Diisoprenyl-cyclohexene/ane-Type Meroterpenoids from Biscogniauxia sp. and Their Anti-inflammatory Activities.
J Org Chem
; 86(16): 11177-11188, 2021 08 20.
Article
em En
| MEDLINE
| ID: mdl-34043349
ABSTRACT
A secondary metabolites investigation on Biscogniauxia sp. 71-10-1-1 was carried out, which led to the obtention of nine new diisoprenyl-cyclohexene/ane-type meroterpenoids (1-9) and two new isoprenylbenzoic acid-type meroterpeniods (10-11). The structures of these isolates were established on the basis of multispectroscopic analyses, ECD, and 13C chemical shifts calculations, and single-crystal X-ray diffraction. Among them, biscognin A (1) is the first diisoprenyl-cyclohexene-type meroterpenoid with a unique 2-isopropyl-6'-methyloctahydro-1'H-spiro[cyclopropane-1,2'-naphthalene] skeleton. Biscognienyne F (5) is the first diisoprenyl-cyclohexene-type meroterpenoid with a cyclic carbonate. The anti-inflammatory assays of the majority of compounds were evaluated, which exhibited that compounds 3 and 5 can obviously inhibit pro-inflammatory cytokines TNF-α and IL-6 productions. This is the first report for diisoprenyl-cyclohexene-type meroterpenoids with anti-inflammatory activity. Moreover, the possible biogenetic pathways of the majority of compounds (1-5) are proposed.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Terpenos
/
Cicloexenos
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2021
Tipo de documento:
Article