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巴利沙宁 A-E,3,4-亚甲二氧基喹啉生物碱与来源于 var. 的苯基-14-氧杂双环[3.2.1]辛烷单元稠合

Paliasanines A-E, 3,4-Methylenedioxyquinoline Alkaloids Fused with a Phenyl-14-oxabicyclo[3.2.1]octane Unit from var. .

机构信息

School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, 920-1192, Japan.

Department of Pharmacognosy-Phytochemistry, Faculty of Pharmacy, Hasanuddin University, Makassar, 90245, Indonesia.

出版信息

J Nat Prod. 2020 Oct 23;83(10):2931-2939. doi: 10.1021/acs.jnatprod.0c00454. Epub 2020 Sep 18.

Abstract

Five new quinoline alkaloids, paliasanines A-E (-), and 17 known compounds (-) were isolated from a methanol extract of var. leaves. Their chemical structures were elucidated by analysis of HRMS and 1D and 2D NMR spectroscopic data. Compounds - are the first naturally occurring 3,4-methylenedioxyquinolines incorporating an oxabicyclo[3.2.1]octane unit. Compounds and displayed selective cytotoxicity (IC 5.9-8.4 μM) against A549 and MCF-7 cell lines, while compounds - were not active. Compounds - did not exhibit an anti-HIV effect in MT4 cells, although the related quinolone derivative waltherione A exhibited significant activity. These preliminary results indicate that the 3-methoxy-4-quinolone skeleton might be preferred for both antiproliferative and anti-HIV activities.

摘要

从 var. 叶的甲醇提取物中分离得到五个新的喹啉生物碱,即 paliasanines A-E(-),以及 17 个已知化合物(-)。通过 HRMS 和 1D 和 2D NMR 光谱数据分析,阐明了它们的化学结构。化合物-是第一个含有氧杂双环[3.2.1]辛烷单元的天然存在的 3,4-亚甲二氧基喹啉。化合物-对 A549 和 MCF-7 细胞系表现出选择性细胞毒性(IC50.9-8.4 μM),而化合物-则没有活性。化合物-在 MT4 细胞中没有表现出抗 HIV 作用,尽管相关的喹诺酮衍生物 waltherione A 表现出显著的活性。这些初步结果表明,3-甲氧基-4-喹啉酮骨架可能对增殖抑制和抗 HIV 活性都有偏好。

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