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Comatulins A-E, Taurine-Conjugated Anthraquinones from the Australian Crinoid Comatula rotalaria.
Journal of Natural Products ( IF 5.1 ) Pub Date : 2020-06-01 , DOI: 10.1021/acs.jnatprod.0c00267
Kah Yean Lum 1 , Aya C Taki 2 , Robin B Gasser 2 , Ian Tietjen 3, 4 , Merrick G Ekins 1, 5 , Jonathan M White 6 , Russell S Addison 1 , Sasha Hayes 1 , James St John 1, 7 , Rohan A Davis 1
Affiliation  

Chemical investigations of two specimens of the Australian crinoid Comatula rotalaria afforded five new taurine-conjugated anthraquinones, comatulins A–E (15), together with 11 known marine natural products (616). The chemical structures of all the compounds were elucidated by detailed spectroscopic and spectrometric data analysis. The first X-ray crystal structure of a crinoid-derived acyl anthraquinone, rhodocomatulin 5,7-dimethyl ether (8), is reported here. Compounds 1, 2, 613, and two additional naphthopyrone derivatives, 17 and 18, were evaluated for their ability to inhibit HIV-1 replication in vitro; none of the compounds were active at 100 μM. Furthermore, compounds 1, 2, 610, 14, 15, 17, and 18 were screened for nematocidal activity against exsheathed third-stage larvae of Hemonchus contortus, a highly pathogenic parasite nematode of ruminants. Compound 17, known as 6-methoxycomaparvin 5,8-dimethyl ether, showed an inhibitory effect on larval motility (IC50 = 30 μM) and development (IC50 = 31 μM) and induced the eviscerated (Evi) phenotype.

中文翻译:

Comatulins AE,来自澳大利亚海百合 Comatula rotalaria 的牛磺酸共轭蒽醌。

澳大利亚海百合的两个试样的化学调查Comatula rotalaria得到五个新的牛磺酸共轭的蒽醌,comatulins A-E(1 - 5)中,用11个已知的海洋天然产物(一起6 - 16)。通过详细的光谱和光谱数据分析阐明了所有化合物的化学结构。本文报道了海百合衍生的酰基蒽醌、红豆马素 5,7-二甲醚 ( 8 )的第一个 X 射线晶体结构。化合物12613和另外两种萘并吡喃酮衍生物1718, 评估了它们在体外抑制 HIV-1 复制的能力;没有一种化合物在 100 μM 时具有活性。此外,化合物126 - 10141517,和18进行了筛选针对的出鞘第三期幼虫杀线虫活性Hemonchus线虫,反刍动物的高致病性寄生虫线虫。化合物17,称为 6-甲氧基康马帕文 5,8-二甲醚,对幼虫运动 (IC 50 = 30 μM) 和发育 (IC 50= 31 μM) 并诱导内脏 ( Evi ) 表型。
更新日期:2020-06-26
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