Natural and Engineered Xylosyl Products from Microbial Source

Overview

Journal Nat Prod Bioprospect

Publisher Springer

Specialty Biology

Date 2024 Jan 31

PMID 38296905

Authors

Jianzhao Qi

Shi-Jie Kang

Ling Zhao

Jin-Ming Gao

Chengwei Liu

Affiliations

Soon will be listed here.

Abstract

Glycosylation is a prevalent post-modification found in natural products and has a significant impact on the structural diversity and activity variation of natural products. Glucosylation is the most common type of glycosylation, whereas xylosylation is relatively rare. Despite their unique chemical structures and beneficial activities, xylosylated natural products from microorganisms have received little attention. This review provides, for the first time, a comprehensive summary of 126 microbial-derived xylosylated natural products, including xylosyl-cyathane diterpenes, xylosylated triterpenes, xylosyl aromatic compounds, and others. Among these compounds, xylosyl-cyathane diterpenes represent the highest number of derivatives, followed by xylosylated triterpenes. Xylosyl compounds from bacterial sources have less defined structural profiles compared to those from fungi. The characterization of xylosyltransferase EriJ from Basidiomycota extended the structural diversity of xylosyl cyathane diterpenes. This work provides a valuable reference for the research and use of xylosyltransferase for drug discovery and synthetic chemistry. Further work is needed to explore the potential applications of microbial derived xylosyl compounds and to develop novel xylosyl transferases. With the deepening of genomic sequencing of medicinal fungi, more biosynthesis of bioactive xylosyl compounds is expected to be elucidated in the future.

References

Chen C, Tzeng T, Chen C, Ni C, Lee L, Chen W . Erinacine S, a Rare Sesterterpene from the Mycelia of Hericium erinaceus. J Nat Prod. 2016; 79(2):438-41. DOI: 10.1021/acs.jnatprod.5b00474. View

Kondo S, Gomi S, Uotani K, Inouye S, Takeuchi T . Isolation of new minor benanomicins. J Antibiot (Tokyo). 1991; 44(2):123-9. DOI: 10.7164/antibiotics.44.123. View

Kondo R, Yamagami H, Sakai K . Xylosylation of Phenolic Hydroxyl Groups of the Monomeric Lignin Model Compounds 4-Methylguaiacol and Vanillyl Alcohol by Coriolus versicolor. Appl Environ Microbiol. 1993; 59(2):438-41. PMC: 202124. DOI: 10.1128/aem.59.2.438-441.1993. View

Li X, Wang Y, Fan Z, Wang Y, Wang P, Yan X . High-level sustainable production of the characteristic protopanaxatriol-type saponins from Panax species in engineered Saccharomyces cerevisiae. Metab Eng. 2021; 66:87-97. DOI: 10.1016/j.ymben.2021.04.006. View

Dong W, Wang Z, Feng X, Zhang R, Shen D, Du S . Chromosome-Level Genome Sequences, Comparative Genomic Analyses, and Secondary-Metabolite Biosynthesis Evaluation of the Medicinal Edible Mushroom Laetiporus sulphureus. Microbiol Spectr. 2022; 10(5):e0243922. PMC: 9602373. DOI: 10.1128/spectrum.02439-22. View

Hundt K, Martin D, Hammer E, Jonas U, Kindermann M, Schauer F . Transformation of triclosan by Trametes versicolor and Pycnoporus cinnabarinus. Appl Environ Microbiol. 2000; 66(9):4157-60. PMC: 92278. DOI: 10.1128/AEM.66.9.4157-4160.2000. View

Galappaththi M, Patabendige N, Premarathne B, Hapuarachchi K, Tibpromma S, Dai D . A Review of Triterpenoids and Their Bioactivities. Biomolecules. 2023; 13(1). PMC: 9856212. DOI: 10.3390/biom13010024. View

He B, Bai X, Tan Y, Xie W, Feng Y, Yang G . Glycosyltransferases: Mining, engineering and applications in biosynthesis of glycosylated plant natural products. Synth Syst Biotechnol. 2022; 7(1):602-620. PMC: 8883072. DOI: 10.1016/j.synbio.2022.01.001. View

Hasegawa T, Kakushima M, Hatori M, Aburaki S, Kakinuma S, FURUMAI T . Pradimicins T1 and T2, new antifungal antibiotics produced by an actinomycete. II. Structures and biosynthesis. J Antibiot (Tokyo). 1993; 46(4):598-605. DOI: 10.7164/antibiotics.46.598. View

10.

Wei J, Ye M, Wang Z, Zhang Y, Hu X, Hui H . Molecular properties, structure, neurotrophic and anti-inflammatory activities of cultured secondary metabolites from the cultures of the mushroom CBPFE A06. Nat Prod Res. 2023; 38(23):4280-4285. DOI: 10.1080/14786419.2023.2273911. View

11.

Li K, Cai J, Su Z, Yang B, Liu Y, Zhou X . Glycosylated Natural Products From Marine Microbes. Front Chem. 2020; 7:879. PMC: 6965366. DOI: 10.3389/fchem.2019.00879. View

12.

Yoshikawa K, Inoue M, Matsumoto Y, Sakakibara C, Miyataka H, Matsumoto H . Lanostane triterpenoids and triterpene glycosides from the fruit body of Fomitopsis pinicola and their inhibitory activity against COX-1 and COX-2. J Nat Prod. 2005; 68(1):69-73. DOI: 10.1021/np040130b. View

13.

Wei J, Cheng M, Zhu J, Zhang Y, Cui K, Wang X . Comparative Genomic Analysis and Metabolic Potential Profiling of a Novel Culinary-Medicinal Mushroom, (Basidiomycota). J Fungi (Basel). 2023; 9(10). PMC: 10608310. DOI: 10.3390/jof9101018. View

14.

Ma K, Zhang Y, Guo C, Yang Y, Han J, Yu B . Reconstitution of biosynthetic pathway for mushroom-derived cyathane diterpenes in yeast and generation of new "non-natural" analogues. Acta Pharm Sin B. 2021; 11(9):2945-2956. PMC: 8463280. DOI: 10.1016/j.apsb.2021.04.014. View

15.

Lee E, Shizuki K, Hosokawa S, Suzuki M, Suganuma H, Inakuma T . Two novel diterpenoids, erinacines H and I from the mycelia of Hericium erinaceum. Biosci Biotechnol Biochem. 2001; 64(11):2402-5. DOI: 10.1271/bbb.64.2402. View

16.

Oki T, Saitoh K, Tomatsu K, Tomita K, Konishi M, Kawaguchi H . Novel antifungal antibiotic BMY-28567. Structural study and biological activities. Ann N Y Acad Sci. 1988; 544:184-7. DOI: 10.1111/j.1749-6632.1988.tb40402.x. View

17.

Wang X, Xie Q, Liu Y, Jiang S, Li W, Li B . and chikusetsusaponins: A review of diverse biological activities and pharmacology mechanism. Chin Herb Med. 2022; 13(1):64-77. PMC: 9476776. DOI: 10.1016/j.chmed.2020.12.003. View

18.

Fujimoto H, Hagiwara H, Suzuki K, Yamazaki M . New toxic metabolites from a mushroom, Hebeloma vinosophyllum. II. Isolation and structures of hebevinosides VI, VII, VIII, IX, X, and XI. Chem Pharm Bull (Tokyo). 1987; 35(6):2254-60. DOI: 10.1248/cpb.35.2254. View

19.

Lauer U, Anke T, Sheldrick W, Scherer A, Steglich W . Antibiotics from basidiomycetes. XXXI. Aleurodiscal: an antifungal sesterterpenoid from Aleurodiscus mirabilis (Berk. & Curt.) Höhn. J Antibiot (Tokyo). 1989; 42(6):875-82. DOI: 10.7164/antibiotics.42.875. View

20.

Kenmoku H, Shimai T, Toyomasu T, Kato N, Sassa T . Erinacine Q, a new erinacine from Hericium erinaceum, and its biosynthetic route to erinacine C in the basidiomycete. Biosci Biotechnol Biochem. 2002; 66(3):571-5. DOI: 10.1271/bbb.66.571. View