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(+)-Cyclopenol, a new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid from the fungus Penicillium sclerotiorum endogenous with the Chinese mangrove Bruguiera gymnorrhiza.
J Asian Nat Prod Res. 2014; 16(5):542-8.JA

Abstract

One new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid named (+)-cyclopenol (1), along with nine known compounds including viridicatol (2), 3-(dimethylaminomethyl)-1-(1,1-dimethyl-2-propenyl)indole (3), anacine (4), aurantiomide C (5), viridicatin (6), 3-O-methylviridicatin (7), verrucosidin (8), ergosterol (9), and ergosterol peroxide (10), was isolated from the EtOAc extract of fungus Penicillium sclerotiorum, an endophytic fungal strain isolated from Chinese mangrove Bruguiera gymnorrhiza. The chemical structure of the new compound 1 was elucidated on the basis of detailed spectroscopic analysis. The absolute configuration of 1 was determined by single-crystal X-ray analysis with Cu Kα radiation (λ = 1.54178 Å). To our knowledge, (+)-cyclopenol (1) represents the first example of 7-membered 2,5-dioxopiperazine isolated from mangrove endophytic fungus.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li J
a School of Biological and Chemical Engineering, Jiangsu University of Science and Technology , Zhenjiang 212018 , China.
Wang J
No affiliation info available
Jiang CS
No affiliation info available
Li G
No affiliation info available
Guo YW
No affiliation info available

MeSH

AlkaloidsBenzodiazepinonesMolecular StructureNuclear Magnetic Resonance, BiomolecularPenicilliumRhizophoraceaeStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24773150

Citation

Li, Jing, et al. "(+)-Cyclopenol, a New Naturally Occurring 7-membered 2,5-dioxopiperazine Alkaloid From the Fungus Penicillium Sclerotiorum Endogenous With the Chinese Mangrove Bruguiera Gymnorrhiza." Journal of Asian Natural Products Research, vol. 16, no. 5, 2014, pp. 542-8.
Li J, Wang J, Jiang CS, et al. (+)-Cyclopenol, a new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid from the fungus Penicillium sclerotiorum endogenous with the Chinese mangrove Bruguiera gymnorrhiza. J Asian Nat Prod Res. 2014;16(5):542-8.
Li, J., Wang, J., Jiang, C. S., Li, G., & Guo, Y. W. (2014). (+)-Cyclopenol, a new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid from the fungus Penicillium sclerotiorum endogenous with the Chinese mangrove Bruguiera gymnorrhiza. Journal of Asian Natural Products Research, 16(5), 542-8. https://doi.org/10.1080/10286020.2014.911290
Li J, et al. (+)-Cyclopenol, a New Naturally Occurring 7-membered 2,5-dioxopiperazine Alkaloid From the Fungus Penicillium Sclerotiorum Endogenous With the Chinese Mangrove Bruguiera Gymnorrhiza. J Asian Nat Prod Res. 2014;16(5):542-8. PubMed PMID: 24773150.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - (+)-Cyclopenol, a new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid from the fungus Penicillium sclerotiorum endogenous with the Chinese mangrove Bruguiera gymnorrhiza. AU - Li,Jing, AU - Wang,Jun, AU - Jiang,Cheng-Shi, AU - Li,Gang, AU - Guo,Yue-Wei, Y1 - 2014/04/29/ PY - 2014/4/30/entrez PY - 2014/4/30/pubmed PY - 2014/7/12/medline KW - 2,5-dioxopiperazine KW - Bruguiera gymnorrhiza KW - Penicillium sclerotiorum KW - alkaloid KW - mangrove fungus SP - 542 EP - 8 JF - Journal of Asian natural products research JO - J Asian Nat Prod Res VL - 16 IS - 5 N2 - One new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid named (+)-cyclopenol (1), along with nine known compounds including viridicatol (2), 3-(dimethylaminomethyl)-1-(1,1-dimethyl-2-propenyl)indole (3), anacine (4), aurantiomide C (5), viridicatin (6), 3-O-methylviridicatin (7), verrucosidin (8), ergosterol (9), and ergosterol peroxide (10), was isolated from the EtOAc extract of fungus Penicillium sclerotiorum, an endophytic fungal strain isolated from Chinese mangrove Bruguiera gymnorrhiza. The chemical structure of the new compound 1 was elucidated on the basis of detailed spectroscopic analysis. The absolute configuration of 1 was determined by single-crystal X-ray analysis with Cu Kα radiation (λ = 1.54178 Å). To our knowledge, (+)-cyclopenol (1) represents the first example of 7-membered 2,5-dioxopiperazine isolated from mangrove endophytic fungus. SN - 1477-2213 UR - https://www.unboundmedicine.com/medline/citation/24773150/_+__Cyclopenol_a_new_naturally_occurring_7_membered_25_dioxopiperazine_alkaloid_from_the_fungus_Penicillium_sclerotiorum_endogenous_with_the_Chinese_mangrove_Bruguiera_gymnorrhiza_ DB - PRIME DP - Unbound Medicine ER -