Trichothecrotocins A–C, Antiphytopathogenic Agents from Potato Endophytic Fungus Trichothecium crotocinigenum

Abstract

Two trichothecene sesquiterpenoids, trichothecrotocins A (1) and B (2), and a merosesquiterpenoid racemate, (±)-trichothecrotocin C (3), were obtained from potato endophytic fungus Trichothecium crotocinigenum by bioguided isolation. Their structures were elucidated by extensive spectroscopic methods, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Compounds 1 and 2 are trichothecenes possessing new ring systems. Compound 3 possesses a novel 6/6−5/5/5 fused ring system. Compounds 1−3 showed antiphytopathogenic activities with MIC values of 8−128 μg/ mL.

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

“…Two sesquiterpenoids derived from the trichodiene precursor, trichothecrotocin A ( 111 ) and B ( 112 ), were isolated from potato endophytic fungus Trichothecium crotocinigenum . Compounds 111 and 112 are unusual trichothecenes that showed potent inhibitory effects against Alternaria solani and Fusarium oxysporum [ 75 ].…”

“…The racemate mixture of (±)–trichothecrotocin C ( 130 ) was isolated from Trichothecium crotocinigenum, has a novel 6/6–5/5/5 fused ring system, showed potent inhibitory effects against Alternaria solani , Fusarium oxysporum, and weakly inhibited Phytophthora infestans and Rhizoctonia solani [ 75 ]. Peyronellins A–C ( 131 – 133 ) were isolated from Peyronellea coffeae-arabicae and represent unusual polyketide–sesquiterpene metabolites.…”

Progress on Terpenoids With Biological Activities Produced by Plant Endophytic Fungi in China Between 2017 and 2019

“…Two trichothecene sesquiterpenoids, trichothecrotocins A and B (110-111), and a merosesquiterpenoid racemate, (+)-trichothecrotocin C (112), were obtained from the potato endophytic fungus Trichothecium crotocinigenum by bioguided isolation. 49 Compounds 110 to 112 all showed potent inhibitory activities toward Alternaria solani and Fusarium oxysporum. 49 A pair of enantiomeric norsesquiterpenoids, (+)and (−)-preuisolactone A (113-114), featuring a tricyclo[4.4.0 1,6 .0 2,8 ]decane carbon scaffold were isolated from Preussia isomera XL-1326, an endophytic fungi from the stems of P. notoginseng.…”

“…49 Compounds 110 to 112 all showed potent inhibitory activities toward Alternaria solani and Fusarium oxysporum. 49 A pair of enantiomeric norsesquiterpenoids, (+)and (−)-preuisolactone A (113-114), featuring a tricyclo[4.4.0 1,6 .0 2,8 ]decane carbon scaffold were isolated from Preussia isomera XL-1326, an endophytic fungi from the stems of P. notoginseng. 50 Additionally, compounds 113 and 114 exhibited remarkable antibacterial activity against Micrococcus luteus with an MIC value of 10.2 µM.…”

3-Decalinoyltetramic acids from kiwi-associated fungus Zopfiella sp. and their antibacterial activity against Pseudomonas syringae

“…Our recent chemical investigations on endophytic fungi reported a number of bioactive secondary metabolites including terpenoids, cytochalasans, and epsidones. [4][5][6][7] Zopella sp. is an endophytic fungus that was isolated from kiwi plant (Actinidia chinensis Planch).…”