Details

Autor(en) / Beteiligte

• Hsu, Yu-Ming
• Wu, Tung-Ying
• Du, Ying-Chi
• El-Shazly, Mohamed
• Beerhues, Ludger
• Thang, Tran Dinh
• Van Luu, Hoang
• Hwang, Tsong-Long
• Chang, Fang-Rong
• Wu, Yang-Chang

Titel

3-Methyl-4,5-dihydro-oxepine, polyoxygenated seco-cyclohexenes and cyclohexenes from Uvaria flexuosa and their anti-inflammatory activity

Ist Teil von

• Phytochemistry (Oxford), 2016-02, Vol.122, p.184-192

Ort / Verlag

England: Elsevier Ltd

Erscheinungsjahr

2016

Quelle

MEDLINE

Beschreibungen/Notizen

• 3-Methyl-4,5-dihydro-oxepine (1), four polyoxygenated seco-cyclohexenes (2–5) and two polyoxygenated cyclohexenes (6–7), along with four known compounds, were isolated from Uvaria flexuosa. [Display omitted] •A rare 3-methyl-4,5-dihydro-oxepine derivative was isolated from Uvaria flexuosa.•Isolation of four seco-cyclohexenes with a characteristic skeleton from Uvaria sp.•Two cyclohexenes were isolated with promising antiinflammatory activity.•Benzyl alcohol benzoyl transferase is a key enzyme in the biosynthesis of these isolates. The phytochemical investigation of the methanolic extract of Uvaria flexuosa (Annonaceae) leaves led to the isolation of seven compounds including, 3-methyl-4,5-dihydro-oxepine (flexuvaroxepine A), four polyoxygenated seco-cyclohexene (flexuvarin A–D) and two polyoxygenated cyclohexene (flexuvarol A–B) derivatives, together with four known flavones. The structures of the isolated compounds were elucidated using different spectroscopic techniques. A plausible biogenetic route of the new compounds was discussed. The anti-inflammatory activity of the isolated compounds was evaluated by superoxide anion generation and elastase release assays. Among the tested compounds, flexuvarol B and chrysin showed the most potent anti-inflammatory effect by inhibiting superoxide anion generation and elastase release from human neutrophils in response to fMLP with IC50 2.25–5.55μM. Moreover, 5-hydroxy-6,7-dimethoxy-flavone showed selective inhibitory activity on superoxide anion generation (IC50=1.19±0.34μM).