Identification of a Novel Pyrrole Alkaloid from the Edible Mushroom Basidiomycetes-X (Echigoshirayukidake)

Abstract

Three pyrrole alkaloid derivatives were isolated from the edible mushroom Basidiomycetes-X (Echigoshirayukidake) by water extraction followed by ethyl acetate fractionation. The chemical structures determined by MS and NMR were 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid (compound I), 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanamide (compound II), and 5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde (compound III). Compound I was found to be the major component, followed by compound II, and compound III was the minor component. The dry powder of Basidiomycetes-X contained approximately 825 μg g−1 compound I and 484 μg g−1 compound II. Compound II was found to be a novel pyrrole aldehyde homologue not previously reported and thus is a specific component of this mushroom.

Mushrooms as a Resource for Mibyou-Care Functional Food; The Role of Basidiomycetes-X (Shirayukidake) and Its Major Components

“…The metabolome data suggest that the major polyphenolics in BDM-X are flavonoids, and not simple phenolic compounds. Moreover, antioxidant compounds such as ergothioneine and vitamin E, which are another group of antioxidant components found in edible mushrooms [35], were also not found in BDM-X by metabolomics and subsequent selective isolation studies [28,29]. Although the flavonoids listed above were not detected as a major ingredient in BDM-X through the isolation study, this wide variety of flavonoid distribution is unique and will significantly contribute not only to the antioxidant potential of BDM-X, but also to other physiological functions, which are both already cleared or yet to be uncovered.…”

“…Functional studies of BDM-X are currently progressing and have unveiled several physiological and pharmacological functions such as being anti-oxidative, anti-obesity and diabetic, and offering liver damage protection including NASH, as reviewed elsewhere [27]. The search for a functional component is also simultaneously being developed [28,29].…”

“…A further analysis of the specific components which may play significant roles in the beneficial health functions of BDM-X was carried out by solvent extraction following HPLC and TLC. The major components with UV absorption and/or DPPH radical scavenging activity were targeted for isolation, and the structures of purified compounds were assigned using mass spectrometry (MS) and nuclear magnetic resonance (NMR) [28,29]. From these studies, three types of formyl pyrrole alkaloids (FPA), ergosterol, (10E,12Z)-octadeca-10,12-dienoic acid ((10E,12Z)-CLA), 2,3-dihydro-3,5dihydroxy-6-methyl-4H-pyran-4-one (DDMP), and two nucleosides, adenosine and uridine, were determined as the major ingredients existing at relatively high amounts and showing high or moderate DPPH radical scavenging activities in BDM-X.…”

“…A further analysis of the specific components which may play significant roles in the beneficial health functions of BDM-X was carried out by solvent extraction following HPLC and TLC. The major components with UV absorption and/or DPPH radical scavenging activity were targeted for isolation, and the structures of purified compounds were assigned using mass spectrometry (MS) and nuclear magnetic resonance (NMR) [28,29]. From these studies, three types of formyl pyrrole alkaloids (FPA), ergoste- 1).…”

Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

“…Compounds 51 – 53 showed a poor cytotoxicity [ 42 ]. Compound 53 had been already isolated from the plant Lycium chinense [ 44 ] and successively from the mushroom Basidiomycetes-X [ 43 ]. Compound 53 showed a remarkable hepatoprotective activity, suggesting that the carboxylic group of this pyrrole plays an important role in this biological activity [ 44 ].…”