Medicinal Flowers. XIV.1) New Acylated Oleanane-Type Triterpene Oligoglycosides with Antiallergic Activity from Flower Buds of Chinese Tea Plant (Camellia sinensis)

Abstract

In the course of our characterization studies on the bioactive saponin constituents from Camellia (C.) sinensis (Theaceae), we have reported the isolation and structure elucidation of theasaponins A 1 -A 5 , C 1 , E 1 -E 13 , F 1 -F 3 , G 1 , G 2 , and H 1 , 2-6) assamsaponins A-I, 7,8) and camelliasaponins B 1 and C 1 9) from the seeds of Japanese C. sinensis (L.) O. KUNTZE and Sri Lankan C. sinensis L. var. assamica PERRE, and foliatheasaponins I-V 10) from the leaves of Japanese C. sinensis. Among the saponin constituents, theasaponin E 1 showed antisweet activity, 2) while theasaponins A 2 , E 1 , E 2 , and E 5 and assamsaponins A, C, and D were found to exhibit potent inhibitory effects on gastric lesions in rats. 4,5) In addition, floratheasaponins A-C (1-3) were isolated from the flower buds of Japanese C. sinensis and these acylated polyhydroxyoleanane-type triterpene oligoglycosides showed inhibitory effects on serum triglyceride elevation in olive oil-treated mice.11) As a continuation of our studies on bioactive constituents of medicinal flowers, 1,11-13) the methanolic extract of the flower buds of Chinese C. sinensis was found to inhibit an immediate allergic reaction by monitoring the release of b-hexosaminidase from rat basophilic leukemia (RBL-2H3) cells. From the methanolic extract, we have isolated six new acylated oleanane-type triterpene oligoglycosides, floratheasaponins D (4), E (5), F (6), G (7), H (8), and I (9), together with 21 known compounds including floratheasaponins A-C (1-3). Furthermore, we examined the inhibitory effects of principal floratheasaponins (1-6) on the release of b-hexosaminidase from RBL-2H3 cells. In this paper, we describe the isolation and structure elucidation of the new constituents (4-9) and the inhibitory effect of major floratheasaponins (1-6) from the flower buds of Chinese C. sinensis on the release of b-hexosaminidase from RBL-2H3 cells.14)The methanolic extract (38.5% from the dried flower buds of C. sinensis cultivated in Anhui province of China) with the inhibitory effect on the release of b-hexosaminidase from

Medicinal Flowers. XXXI. Acylated Oleanane-Type Triterpene Saponins, Sasanquasaponins I-V, with Antiallergic Activity from the Flower Buds of Camellia sasanqua

“…8,14) As a continuation of this study, we examined the effects of acylated oleanane-type triterpene saponins, sasanquasaponins, on the release of b-hexosaminidase from RBL-2H3 cells. As shown in Table 2, sasanquasaponins I-III (1-3) with the 22-acyl group were found to exhibit strong activities regardless of the structures of their acyl groups.…”

“…However, the pharmacological activities of the flower buds of this plant have not yet characterized. Recently, we have reported the isolation and structure elucidation of triterpene saponins from the flower buds of C. japonica L. (camelliosides A-D), 5,6) C. sinensis L. (chakasaponins I-VI, floratheasaponins A-J), [7][8][9][10][11][12] and C. oleifera ABEL (yuchasaponins A-D).…”

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 ].…”

“…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.…”