Antiviral saponins from Tieghemella heckelii.
Arganine C (1) and a new saponin, tieghemelin (2), were isolated from Tieghemella heckelii fruits. Arganine C (1) strongly inhibited HIV entry into cells in a cell fusion assay. The less potent tieghemelin (2) was converted into arganine C (1) by reduction of its ethyl ester with sodium borohydride. The removal of the four-sugar chains from arganine C (1) and tieghemelin (2) to give 16alpha-hydroxyprotobassic acid 3-O-beta-D-glucopyranoside (3) and 16alpha-hydroxyprotobassic acid 3-O-beta-D-glucuronopyranoside (4), respectively, caused total loss of activity in both cases. Arganine C (1) was not significantly cytotoxic to HeLa-CD4(+) cells at the level required to reduce the syncytium count to zero, suggesting it to be a promising candidate for further study as an antiviral drug.
Gosse
Benjamin
B
Departement de Chemie, Institut National Polytechnique, Hoouphouet Boigny, BP 1083 Yamoyussokro, Ivory Coast.
Gnabre
John
J
Bates
Robert B
RB
Dicus
Christopher W
CW
Nakkiew
Pichaya
P
Huang
Ru Chih C
RC
D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015704:CD4 Antigens / Q000187:drug effects; D007560:Cote d'Ivoire; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005638:Fruit / Q000737:chemistry; D006678:HIV / Q000187:drug effects; D006367:HeLa Cells / Q000187:drug effects; D006801:Humans; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029632:Sapotaceae / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects
D019380:Anti-HIV Agents; D015704:CD4 Antigens; D012503:Saponins; C473293:arganine C; C473294:tieghemelin; D009828:Oleanolic Acid