title: Paviosides A-H, eight new oleane type saponins from Aesculus pavia with cytotoxic activity.
abstract: A phytochemical analysis of Aesculus pavia has led to the isolation of eight novel triterpenoid saponins, based on oleane type skeleton and named paviosides A-H (1a, 1b-4a, 4b). On the basis of chemical, and 2D NMR and mass spectrometry data, the structures of the new compounds were elucidated as 3-O-[β-D-xylopyranosyl (1 → 2)] [-β-d-glucopyranosyl (1 → 4)]-β-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (1a), 3-O-[β-D-xylopyranosyl (1 → 2)] [-β-D-glucopyranosyl (1 → 4)]-β-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (1b), 3-O-[β-D-xylopyranosyl (1 → 2)] [-β-D-galactopyranosyl (1 → 4)]-β-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (2a), 3-O-[β-D-xylopyranosyl (1 → 2)] [-β-D-galactopyranosyl (1 → 4)]-β-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (2b), 3-O-[β-D-xylopyranosyl (1 → 2)] [-β-D-xylopyranosyl (1 → 4)]-β-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (3a), 3-O-[β-D-xylopyranosyl (1 → 2)] [-β-D-xylopyranosyl (1 → 4)]-β-d-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (3b), 3-O-[β-D-xylopyranosyl (1 → 2)] [-β-D-xylopyranosyl (1 → 4)]-β-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl protoaescigenin (4a), and 3-O-[β-D-xylopyranosyl (1 → 2)] [-β-D-xylopyranosyl (1 → 4)]-β-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl protoaescigenin (4b). The compounds showed cytotoxic activity on J-774, murine monocyte/macrophage, and WEHI-164, murine fibrosarcoma, cell lines. Among them, paviosides E-H (3a, 3b and 4a, 4b) showed higher activity with values ranging from 2.1 to 3.6 μg/mL. Structure-activity relationship studies indicated the positive effect on the activity of xylose unit in the place of glucose, while a little detrimental effect is observed when glucose is substituted by galactose. The aglycone structure and the presence of a tigloyl or an angeloyl group at C-21 do not affect significantly the inhibitory activity on both tested cell lines.
authors.affiliation: Dipartimento di Scienza degli Alimenti, Università di Napoli Federico II, Via Università 100, 80055 Portici, Napoli, Italy. lanzotti@unina.it
authors.forename: Virginia
authors.initials: V
authors.lastname: Lanzotti
authors.forename: Pasquale
authors.initials: P
authors.lastname: Termolino
authors.forename: Marcello
authors.initials: M
authors.lastname: Dolci
authors.forename: Paolo
authors.initials: P
authors.lastname: Curir
mesh_terms: D031319:Aesculus / Q000737:chemistry*; D000818:Animals; D002240:Carbohydrate Sequence; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects*; D005354:Fibrosarcoma / Q000188:drug therapy; D008264:Macrophages / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008969:Molecular Sequence Data; D009828:Oleanolic Acid / Q000737:chemistry / Q000633:toxicity; D035261:Plant Components, Aerial / Q000737:chemistry*; D010936:Plant Extracts / Q000633:toxicity*; D012503:Saponins / Q000737:chemistry* / Q000633:toxicity*
chemical_list: D010936:Plant Extracts; D012503:Saponins; D009828:Oleanolic Acid