Secondary Metabolites from the Endolichenic Fungus

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 6

PMID 35520149

Authors

Yue-Lan Li

Rong-Xiu Zhu

Gang Li

Ning-Ning Wang

Chun-Yu Liu

Zun-Tian Zhao

Hong-Xiang Lou

Affiliations

Soon will be listed here.

Abstract

The isolation of the cytotoxic fractions from the endolichenic fungus yielded six new metabolites, including five polyketides (ophiofuranones A (1) and B (2), with unusual furopyran-3,4-dione-fused heterocyclic skeletons, ophiochromanone (3), ophiolactone (4), and ophioisocoumarin (5)), one sesquiterpenoid ophiokorrin (10), and nine known compounds. Their structures were established on the basis of the analysis of HRESIMS and NMR spectroscopic data. ECD calculations, GIAO NMR shift calculations and single-crystal X-ray diffraction were employed for the stereo-structure determination. A plausible biogenetic pathway for the ophiofuranones A (1) and B (2) was proposed. The cytotoxic assay suggested that the five known perylenequinones mainly contributed to the cytoxicity of the extract. Further phytotoxic studies indicated that ophiokorrin inhibited root elongation in the germination of with an IC value of 18.06 μg mL.

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References

Asai T, Tsukada K, Ise S, Shirata N, Hashimoto M, Fujii I . Use of a biosynthetic intermediate to explore the chemical diversity of pseudo-natural fungal polyketides. Nat Chem. 2015; 7(9):737-43. DOI: 10.1038/nchem.2308. View

Grimblat N, Zanardi M, Sarotti A . Beyond DP4: an Improved Probability for the Stereochemical Assignment of Isomeric Compounds using Quantum Chemical Calculations of NMR Shifts. J Org Chem. 2015; 80(24):12526-34. DOI: 10.1021/acs.joc.5b02396. View

Slade D, Ferreira D, Marais J . Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. Phytochemistry. 2005; 66(18):2177-215. DOI: 10.1016/j.phytochem.2005.02.002. View

Aquea F, Federici F, Moscoso C, Vega A, Jullian P, Haseloff J . A molecular framework for the inhibition of Arabidopsis root growth in response to boron toxicity. Plant Cell Environ. 2011; 35(4):719-34. DOI: 10.1111/j.1365-3040.2011.02446.x. View

Anke H, Casser I, Schrage M, Steglich W . Cyclogregatin, a new metabolite from Aspergillus panamensis. J Antibiot (Tokyo). 1988; 41(11):1681-4. DOI: 10.7164/antibiotics.41.1681. View

Xie F, Chang W, Zhang M, Li Y, Li W, Shi H . Quinone derivatives isolated from the endolichenic fungus Phialocephala fortinii are Mdr1 modulators that combat azole resistance in Candida albicans. Sci Rep. 2016; 6:33687. PMC: 5030645. DOI: 10.1038/srep33687. View

Singh B, Upreti D, Gupta V, Dai X, Jiang Y . Endolichenic Fungi: A Hidden Reservoir of Next Generation Biopharmaceuticals. Trends Biotechnol. 2017; 35(9):808-813. DOI: 10.1016/j.tibtech.2017.03.003. View

Stephens P, Harada N . ECD cotton effect approximated by the Gaussian curve and other methods. Chirality. 2009; 22(2):229-33. DOI: 10.1002/chir.20733. View

Oritani T, Kiyota H . Biosynthesis and metabolism of abscisic acid and related compounds. Nat Prod Rep. 2003; 20(4):414-25. DOI: 10.1039/b109859b. View

10.

Miteva M, Guyon F, Tuffery P . Frog2: Efficient 3D conformation ensemble generator for small compounds. Nucleic Acids Res. 2010; 38(Web Server issue):W622-7. PMC: 2896087. DOI: 10.1093/nar/gkq325. View

11.

Sarotti A . Structural revision of two unusual rhamnofolane diterpenes, curcusones I and J, by means of DFT calculations of NMR shifts and coupling constants. Org Biomol Chem. 2018; 16(6):944-950. DOI: 10.1039/c7ob02916k. View

12.

Gerea A, Branscum K, King J, You J, Powell D, Miller A . Secondary metabolites produced by fungi derived from a microbial mat encountered in an iron-rich natural spring. Tetrahedron Lett. 2012; 53(32):4202-4205. PMC: 3404852. DOI: 10.1016/j.tetlet.2012.05.156. View

13.

Li W, Gao W, Zhang M, Li Y, Li L, Li X . p-Terphenyl Derivatives from the Endolichenic Fungus Floricola striata. J Nat Prod. 2016; 79(9):2188-94. DOI: 10.1021/acs.jnatprod.6b00197. View

14.

Li Y, Zhu R, Zhang J, Xie F, Wang X, Xu K . Ophiosphaerellins A-I, Polyketide-Derived Compounds from the Endolichenic Fungus . ACS Omega. 2018; 3(1):176-180. PMC: 6045351. DOI: 10.1021/acsomega.7b01668. View

15.

Li G, Wang H, Zhu R, Sun L, Wang L, Li M . Phaeosphaerins A-F, cytotoxic perylenequinones from an endolichenic fungus, Phaeosphaeria sp. J Nat Prod. 2012; 75(2):142-7. DOI: 10.1021/np200614h. View

16.

Yin G, Wu Y, Yang M, Li T, Wang X, Zhou M . Citrifurans A-D, Four Dimeric Aromatic Polyketides with New Carbon Skeletons from the Fungus Aspergillus sp. Org Lett. 2017; 19(15):4058-4061. DOI: 10.1021/acs.orglett.7b01823. View

17.

Tayone W, Kanamaru S, Honma M, Tanaka K, Nehira T, Hashimoto M . Absolute stereochemistry of novel isochromanone derivatives from Leptosphaeria sp. KTC 727. Biosci Biotechnol Biochem. 2011; 75(12):2390-3. DOI: 10.1271/bbb.110621. View

18.

Zhou Y, Zhang M, Zhu R, Zhang J, Xie F, Li X . Heptaketides from an Endolichenic Fungus Biatriospora sp. and Their Antifungal Activity. J Nat Prod. 2016; 79(9):2149-57. DOI: 10.1021/acs.jnatprod.5b00998. View

19.

Song Y, Wang J, Li S, Cheng B, Li L, Chen B . Metabolites of the mangrove fungus Xylaria sp. BL321 from the South China Sea. Planta Med. 2011; 78(2):172-6. DOI: 10.1055/s-0031-1280347. View

20.

Li X, Li L, Zhu R, Li W, Chang W, Zhang L . Tetramic Acids and Pyridone Alkaloids from the Endolichenic Fungus Tolypocladium cylindrosporum. J Nat Prod. 2015; 78(9):2155-60. DOI: 10.1021/np501018w. View