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

Overview

Journal J Fungi (Basel)

Date 2022 Jan 20

PMID 35050002

Authors

Xuwen Hou

Xuping Zhang

Mengyao Xue

Zhitong Zhao

Huizhen Zhang

Dan Xu

Daowan Lai

Ligang Zhou

Affiliations

Soon will be listed here.

Abstract

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 , , , and , 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.

Citing Articles

Detoxification of Ustiloxin A Through Oxidative Deamination and Decarboxylation by Endophytic Fungus .

Li P, Gu G, Hou X, Xu D, Dai J, Kuang Y Toxins (Basel). 2025; 17(2).

PMID: 39998066 PMC: 11861864. DOI: 10.3390/toxins17020048.

Antifungal Natural Products Originating from Endophytic and Rhizospheric Microbes Isolated from Coastal Vegetation.

Jayaweera S, Van T, Dias D J Xenobiot. 2025; 15(1).

PMID: 39997375 PMC: 11856389. DOI: 10.3390/jox15010032.

Regulation of Histone Acetylation Modification on Biosynthesis of Secondary Metabolites in Fungi.

Hou X, Liu L, Li Y, Wang P, Pan X, Xu D Int J Mol Sci. 2025; 26(1.

PMID: 39795886 PMC: 11720177. DOI: 10.3390/ijms26010025.

Involvement of LaeA and Velvet Proteins in Regulating the Production of Mycotoxins and Other Fungal Secondary Metabolites.

Hou X, Liu L, Xu D, Lai D, Zhou L J Fungi (Basel). 2024; 10(8).

PMID: 39194887 PMC: 11355368. DOI: 10.3390/jof10080561.

Rice false smut pathogen: implications for mycotoxin contamination, current status, and future perspectives.

Zhou L, Mubeen M, Iftikhar Y, Zheng H, Zhang Z, Wen J Front Microbiol. 2024; 15:1344831.

PMID: 38585697 PMC: 10996400. DOI: 10.3389/fmicb.2024.1344831.

References

Chen G, Chu J . Characterization of Two Polyketide Synthases Involved in Sorbicillinoid Biosynthesis by Acremonium chrysogenum Using the CRISPR/Cas9 System. Appl Biochem Biotechnol. 2019; 188(4):1134-1144. DOI: 10.1007/s12010-019-02960-z. View

Supratman U, Suzuki T, Nakamura T, Yokoyama Y, Harneti D, Maharani R . New metabolites produced by endophyte B5 - 2. Nat Prod Res. 2019; 35(9):1525-1531. DOI: 10.1080/14786419.2019.1656629. View

Han P, Zhang X, Xu D, Zhang B, Lai D, Zhou L . Metabolites from Fungi and Their Biological Activities. J Fungi (Basel). 2020; 6(4). PMC: 7712584. DOI: 10.3390/jof6040229. View

Meng J, Zhao S, Dang P, Zhou Z, Lai D, Zhou L . Ustilaginoidin M, a new bis-naphtho-γ-pyrone from the fungus . Nat Prod Res. 2019; 35(9):1555-1560. DOI: 10.1080/14786419.2019.1652289. View

Fahad A, Abood A, Fisch K, Osipow A, Davison J, Avramovic M . Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis†Electronic supplementary information (ESI) available: Containing all experimental details. See DOI: 10.1039/c3sc52911hClick here for additional data file. Chem Sci. 2015; 5(2):523-527. PMC: 4285102. DOI: 10.1039/c3sc52911h. View

Abe N, Murata T, Hirota A . Novel DPPH Radical Scavengers, Bisorbicillinol and Demethyltrichodimerol, from a Fungus. Biosci Biotechnol Biochem. 2016; 62(4):661-6. DOI: 10.1271/bbb.62.661. View

Harned A, Volp K . The sorbicillinoid family of natural products: isolation, biosynthesis, and synthetic studies. Nat Prod Rep. 2011; 28(11):1790-810. DOI: 10.1039/c1np00039j. View

Monroy A, Stappler E, Schuster A, Sulyok M, Schmoll M . A CRE1- regulated cluster is responsible for light dependent production of dihydrotrichotetronin in Trichoderma reesei. PLoS One. 2017; 12(8):e0182530. PMC: 5557485. DOI: 10.1371/journal.pone.0182530. View

Lai D, Meng J, Xu D, Zhang X, Liang Y, Han Y . Determination of the absolute configurations of the stereogenic centers of ustilaginoidins by studying the biosynthetic monomers from a gene knockout mutant of Villosiclava virens. Sci Rep. 2019; 9(1):1855. PMC: 6372653. DOI: 10.1038/s41598-018-37941-5. View

10.

Guzman-Chavez F, Salo O, Nygard Y, Lankhorst P, Bovenberg R, Driessen A . Mechanism and regulation of sorbicillin biosynthesis by Penicillium chrysogenum. Microb Biotechnol. 2017; 10(4):958-968. PMC: 5481523. DOI: 10.1111/1751-7915.12736. View

11.

Wang A, Li P, Han P, Gu G, Shan T, Lai D . New nitrogen-containing metabolites from cultures of rice false smut pathogen . Nat Prod Res. 2019; 35(2):272-281. DOI: 10.1080/14786419.2019.1627354. View

12.

Yang Z, Qiao Y, Li J, Wu F, Lin F . Novel Type of Water-Soluble Photosensitizer from for Photodynamic Inactivation of Gram-Positive Bacteria. Langmuir. 2020; 36(44):13227-13235. DOI: 10.1021/acs.langmuir.0c02109. View

13.

Ramesh C, Vinithkumar N, Kirubagaran R, Venil C, Dufosse L . Multifaceted Applications of Microbial Pigments: Current Knowledge, Challenges and Future Directions for Public Health Implications. Microorganisms. 2019; 7(7). PMC: 6680428. DOI: 10.3390/microorganisms7070186. View

14.

McMullin D, Renaud J, Barasubiye T, Sumarah M, Miller J . Metabolites of Trichoderma species isolated from damp building materials. Can J Microbiol. 2017; 63(7):621-632. DOI: 10.1139/cjm-2017-0083. View

15.

Sun W, Dong X, Xu D, Meng J, Fu X, Wang X . Preparative Separation of Main Ustilaginoidins from Rice False Smut Balls by High-Speed Counter-Current Chromatography. Toxins (Basel). 2016; 8(1). PMC: 4728542. DOI: 10.3390/toxins8010020. View

16.

Lai D, Meng J, Zhang X, Xu D, Dai J, Zhou L . Ustilobisorbicillinol A, a Cytotoxic Sorbyl-Containing Aromatic Polyketide from Ustilaginoidea virens. Org Lett. 2019; 21(5):1311-1314. DOI: 10.1021/acs.orglett.8b04101. View

17.

Jiang C, Zhou Z, Yang X, Lan L, Gu Y, Ye B . Antibacterial sorbicillin and diketopiperazines from the endogenous fungus Penicillium sp. GD6 associated Chinese mangrove Bruguiera gymnorrhiza. Chin J Nat Med. 2018; 16(5):358-365. DOI: 10.1016/S1875-5364(18)30068-2. View

18.

Sun W, Wang A, Xu D, Wang W, Meng J, Dai J . New Ustilaginoidins from Rice False Smut Balls Caused by Villosiclava virens and Their Phytotoxic and Cytotoxic Activities. J Agric Food Chem. 2017; 65(25):5151-5160. DOI: 10.1021/acs.jafc.7b01791. View

19.

Ngo M, Nguyen M, Han J, Park M, Kim H, Choi G . In Vitro and In Vivo Antifungal Activity of Sorbicillinoids Produced by . J Fungi (Basel). 2021; 7(6). PMC: 8229967. DOI: 10.3390/jof7060428. View

20.

Li C, Lin F, Sun W, Yuan S, Zhou Z, Wu F . Constitutive hyperproduction of sorbicillinoids in ZC121. Biotechnol Biofuels. 2018; 11:291. PMC: 6202828. DOI: 10.1186/s13068-018-1296-4. View