Wortmannines A–C, three novel wortmannin derivatives with an unusual five-membered B ring from the endophytic fungus Talaromyces wortmannii LGT-4

Fu, Guang-Chao; Yang, Zhiwei; Zhou, Shuangyan; Li, Xinming; Yu, Hongwei; Yao, Xiaojun; Fang, Jianguo; Shu, Zong-Mei; Xue, Hongyan; Wang, Yonggang

doi:10.1016/j.tetlet.2016.09.004

Cited by 21 publications

(6 citation statements)

References 13 publications

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“…The culture of Talaromyces wortmanni resulted in the isolation of wortmannin scaffold derivatives, all of which possess an unusual five-membered B ring as in wortmannin A ( 134 ); wortmannin B ( 135 ) and C ( 136 ), additional to ring B, have a lactam and a lactone E-ring, respectively. Compounds 134 – 136 were evaluated for cytotoxicity but showed no activity [ 83 ]. Among compounds isolated from the culture of Guignardia sp., a series of structurally similar meroterpenoids to uncommon tricycloalternarenes ( 137 – 142 ) were characterized to be containing an additional tetrahydrofuran ring.…”

Section: Resultsmentioning

confidence: 99%

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Ortega

Torres-Mendoza

et al. 2021

JoF

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Among microorganisms, endophytic fungi are the least studied, but they have attracted attention due to their high biological diversity and ability to produce novel and bioactive secondary metabolites to protect their host plant against biotic and abiotic stress. These compounds belong to different structural classes, such as alkaloids, peptides, terpenoids, polyketides, and steroids, which could present significant biological activities that are useful for pharmacological or medical applications. Recent reviews on endophytic fungi have mainly focused on the production of novel bioactive compounds. Here, we focus on compounds produced by endophytic fungi, reported with uncommon bioactive structures, establishing the neighbor net and diversity of endophytic fungi. The review includes compounds published from January 2015 to December 2020 that were catalogued as unprecedented, rare, uncommon, or possessing novel structural skeletons from more than 39 different genera, with Aspergillus and Penicillium being the most mentioned. They were reported as displaying cytotoxic, antitumor, antimicrobial, antiviral, or anti-inflammatory activity. The solid culture, using rice as a carbon source, was the most common medium utilized in the fermentation process when this type of compound was isolated.

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Section: Resultsmentioning

confidence: 99%

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Ortega

Torres-Mendoza

et al. 2021

JoF

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“…Asterogynins A ( 66 ) and B ( 67 ) ( Figure 12 ), two unusual steroid-like metabolites with a tetracyclic carbocyclic ring system [ 95 ], were purified from the culture of Chalara alabamensis isolated from the host plant Asterogyne martiana [ 96 ]. More recently, four structurally related steroids, wortmannines A–C ( 68 – 70 , Figure 12 ) and secovironolide ( 71 , Figure 12 ) bearing an unusual five-membered B ring [ 97 , 98 ], were discovered from an endophytic fungus Talaromyces wortmannii living in Tripterygium wilfordii by the group of Yang.…”

Section: Isoprenoidsmentioning

confidence: 99%

Structural Diversity and Biological Activities of Novel Secondary Metabolites from Endophytes

Han

Lou

2018

Molecules

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Exploration of structurally novel natural products greatly facilitates the discovery of biologically active pharmacophores that are biologically validated starting points for the development of new drugs. Endophytes that colonize the internal tissues of plant species, have been proven to produce a large number of structurally diverse secondary metabolites. These molecules exhibit remarkable biological activities, including antimicrobial, anticancer, anti-inflammatory and antiviral properties, to name but a few. This review surveys the structurally diverse natural products with new carbon skeletons, unusual ring systems, or rare structural moieties that have been isolated from endophytes between 1996 and 2016. It covers their structures and bioactivities. Biosynthesis and/or total syntheses of some important compounds are also highlighted. Some novel secondary metabolites with marked biological activities might deserve more attention from chemists and biologists in further studies.

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“…2 Wortmannines A (1), B (2), and C (3) were isolated from the zeistic culture of Talaromyces wortmannii LGT-4 by Yang and co-workers in 2016. 3 Recently, structural analogues, such as wortmannines B1(4) and B3 ( 5), were discovered from the genus Niesslia (TTI-0426) by Gloer and co-workers. 4 Moreover, the unprecedented trans−anti−trans decahydro-1H-fluoren-9-ol (II) (Figure 1A) comprises the core skeleton of a family of complex molecules, isolated from different fungal sources in the past decades.…”

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confidence: 99%

“…For instance, the core cis -decahydro-9 H -fluoren-9-one ( I ) was found in a small group of steroid wortmannines (Figure B) . Wortmannines A ( 1 ), B ( 2 ), and C ( 3 ) were isolated from the zeistic culture of Talaromyces wortmannii LGT-4 by Yang and co-workers in 2016 . Recently, structural analogues, such as wortmannines B1( 4 ) and B3 ( 5 ), were discovered from the genus Niesslia (TTI-0426) by Gloer and co-workers …”

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confidence: 99%

Stereoselective Synthesis of the Core Structures of Pyrrocidines and Wortmannines through the Excited-State Nazarov Reactions

et al. 2021

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The reaction conditions and scope of the excitedstate Nazarov reaction of dicyclicvinyl ketones were studied. The stereochemistry of this electrocyclization is consistent with the mechanism of the pericyclic reaction and Woodward−Hoffmann rule. UV-light-promoted excited-state Nazarov reactions gave hydrofluorenones bearing a syn−cis configuration via a disrotatory cyclization. The core tricyclic hydrofluorenones of pyrrocidines and wortmannines were constructed via the excited-state Nazarov reactions, which demonstrated their synthetic potential in complex natural product total synthesis.

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Wortmannines A–C, three novel wortmannin derivatives with an unusual five-membered B ring from the endophytic fungus Talaromyces wortmannii LGT-4

Cited by 21 publications

References 13 publications

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Structurally Uncommon Secondary Metabolites Derived from Endophytic Fungi

Structural Diversity and Biological Activities of Novel Secondary Metabolites from Endophytes

Stereoselective Synthesis of the Core Structures of Pyrrocidines and Wortmannines through the Excited-State Nazarov Reactions

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