Xia Dan-Dan, Chen Jing-Xin, Xie Fei, Geng Yan, Dong Hai-Xia, Zhou Hao, Ding Zhong-Tao
Yunnan Characteristic Plant Extraction Laboratory, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China; Institute of International Rivers and Eco-security, Yunnan University, Kunming 650500, China.
Yunnan Characteristic Plant Extraction Laboratory, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China.
Fitoterapia. 2025 Jul;184:106619. doi: 10.1016/j.fitote.2025.106619. Epub 2025 May 12.
Two new sesquiterpenoids asperpenoids A-B (1-2) and one new ergostane-type steroid aspergteroid (3) were isolated from the fungus Aspergillus sp. YUD20004 which was derived from the tuber of Zingiber officinale Roscoe. Their structures and absolute configurations were elucidated by comprehensive spectroscopic analyses, electronic circular dichroism (ECD) spectra and consideration of the biogenetic origins. Especially, asperpenoid A was featured as a rare spiro[6-oxabicyclo[3.2.1]octane-2,2'-oxirane] 5/6/3 tricyclic skeleton. In vitro cytotoxic activity assays, aspergteroid (3) exhibited significant cytotoxic activities against five human cancer cell lines (SMMC-7721, HL-60, A549, SW480 and MDA-MB-231) with IC values ranging from 0.40 to 34.24 μM. Most significantly, compound 3 reduced the viability of SMMC-7721 cells in a concentration-dependent manner with an IC value of 0.40 μM.
从来源于姜科植物姜(Zingiber officinale Roscoe)块茎的曲霉属真菌Aspergillus sp. YUD20004中分离得到了两种新的倍半萜类化合物asperpenoids A - B(1 - 2)和一种新的麦角甾烷型甾体化合物aspergteroid(3)。通过综合光谱分析、电子圆二色(ECD)光谱以及生源合成途径的考虑,阐明了它们的结构和绝对构型。特别地,asperpenoid A具有罕见的螺[6 - 氧杂双环[3.2.1]辛烷 - 2,2'-环氧乙烷]5/6/3三环骨架。体外细胞毒性活性测定表明,aspergteroid(3)对五种人类癌细胞系(SMMC - 7721、HL - 60、A549、SW480和MDA - MB - 231)表现出显著的细胞毒性活性,IC值范围为0.40至34.24 μM。最显著的是,化合物3以浓度依赖的方式降低了SMMC - 7721细胞的活力,IC值为0.40 μM。