来自 Trichoderma strigosum 的细胞毒性 Peptaibols。
Cytotoxic Peptaibols from Trichoderma strigosum.
发表日期:2024 Jul 22
作者:
Yun Seo Park, Eun-Sook Kim, Stephen T Deyrup, Jin Woo Lee, Sang Hee Shim
来源:
JOURNAL OF NATURAL PRODUCTS
摘要:
从 Trichoderma strigosum 中分离出五种新的脂肽醇 (1-5) 和八种新的 19 残基肽醇 (8-15) 以及两种已知的脂肽醇,脂肽醇 C (6) 和 D (7)。使用 1D 和 2D NMR 以及 UPLC-MS/MS 数据阐明了新发现的 peptaibols (1-5、8-15) 的平面结构。使用先进的 Marfey 方法和 GITC(2,3,4,6-四-O-乙酰基-β-d-吡喃葡萄糖基异硫氰酸酯)衍生化阐明了新 peptaibols (1-5, 8-15) 的绝对构型。通过CD光谱分析,发现这些peptabols具有右手螺旋构象。虽然大多数新化合物的活性显着高于阳性对照,但在 10 位和 11 位分别含有 Ser 和 Leu 的 9、10、12 和 15 对 MDA-MB-231、SNU449、SKOV3、 DU145 和 HCT116 癌细胞系以及 19 残基肽醇通常比脂肽醇更有效。
Five new lipopeptaibols (1-5) and eight new 19-residue peptaibols (8-15) along with two known lipopeptaibols, lipovelutibols C (6) and D (7) were isolated from Trichoderma strigosum. The planar structures of the newly discovered peptaibols (1-5, 8-15) were elucidated using 1D and 2D NMR, and UPLC-MS/MS data. The absolute configurations for new peptaibols (1-5, 8-15) were elucidated using the advanced Marfey's method and GITC (2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate) derivatization. Through analysis of CD spectra, these peptabols were found to have right-handed helical conformations. While most of the new compounds were significantly more active than the positive control, 9, 10, 12, and 15 containing Ser and Leu at positions 10 and 11, respectively, were the most cytotoxic against MDA-MB-231, SNU449, SKOV3, DU145, and HCT116 cancer cell lines, and the 19-residue peptaibols were generally more potent than lipopeptaibols.