Medicinal Flowers. XVII. New Dammarane-Type Triterpene Glycosides from Flower Buds of American Ginseng, Panax quinquefolium L.

Abstract

The Araliaceae plant, Panax (P.) quinquefolium L., which is called as American ginseng or North American ginseng, is widely cultivated in U.S.A., Canada, and China. The roots of this plant are used for the same medicinal purposes as Ginseng, the roots of P. ginseng C. A. MEYER. The biologically active constituents of the roots have been pursued extensively and many dammarane-type triterpene oligoglycosides have been characterized as the principal ingredients.2-6) On the other hand, the flower buds of P. quinquefolium have been used as an exhilarant and tonic in the form of health tea. However, chemical and pharmacological studies on the bioactive constituents from the flower buds were yet left uncharacterized. Recently, we have reported the isolation and structure elucidation of dammarane-type triterpene oligoglycosides from the flower buds of P. ginseng 1,7,8) and P. notoginseng.9) Among them, ginsenoside Rd, which is principal constituent from the flower buds of P. ginseng, was found to show gastroprotective effect and ginsenosides-Rb 3 (6) and Rc, which are principal constituents from the flower buds of P. notoginseng, were found to show hepatoprotective effects. As a continuing study on the bioactive constituents of medicinal flowers, 1,[7][8][9][10][11][12][13][14][15] we have isolated new dammarane-type triterpene glycosides named floralquinquenosides A (1), B (2), C (3), D (4), and E (5) from the flower buds of P. quinquefolium together with 18 known dammarane-type triterpene oligoglycosides and three flavonoid glycosides. In this paper, we describe the isolation and structure elucidation of new floralquinquenosides (1-5).Isolation of Floralquinquenosides The methanolic extract from the flower buds of P. quinquefolium cultivated in Jilin province of China was partitioned into an ethyl acetate (EtOAc)-water mixture to furnish an EtOAc-soluble portion and an aqueous layer. The aqueous layer was further extracted with n-butanol (n-BuOH) to give an n-BuOH-soluble portion. The EtOAc-soluble fraction was subjected to normal-phase and reversed-phase silica gel column chromatography and finally HPLC to afford floralquinquenoside A (1, 0.0015% from the dried flower buds) together with 11 known compounds, ginsenoside Rb 3 (6,9,16) -rhamnopyranoside (26, 22) 0.0018%). The n-BuOH-soluble portion was subjected to normal-phase and reversed-phase silica gel column chromatography and finally HPLC to afford floralquinquenosides B (2, 0.0011%), C (3, 0.0036%), D (4, 0.0046%), and E (5, 0.0062%) together with 18 known compounds, ginsenoside Rb 3 (6, 9,16) 0.11%), ginsenoside Rd (7, 17) 0.23%), ginsenoside Rs 1 (8,18) 0.034%), pseudo-ginsenoside-RC 1 (9, 23) 0.0096%), pseudo-ginsenoside-F 8 (10, 18) 0.030%), quinquenoside III (11,2) (20,20) 0.0066%), pseudo-ginsenoside F 11 (21,20) 6.1%), 24(S)-pseudo-ginsenoside F 11 (22,20) 0.015%), and kaempferol 3-O-b-D-sophoroside-7-O-a-Lrhamnopyranoside (24, 27) 0.0042%).

Dammarane-Type Glycosides from the Steamed Flower-Buds of Panax ginseng

“…Subsequently, in continuation of our research on P. ginseng, 6,7 the present study on chemical components of the steamed flower-buds led to the isolation of one new damarane-type saponin, named ginsenoside SF (1) (Fig. 1), and nineteen known saponins (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) (Fig. 2), including ginsenoside Rh4 (2), 8 ginsenoside Rk3 (3), 8 ginsenoside F1 (4), 9 (20E)-ginsenoside F4 (5), 10 ginsenoside Rg2 (6), pseudoginsenoside RC1 (7), 4 ginsenoside Rg6 (8), 12 ginsenoside F4 (9), 12 ginsenoside Rg1 (10), 13 6'-acetyl-ginsenoside Rg1 (11), 14 ginsenoside Rd (12), 6 ginsenoside Rc (13), 6 ginsenoside Rb 2 (14), 6 ginsenoside Re (15), 6 vinaginsenoside R4 (16), 6 ginsenoside Mb (17), 15 ginsenoside Rb1 (18), 6 ginsenoside Rs4 (19), 16 and 6'-acetyl-ginsenoside F1 (20), 14 respectively, on the basis of NMR, ESI-MS data, and comparison with those reported in the literature.…”

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;

“…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. The 1-BuOH-and ethyl acetate (EtOAc)-soluble fractions exhibited inhibitory activities on rat lens aldose reductase and scavenging effects on 1,1-diphenylpicryl-2-hydrazyl (DPPH) radical and superoxide.…”

Preventive and Therapeutic Roles of Ginseng - Focus on Colon Cancer

“…It has been shown that ginsenosides are the most effective agents in the treatment and prevention of cancer in ginseng. More than 60 different types of ginseng have been identified (Nakamura et al, 2007;Qu et al, 2009). that are in different parts of the plant including roots, leaves and fruits.…”