Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea.
Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea.
J Nat Prod. 2022 Sep 23;85(9):2177-2183. doi: 10.1021/acs.jnatprod.2c00398. Epub 2022 Aug 30.
Four previously undescribed ergostane-type sterols, aspersterols A-D (-), were isolated from a deep-sea-derived fungus, IV17-109. The structures of the new compounds were determined by extensive analyses of their spectroscopic data, pyridine-induced deshielding effect, Mosher's method, and electronic circular dichroism calculations. The key feature of these sterols is the presence of a rare unsaturated side chain with conjugated double bonds at Δ and Δ. The absolute configuration of C-24 in the side chain was determined by hydrogenation and comparing C NMR chemical shifts of the hydrogenated products with literature values. In addition, aspersterol A () is the second representative of anthrasteroids with a hydroxy group at the C-2 position. Compound showed cytotoxicity against six cancer cell lines, with GI values of 3.4 ± 0.3 to 4.5 ± 0.7 μM, while - showed anti-inflammatory activity, with IC values ranging from 11.6 ± 1.6 to 19.5 ± 1.2 μM.
从深海来源的真菌 IV17-109 中分离到四种以前未描述的麦角甾烷型甾体，即aspersterols A-D (-)。通过对其光谱数据、吡啶诱导去屏蔽效应、Mosher 法和电子圆二色谱计算的广泛分析，确定了这些新化合物的结构。这些甾体的主要特征是存在一个罕见的不饱和侧链，在 Δ 和 Δ 处具有共轭双键。侧链中 C-24 的绝对构型通过氢化确定，并将氢化产物的 C NMR 化学位移与文献值进行比较。此外，aspersterol A () 是具有 C-2 位羟基的 anthrasteroids 的第二个代表。化合物 () 对六种癌细胞系表现出细胞毒性，GI 值为 3.4 ± 0.3 至 4.5 ± 0.7 μM，而 - 表现出抗炎活性，IC 值范围为 11.6 ± 1.6 至 19.5 ± 1.2 μM。
