Quinazolinone nitriles and related metabolites from the deep-sea-derived fungus <i>Penicillium viridicatum</i> MCCC 3A00265

Two new quinazolinone nitriles (1 and 2) and one new indole alkaloid (3), together with 13 known compounds, were isolated from the deep-sea-derived <i>Penicillium viridicatum</i> MCCC 3A00265. Their structures were determined by extensive spectroscopic analysis, with the absolute configurations established by comparing experimental and calculated electronic circular dichroism (ECD) and optical rotation (OR) data as well as biogenetic considerations. Viricyanoamides A and B (1 and 2) are the sole representatives of quinazolinones featuring a nitrile group, while solitumidine F (3) incorporates a rare pyrrolidinedione unit as an indole terpenoid. In particular, compounds 2 and 10 exhibit significant activity in reactivating mutant p53 at 10 μM, indicating their potential for application in cancer therapy.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2024-12-24
DOI
https://doi.org/10.1039/d4ob01795a
Citations
2
Primary Topic
Microbial Natural Products and Biosynthesis
Type
article
Field-Weighted Citation Impact
0.90

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article

Quinazolinone nitriles and related metabolites from the deep-sea-derived fungus Penicillium viridicatum MCCC 3A00265

Xian‐Wen Yang, Taizong Wu, Jiajian Wang, Dali Meng et al.
2 citations
Organic & Biomolecular Chemistry
Microbial Natural Products and Biosynthesis
0.90
article

Quinazolinone nitriles and related metabolites from the deep-sea-derived fungus Penicillium viridicatum MCCC 3A00265

Xian‐Wen Yang, Taizong Wu, Jiajian Wang, Dali Meng, Meng Zhang, Haoyu Yu, Jihong Zhang
article en
2 citations

Abstract

Two new quinazolinone nitriles (1 and 2) and one new indole alkaloid (3), together with 13 known compounds, were isolated from the deep-sea-derived <i>Penicillium viridicatum</i> MCCC 3A00265. Their structures were determined by extensive spectroscopic analysis, with the absolute configurations established by comparing experimental and calculated electronic circular dichroism (ECD) and optical rotation (OR) data as well as biogenetic considerations. Viricyanoamides A and B (1 and 2) are the sole representatives of quinazolinones featuring a nitrile group, while solitumidine F (3) incorporates a rare pyrrolidinedione unit as an indole terpenoid. In particular, compounds 2 and 10 exhibit significant activity in reactivating mutant p53 at 10 μM, indicating their potential for application in cancer therapy.

Organic & Biomolecular ChemistryVol. 23(6)
Shenyang Pharmaceutical University (CN), Kunming University of Science and Technology (CN), Fujian Institute of Oceanography (CN), Hainan Medical University (CN)
National Key Research and Development Program of China
Life below water
Openalex Percentile: Top 22%
Microbial Natural Products and Biosynthesis
0.90
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Quinazolinone nitriles and related metabolites from the deep-sea-derived fungus <i>Penicillium viridicatum</i> MCCC 3A00265 — Xian‐Wen Yang, Taizong Wu, et al. · Organic & Biomolecular Chemistry (2024) | TGRS Research Map | TGRS