Floratheasaponins A−C, Acylated Oleanane-Type Triterpene Oligoglycosides with Anti-hyperlipidemic Activities from Flowers of the Tea Plant (Camellia sinensis)

Abstract

The methanolic extract and its n-butanol-soluble fraction from the flowers of the tea plant (Camellia sinensis) were found to suppress serum triglyceride elevation in olive oil-treated mice. From the n-butanol-soluble fraction, three new acylated oleanane-type triterpene oligoglycosides, floratheasaponins A-C (1-3), were isolated together with several flavonol glycosides and catechins. The structures of 1-3 were elucidated on the basis of chemical and physicochemical evidence as 21-O-angeloyl-22-O-acetyltheasapogenol B 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, 21,22-di-O-angeloyl-R1-barrigenol 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, and 21-O-angeloyl-22-O-2-methylbutyryl-R1-barrigenol 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, respectively. Floratheasaponins (1-3) showed inhibitory effects on serum triglyceride elevation, with their activities being more potent than those of theasaponins E1 (4) and E2 (5) obtained previously from the seeds of C. sinensis.

Medicinal Flowers. XXVI. Structures of Acylated Oleanane-Type Triterpene Oligoglycosides, Yuchasaponins A, B, C, and D, from the Flower Buds of <i>Camellia oleifera</i>&mdash;Gastroprotective, Aldose Reductase Inhibitory, and Radical Scavenging Effects&mdash;

“…Isolation of Yuchasaponins The 1-BuOH-soluble fraction was subjected to ordinary-and reversed-phase silica gel column chromatographies and finally HPLC to furnish yuchasaponins A (1, 0.00012%), B (2, 0.00006%), C (3, 0.00006%), and D (4, 0.00010%) together with jegosaponin 5,6,29) and four mucosaccharides, D-galactose, Dglucose, D-glucuronic acid, and L-rhamnose, which were identified by GLC analysis of their trimethylsilyl thiazolidine derivatives. [30][31][32] The 1 H-(pyridine-d 5 ) and 13 C-NMR (Table 5) spectra of 1, which were assigned by various NMR experiments, 33) showed signals assignable to a R ].…”

“…yuchasaponin A was determined to be 21 34) and tiglic acid, which was identified by HPLC. [26][27][28] Acid hydrolysis of 2a with 5% aqueous H 2 SO 4 in 1,4-dioxane [1 : 1 (v/v)] liberated barringtogenol C (2b) 35) and four mucosaccharides (D-galactose, Dglucose, D-glucuronic acid, and L-rhamnose), which were identified by GLC. [30][31][32] The 1 H-(pyridine-d 5 ) and 13 C-NMR (Table 5) …”

“…Alkaline hydrolysis of 3, and 4 furnished desacyl-derivatives (3a, 4a) and tiglic acid, which was identified by HPLC. [26][27][28] On the acid hydrolysis, 3a and 4a liberated 1b (from 3a) and 2b (from 4a) together with D-galactose, D-glucuronic acid, and L-rhamnose, which were identified by GLC. [30][31][32] The 1 H-(pyridined 5 ) and 13 C-NMR (Table 5) Next, we examined the gastroprotective effects of the principal constituents (6, 7, 8, gallic acid) from the flower buds of C. oleifera and the flavonoid constituents (6, 7) were found to show moderate activities as shown in Table 6.…”

“…However, the chemical constituents and biological activities of the flower buds of this plant have not yet characterized. Recently, we have reported the isolation and structure elucidation of acylated polyhydroxyoleanane-type triterpene oligoglycosides from the flower buds of C. sinensis 1,[5][6][7][8][9] and C. japonica. 10,11) Furthermore, those oligoglycosides were found to exhibit antiallergic, 6) antidiabetic, 7) antiobesitic, 5,8) gastroprotective, 7,10,11) and platelet aggregation 10,11) activities.…”

“…Recently, we have reported the isolation and structure elucidation of acylated polyhydroxyoleanane-type triterpene oligoglycosides from the flower buds of C. sinensis 1,[5][6][7][8][9] and C. japonica. 10,11) Furthermore, those oligoglycosides were found to exhibit antiallergic, 6) antidiabetic, 7) antiobesitic, 5,8) gastroprotective, 7,10,11) and platelet aggregation 10,11) activities. In the course of our characterization studies on Camellia speicies [12][13][14][15] and medicinal flowers, [16][17][18][19][20][21] we found that the methanolic (MeOH) extract and its 1-butanol (1-BuOH)-soluble fraction from the flower buds of C. oleifera showed gastroprotective effects on ethanol-or indomethacin-induced gastric mucosal lesions in rats.…”