Talarmalnoids A-F: Fusicoccane diterpenoids from an arthropod-derived endophytic fungus Talaromyces malicola.

IF 2.5 3区 医学 Q3 CHEMISTRY, MEDICINAL
Chen-Yu Yang, Ke-Liang Chen, Yang Liu, Xing-Bao Jia, Cheng Yi, Yu-Wei Niu, Ya-Nan Tian, Yun-Bao Liu
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Abstract

The metabolites from the endophytic fungus Talaromyces malicola hosted in the gastrointestinal tract of the arthropods Armadillidium vulgare were investigated, and six undescribed fusicoccane diterpenoids, talarmalnoids A-F (1-6), along with three known analogs were isolated. Talarmalnoid C (3) was an unprecedented fusicoccane diterpenoid with two sugar units, i.e., 6-O-methyl-α-d-glucose and α-d-glucose. Talarmalnoids D and E (4 and 5) were fusicoccane-type diterpenoids with unusual seven-membered rings attached at the C-3' and C-4' positions. Their structures and absolute configurations were identified by NMR, HRESIMS analyses, X-ray single crystal diffraction, GC-MS, ECD analyses, 13C NMR calculations, and DP4+ probability analyses. Bioassay results showed that talarmalnoid B (2) exhibited significant inhibitory activities against the LPS-inducted production of NO in RAW 264.7 cells, with IC50 value of 0.83 μM.

Talarmalnoids A-F: Fusicoccane diterpenoids from an arthropod-derived endophytic fungus Talaromyces malicola.
研究人员对寄生在节肢动物犰狳胃肠道中的内生真菌 Talaromyces malicola 的代谢物进行了调查,并分离出了六种未曾描述过的 fusicoccane 二萜,即 Talarmalnoids A-F(1-6),以及三种已知的类似物。Talarmalnoids C(3)是一种前所未有的含有两个糖单位(即 6-O-甲基-α-d-葡萄糖和α-d-葡萄糖)的草杉烷二萜类化合物。Talarmalnoids D 和 E(4 和 5)是在 C-3' 和 C-4' 位置上连接有不寻常的七元环的 fusicoccane 型二萜类化合物。通过核磁共振、HRESIMS 分析、X 射线单晶衍射、气相色谱-质谱、ECD 分析、13C 核磁共振计算和 DP4+ 概率分析,确定了它们的结构和绝对构型。生物测定结果表明,talarmalnoid B (2) 对 RAW 264.7 细胞在 LPS 诱导下产生的 NO 具有显著的抑制活性,IC50 值为 0.83 μM。
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来源期刊
Fitoterapia
Fitoterapia 医学-药学
CiteScore
5.80
自引率
2.90%
发文量
198
审稿时长
1.5 months
期刊介绍: Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.
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