/Cytotoxic activity

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基金项目

国家重点研发计划(2019YFA0905700)

国家自然科学基金(82173703)

国家自然科学基金(81874293)

Major Basic Research Program of Shandong Provincial Natural Science Foundation(ZR2019ZD26)

出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCDCSCD
影响因子:0.771
ISSN:1001-8417
参考文献量22
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