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-[beta-D-xylopyranosyl(1 -> 2)] [-beta-D-glucopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (1a), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-glucopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (1b), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-galactopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (2a), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-galactopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (2b), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (3a), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (3b), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl protoaescigenin (4a), and 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl protoaescigenin (4b). The compounds showed cytotoxic activity on J-774, murinemonocyte/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 mu g/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. (C) 2012 Elsevier Ltd. All rights reserved.
Paviosides A-H, eight new oleane type saponins from Aesculus pavia with cytotoxic activity / Lanzotti, Virginia; Termolino, Pasquale; M., Dolci; P., Curir. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 20:(2012), pp. 3280-3286. [10.1016/j.bmc.2012.03.048]
Paviosides A-H, eight new oleane type saponins from Aesculus pavia with cytotoxic activity
LANZOTTI, VIRGINIA;TERMOLINO, PASQUALE;
2012
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-[beta-D-xylopyranosyl(1 -> 2)] [-beta-D-glucopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (1a), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-glucopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (1b), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-galactopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (2a), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-galactopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (2b), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (3a), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (3b), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl protoaescigenin (4a), and 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl protoaescigenin (4b). The compounds showed cytotoxic activity on J-774, murinemonocyte/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 mu g/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. (C) 2012 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
