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与番荔枝果实相关的内生真菌层出镰刀菌 Ann-B-2 中具有细胞毒性的萘并呋喃和苯并呋喃。

Cytotoxic naphtho- and benzofurans from an endophytic fungus Epicoccum nigrum Ann-B-2 associated with Annona squamosa fruits.

机构信息

Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, Cairo, 11566, Egypt.

出版信息

Sci Rep. 2024 Feb 28;14(1):4940. doi: 10.1038/s41598-024-55168-5.

Abstract

Chemical exploration of the total extract derived from Epicoccum nigrum Ann-B-2, an endophyte associated with Annona squamosa fruits, afforded two new metabolites, epicoccofuran A (1) and flavimycin C (2), along with four known compounds namely, epicocconigrone A (3), epicoccolide B (4), epicoccone (5) and 4,5,6-trihydroxy-7-methyl-1,3-dihydroisobenzofuran (6). Structures of the isolated compounds were elucidated using extensive 1D and 2D NMR along with HR-ESI-MS. Flavimycin C (2) was isolated as an epimeric mixture of its two diastereomers 2a and 2b. The new compounds 1 and 2 displayed moderate activity against B. subtilis, whereas compounds (2, 3, 5, and 6) showed significant antiproliferative effects against a panel of seven different cancer cell lines with IC values ranging from 1.3 to 12 µM.

摘要

从与番荔枝果实相关的内生真菌青霉菌属(Ann-B-2)的总提取物中进行化学探索,得到了两种新的代谢产物,即 epicoccofuran A(1)和 flavimycin C(2),以及四种已知化合物,即 epicocconigrone A(3)、epicoccolide B(4)、epicoccone(5)和 4,5,6-三羟基-7-甲基-1,3-二氢异苯并呋喃(6)。通过广泛的 1D 和 2D NMR 以及 HR-ESI-MS 确定了分离化合物的结构。flavimycin C(2)作为其两个非对映异构体 2a 和 2b 的外消旋混合物被分离出来。新化合物 1 和 2 对枯草芽孢杆菌显示出中等的活性,而化合物(2、3、5 和 6)对七种不同的癌细胞系显示出显著的抗增殖作用,IC 值范围为 1.3 至 12 μM。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c7d6/10901772/8c78f705545c/41598_2024_55168_Fig1_HTML.jpg

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