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Structurally Diverse Metabolites from the Soft Coral Sinularia verruca Collected in the South China Sea

机译:南中国海采集的软珊瑚奇律藻的结构多样的代谢产物

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摘要

Nineteen metabolites with diverse structures, including the rare pyrroloindoline alkaloid verrupyrroloindoline (>1), the unprecedented highly fused benzosesquiterpenoid verrubenzospirolactone (>2), the new asteriscane-type sesquiterpenoid 10-deoxocapillosanane D (>3), and the two new cyclopentenone derivatives (4S*,5S*)-4-hydroxy-5-(hydroxymethyl)-2,3-dimethyl-4-pentylcyclopent-2-en-1-one (>4) and (S)-4-hydroxy-5-methylene-2,3-dimethyl-4-pentylcyclopent-2-en-1-one (>5), were isolated from a South China Sea collection of the soft coral Sinularia verruca. Eleven previously described marine metabolites (>7–>15, >18, and >19) were also obtained as well as three new EtOH-adduct artifacts (>6, >16, and >17). The structures of the new compounds were elucidated by extensive spectroscopic analysis and by comparison with previously reported data. Compounds >4, >5, and >16 showed protection against the cytopathic effects of HIV-1 infection with EC50 values of 5.8–34 μM, and >4, >6, and >16 exhibited inhibition against LPS-induced NO production with IC50 values of 24–28 μM.
机译:19种具有多种结构的代谢物,包括稀有的吡咯并吲哚碱生物碱verrupyrroloindoline(> 1 ),前所未有的高度融合的苯并半萜类Verrubenzospirolactone(> 2 ),新的甾体类倍半萜类10-脱氧己酰环己烷D (> 3 ),以及两个新的环戊烯酮衍生物(4S *,5S *)-4-羟基-5-(羟甲基)-2,3-二甲基-4-戊基环戊-2-烯-1 -一个(> 4 )和(S)-4-羟基-5-亚甲基-2,3-二甲基-4-戊基环戊-2-烯-1-一(> 5 ),是从南中国海收集的软珊瑚Sinularia verruca中分离出来的。还获得了先前描述的11种海洋代谢物(> 7 – > 15 ,> 18 和> 19 ),还有3种新的EtOH加成物(> 6 ,> 16 和> 17 )。通过广泛的光谱分析和与先前报道的数据比较,阐明了新化合物的结构。化合物> 4 ,> 5 和> 16 显示出对HIV-1感染的细胞病变作用的保护,其EC50值为5.8–34μM,而<50 strong> 4 ,> 6 和> 16 对LPS诱导的NO产生抑制作用,IC50值为24–28μM。

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