Zhong Lin-Fang, Zou Qing-Hui, Ren Xu-Meng, Ling Juan, Qi Shu-Hua
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, Guangdong, China; University of Chinese Academy of Sciences, Beijing 100049, China.
School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China.
Fitoterapia. 2025 Jun;183:106580. doi: 10.1016/j.fitote.2025.106580. Epub 2025 Apr 30.
Thirteen new sorbicillinoids including trichosorbicilloid A (1), 12-epi- trichosorbicilloid A (2), trichosorbicilloids B - C (3-4), 24-hydroxy-12-epi-trichobisvertinol D (5), 15,24-dihydroxy-12-epi-trichobisvertinol D (6), 15,24-dihydroxy-13,14-tetrahydro-12-epi-trichobisvertinol D (7), 15-hydroxy-13,14-tetrahydro-12-epi-trichobisvertinol D (8), 24-hydroxy-trichobisvertinol D (9), 15,24-hydroxy-trichobisvertinol D (10), 13,20-dihydroxy-trichodermolide (11), 20-hydroxy-13-trichodermolide acid (12), and trichosorbicilloid D (13) were isolated from the mangrove sediment-derived fungus Trichoderma reesei SCSIO 41705. Their structures were determined by extensive spectroscopic analysis, and their absolute configurations were established by quantum chemical calculations of electronic circular dichroism (ECD) spectra or comparison of experimental ECD spectra. Compounds 1 and 2 possess a novel cagelike polycyclic skeleton with a unique 5/5/5/5/6 ring system. Compound 3 was the first example of hybrid sorbicillinoid fused vertinolide with a 3-propyl-1H-indole unit by Michael-addition. Compounds 5-13 as dimeric sorbicillinoids have different sorbyl side chains. Biologically, compounds 3, 11 and 13 showed potent anti-inflammatory activity by inhibiting the LPS-induced NO production in RAW 264.7 cells. A preliminary structure-anti-inflammatory activity relationship of sorbicillinoids was also discussed.
从来源于红树林沉积物的里氏木霉Trichoderma reesei SCSIO 41705中分离得到13个新的山梨醇类化合物，包括曲霉菌素A（1）、12-表-曲霉菌素A（2）、曲霉菌素B - C（3 - 4）、24-羟基-12-表-曲双戊醇D（5）、15,24-二羟基-12-表-曲双戊醇D（6）、15,24-二羟基-13,14-四氢-12-表-曲双戊醇D（7）、15-羟基-13,14-四氢-12-表-曲双戊醇D（8）、24-羟基-曲双戊醇D（9）、15,24-二羟基-曲双戊醇D（10）、13,20-二羟基-木霉内酯（11）、20-羟基-13-木霉内酯酸（12）和曲霉菌素D（13）。通过广泛的光谱分析确定了它们的结构，并通过电子圆二色光谱（ECD）的量子化学计算或实验ECD光谱的比较确定了它们的绝对构型。化合物1和2具有一种新型的笼状多环骨架，带有独特的5/5/5/5/6环系。化合物3是通过迈克尔加成将山梨醇类与维蒂诺内酯稠合的3-丙基-1H-吲哚单元的首个杂合山梨醇类化合物实例。化合物5 - 13作为二聚体山梨醇类化合物具有不同的山梨醇侧链。在生物学方面，化合物3、11和13通过抑制RAW 264.7细胞中脂多糖诱导的一氧化氮产生而表现出较强的抗炎活性。还讨论了山梨醇类化合物初步的构效关系。
