Structural Features of Herqueinone, a Red Pigment From Penicillium Herquei

Abstract

Isolation of a red pigment from P . herquei has been reported in an earlier paper (1). Further examination of this pigment and purification by adsorption chromatography has verified its homogeneity and the empirical formula CmHzoO,, although there remains the possibility of a slightly Merent ratio of hydrogen to carbon. Since the infrared spectrum of this pigment indicates the presence of a t least one carbonyl group, and since Burton (2) has applied the name, herquein, to a yellow acid also isolated from P . herqwi, the name herqueinone is proposed for the red pigment with a coppery lustre, which is the subject of the present study.The infrared spectrum of herqueinone, Fig. 1, shows a band at 3.1 p, characteristic of a hydrogen-bonded hydroxyl (3). For example, salicylaldehyde shows the band from the stretching vibration of the hydroxyl a t 3.05 p . The absence of absorption in the 5.5-6 p region and occurrence of a strong band at 6.1 p suggests carbonyl in an aromatic or quinonoid system which also contains hydroxyl. Among the few types of carbonyl compounds absorbing beyond 6 p are hydroxyphenyl aldehydes (3) and ketones (4), and 2-hydroxy-l14-naphthoquinones (5). Ettlinger (5) has noted that 2-hydroxy-1 , 4-naphthoquinones and their 3-alkyl derivatives are characterized by bands at 2.95-3.1 p, 5.98-6.08 p, and 6.23-6.3 p. The spectrum of herqueinone exhibits bands in each of these three regions; however, all efforts to secure carbonyl derivatives of herqueinone have been unsuccessful. The 1,2-naphthoquinones (5) show a shorter wavelength band, below 6 p, as do all types of y-and &lactones. Further indication of absence of a 1,2-quinone system is furnished by failure of herqueinone to react with o-phenylenediamine under conditions which yield a quinoxaline with

Phenalenones from a Marine-Derived Fungus Penicillium sp.

“…In addition to 1 – 6 , five previously reported phenalenones ( 7 – 11 ) were also isolated. Based on a combination of spectroscopic analyses and a literature survey, these compounds were identified as an acetone adduct of the triketone ( 7 ) [14], herqueinone ( 8 ) [3,17,18], isoherqueinone ( 9 ) [19,20], sclerodin ( 10 ) [14], and scleroderolide ( 11 ) [21]. The NMR data of these compounds were in good agreement with the reported values in the literature.…”

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

“…Extrolites : Species in ser. Herqueorum produce atrovenetin, herqueinone, herqueichrysin, peniciherqueinone, peniciphenalines, sclerodin, scleroderolide, sclerodione, sculenonone A & B, and xanthoherquein ( Stodola et al., 1951 , Galarraga et al., 1955 , Harman et al., 1955 , Barton et al., 1959 , Narasimhachari et al., 1963 , Narasimhachari and Vining, 1963 , Narasimhachari and Ramaswami, 1966 , Narasimhachari and Vining, 1972 , Simpson, 1976 , Robinson et al., 1992 , Trotter, 1992 , Tansakul et al., 2014 , Nishikori et al., 2016 , Li et al., 2018a ), herqulines ( Furusaki et al., 1980 , Enomoto et al., 1996 , Chiba et al., 2017 , Yang et al., 2018 ), neocyclocitrinol ( Marinho et al. 2009 ), peniciherquamides ( Nishikori et al.…”

Anti-hepatitis C Virus Natural Product from a Fungus, Penicillium herquei

“…In this study, we report the isolation, structural elucidation, and anti-HCV activities of new diazabicyclo[2.2.2]­octane derivatives, peniciherquamide A–C ( 1 – 3 ), and a novel herqueinone derivative, neoherqueinone ( 5 ). Additionally, the isolation and characterization of known compounds preparaherquamide ( 4 ), peniciherqueinone ( 6 ), and herqueinone/isoherqueinone ( 7 / 7a ) , are also described.…”