Benzopyran Derivatives and a Aliphatic Compound from a Mangrove Endophytic Fungus Penicillium citrinum QJF-22,Chemistry & Biodiversity

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Benzopyran Derivatives and a Aliphatic Compound from a Mangrove Endophytic Fungus Penicillium citrinum QJF-22
Chemistry & Biodiversity ( IF 2.3 ) Pub Date : 2020-05-08 , DOI: 10.1002/cbdv.202000192
Wencong Yang ₁ , Yan Chen _{1,

2} , Runlin Cai ₁ , Ge Zou ₁ , Bo Wang ₁ , Zhigang She _{1,

3}

Affiliation

Two new benzopyran derivatives, (2R,4S)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol and (2S,4R,2′S,4′R)‐4,4′‐oxybis(5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran), and a new aliphatic compound, (3E,5Z,8S,10E)‐8‐hydroxytrideca‐3,5,10,12‐tetraen‐2‐one, together with three known benzopyran derivatives, were obtained from a mangrove endophytic fungus Penicillium citrinum QJF‐22 collected in Hainan island. Their structures were determined by analysis of spectroscopic data and the relative configuration of (2R,4S)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol was also confirmed by single‐crystal X‐ray diffraction. The absolute configurations of four compounds were established by comparison of ECD spectra to calculations. The configuration of (3E,5Z,8S,10E)‐8‐hydroxytrideca‐3,5,10,12‐tetraen‐2‐one was confirmed by comparison of optical value to the similar compound. The configurations of the compounds (2S,4S)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol and (2R,4R)‐5‐methoxy‐2‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐ol were first determined. (3R,4S)‐3,4,8‐Trihydroxy‐3,4‐dihydronaphthalen‐1(2H)‐one exhibited moderate inhibitory effects on LPS‐induced NO production in RAW264.7 cells with IC50 of 44.7 μM, and without cytotoxicity to RAW264.7 cells within 50 μM.

中文翻译：

来自红树林内生真菌 Penicillium citrinum QJF-22 的苯并吡喃衍生物和脂肪族化合物

两种新的苯并吡喃衍生物，(2R,4S)-5-甲氧基-2-甲基-3,4-二氢-2H-1-苯并吡喃-4-醇和(2S,4R,2'S,4'R)-4 ,4'-oxybis(5-methoxy-2-methyl-3,4-dihydro-2H-1-benzopyran), 和一个新的脂肪族化合物, (3E,5Z,8S,10E)-8-hydroxytrideca-3,5 ,10,12-tetraen-2-one 以及三种已知的苯并吡喃衍生物是从海南岛采集的红树林内生真菌 Penicillium citrinum QJF-22 中获得的。它们的结构通过光谱数据分析确定，(2R,4S)-5-甲氧基-2-甲基-3,4-二氢-2H-1-苯并吡喃-4-醇的相对构型也通过单晶证实X射线衍射。四种化合物的绝对构型是通过比较 ECD 光谱与计算结果来确定的。(3E,5Z,8S,10E)-8-hydroxytrideca-3,5,10 的构型，12-tetraen-2-one 通过与类似化合物的光学值比较得到证实。(2S,4S)-5-甲氧基-2-甲基-3,4-二氢-2H-1-苯并吡喃-4-醇和(2R,4R)-5-甲氧基-2-甲基-3的构型,4-二氢-2H-1-苯并吡喃-4-醇首先被测定。(3R,4S)-3,4,8-Trihydroxy-3,4-dihydronaphthalen-1(2H)-one 对 RAW264.7 细胞中 LPS 诱导的 NO 产生具有中等抑制作用，IC50 为 44.7 μM，且无细胞毒性到 50 μM 内的 RAW264.7 细胞。

更新日期：2020-05-08

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