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      Dimeric Pimprinine Alkaloids From Soil-Derived Streptomyces sp. NEAU-C99

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          Abstract

          Six new pimprinine alkaloids ( 16), including four dimers, dipimprinines A–D ( 14), and two monomers, (±)-Pimprinol D ( 5), and pimprinone A ( 6), along with six known congeners ( 712), were isolated from a soil-derived actinomycete Streptomyces sp. NEAU-C99. Structures of the new compounds were elucidated by extensive spectroscopic analyses, single-crystal X-ray diffractions, and ECD calculations. Dipimprinines A–D ( 14) showed weak cytotoxic activities against five tumor cell lines, including HL-60, SMMC-7721, A-549, MCF-7, and SW-480, with IC 50 values ranging from 12.7 to 30.7 μM.

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          Most cited references23

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          Novel antibiotic screening methods to awaken silent or cryptic secondary metabolic pathways in actinomycetes

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            Discovery of Pimprinine Alkaloids as Novel Agents against a Plant Virus

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              Isolation of labradorins 1 and 2 from Pseudomonas syringae pv. coronafaciens.

              Investigation of Pseudomonas syringae pv. coronafaciens cancer cell growth inhibitory constituents led to the isolation of 2-isobutyl-5-(3-indolyl)oxazole (1) and 2-n-pentyl-5-(3-indolyl)oxazole (2f), designated labradorins 1 (1) and 2 (2f), related to pimprinine (2a). The structures were deduced by spectroscopic techniques and X-ray crystal structure determinations. Labradorin 1 (1) afforded GI(50) microg/mL values of 9.8 and 6.2 against the human cancer cell lines NCI-H 460 (lung-NSC) and BXPC-3 (pancreas-a).
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                Author and article information

                Contributors
                Journal
                Front Chem
                Front Chem
                Front. Chem.
                Frontiers in Chemistry
                Frontiers Media S.A.
                2296-2646
                18 February 2020
                2020
                : 8
                : 95
                Affiliations
                [1] 1Heilongjiang Provincial Key Laboratory of Agricultural Microbiology, Northeast Agricultural University , Harbin, China
                [2] 2State Key Laboratory of Phytochemistry and Plant Resources in West China, CAS Center for Excellence in Molecular Plant Sciences, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming, China
                Author notes

                Edited by: Huiming Ge, Nanjing University, China

                Reviewed by: Yongbo Xue, Huazhong University of Science and Technology, China; Zhengxi Hu, Huazhong University of Science and Technology, China

                *Correspondence: Wensheng Xiang xiangwensheng@ 123456neau.edu.cn

                This article was submitted to Organic Chemistry, a section of the journal Frontiers in Chemistry

                Article
                10.3389/fchem.2020.00095
                7040024
                fb273aba-1d4c-4f47-8c81-feb978c690db
                Copyright © 2020 Yu, Jiang, Wang, Yang, Huang, Liu, Guo, Xiang and Huang.

                This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

                History
                : 21 November 2019
                : 31 January 2020
                Page count
                Figures: 4, Tables: 3, Equations: 0, References: 26, Pages: 8, Words: 5455
                Categories
                Chemistry
                Original Research

                streptomyces,pimprinine,alkaloids,structural characterization,cytotoxicity

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