New Lignans from Anogeissus acuminata with HIV-1 Reverse Transcriptase Inhibitory Activity

• Published in: Journal of natural products (Washington, D.C.) Vol. 57; no. 7; pp. 896 - 904
• Main Authors: Rimando, Agnes M, Pezzuto, John M, Farnsworth, Norman R, Santisuk, Thawatchai, Reutrakul, Vichai, Kawanishi, Kazuko
• Format: Journal Article
• Language: English
• Published: CINCINNATI American Chemical Society 01.07.1994; AMER SOC PHARMACOGNOSY
• Subjects: AIDS/HIV; Animals; ANOGEISSUS; ANOGEISSUS ACUMINATA VAR. LANCEOLATA; ANOLIGNANS; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Antiviral Agents - isolation & purification; Antiviral Agents - pharmacology; CHEMICAL COMPOSITION; Chemistry, Medicinal; Chromatography, Gel; Chromatography, Thin Layer; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; CYTOTOXIC COMPOUNDS; DRUG PLANTS; Drug Screening Assays, Antitumor; ENZYME INHIBITORS; ESPECTROMETRIA; GENERO HUMANO; GENRE HUMAIN; HERPETOVIRIDAE; HIV Reverse Transcriptase; HIV-1 - drug effects; HIV-1 - enzymology; HUMAN IMMUNODEFICIENCY VIRUS; human immunodeficiency virus 1; Humans; INHIBIDORES DE ENZIMAS; INHIBITEUR D'ENZYME; Life Sciences & Biomedicine; Lignans - isolation & purification; Lignans - pharmacology; LIGNINAS; LIGNINE; LIGNINS; Magnetic Resonance Spectroscopy; MANKIND; MEDICINAL PLANTS; MEDICINAL PROPERTIES; Mice; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; Pharmacology & Pharmacy; Plant Sciences; PLANTAS MEDICINALES; PLANTE MEDICINALE; Plants - chemistry; PROPIEDADES MEDICINALES; PROPRIETE PHARMACOLOGIQUE; Reverse Transcriptase Inhibitors; Science & Technology; SPECTRAL ANALYSIS; SPECTROMETRIE; SPECTROMETRY; STEMS; SUBSTANCE TOXIQUE; SUSTANCIAS TOXICAS; TAILANDIA; TALLO; THAILAND; THAILANDE; TIGE; TOXIC SUBSTANCES; TRANSCRIPTION; Tumor Cells, Cultured; Thailand; NORNEOLIGNANS; NEOLIGNANS; SYNERGY
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np50109a004

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 rested in various cancer cell lines. The structures of 1-5 and 10 were established by spectroscopic methods, especially by 1D and 2D nmr experiments.