A monoacylglyceryltrimethylhomoserine, 21F121-A, containing a branched acyl group from Penicillium glaucoroseum

IF 2.5 4区医学 Q3 CHEMISTRY, MEDICINAL

Journal of Natural Medicines Pub Date : 2023-07-29 DOI:10.1007/s11418-023-01735-5

Ichiro Kimura, Yuki Hitora, Yusaku Sadahiro, Teppei Kawahara, Sachiko Tsukamoto

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Abstract

A new monoacylglyceryltrimethylhomoserine, 21F121-A (1), was isolated from the culture of Penicillium glaucoroseum (21F00121) by LCMS-guided purification. The structure was elucidated by NMR and mass spectrometries. The absolute configuration of the homoserine moiety was analyzed by the ECD spectrum after acid hydrolysis, and the S-configuration of the glycerol moiety was determined based on the spectrum of the 1,2-dibenzoyl derivative after acid hydrolysis. Although a variety of diacylglyceryltrimethylhomoserine is distributed in lower plants and fungi, a limited number of studies on monoacyl derivatives have been reported. This is the fourth sample of monoacylglyceryltrimethylhomoserine discovered from a natural source, and the second sample isolated from a fungus. Compound 1 contains an unusual branched pentaene chain attached at the sn-1 position of glycerol and weakly inhibited the growth of HCT116 cells.

Graphical abstract

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青霉一种单酰基甘油三甲基同丝氨酸，21F121-A，含有青霉的支链酰基

从青铜绿青霉(21F00121)培养物中分离到一种新的单酰基甘油三甲基同丝氨酸21F121-A(1)。结构经核磁共振和质谱鉴定。酸水解后的ECD谱分析了同丝氨酸片段的绝对构型，酸水解后的1,2-二苯甲酰衍生物谱分析了甘油片段的s构型。虽然低等植物和真菌中分布着多种二酰基甘油三甲基同丝氨酸，但关于单酰基衍生物的研究报道有限。这是从自然来源中发现的第四个单酰基甘油三甲基高丝氨酸样本，以及从真菌中分离的第二个样本。化合物1在甘油的sn-1位置含有一个不寻常的支链戊烯链，对HCT116细胞的生长有微弱的抑制作用。图形抽象

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来源期刊

Journal of Natural Medicines 医学-药学

CiteScore

6.90

自引率

3.00%

发文量

审稿时长

1.7 months

期刊介绍： The Journal of Natural Medicines is an international journal publishing original research in naturally occurring medicines and their related foods and cosmetics. It covers: -chemistry of natural products -biochemistry of medicinal plants -pharmacology of natural products and herbs, including Kampo formulas and traditional herbs -botanical anatomy -cultivation of medicinal plants. The journal accepts Original Papers, Notes, Rapid Communications and Natural Resource Letters. Reviews and Mini-Reviews are generally invited.