Anti-HIV-1 and anti-inflammatory lupanes from the leaves, twigs, and resin of Garcinia hanburyi.
Two new lupanes, 2 alpha-acetoxy-3 beta-hydroxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (2-acetoxyalphitolic acid) ( 1) and 2 alpha-hydroxy-3 beta-acetoxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (3-acetoxyalphitolic acid) ( 2), together with the known betulinic acid ( 3), betulin ( 4), and stimasterol-3- O- beta- D-glucopyranoside ( 5), were isolated from the leaves and twigs of GARCINIA HANBURYI. Compounds 1- 3 were also isolated from the resin of this plant. The structure of 2 was confirmed by single-crystal X-ray diffraction analysis. All of the lupanes ( 1- 4) displayed anti-HIV-1 activities in the anti-HIV-1 reverse transcriptase (IC (50) values 16.3-116.9 microg/mL) and syncytium assays (EC (50) 5.6-73.6 microg/mL, SI 1.7-3.3). Moreover compounds 1- 4 exhibited anti-inflammatory activity in an ethyl phenylpropiolate (EPP)-induced ear edema model.
Reutrakul
Vichai
V
Anantachoke
Natthinee
N
Pohmakotr
Manat
M
Jaipetch
Thaworn
T
Yoosook
Chalobon
C
Kasisit
Jittra
J
Napaswa
Chanita
C
Panthong
Ampai
A
Santisuk
Thawatchai
T
Prabpai
Samran
S
Kongsaeree
Palangpon
P
Tuchinda
Patoomratana
P
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D000998:Antiviral Agents / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D004195:Disease Models, Animal; D004487:Edema / Q000188:drug therapy*; D029760:Garcinia / Q000737:chemistry*; D015726:Giant Cells / Q000187:drug effects; D005960:Glucosides / Q000302:isolation & purification; D015497:HIV-1 / Q000187:drug effects*; D007249:Inflammation / Q000188:drug therapy; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D018515:Plant Leaves; D018547:Plant Stems; D012194:RNA-Directed DNA Polymerase / Q000378:metabolism; D012116:Resins, Plant; D013265:Stigmasterol / Q000031:analogs & derivatives / Q000302:isolation & purification; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology* / Q000627:therapeutic use; D014961:X-Ray Diffraction
D000893:Anti-Inflammatory Agents; D000998:Antiviral Agents; D005960:Glucosides; D010936:Plant Extracts; D012116:Resins, Plant; D014315:Triterpenes; C525613:stigmasterol 3-O-beta-D-glucopyranoside; D013265:Stigmasterol; D012194:RNA-Directed DNA Polymerase