Chemical Constituents of Bangia fuscopurpurea

Wu, Jiahui; Rothenberg, Marc E.; Su, Jie; Lu, Haixia; Liu, Zhiyu

doi:10.1007/s10600-019-02731-6

Cited by 7 publications

(1 citation statement)

References 9 publications

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“…4829 was isolated from the ascidian Styela plicata , collected from the South China Sea. Subsequent chemical investigation led to the isolation of a pair of novel N , N ′-ketal quinazolinone enantiomers, (±)-penicamide A [(−)- 1 and (+)- 1 ] and one new biogenetically related compound, penicamide B ( 2 ), along with six known compounds, 2-pyruvamidobenzamide ( 3 ) [11], ( S )-2-(2-hydroxypropanamido)benzamide ( 4 ) [12], pseurotin A( 5 ) [13], niacinamide ( 6 ) [14], citreohybridonol ( 7 ) [15], and citreohybriddione C ( 8 ) [16] (Figure 1). (±)-Penicamide A ( 1 ) is the first example of naturally occurring N , N ′-ketal quinazolinone possessing a unique tetracyclic system having 4-quinazolinone fused with tetrahydroisoquinoline.…”

Section: Introductionmentioning

confidence: 99%

Penicamide A, A Unique N,N′-Ketal Quinazolinone Alkaloid from Ascidian-Derived Fungus Penicillium sp. 4829

et al. 2019

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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.

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