New lignans from Anogeissus acuminata with HIV-1 reverse transcriptase inhibitory activity.
Anolignan A [1] and anolignan B [3] are new dibenzylbutadiene lignans isolated from Anogeissus acuminata. Compounds 1 and 3 were identified as the active HIV-1 reverse transcriptase (RT) inhibitory constituents of this plant obtained by bioassay-guided fractionation. Compound 3, which was very weakly active when tested alone, showed high activity when combined with 1. The activity of 1 was likewise enhanced in the presence of 3. A concave isobole obtained from a plot of data derived from assays with 1 and 3 in combination indicated their synergistic effects. Another new lignan, anolignan C [5], and a known lignan, (-)-secoisolariciresinol [10], were also isolated from this plant. Compounds 5 and 10 did not have activity against HIV-1 RT. Compounds 1, 3 and 5 were either weakly cytotoxic or noncytotoxic when tested in various cancer cell lines. The structures of 1-5 and 10 were established by spectroscopic methods, especially by 1D and 2D nmr experiments.
Rimando
A M
AM
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612.
Pezzuto
J M
JM
Farnsworth
N R
NR
Santisuk
T
T
Reutrakul
V
V
Kawanishi
K
K
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology; D000998:Antiviral Agents / Q000302:isolation & purification* / Q000494:pharmacology; D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D004354:Drug Screening Assays, Antitumor; D054303:HIV Reverse Transcriptase; D015497:HIV-1 / Q000187:drug effects* / Q000201:enzymology; D006801:Humans; D017705:Lignans / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D010944:Plants / Q000737:chemistry*; D018894:Reverse Transcriptase Inhibitors; D013785:Thailand; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D000998:Antiviral Agents; D017705:Lignans; D018894:Reverse Transcriptase Inhibitors; C090325:anolignan A; C090326:anolignan B; D054303:HIV Reverse Transcriptase