Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata.
Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (1) and chalcone derivatives (2-6) from the methanol extract of Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (2), hydroxypanduratin A (3), helichrysetin (4), 2',4',6'-trihydroxyhydrochalcone (5), and uvangoletin (6). The structures of all compounds were elucidated on the basis of chemical and spectroscopic methods. It was found that 3 possessed the most potent anti-HIV-1 PR activity with an IC50 value of 5.6 microM, followed by 2 (IC50 = 18.7 microM), whereas other compounds exhibited only mild activity. Structure-activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4''' reduced activity; and (4) introduction of double bond at C1' and C6' of chalcone gave higher activity. As regards active constituents contained in B. pandurata rhizomes, hydroxypanduratin A (3) and panduratin A (2) are active principles against HIV-1 PR.
Cheenpracha
Sarot
S
Department of Chemistry, Faculty of Sciences, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.
Karalai
Chatchanok
C
Ponglimanont
Chanita
C
Subhadhirasakul
Sanan
S
Tewtrakul
Supinya
S
D047188:Chalcones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D016333:HIV Protease / Q000737:chemistry / Q000187:drug effects; D017320:HIV Protease Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015497:HIV-1 / Q000201:enzymology; D010936:Plant Extracts / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal; D013329:Structure-Activity Relationship; D030521:Zingiberaceae / Q000737:chemistry*
D047188:Chalcones; D017320:HIV Protease Inhibitors; D010936:Plant Extracts; C510460:panduratin C; D016333:HIV Protease