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Penicamide A, A Unique N,N'-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829.
Mar Drugs 2019; 17(9)MD

Abstract

Previously unreported N,N'-ketal quinazolinone enantiomers [(-)-1 and (+)-1] and a new biogenetically related compound (2), along with six known compounds, 2-pyrovoylaminobenzamide (3), N-(2-hydroxypropanoyl)-2 amino benzoic acid amide (4), pseurotin A (5), niacinamide (6), citreohybridonol (7), citreohybridone C (8) were isolated from the ascidian-derived fungus Penicillium sp. 4829 in wheat solid-substrate medium culture. Their structures were elucidated by a combination of spectroscopic analyses (1D and 2D NMR and Electron Circular Dichroism data) and X-ray crystallography. The enantiomeric pair of 1 is the first example of naturally occurring N,N'-ketal quinazolinone possessing a unique tetracyclic system having 4-quinazolinone fused with tetrahydroisoquinoline moiety. The enantiomeric mixtures of 1 displayed an inhibitory effect on NO production in lipopolysaccharide-activated RAW264.7 cells, while the optically pure (-)-1 showed better inhibitory effect than (+)-1.

Authors+Show Affiliations

School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China. chensenh@mail.sysu.edu.cn. Southern Laboratory of Ocean Science and Engineering (Guangdong, Zhuhai), Zhuhai 519000, China. chensenh@mail.sysu.edu.cn.School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China. jiangmh23@mail2.sysu.edu.cn.School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China. chenbin25@mail.sysu.edu.cn.Department of Marine Science, Faculty of Fisheries, Kasetsart University, Bangkok 10900, Thailand. ffisjd@ku.ac.th.School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China. shah_iram2000@yahoo.com. Institute of chemical sciences, Gomal University, Dera Ismail Khan 27100, Pakistan. shah_iram2000@yahoo.com.School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China. lsshjg@mail.sysu.edu.cn.School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China. cesllan@mail.sysu.edu.cn. Southern Laboratory of Ocean Science and Engineering (Guangdong, Zhuhai), Zhuhai 519000, China. cesllan@mail.sysu.edu.cn.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31492051

Citation

Chen, Senhua, et al. "Penicamide A, a Unique N,N'-Ketal Quinazolinone Alkaloid From Ascidian-Derived Fungus Penicillium Sp. 4829." Marine Drugs, vol. 17, no. 9, 2019.
Chen S, Jiang M, Chen B, et al. Penicamide A, A Unique N,N'-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829. Mar Drugs. 2019;17(9).
Chen, S., Jiang, M., Chen, B., Salaenoi, J., Niaz, S. I., He, J., & Liu, L. (2019). Penicamide A, A Unique N,N'-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829. Marine Drugs, 17(9), doi:10.3390/md17090522.
Chen S, et al. Penicamide A, a Unique N,N'-Ketal Quinazolinone Alkaloid From Ascidian-Derived Fungus Penicillium Sp. 4829. Mar Drugs. 2019 Sep 5;17(9) PubMed PMID: 31492051.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Penicamide A, A Unique N,N'-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829. AU - Chen,Senhua, AU - Jiang,Minghua, AU - Chen,Bin, AU - Salaenoi,Jintana, AU - Niaz,Shah-Iram, AU - He,Jianguo, AU - Liu,Lan, Y1 - 2019/09/05/ PY - 2019/08/21/received PY - 2019/09/02/revised PY - 2019/09/02/accepted PY - 2019/9/8/entrez KW - Penicillium KW - anti-inflammatory KW - ascidian-derived fungus KW - quinazolinone alkaloid JF - Marine drugs JO - Mar Drugs VL - 17 IS - 9 N2 - Previously unreported N,N'-ketal quinazolinone enantiomers [(-)-1 and (+)-1] and a new biogenetically related compound (2), along with six known compounds, 2-pyrovoylaminobenzamide (3), N-(2-hydroxypropanoyl)-2 amino benzoic acid amide (4), pseurotin A (5), niacinamide (6), citreohybridonol (7), citreohybridone C (8) were isolated from the ascidian-derived fungus Penicillium sp. 4829 in wheat solid-substrate medium culture. Their structures were elucidated by a combination of spectroscopic analyses (1D and 2D NMR and Electron Circular Dichroism data) and X-ray crystallography. The enantiomeric pair of 1 is the first example of naturally occurring N,N'-ketal quinazolinone possessing a unique tetracyclic system having 4-quinazolinone fused with tetrahydroisoquinoline moiety. The enantiomeric mixtures of 1 displayed an inhibitory effect on NO production in lipopolysaccharide-activated RAW264.7 cells, while the optically pure (-)-1 showed better inhibitory effect than (+)-1. SN - 1660-3397 UR - https://www.unboundmedicine.com/medline/citation/31492051/Penicamide_A,_A_Unique_N,N'-Ketal_Quinazolinone_Alkaloid_from_Ascidian-Derived_Fungus_Penicillium_sp._4829 L2 - http://www.mdpi.com/resolver?pii=md17090522 DB - PRIME DP - Unbound Medicine ER -