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Deconins A–E: Cuparenic and Mevalonic or Propionic Acid Conjugates from the Basidiomycete Deconica sp. 471

Author:
Surup, Frank, Thongbai, Benjarong, Kuhnert, Eric, Sudarman, Enge, Hyde, Kevin D., Stadler, Marc
Source:
Journal of natural products 2015 v.78 no.4 pp. 934-938
ISSN:
1520-6025
Subject:
Basidiomycota, cytotoxicity, fractionation, mevalonic acid, new species, nuclear magnetic resonance spectroscopy, propionic acid, saponification, terpenoids, Thailand
Abstract:
Bioassay-guided fractionation of antibacterial extracts from cultures of a basidiomycete from Northern Thailand, which represents a new species of the genus Deconica, yielded the terpenoid deconin A (1), whose structure was elucidated by spectral methods (NMR, HRMS) as a cuparenic/mevalonic acid conjugate. The absolute configuration of 1 was determined after saponification and comparison of specific rotations of the resulting cuparenic acid and mevalonolactone with authentic standards and literature data. Six minor congeners (2–7) were isolated and identified, and their antimicrobial and cytotoxic effects are reported. Compounds 1–4 are the first natural products featuring an unmodified mevalonic acid residue as a building block.
Agid:
5498163