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Dalestones A and B, two anti-inflammatory cyclopentenones from daldinia eschscholzii with an edited strong promoter for the global regulator LaeA-like gene

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Chinese Journal of Natural Medicines 2019年第5期17卷 387-393页

作者： ZHOU Zhen-Zhen ZHU Hong-Jie YANG Cheng-Long LIU Yan-Jun JIANG Nan XIAO Yong-Sheng SHI Li-Yun JIAO Rui-Hua GE Hui-Ming TAN Ren-Xiang State Key Laboratory of Pharmaceutical Biotechnology Institute of Functional Biomolecules Nanjing University State Key Laboratory Cultivation Base for TCM Quality and Efficacy Nanjing University of Chinese Medicine School of Pharmacy Nanjing Medical University

Replacement of the native promoter of the global regulator Lae A-like gene of daldinia eschscholzii by a strong gpdA promoter led to the generation of two novel cyclopentenone metabolites, named dalestones A and B, whose structures were assigned by a combination of spectroscopic analysis, modified Mosher's reaction, and electronic circular dichroism(ECD). Dalestones A and B inhibit the gene expression of TNF-α and IL-6 in LPS-induced RAW264.7 macrophages.

关键词： daldinia eschscholzii Global regulator Cyclopentenone

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Cytotoxic and antibacterial polyketide-indole hybrids synthesized from indole-3-carbinol by daldinia eschscholzii

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Acta Pharmaceutica Sinica B 2019年第2期9卷 369-380页

作者： Liping Lin Nan Jiang Huimin Wu Yaning Mei Jie Yang Renxiang Tan State Key Laboratory Cultivation Base for TCM Quality and Efficacy Nanjing University of Chinese Medicine State Key Laboratory of Pharmaceutical Biotechnology Nanjing University School of Pharmacy Nanjing Medical University Department of Clinical Laboratory the First Affiliated Hospital of Nanjing Medical University Jiangsu Province Academy of Traditional Chinese Medicine

Two skeletally undescribed polyketide-indole hybrids(PIHs), named indolchromins A and B,were generated from indole-3-carbinol(I3 C) in the fungal culture(daldinia eschscholzii). The indolchromin structures were elucidated mainly by their 1 D and 2 D NMR spectra with the former confirmed by the single-crystal X-ray crystallographic analysis. Each indolchromin alkaloid was chirally separated into four isomers, whose absolute configurations were assigned by comparing the recorded circular dichroism(CD) spectra with the electronic CD(ECD) curves computed for all optional stereoisomers. Furthermore, the indolchromin construction pathways in fungal culture were clarified through enzyme inhibition, precursor feeding experiment, and energy calculation. The cascade reactions,including decarboxylative Claisen condensation catalyzed by 8-amino-7-oxononanoate synthase(AONS),C(sp3)-H activation, double bond migration, and Michael addition, all undergone compatibly during the fungal cultivation. In an MIC range of 1.3–8.6 μmol/L,(2 S,4 R)-and(2 R,4 S)-indolchromin A and(2 R,4 S)-indolchromin B are inhibitory against Clostridium perfringens, Clostridium difficile, Veillonella sp.,Bacteroides fragilis, and Streptococcus pyogenes.(2 R,4 S)-Indolchromin A and(2 S,4 S)-indolchromin B were cytotoxic against the human breast cancer cell line MDA-MB-231 with IC50 values of 27.9 and131.2 nmol/L, respectively, with the former additionally active against another human breast cancer cell line MCF-7(IC_(50)94.4 nmol/L).

关键词： Polyketide-indole hybrids Indole-3-carbinol daldinia eschscholzii 8-Amino-7-oxononanoate synthase Decarboxylative Claisen condensation Antibacterial Anticancer

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广藿香内生真菌daldinia eschscholtzii A630次级代谢产物及其细胞毒活性研究

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天然产物研究与开发 2018年第7期30卷 1176-1180页

作者：卢梦梦陈玉婵刘洪新李赛妮李浩华陶美华郝再彬章卫民广东省微生物研究所省部共建华南应用微生物国家重点实验室广东省菌种保藏与应用重点实验室广东省微生物应用新技术公共实验室广州510070 桂林理工大学化学与生物工程学院桂林541006

采用色谱法从广藿香内生真菌daldinia eschscholtzii发酵液中分离得到9个化合物,通过波谱数据分析分别鉴定为dihydrosphaerolone(1)、2,3-dihydro-5-hydroxy-2-methyl-4H-1-benzopyran-4-one(2)、6-hydroxymellein(3)、4,8-dihydroxy-1-tetralone(4)、8-methoxy-1-naphthol(5)、helicascolide A(6)、1-(2,6-dihydroxyphenyl)butan-1-one(7)、1-(2,6-dihydroxyphenyl)ethan-1-one(8)、diisobutyl phthalate(9),其中化合物5、9为首次从该属真菌中分离得到。细胞毒活性测试显示化合物6、7对肿瘤细胞SF-268、MCF-7、NCI-H460、Hep G-2具有较好的抑制活性,IC50值在16.52~28.42μmol/L之间。

关键词：广藿香内生真菌 daldinia eschscholtzii 次级代谢产物细胞毒活性

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