Triterpenoid saponins from the stem bark of Caryocar villosum.
Five triterpenoid saponins, caryocarosides II-22 (3), III-22 (4), II-23 (5), III-23 (6), and II-24 (7), have been isolated from the methanol extract of the stem bark of Caryocar villosum, along with two known saponins (1-2). The seven saponins are glucuronides of hederagenin (II) or bayogenin (III). Caryocaroside II-24 (7) is an unusual galloyl ester saponin acylated on the sugar chain attached to C-28, the 3-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl hederagenin-28-O-[2-O-galloyl-beta-D-glucopyranosyl] ester. The structures of the saponins were established on the basis of extensive NMR ((13)C, (1)H, COSY, TOCSY, HSQC, HMBC and ROESY) and ESI-MS studies. The cytotoxic activity of saponins 2 and 3 was evaluated in vitro against human keratinocytes. The DOPA-oxidase inhibition and the lipolytic activities were evaluated ex vivo using an explant of human adipose tissue.
Alabdul Magid
Abdulmagid
A
Laboratoire de Pharmacognosie, FRE CNRS 2715, IFR 53 Biomolécules, Bâtiment 18, BP 1039, 51687 Reims Cedex 2, France.
Voutquenne-Nazabadioko
Laurence
L
Renimel
Isabelle
I
Harakat
Dominique
D
Moretti
Christian
C
Lavaud
Catherine
C
D000273:Adipose Tissue / Q000187:drug effects / Q000378:metabolism; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D006801:Humans; D015603:Keratinocytes / Q000166:cytology / Q000187:drug effects; D008066:Lipolysis / Q000187:drug effects; D019684:Magnoliopsida / Q000737:chemistry*; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D018547:Plant Stems / Q000737:chemistry*; D012502:Sapogenins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D046509:Tissue Culture Techniques; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D010936:Plant Extracts; D012502:Sapogenins; D012503:Saponins; D014315:Triterpenes; D009828:Oleanolic Acid; C025763:hederagenin