Anti-HIV activity of dibenzylbutyrolactone-type lignans from Phenax species endemic in Costa Rica.
Previously, we isolated two new dibenzylbutyrolactone-type lignans, named phenaxolactones and, from the leaves of Phenax angustifolius Wedd. (Urticaceae). In this investigation three new dibenzylbutyrolactone lignans (phenaxolactones), together with phenaxolactone, and flavones vitexin, isovitexin, were isolated from Phenax rugosus Wedd. leaves collected in Santa Ana, Costa Rica. The structures were elucidated using 1D and 2D NMR spectroscopy as well as mass spectrometry. Phenaxolactones and flavones and were evaluated for their inhibitory activity against HIV-1MN in infected C8166 cells. The most promising compound was phenaxolactone with an EC50 value of 3.0 microM, no cytotoxicity at 112 microM and a therapeutic index value of 37.3.
Piccinelli
A L
AL
Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano, Salerno, Italy.
Mahmood
N
N
Mora
G
G
Poveda
L
L
De Simone
F
F
Rastrelli
L
L
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D019380:Anti-HIV Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D047310:Apigenin / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods; D003364:Costa Rica / Q000208:ethnology; D000431:Ethanol / Q000302:isolation & purification / Q000494:pharmacology; D005843:Geography; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018515:Plant Leaves / Q000737:chemistry; D013329:Structure-Activity Relationship; D013678:Technology, Pharmaceutical / Q000379:methods; D027003:Urticaceae / Q000737:chemistry*
D019380:Anti-HIV Agents; D007783:Lactones; D017705:Lignans; D010936:Plant Extracts; C506849:phenaxolactone; D000431:Ethanol; D047310:Apigenin; C032731:vitexin; C049772:isovitexin; D015107:4-Butyrolactone