Cytotoxic Peptaibols from Trichoderma strigosum.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-08-23 Epub Date: 2024-07-22 DOI:10.1021/acs.jnatprod.4c00590

Yun Seo Park, Eun-Sook Kim, Stephen T Deyrup, Jin Woo Lee, Sang Hee Shim

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Abstract

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.

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从绞股蓝毛霉中提取具有细胞毒性的 Peptaibols。

从链霉菌（Trichoderma strigosum）中分离出了五种新的脂庚二醇（1-5）和八种新的 19 位元的脂庚二醇（8-15），以及两种已知的脂庚二醇，即脂藜芦醇 C（6）和 D（7）。利用 1D 和 2D NMR 以及 UPLC-MS/MS 数据阐明了新发现的七叶皂糖醇（1-5、8-15）的平面结构。采用先进的马菲法和 GITC（2,3,4,6-四-O-乙酰基-β-d-吡喃葡萄糖基异硫氰酸酯）衍生法阐明了新发现的庚二醇（1-5、8-15）的绝对构型。通过分析 CD 光谱，发现这些肽醇具有右手螺旋构象。虽然大多数新化合物的活性明显高于阳性对照，但分别在第 10 位和第 11 位含有 Ser 和 Leu 的 9、10、12 和 15 号化合物对 MDA-MB-231、SNU449、SKOV3、DU145 和 HCT116 癌细胞株的细胞毒性最强，而且 19 位元的肽多酚一般比脂肽多酚更有效。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.