Elucidation of ustilaginoidin biosynthesis reveals a previously unrecognised class of ene-reductases

Xu, Dan; Yin, Ruya; Zhou, Zijiang; Gu, Gan; Zhao, Siji; Xu, Jin‐Rong; Liu, Junfeng; Peng, You-Liang; Lai, Daowan; Zhou, Ligang

doi:10.1039/d1sc02666f

Cited by 15 publications

(20 citation statements)

References 18 publications

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“…The PKS BGC is highly conserved in terms of both similarity and synteny to the UstP/UvPKS1 cluster of U. virens . The latter has been characterized for the biosynthesis of ustilaginoidins ( 13 , 14 ). The remaining clustered genes are conserved with mesosyntenic relationships to the intertwined-cluster members of A. fumigatus for the productions of fumagillin and pseurotin ( 3 ).…”

Section: Resultsmentioning

confidence: 99%

Orchestrated Biosynthesis of the Secondary Metabolite Cocktails Enables the Producing Fungus to Combat Diverse Bacteria

Sun

Chen

et al. 2022

mBio

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Section: Resultsmentioning

confidence: 99%

Orchestrated Biosynthesis of the Secondary Metabolite Cocktails Enables the Producing Fungus to Combat Diverse Bacteria

Sun

Chen

et al. 2022

mBio

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“…This provides a basis for fungal chemotaxonomy, which should be further studied in detail. It is worth mentioning that 21 sorbicillinoids were firstly isolated from the rice false smut pathogen Ustilaginoidea virens [14,19], which can produce many types of bioactive secondary metabolites [49][50][51][52][53][54][55][56][57][58]. Some sorbicillinoids exhibited cytotoxic (Table S4), antibacterial (Table S5), antifungal (Table S6), anti-inflammatory (Table S7), phytotoxic (Table S8), and α-glucosidase-inhibitory (Table S9) and PTP1B-inhibitory activities (Table S10).…”

Section: Discussionmentioning

confidence: 99%

“…It was isolated from a culture of Ustilaginoidea virens, the rice false smut pathogen [19]. Three other bisorbicillinoids, namely ustisorbicillinols C (57), D (58), and E (59), were also isolated from Ustilaginoidea virens. Both ustisorbicillinols C (57) and D ( 58) are epimeric to each other [14].…”

Section: Bisorbicillinoidsmentioning

confidence: 99%

Recent Advances in Sorbicillinoids from Fungi and Their Bioactivities (Covering 2016–2021)

Hou

Zhang

Xue

et al. 2022

JoF

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Sorbicillinoids are a family of hexaketide metabolites with a characteristic sorbyl side chain residue. Sixty-nine sorbicillinoids from fungi, newly identified from 2016 to 2021, are summarized in this review, including their structures and bioactivities. They are classified into monomeric, dimeric, trimeric, and hybrid sorbicillinoids according to their basic structural features, with the main groups comprising both monomeric and dimeric sorbicillinoids. Some of the identified sorbicillinoids have special structures such as ustilobisorbicillinol A, and sorbicillasins A and B. The majority of sorbicillinoids have been reported from fungi genera such as Acremonium, Penicillium, Trichoderma, and Ustilaginoidea, with some sorbicillinoids exhibiting cytotoxic, antimicrobial, anti-inflammatory, phytotoxic, and α-glucosidase inhibitory activities. In recent years, marine-derived, extremophilic, plant endophytic, and phytopathogenic fungi have emerged as important resources for diverse sorbicillinoids with unique skeletons. The recently revealed biological activities of sorbicillinoids discovered before 2016 are also described in this review.

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“…In addition to its negative impacts on rice yield and quality, U. virens can produce poisonous mycotoxins to threaten the health of humans and animals [ 11 , 12 , 13 ] and can also inhibit the radicle and plumule growth of plant seedlings [ 14 , 15 , 16 ]. Up to now, three main types of mycotoxins, including 7 ustiloxins [ 15 , 17 , 18 ], 27 ustilaginoidins [ 14 , 19 , 20 , 21 , 22 ], and 21 sorbicillinoids [ 16 , 23 ] have been identified in U. virens . These mycotoxins were screened to show cytotoxic, antimicrobial and phytotoxic activities [ 15 , 16 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

UvSorA and UvSorB Involved in Sorbicillinoid Biosynthesis Contribute to Fungal Development, Stress Response and Phytotoxicity in Ustilaginoidea virens

Zhang

Hou

et al. 2022

IJMS

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Ustilaginoidea virens (teleomorph: Villosiclava virens) is an important fungal pathogen that causes a devastating rice disease. It can produce mycotoxins including sorbicillinoids. The biosynthesis and biological functions of sorbicillinoids have not been reported in U. virens. In this study, we identified a sorbicillinoid biosynthetic gene cluster in which two polyketide synthase genes UvSorA and UvSorB were responsible for sorbicillinoid biosynthesis in U. virens. In ∆UvSorA and ∆UvSorB mutants, the mycelial growth, sporulation and hyphal hydrophobicity were increased dramatically, while the resistances to osmotic pressure, metal cations, and fungicides were reduced. Both phytotoxic activity of rice germinated seeds and cell wall integrity were also reduced. Furthermore, mycelia and cell walls of ∆UvSorA and ∆UvSorB mutants showed alterations of microscopic and submicroscopic structures. In addition, feeding experiment showed that sorbicillinoids could restore mycelial growth, sporulation, and cell wall integrity in ∆UvSorA and ∆UvSorB mutants. The results demonstrated that both UvSorA and UvSorB were responsible for sorbicillinoid biosynthesis in U. virens, and contributed to development (mycelial growth, sporulation, and cell wall integrity), stress responses, and phytotoxicity through sorbicillinoid mediation. It provides an insight into further investigation of biological functions and biosynthesis of sorbicillinoids.

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Elucidation of ustilaginoidin biosynthesis reveals a previously unrecognised class of ene-reductases

Abstract: The 2,3-double bond reduction of the pyrenone ring in linear naphtho-γ-pyrenones was catalyzed by a phospholipid methyltransferase-like enzyme, namely UsgR, which is a previously unrecognised class of ene-reductases.

Cited by 15 publications

References 18 publications

Orchestrated Biosynthesis of the Secondary Metabolite Cocktails Enables the Producing Fungus to Combat Diverse Bacteria

Orchestrated Biosynthesis of the Secondary Metabolite Cocktails Enables the Producing Fungus to Combat Diverse Bacteria

Recent Advances in Sorbicillinoids from Fungi and Their Bioactivities (Covering 2016–2021)

UvSorA and UvSorB Involved in Sorbicillinoid Biosynthesis Contribute to Fungal Development, Stress Response and Phytotoxicity in Ustilaginoidea virens

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