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Trimeric and dimeric Aspidosperma-type alkaloids from leaves of Tabernaemontana divaricata 'Dwaft'
Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2021-09-01 , DOI: 10.1016/j.bioorg.2021.105314
Jing Chen 1 , Yang Yu 2 , Jing Wu 1 , Mei-Fen Bao 2 , Sumet Kongkiatpaiboon 3 , Johann Schinnerl 4 , Xiang-Hai Cai 2
Affiliation  

Continued interest in bioactive monoterpenoid indole alkaloids and the purpose to explore the artificial cultivation influence on the chemical composition in the same plant species, 8 undescribed Aspidosperma-type alkaloids including two unprecedented trimers, taberdivarines A–B (12), and six new dimers, taberdivarines Csingle bondH (38), together with 9 known bisindoles were isolated from the leaves of Tabernaemontana divaricata 'Dwaft'. Notably, taberdivarines A and B were the first cases of Aspidosperma-Aspidosperma-Aspidosperma-type alkaloids with furan ring linkage patterns of the natural products. Their structures were elucidated by comprehensive spectroscopic analyse. Compounds 18 were screened for the cytotoxicity against three human cancer cell lines, SMMC-7721, HT-29 and A549. Among them, Compound 6 exhibited significant activity against three cell lines with IC50 values of 0.30, 0.75 and 3.41 μM, respectively (IC50 = 3.02, 0.14 and 2.23 μM for the positive control, vinorelbine). Compound 1, 3, 4, 6, 7 and 8 also expressed varying degrees of activity. The structure–activity relationships (SARs) of these alkaloids were discussed.



中文翻译:

来自 Tabernaemontana divaricata 'Dwaft' 叶子的三聚体和二聚体 Aspidosperma 型生物碱

在续感兴趣的生物活性单萜吲哚生物碱,并探讨在相同植物物种的化学成分的人工栽培影响的目的,未描述的8白坚木属型生物碱包括二前所未有三聚体,taberdivarines A-B(1 - 2),以及六个新从Tabernaemontana divaricata 'Dwaft'的叶子中分离出二聚体、taberdivarines C 单键H ( 38 ) 以及 9 种已知的双吲哚。值得注意的是,taberdivarines A 和 B 是最早出现的Aspidosperma-Aspidosperma-Aspidosperma-具有天然产物呋喃环连接模式的类型生物碱。通过综合光谱分析阐明了它们的结构。化合物1 - 8筛选抗三种人癌细胞系的杀伤,SMMC-7721,HT-29和A549。其中,化合物6对三种细胞系表现出显着的活性,IC 50值分别为0.30、0.75和3.41 μM( 阳性对照长春瑞滨的IC 50 = 3.02、0.14和2.23 μM)。化合物134678也表现出不同程度的活跃度。讨论了这些生物碱的构效关系 (SAR)。

更新日期:2021-09-07
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