Dammarane Saponins Research Articles

New Dammarane Saponins from the Steamed Ginseng Leaves

indicated the presence of partial structures written in bold lines; and in the HMBC spectrum, the long-range correlations were observed between the follow-ing protons and carbons: H-6 and C-8; H-12 and C-9,17; H-18 and C-7,9,14; H-19 and C-1,5,9; H-21 C-22; H-22C-17,24; H-24 and C-22,26; H-26 and C-24; H-27 and C-24; H-1' and C-6, respectively. Consequently, the structure of gin-senoside ST

Attenuation of Hepatic Oxidative Damages in Exhaustive Exercised Rats by Dammarane Saponins Supplementation

PURPOSE: Oxidative damage of proteins and lipids may further impair other cellular functions after exhaustive exercise. This study investigated the effect of different concentrations of Dammarane Saponins supplementation to cope the exhaustive exercise-induced oxidative damages in liver of rats. METHODS: Dammarane saponins (DS), exclusively extracted from ginseng were given to rats at different dosages (20, 60 and 120 mg/kg b.w.) for 2 months and treated as placebo, DS-20, DS-60 and DS-120 groups. Each group consists ten and five rats performed exhausted swimming exercise from each group. RESULTS: Glutathione (GSH), a foot marker of oxidative stress was dramatically decreased after exhausted exercise in placebo group, and the same was elevated in DS treated groups even after exercise. No significant changes in oxidized GSH (GSSG) levels were reported after exercise. In this study proteins and lipids peroxidation was clearly observed in exercised liver as shown as elevated protein carbonyls and MDA (malondialdehyde) levels respectively. However, we found that elevated protein and lipid peroxidation levels were attenuated in all DS pretreated groups after exercise. Furthermore, we also found significant (p <0.05) increase in xanthine oxidase (XO) activities after exercise in placebo groups. Whereas, XO activities were controlled in DS pretreated groups than placebo exercised rats, which indicates diminished free radical production. CONCLUSIONS: For the first time, we demonstrated that exhausted exercise-induced oxidative damage in liver was significantly reversed by DS pre-supplementation. This was evidenced by improved intracellular GSH status, controlled protein and lipids oxidation, and XO values. These results further suggest that DS as a nutritional supplement to athletes could be helpful to cope with the oxidative damages induced by exhaustive performance.

Dammarane Saponins Prevents the Loss of Antioxidant Enzyme in Liver after Exhausted Swimming

Dammarane Saponins Prevents the Loss of Antioxidant Enzyme in Liver after Exhausted Swimming

Dose-dependency of Dammarane Saponins on Blood Inflammatory and Oxidative Stress makers After Exhaustive Exercise

Dose-dependency of Dammarane Saponins on Blood Inflammatory and Oxidative Stress makers After Exhaustive Exercise

Three new triterpenoid saponins from the leaves and stems of Panax quinquefolium

Three new minor dammarane saponins, quinquenosides L10 (1), L14 (2), and L16 (3), were isolated from the leaves and stems of Panax quinquefolium L. By the combination of one- and two-dimensional NMR techniques and MS spectroscopic analysis, their structures were established as 20-O-(α-l-arabinopyranosyl-(1-6)-O-β-d-glucopyranosyl)-3-O-β-d-glucopyranosyl-dammar-24-ene-3,12, 20-triol (1), 20-O-α-l-arabinopyranosyl-3-O-(β-d-glucopyranosyl-(1-2)-O-β-d-glucopyranosyl)-dammar-24-ene-3,12,20-triol (2), 3-O-(β-d-glucopyranosyl-(1-2)-O-β-d-glucopyranosyl)-20-O-(β-d-glucopyranosyl-(1-6)-β-d-glucopyranosyl)-dammarane-3,12,20,24,25-pentaol (3). The content of artemisinin was significantly enhanced by 3.0 mg l− 1 of compounds 1, 2, and 3 in the callus of Artemisia annua.

Simultaneous determination of ginsenosides and polyacetylenes in American ginseng (Panax quinquefolium L.) using high-performance liquid chromatography

Panax quinquefolium L. (American ginseng) is native to North America, and is one of the most widely used medicinal herbs in the world together with other ginseng species. The alcoholic extract of ginseng roots has been widely used as a tonic against cancer, diabetes, cardiovascular disorders, and immune functions [1]. The active principles of ginseng roots appear to be polyacetylenes and dammarane saponins (ginsenosides), which are normally determined by different analytical methods. The aim of this study was to develop a method for simultaneous determination of both ginsenosides and polyacetylenes of P. quinquefolium roots.

Nine New Dammarane Saponins from Gynostemma pentaphyllum

Nine new dammarane saponins, 1-9, were isolated from the MeOH extract of the aerial part of Gynostemma pentaphyllum, an edible plant of the Cucurbitaceae family, that grows wildly in China. Their structures were elucidated by 1D- and 2D-NMR analysis, as well as by chemical degradation. Aglycons 21,24-cyclopentyldammar-25-ene of 6 and 7, and 21,24-cyclopentyldammarane of 8 and 9, were novel. Compounds 1, 4, and 8 showed moderate antitumor activities against stomach cancer cells SGC-7901 and liver cancer cells BEL-7402.

Phytochemical and analytical studies of Panax notoginseng (Burk.) F.H. Chen

Panax notoginseng (Burk.) F.H. Chen is distributed throughout the southwest of China, Burma and Nepal. The root of this plant, called notoginseng or sanchi, has a long history of use as a remedy in Oriental traditional medicine. Modern studies have found that extracts and compounds from notoginseng exert various physiological effects. The active constituents are mainly recognized as saponins. In this review, we summarized the discovery and analysis of chemical constituents in notoginseng. Fifty-six saponins from notoginseng were isolated and elucidated. All of them are dammarane saponins, 35 of which can be classified as belonging to the protopanaxadiols group, and 21 as belonging to the protopanaxatriols group. Evidence from phytochemical studies on notoginseng demonstrated that no oleanane-type saponin, which exists in Asian ginseng (Panax ginseng) and American ginseng (Panax quinquefolius), was found. Other types of compounds such as non-protein amino acids, polyacetylenes, phytosterols, flavonoids, and polysaccharides, many of which have pharmacological activities, were also isolated from notoginseng. Analytical studies on notoginseng were carried out based on botanical and phytochemical advances. In the qualitative studies, identification of the herbal materials and extracts was the main objective. The utilization of high-performance liquid chromatography (HPLC) fingerprint and molecular biological methods made the identification accurate and efficient. Spectral, chromatographic and immunoassay methods were used for the quantitative analysis. HPLC methods are the main authority regarding the determination of saponins and other types of constituents. The chromatographic conditions and detectors employed in the HPLC are discussed.

Chemistry and Pharmacology of Gynostemma pentaphyllum

In traditional Chinese medicine, Gynostemma pentaphyllum (Thunb.) Makino is a herbal drug of extreme versatility and has been extensively researched in China. The dammarane saponins isolated from Gynostemma pentaphyllum, namely gypenosides or gynosaponins, are believed to be the active components responsible for its various biological activities and reported clinical effects. This review attempts to encompass the available literature on Gynostemma pentaphyllum, from its cultivation to the isolation of its chemical entities and a summary of its diverse pharmacological properties attributed to its gypenoside content. Other aspects such as toxicology and pharmacokinetics are also discussed. In vitro and in vivo evidence suggests that Gynostemma pentaphyllum may complement the popular herbal medicine, Panax ginseng, as it also contains a high ginsenoside content and exhibits similar biological activities.

Isolation of dammarane saponins from Panax notoginseng by high-speed counter-current chromatography

The Chinese phytomedicinal formulation Sanqi Zongdai Pian, traditionally prepared from crude extracts from roots of Panax notoginseng (Araliaceae), contains highly polar dammarane saponins which were separated at a preparative scale using high-speed counter-current chromatography (HSCCC). In each operation, 283 mg methanolic extract of five tablets was separated and yielded pure 157, 17, 13 and 56 mg of ginsenoside-Rb 1, notoginsenoside-R 1, ginsenoside-Re and ginsenoside-Rg 1, respectively, n-hexane– n-butanol–water (3:4:7, v/v/v) was used for the two-phase solvent system of the HSCCC separation. The chemical structures of three ginsenosides and one notoginsenoside were elaborated by means of electrospray ionization MS–MS and NMR analysis.

Separation of Dammarane‐Saponins from Notoginseng, Root of Panax notoginseng (Burk.) F. H. Chen, by HSCCC Coupled with Evaporative Light Scattering Detector

High‐speed countercurrent chromatography (HSCCC) coupled with evaporative light scattering detection, was applied to the separation of saponins from notoginseng, the main root of Panax notoginseng (Burk.) F. H. Chen. Five individual dammarane saponins have been isolated with the solvent systems composed of CHCl3/MeOH/2‐BuOH/H2O (5:6:1:4, v/v/v/v) and EtOAc/1‐BuOH/H2O (1:1:2, v/v/v), successively. They were identified as ginsenoside‐Rg1, ginsenoside‐Rd, notoginsenoside‐R1, ginsenoside‐Re, and ginsenoside‐Rb1 by FAB‐MS and 13C NMR, together with HPLC and TLC analysis.

Quinquenoside L9 from Leaves and Stems of Panax Quinquefolium L

During additional chemical investigation on the saponin composition of leaves and stems of Panax quinquefolium L, a new minor dammarane saponin, quinquenoside L9 (1) has been obtained. By means of physico-chemical evidences and spectral analysis, its structure was elucidated as 6-O-[α-L-rhamnopyranosyl-(1–2)-β-D-glucopyranosyl]-dammara-3β,6β,12β,20(S),24ζ,25-hexaol (1).

A Pair of 24-hydroperoxyl Epimeric Dammarane Saponins from Flower-buds of Panax Ginseng

Further investigation on the saponins of the flower-buds of Panax ginseng C. A. Meyer has resulted in the isolation and structural elucidation of a pair of new 24-epimers of dammarane type saponins named ginsenoside I and II. The structures of the epimers were characterized on the basis of chemical and spectral evidence as 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosyl]-20-S-O-β-D-glucopyranosyl-3β12β20(S)-trihydroxy-24ξ-hydroperoxydammar-25-ene, except for their C-24 configurations. Ginsenoside I is a new triterpene glycoside, and ginsenoside II is a known compound first isolated from a natural plant.

Triterpenoid Saponins from Leaves and Stems of Panax Quinquefolium L

In the chemical investigation on the saponin composition of leaves and stems of Panax quinquefolium L., two new minor dammarane saponins, quinquenoside L1 (1) and L2 (2) have been isolated. By means of physico-chemical evidences and spectral analysis their structures were established as 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranosy-dammara-23,25-diene-3β, 12β, 20(S)-triol (1) and 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-D-glucopyranosyl-(24Z)-dammar-24-ene-3β, 12β, 20(S), 26-tetraol (2).

Saponins of plants of Panax species collected in Central Nepal, and their chemotaxonomical significance. III.

Panax pseudo-ginseng subsp. pseudo-ginseng has a carrot like root with a small rhizome. It was shown that the saponin composition of roots and rhizomes of this subspecies collected in Tibet and China was extremely poor. From the roots and rhizomes collected in Central Nepal, (specimen-PNct), only a small amount of an oleanolic acid saponin, beta-D-glucopyranosyl-oleanolate (2) was isolated together with a polyacetylene-alcohol, panaxynol (3). In another specimen (specimen-PNs), also collected in Central Nepal, two oleanolic acid saponins, stipleanoside R2 (4) and chikusetsusaponin IV (5) were detected. No dammarane saponin was identified in either specimen. P. pseudo-ginseng subsp. himalaicus (Subsp-H) has a big rhizome with a small round root. From rhizomes and roots of this subsp. collected in Central Nepal (specimen-HNct), a fairly large amount of dammarane saponins, ginsenosides-Rb1 (6), -Rd (7), -Re (9) and -Rg1 (10), gypenoside XVII (8), notoginsenoside-R1 (11), majonoside-R2 (12) and pseudo-ginsenoside-F11 (13) were isolated, while no oleanane saponin (oleanolic acid saponin) was identified in this subsp. Based on the present and previous studies, medicinal evaluation and chemogeographical correlation of Himalayan Panax spp. are discussed.

Dammarane saponins from Zizyphus lotus

Four dammarane-type saponins were isolated by means of centrifugal partition chromatography from the root bark of Zizyphus lotus. Their structures were elucidated using a combination of 1D and 2D 1H and 13C NMR spectra and mass spectroscopy. One of these glycosides is the known jujuboside A. The others are three new dammarane saponins, identified as 3-O-β- d-glucopyranosyl(1 → 6)-β- d-glucopyranosyl (1 → 3)-[α- l-rhamnopyranosyl(1 → 2)]-α- l-arabinopyranosyl jujubogenin = jujuboside C, 3-O-α- l-rhamnopyranosyl(1 → 2)-[β- d-glucopyranosyl(1 → 3)]-β- d-galactopyranosyl lotogenin = lotoside I, and 3-O-α- l-rhamnopyranosyl(1 → 2)-[β- d-glucopyranosyl(1 → 3)]-β- d-glucopyranosyl lotogenin = lotoside II. Lotogenin is a new dammarane derivative identified as (15 R, 16 R, 20 R, 22 R)-16 β,22-epoxydammar-24-ene-3β,15α,16α,20β-tetraol.

Minor dammarane saponins from Panax notoginseng

Further investigation of the roots of Panax notoginseng yielded two new minor dammarane saponins, notoginsenosides R 8 and R 9, whose structures were established by means of spectral evidence as (20 S)-dammar-22-ene-3 β, 6α, 12β, 20, 25-pentol 6-O-β- d-glucopyranoside and its (20 R)-epimer analogue, respectively.

Dammarane saponins from Panax ginseng

From the dried roots of Panax ginseng two new minor dammarane saponins named koryoginsenoside-R 1 and -R 2 were isolated, along with fourteen known saponins. On the basis of spectral and chemical evidence, the structures of the new saponins were elucidated as 6-O-[ trans butenoyl-(1 → 6)-β- d-glucopyranosyl ]-20-O-β- d-glucopyranosyl dammar-24-en-3β,6α,12β,20( S)-tetrol and 3-O-[β- d-glucopyranosyl-(1 → 2)-β- d-glucopyranosyl ]-20-O-[β- d-glucopyranosyl-(1 → 6)-β- d-glucopyranosyl ] dammar-22-en-3β,12β,20( S),-25-tetrol, respectively.

Antiviral Activity of Dammarane Saponins Against Herpes Simplex Virus I

AbstractTwo dammarane saponins, ginsenoside Rb1 (GRb1) and chikusetsusaponin III (Chi III), were investigated for antiviral activity against herpes simplex virus type I using an in vitro plaque elimination assay. Chi III prevented plaque formation at 50 μM, while GRb1 had no effect at 100 μM. Chi III was further examined for effects on virus yield and for cytotoxicity. The ID50 value for virus yield reduction was 29 μM, and cell growth was inhibited by 50% at 66 μM, indicating that Chi III exhibited marginal antiviral selectivity with a therapeutic index of about 2-fold. Although Chi III exhibited an in vitro virucidal effect with an ID50 value of 62 μM, drug treatment for 24 h reduced production of the cell-associated virus as well as the virus present in the medium, indicating Chi III has intracellular inhibitory activity. Intracellular levels of viral proteins were marginally affected at five hours post-infection, indicating Chi III has a minor impact on the early events of infection.

Saponins from Vietnamese ginseng, Panax vietnamensis Ha et Grushv. collected in central Vietnam. III.

Five new dammarane saponins derived from four new aglycones were isolated from the rhizomes and roots of Panax vietnamensis Ha et Grushv. On the basis of physicochemical and spectral evidence, the structures of these compounds were established as 6-O-beta-D-glucopyranosyl 20(S),25-epoxydammarane-3 beta,6 alpha,12 beta,24 alpha-tetrol (1), 6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranosyl 20(S),25-epoxydammarane-3 beta,6 alpha,12 beta,24 alpha-tetrol (2), 6-O-beta-D-glucopyranosyl dammarane-3 beta,6 alpha,12 beta,20(S),24 xi,25-hexol (5), 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-20-O-beta-D- glucopyranosyl dammarane-3 beta,12 beta,20(S),24 xi,25-pentol (8) and 6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranosyl 20(S),24(S)-epoxydammarane-3 beta,6 alpha,12 beta,25 xi,26-pentol (10). The trivial names, vina-ginsenoside-R10, -R11, -R12, -R13 and -R14, respectively, were assigned to the new saponins.