New Terpenoids from the Corticioid Fungus Punctularia atropurpurascens and their Antimycobacterial Evaluation^{[ # ]}

Abstract

Chemical investigation of Punctularia atropurpurascens strain HM1 (Punctulariaceae), a corticioid isolated from a decorticated piece of Quercus bark collected in Bosque de Tlalpan, Mexico City, led to the isolation of a new drimane, 1-α-hydroxy-isodrimenine (1) and a new tetrahydroxy kauranol, 16-hydroxy-phlebia-nor-kauranol (2), together with the known N-phenylacetamide (3). Structures of all compounds were elucidated by spectroscopic and spectrometric methods, and the absolute configuration of 1 and 2 was confirmed via single-crystal X-ray crystallography. The isolated compounds showed modest antimycobacterial activity.

Key words

Punctularia atropurpurascens - corticioid - drimane - nor-kaurane - antitubercular activity - Punctulariaceae

^# Dedicated to Professor Dr. A. Douglas Kinghorn on the occasion of his 75th birthday.

Publikationsverlauf

Eingereicht: 15. Dezember 2021

Angenommen nach Revision: 22. Februar 2022

Artikel online veröffentlicht:
30. März 2022

• References

• 1 Guan QH, Zhao W, Zhao ChL. A new species of Punctularia (Punctulariaceae, Basidiomycota) from southwest China. Phytotaxa 2021; 489: 285-292
• 2 Knijn A, Saar I, Ferretti A. Biological characteristics of Punctularia atropurpurascens through morphological and molecular analyses during development. Ital J Mycol 2019; 48: 39-49
• 3 Ginns J. Genera of the North American Corticiaceae sensu lato. Mycologia 1998; 90: 1-35
• 4 Anke H, Casser I, Steglich W, Pommer EH. Antibiotics from basidiomycetes. Phlebiakauranol aldehyde an antifungal and cytotoxic metabolite from Punctularia atropurpurascens . J Antibiotic 1987; 40: 443-449
• 5 Cali V, Spatafora C, Tringali C. Polyhydroxy-p-terphenyls and related p-terphenylquinones from fungi: Overview and biological properties. Stud. Nat Prod Chem 2003; 29 (part J): 263-307
• 6 Aparicio-Cuevas MA, González MDC, Raja HA, Rivero-Cruza I, Kurina JS, Burdette JE, Oberlies NH, Figueroa M. Metabolites from the marine-facultative Aspergillus sp. MEXU 27854 and Gymnoascus hyalinosporus MEXU 29901 from Caleta Bay, Mexico. Tetrahedron Lett 2019; 60: 1649-1652
• 7 Maurs M, Azerad R, Cortés M, Aranda G, Bertranne-Delahaye M, Ricard L. Microbial hydroxylation of natural drimenic lactones. Phytochemistry 1999; 52: 291-296
• 8 Lisy JM, Clardy J. X-Ray structures of phlebiakauranol and phlebianorkauranol, highly oxygenated antibacterial metabolites of Phlebia strigosozonata . J Chem Soc Chem Commun 1975; 406-407
• 9 Chen S, Yong T, Xiao C, Su J, Zhang Y, Jiao C, Xie Y. Pyrrole alkaloids and ergosterols from Grifola frondosa exert anti-α-glucosidase and anti-proliferative activities. J Funct Foods 2018; 43: 196-205
• 10 Wu HH, Tian L, Chen G, Xu N, Wang YN, Sun S, Pei YH. Six compounds from marine fungus Y26-02. J Asian Nat Prod Res 2009; 11: 748-751
• 11 Zou X, Liu S, Zheng Z, Zhang H, Chen X, Liu X, Li E. Two new imidazolone-containing alkaloids and further metabolites from the ascomycete fungus Tricladium sp. Chem Biodivers 2011; 8: 1914-1920
• 12 Cho S, Lee HS, Franzblau S. Microplate Alamar Blue Assay (MABA) and Low Oxygen Recovery Assay (LORA) for Mycobacterium tuberculosis . In: Parish T, Roberts DM. eds. Mycobacteria Protocols. New York, USA: Springer; 2015: 281-292
• 13 Wube AA, Bucar F, Gibbons S, Asres K. Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. Phytochemistry 2005; 66: 2309-2315
• 14 Clarkson C, Madikane EV, Hansen SH, Smith PJ, Jaroszewski JW. HPLC-SPE-NMR characterization of sesquiterpenes in an antimycobacterial fraction from Warburgia salutaris. Planta Med 2007; 73: 578-584
• 15 Maroyi A. The genus Warburgia: A review of its traditional uses and pharmacology. Pharm Biol 2014; 52: 378-391
• 16 Isaka M, Chinthanom P, Danwisetkanjana K, Choeyklin R. A new cryptoporic acid derivative from cultures of the basidiomycete Poria albocincta BCC 26244. Phytochem Lett 2014; 7: 97-100
• 17 Xu S, Li D, Pei L, Yao H, Wang C, Cai H, Yao H, Wu X, Xu J. Design, synthesis and antimycobacterial activity evaluation of natural oridonin derivatives. Bioorg Med Chem Lett 2014; 24: 2811-2814
• 18 Xu S, Pei L, Li D, Yao H, Cai H, Yao H, Wu X, Xu J. Synthesis and antimycobacterial evaluation of natural oridonin and its enmein-type derivatives. Fitoterapia 2014; 99: 300-306
• 19 Jang WS, Jyoti MA, Kim S, Nam KW, Ha TKQ, Oh WK, Song HY. In vitro antituberculosis activity of diterpenoids from the Vietnamese medicinal plant Croton tonkinensis . J Nat Med 2016; 70: 127-132
• 20 Raja HA, Miller AN, Pearce CJ, Oberlies NH. Fungal identification using molecular tools: A primer for the natural products research community. J Nat Prod 2017; 80: 756-770
• 21 Zhang D, Gao F, Jakovlić I, Zou H, Zhang J, Li WX, Wang GT. PhyloSuite: An integrated and scalable desktop platform for streamlined molecular sequence data management and evolutionary phylogenetics studies. Mol Ecol Resour 2020; 20: 348-435
• 22 CCDC 2128612 (1) and 2128613 (2) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at: www.ccdc.cam.ac.uk/data_request/cif (accessed March 14, 2022), or by emailing [e-mail]
• 23 Sheldrick GM. SHELXL-2018: Program for Crystal Structure Refinement. Göttingen, Germany: University of Göttingen; 2018. Accessed March 14, 2022 at: http://www.shelx.uni-goettingen.de/