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

Structurally Diverse Metabolites from the Soft Coral Sinularia verruca Collected in the South China Sea.
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DOI:
10.1021/acs.jnatprod.6b00031
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发表时间:
2016-04-22
影响因子:
5.1
通讯作者:
Yan P
Yan P
中科院分区:
生物学2区
文献类型:
--
作者:
Yuan W;Cheng S;Fu W;Zhao M;Li X;Cai Y;Dong J;Huang K;Gustafson KR;Yan P

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19种具有不同结构的代谢产物,包括罕见的吡咯并吲哚啉生物碱verrupyrroloindoline(1)、前所未有的高度稠合的苯并倍半萜verrubenzobenzopirolactone(2)、新的倍半萜型倍半萜10-deoxocapillosanane D(3)和两种新的环戊烯酮衍生物(4S*,5S*)-4-羟基-5-从中国南海软珊瑚Sinulariaverruca中分离得到2个新化合物(4)和(S)-4-羟基-5-亚甲基-2,3-二甲基-4-戊基环庚烯-2-酮(5),分别为(羟甲基)-2,3-二甲基-4-戊基环庚烯-2-酮(4)和(S)-4-羟基-5-亚甲基-2,3-二甲基-4-戊基环庚烯-2-酮(5)。还获得了11种先前描述的海洋代谢物(7-15、18和19)以及3种新的乙醇加合物人工产物(6、16和17)。通过广泛的光谱分析并与先前报道的数据进行比较,阐明了新化合物的结构。化合物4、5和16显示出对HIV-1感染的细胞病变效应的保护作用,其EC 50值为5.8-34 μM,化合物4、6和16显示出对LPS诱导的NO产生的抑制作用,其IC 50值为24-28 μM。
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.
Flexibilisquinone,是一种来自培养的软珊瑚脆性柔韧性的新型抗炎醌。
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