Bipolarithizole A, an antifungal phenylthiazole-sativene merosesquiterpenoid from the potato endophytic fungus Bipolaris eleusines

Abstract

Bipolarithizole A (1) is a phenylthiazole-sativene sesquiterpenoid hybrid isolated from the fungus Bipolaris eleusines. It shows anti-pathogenic fungi activity against Rhizoctonia solani with an MIC value of 16 μg mL−1.

6-Exo-dig cyclization/dearomatization cascade towards N–O fused spiro polyheterocycles

“…Pathogenic fungi have been obstructing the progress of agriculture and forestry products. [41][42][43] Developing hypotoxic and efficient novel antifungal agents is still demanded. In view of the remarkable bioactivities of polyheterocycles, we subsequently launched the antifungal activity tests of N-O fused spiro polyheterocycles towards three crop pathogenic fungi and a forest pathogenic fungus employing boscalid as the positive control (Table 3).…”

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“…A biocatalytic [1,2]-Stevens rearrangement of aziridines to give azetidines has been developed using an evolved variant of cytochrome P450 BM3 (P411-AzetS). 27 Reaction of ethyl diazoacetate with carbamate protected aziridines allowed efficient, stereocontrolled one-carbon ring expansion, which could be performed on a preparative scale, generating gram quantities of product (Scheme 1).…”

“…Bipolarithizole A 2 is a metabolite of the potato-endophytic fungus Bipolaris eleusines and is the first example of a phenylthiazole linked to a sativene sesquiterpenoid. 2 Lycophlegmarinine A 3 , from Phlegmariurus phlegmaria , is a cleaved Lycodpodium alkaloid with a new ring system. 3 Massinidine 4 is an antiplasmodial metabolite of Massilia sp.…”

Bipodonines A–J, a new class of natural sesquiterpenes with a 2-(tetrahydro-2H-pyran-2-yl)propan-2-ol system from the fungus Bipolaris cynodontis DJWT-01

“…Bipolaris species are known to produce a wide array of bioactive metabolites including polyketide–terpenoids, 5 sesquiterpenes, 6 and sesterterpenes. 7 In our previous work, we characterized a series of bioactive compounds including sesterterpenoids with novel skeletons, 8 isoprenoid epoxycyclohexenone, 9 indole alkaloid, 10 and cytochalasin, 11 which were obtained from an endophytic fungus isolated from the Aconitum species.…”