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别链吡咯A - E,一种放线菌属sp. RD068384产生的β - 烷基吡咯衍生物。

Allostreptopyrroles A-E, β-alkylpyrrole derivatives from an actinomycete sp. RD068384.

作者信息

Elsbaey Marwa, Oku Naoya, Abdel-Mottaleb Mohamed S A, Igarashi Yasuhiro

机构信息

Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt.

Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan.

出版信息

Beilstein J Org Chem. 2024 Aug 13;20:1981-1987. doi: 10.3762/bjoc.20.174. eCollection 2024.

DOI:10.3762/bjoc.20.174
PMID:39161712
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11331545/
Abstract

Five new β-alkylpyrrole derivatives, allostreptopyrroles A-E (-), were isolated from the culture broth of RD068384. Their structures were elucidated by 1D and 2D NMR spectroscopic analyses, HRESIMS, and chemical derivatization. The absolute configurations of compounds and were predicted by comparison of experimental and calculated specific rotation data. Compounds - are the first examples of natural pyrroles substituted by formyl and carboxyl functionalities. Compounds , , and showed cytotoxicity against Kasumi-1 human acute myeloblastic leukemia cells with IC values of 103, 105, and 105 μM, respectively, which are less active than the anticancer agent cisplatin, with an IC value of 70 μM.

摘要

从RD068384的培养液中分离出了5种新的β-烷基吡咯衍生物,即别链霉吡咯A-E(-)。通过一维和二维核磁共振光谱分析、高分辨电喷雾电离质谱以及化学衍生化确定了它们的结构。通过比较实验和计算的比旋光度数据预测了化合物和的绝对构型。化合物-是天然存在的被甲酰基和羧基官能团取代的吡咯的首个实例。化合物、和对Kasumi-1人急性髓性白血病细胞显示出细胞毒性,IC值分别为103、105和105 μM,活性低于抗癌剂顺铂,其IC值为70 μM。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e498/11331545/33e48a31fce6/Beilstein_J_Org_Chem-20-1981-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e498/11331545/6d4971a04aa4/Beilstein_J_Org_Chem-20-1981-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e498/11331545/33e48a31fce6/Beilstein_J_Org_Chem-20-1981-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e498/11331545/6d4971a04aa4/Beilstein_J_Org_Chem-20-1981-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e498/11331545/33e48a31fce6/Beilstein_J_Org_Chem-20-1981-g003.jpg

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