New 3-<i>O</i>-Alkyl-4a,10a-dihydrofusarubins Produced by <i>Fusarium</i> sp. Mj-2

Abstract

Five new 3-O-alkyl-4a,10a-dihydrofusarubins (2-6) were isolated from the culture filtrate of a strain of Fusarium sp. (Mj-2), together with the known metabolite, anhydrofusarubin (1). The structures of the new metabolites were elucidated by spectroscopic analyses to be 3-O-butyl, 3-O-3'-methylbutyl, 3-O-2'-methylbutyl and 3-O-2'-phenylethyl-4a,10a-dihydrofusarubin A, and an isomer of 3-O-2'-phenylethyl-4a,10a-dihydrofusarubin A. Their antifungal and antibacterial activities were evaluated together with a 3-O-methyl derivative (7) prepared from 3-O-butyl-4a,10a-dihydrofusarubin A (2), indicating that the size of the O-substituent at C-3 in the 4a,10a-dihydrofusarubins negatively affected the metabolites' antimicrobial activity.

Association between dipsacus saponin VI level and diversity of endophytic fungi in roots of Dipsacus asperoides

“…Many active pharmaceutical compounds have been isolated from filtrates of Fusarium sp. cultures (Suzuki et al 2013). The leptosins I and J have been isolated from Leptosphaeria mycelium (Takahashi et al 1994).…”

Pyranonaphthoquinones and Naphthoquinones from the Stem Bark of Ventilago harmandiana and Their Anti-HIV-1 Activity

“…These assignments were supported by the correlations of H-10a/C-1, C-4, C-4a, and C-5 as well as H-4a/C-10a, C-4, and C-5 in the HMBC experiments (Figure ). The magnitude of the vicinal coupling constant observed between H-4a and H-10a ( 3 J = 13.4 Hz) established a trans -diaxial relationship similar to those of dihydrofusarubin. − The relative configuration of compound 1 was also confirmed by NOESY experiments and led to the assignment of the relative configuration of compound 1 as shown in Figure . The NOESY correlations of H-1 and H-4a with H-3 suggested that they were oriented on the same face of the preferred chairlike conformation (Figure ).…”

“…The 4a,10a-dihydropyranonaphthoquinones are a unique class of compounds and are commonly found in fungi and related microorganisms. − Some of the 4a,10a-dihydropyranonaphthoquinones possessed potent biological activities, e.g., cytotoxicity and anti-HIV-1 and antibacterial activities. − Dihydrofusarubin, a 4a,10a-dihydropyranonaphthoquinone derivative, is a secondary metabolite obtained from various species of Fusarium and exhibited antifungal activity . From our exhaustive search (SciFinder Scholar database), this work is the first report on the isolation of 4a,10a-dihydropyranonaphthoquinone derivatives from plants in the Ventilago genus.…”

“…28−31 Dihydrofusarubin, a 4a,10a-dihydropyranonaphthoquinone derivative, is a secondary metabolite obtained from various species of Fusarium and exhibited antifungal activity. 20 From our exhaustive search (SciFinder Scholar database), this work is the first report on the isolation of 4a,10adihydropyranonaphthoquinone derivatives from plants in the Ventilago genus.…”

Anti-nemic secondary metabolites produced by Fusarium oxysporum f. sp. ciceris

“…Naphthoquinone and related metabolites are widely distributed in nature and have been found in various fungi. This class of compounds has attracted interest due to their broad range of biological action like insecticidal, antibacterial and fungicidal activity (Medentsev and Akimenko, 1998;Suzuki et al, 2013). Fusarium sp.…”