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

Yu, Zhiyin; Jiang, Hao; Wang, Li; Fan, Yang; Huang, Jianping; Liu, Chongxi; Guo, Xiaowei; Xiang, Wensheng; Huang, Sheng‐Xiong

doi:10.3389/fchem.2020.00095

Cited by 6 publications

(2 citation statements)

References 27 publications

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“…Those new derivatives were depicted in Figure 4. Based on our results and the previous literature [10,11], we postulated a possible BGC for pimprinine (Figure S37). Unfortunately, gene inactivation experiments in S. netropsis WLXQSS-4 have been so far unsuccessful in confirming our hypothesis.…”

Section: Analysis Of the Secondary Metabolites Of S Netropsis Wlxqss-4supporting

confidence: 79%

Genomic and Metabolomic Investigation of a Rhizosphere Isolate Streptomyces netropsis WLXQSS-4 Associated with a Traditional Chinese Medicine

Zhang

Zhu

et al. 2021

Molecules

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Rhizosphere microorganisms play important ecological roles in promoting herb growth and producing abundant secondary metabolites. Studies on the rhizosphere microbes of traditional Chinese medicines (TCMs) are limited, especially on the genomic and metabolic levels. In this study, we reported the isolation and characterization of a Steptomyces netropsis WLXQSS-4 strain from the rhizospheric soil of Clematis manshurica Rupr. Genomic sequencing revealed an impressive total of 40 predicted biosynthetic gene clusters (BGCs), whereas metabolomic profiling revealed 13 secondary metabolites under current laboratory conditions. Particularly, medium screening activated the production of alloaureothin, whereas brominated and chlorinated pimprinine derivatives were identified through precursor-directed feeding. Moreover, antiproliferative activities against Hela and A549 cancer cell lines were observed for five compounds, of which two also elicited potent growth inhibition in Enterococcus faecalis and Staphylococcus aureus, respectively. Our results demonstrated the robust secondary metabolism of S. netropsis WLXQSS-4, which may serve as a biocontrol agent upon further investigation.

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Section: Analysis Of the Secondary Metabolites Of S Netropsis Wlxqss-4supporting

confidence: 79%

Genomic and Metabolomic Investigation of a Rhizosphere Isolate Streptomyces netropsis WLXQSS-4 Associated with a Traditional Chinese Medicine

Zhang

Zhu

et al. 2021

Molecules

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“…The cytotoxic bioassays of compounds 1 and 2 were conducted using the method reported by us previously …”

Section: Methodsmentioning

confidence: 99%

Bisaspochalasins D and E: Two Heterocycle-Fused Cytochalasan Homodimers from an Endophytic Aspergillus flavipes

Wang

Guo

et al. 2021

J. Org. Chem.

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Two heterocycle-fused cytochalasan homodimers, bisaspochalasins D (1) and E (2), were isolated from an endophytic Aspergillus f lavipes. Their chemical structures were elucidated using a combination of HRESIMS, NMR, theoretical calculations, and crystallographic techniques. Bisaspochalasin D (1) is dimerized by the first reported naturally occurring triple heterobridged 3,8-dioxa-6-azabicyclo[3.2.1]octane framework, while bisaspochalasin E (2) employs a pyrrole ring as the linking moiety. Possible dimerization mechanisms of bisaspochalasins D and E were proposed. The bioassay screening revealed that bisaspochalasin D showed cytotoxic activities against five cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480) with IC 50 values ranging from 4.45 to 22.99 μM. Additionally, bisaspochalasin D exhibited neurotrophic activities in a PC12 cell-based assay. At a concentration of 10 μM, bisaspochalasin D can promote neurite growth by inducing a differentiation rate of 12.52% for PC12 cells.

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Natural and synthetic 5‐(3′‐indolyl)oxazoles: Biological activity, chemical synthesis and advanced molecules

Liu,

Jiang,

Sukhbaatar

et al. 2024

Medicinal Research Reviews

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Abstract5‐(3′‐Indolyl)oxazole moiety is a privileged heterocyclic scaffold, embedded in many biologically interesting natural products and potential therapeutic agents. Compounds containing this scaffold, whether from natural sources or synthesized, have demonstrated a wide array of biological activities. This has piqued the interest of synthetic chemists, leading to a large number of reported synthetic approaches to 5‐(3′‐indolyl)oxazole scaffold in recent years. In this review, we comprehensively overviewed the different biological activities and chemical synthetic methods for the 5‐(3′‐indolyl)oxazole scaffold reported in the literatures from 1963 to 2024. The focus of this study is to highlight the significance of 5‐(3′‐indolyl)oxazole derivatives as the lead compounds for the lead discovery of anticancer, pesticidal, antimicrobial, antiviral, antioxidant and anti‐inflammatory agents, to summarize the synthetic methods for the 5‐(3′‐indolyl)oxazole scaffold. In addition, the reported mechanism of action of 5‐(3′‐indolyl)oxazoles and advanced molecules studied in animal models are also reviewed. Furthermore, this review offers perspectives on how 5‐(3′‐indolyl)oxazole scaffold as a privileged structure might be exploited in the future.

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

Cited by 6 publications

References 27 publications

Genomic and Metabolomic Investigation of a Rhizosphere Isolate Streptomyces netropsis WLXQSS-4 Associated with a Traditional Chinese Medicine

Genomic and Metabolomic Investigation of a Rhizosphere Isolate Streptomyces netropsis WLXQSS-4 Associated with a Traditional Chinese Medicine

Bisaspochalasins D and E: Two Heterocycle-Fused Cytochalasan Homodimers from an Endophytic Aspergillus flavipes

Natural and synthetic 5‐(3′‐indolyl)oxazoles: Biological activity, chemical synthesis and advanced molecules

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