Identification of ent-16 beta, 17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa.
Phytochemical analysis of the fruits of Annona squamosa yielded 12 known kaurane derivatives (1-11, 13) and two new kaurane diterpenoids, which have been named annosquamosin A (16 beta-hydroxy-17-acetoxy-ent-kauran-19-al) (12) and annosquamosin B (19-nor-ent-kaurane-4 alpha,16 beta,-17-triol) (14). The structures of the new compounds were established by spectral analyses and chemical evidence. Among these 14 compounds, 16 beta, 17-dihydroxy-ent-kauran-19-oic acid (2) showed significant activity against HIV replication in H9 lymphocyte cells with an EC50 value of 0.8 microgram/mL (therapeutic index > 5).
Wu
Y C
YC
Graduate Institute of Natural Products, Kaohsiung Medical College, Taiwan, Republic of China.
Hung
Y C
YC
Chang
F R
FR
Cosentino
M
M
Wang
H K
HK
Lee
K H
KH
D000998:Antiviral Agents / Q000302:isolation & purification* / Q000494:pharmacology; D004224:Diterpenes / Q000302:isolation & purification* / Q000494:pharmacology; D045786:Diterpenes, Kaurane; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D008214:Lymphocytes / Q000821:virology; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry*; D014779:Virus Replication / Q000187:drug effects
D000998:Antiviral Agents; D004224:Diterpenes; D045786:Diterpenes, Kaurane; C100908:annosquamosin A; C100909:annosquamosin B