• Journal of Ginseng Research
• /
• v.44 no.5
• /
• pp.673-679
• /
• 2020

Background: Panax notoginseng saponin (PNS) is the extraction from the roots and rhizomes of Panax notoginseng (Burk.) F. H. Chen. PNS is the main bioactive component of Xuesaitong, Xueshuantong, and other Chinese patent medicines, which are all bestselling prescriptions in China to treat cardiocerebrovascular diseases. Notoginsenoside R₁ and ginsenoside Rg₁, Rd, Re, and Rb₁ are the principal effective constituents of PNS, but a systematic research on the rare saponin compositions has not been conducted. Objective: The objective of this study was to conduct a systematic chemical study on PNS and establish the HPLC fingerprint of PNS to provide scientific evidence in quality control. In addition, the cytotoxicity of the new compounds was tested. Methods: Pure saponins from PNS were isolated by means of many chromatographic methods, and their structures were determined by extensive analyses of NMR and HR-ESI-MS studies. The fingerprint was established by HPLC-UV method. The cytotoxicity of the compounds was tested by 3-(4,5-dimethylthiazol-2-yl)-2,5 -diphenyltetrazolium bromide assay. Results and Conclusion: Three new triterpenoid saponins (1-3) together with 25 known rare saponins (4-28) were isolated from PNS, except for the five main compounds (notoginsenoside R1 and ginsenoside Rg1, Rd, Re, and Rb1). In addition, the HPLC fingerprint of PNS was established, and the peaks of the isolated compounds were marked. The study of chemical constituents and fingerprint was useful for the quality control of PNS. The study on antitumor activities showed that new Compound 2 exhibited significant inhibitory activity against the tested cell lines.

• Journal of Ginseng Research
• /
• v.41 no.3
• /
• pp.373-378
• /
• 2017

Ocotillol-type saponins are one kind of tetracyclic triterpenoids, sharing a tetrahydrofuran ring. Natural ocotillol-type saponins have been discovered in Panax quinquefolius L., Panax japonicus, Hana mina, and Vietnamese ginseng. In recent years, the semisynthesis of 20(S/R)-ocotillol-type saponins has been reported. The biological activities of ocotillol-type saponins include neuroprotective effect, antimyocardial ischemia, antiinflammatory, antibacterial, and antitumor activities. Owing to their chemical structure, pharmacological actions, and the stereoselective activity on antimyocardial ischemia, ocotillol-type saponins are subjected to extensive consideration. In this review, we sum up the discovery, semisynthesis, biological activities, and metabolism of ocotillol-type saponins.

• Journal of Ginseng Research
• /
• v.44 no.1
• /
• pp.14-23
• /
• 2020

Ginseng has been used as a popular herbal medicine in East Asia for at least two millennia. However, 20(R)-ginseng saponins, one class of important rare ginsenosides, are rare in natural products. 20(R)-ginseng saponins are generally prepared by chemical epimerization and microbial transformation from 20(S)-isomers. The C20 configuration of 20(R)-ginseng saponins are usually determined by ¹³C NMR and X-ray single-crystal diffraction. 20(R)-ginseng saponins have antitumor, antioxidative, antifatigue, neuroprotective, and osteoclastogenesis inhibitory effects, among others. Owing to the chemical structure and pharmacological and stereoselective properties, 20(R)-ginseng saponins have attracted a great deal of attention in recent years. In this study, the discovery, identification, chemical epimerization, microbial transformation, pharmacological activities, and metabolism of 20(R)-ginseng saponins are summarized.

• Asian-Australasian Journal of Animal Sciences
• /
• v.19 no.11
• /
• pp.1580-1587
• /
• 2006

Several researchers have demonstrated that the rumen microbial community rapidly adapts to saponins and proposed interval feeding to prevent this rapid adaptation. An in vivo experiment was carried out to examine the effect of daily versus application every third day (interval feeding) of Sapindus rarak saponins (SE) on rumen fermentation end products, protozoal counts and nutrient digestibility. Thirty sheep were allocated into 5 groups. Sheep were fed daily or every third day with two levels of SE (0.48 and 0.72 g/kg body mass). One group received no saponin and served as control. All sheep received the same diet, a mixture of elephant grass and wheat pollard (65:35 w/w). Independent of the feeding regime and the level of inclusion, the addition of SE decreased protozoal counts and rumen ammonia concentrations (p<0.01). Microbial N supply and N retention were not affected by the high feeding regime. Daily feeding negatively influenced rumen xylanase and cellulase activity, but only when the high level of saponins was fed. However, these negative effects on rumen cell wall degradation were not reflected in decreasing total tract digestibility of the organic matter or the plant cell walls. Our results show that rumen microorganisms do not rapidly adapt to S. rarak saponins.

• Biomolecules & Therapeutics
• /
• v.8 no.1
• /
• pp.32-37
• /
• 2000

Recently new soybean saponins with D DMP (2,5-dihydroxy-6-methyl-2,3,- dihydro-4H-pyran-4-one) moiety have been isolated from legumes. The purpose of this study is to characterize ROS scavenging activities of DDMP saponins ($\alpha$g, $\beta$g saponin) isolated from Glycine max (L.) Merrill. The scavenging activity on OH was examined in terms of lipid peroxidation in the rat liver homogenates and the same activity on $O_2$ was also determined in the xanthine-xanthine oxidase system, respectively. Up to 0.25 mg DDMP saponins ($\alpha$g and $\beta$g saponins) did not cause any significant effects on the prevention of lipid peroxidation as compared with the control group. In terms of superoxide scavenging activities, 0.25 and 0.5 mg $\alpha$g saponin inhibits only 2.6% and 5.5% (p<0.05) of the control group, respectively. However, $\alpha$g saponin dose-dependently (p<0.01, r=0.955) inhibits the formation of superoxide radical unto 21.3% of the control group with a maximal dose of 0.5 mg (p<0.01), equivalent to 0.17 units of superoxide dismutase activity.

• Proceedings of the Ginseng society Conference
• /
• 1993.09a
• /
• pp.206-214
• /
• 1993

Ginseng saponins have been known as main active principles and analyzed as the index components in ginseng and its products for quality control. But it is generally difficult to analyze the saponins in crude drug preparations. Saponins, Prosapogenins and sapogenins of crude drug preparation were identified by TLC and determined quantitatively by HPLC. $Prosapogemins-Rg_3\;-Rg_2\;and\;{\Delta}^{20}-prosapogenin$ were extracted with ethyl acetate from $50\%$ acetic acid hydrolyzates of saponin fractions and identified by TLC with lower phase of $CHCl_3/MeOH/H_2$ O\65:35:10. v/v)on silica gel plate, and quantified by HPLC on $Lichrosorb-NH_2$ column with $CH_3CN/H_2O(90:10,\;v/v).$ Sapogenins. panaxadiol and panaxatriol. were extracted with ethyl ether from $7\%-sulfuric$ acid hydrolyzates of saponin fractions and identified by TLC with chloroform/acetone(1 : 1 v/v) on silica gel plate. and quantified by HPLC on u - Bondapak $C^{18}$ column with $CH_3CN/MeOH/CHCl_3(83:10:7.\;v/v).$ These analyses of prosapogenins and sapogenins are more useful for quality control than those of saponins in crude drug preparations such as So - Shi - Ho - Tang(소시호탕), Sa - Kun - Ja - Tang(사군자탕), Yook - Kun - Ja - Tang(육군자탕), and In - Sam -Tang(인삼탕)

• Natural Product Sciences
• /
• v.14 no.1
• /
• pp.37-46
• /
• 2008

From the 70% EtOH extract of the roots of Astragalus membranaceus (Leguminosae), fifteen saponins were isolated and identified as astragaloside I (1), isoastragaloside II (2), astragaloside II (3), agroastragaloside I (4), cyclogaleginoside B (5), cycloaraloside A (6), brachyoside B (7), agroastragaloside II (8), astragaloside III (9), astragaloside IV (10), astramembranoside A (11), astramembranoside B (12), cylocanthoside E (13), cyclounifolioside B (14) and azukisaponin V methyl ester (15) by spectroscopic methods. Ten compounds 1 - 3, 5 - 7, 9 - 11 and 14 have cycloastragenol as an aglycon, and four compounds 4, 8 , 12, and 13 have cyclocanthogenin as an aglycon. The hairy roots of A. membranaceus were shown to produce previously unreported cycloartane-type saponins such as agroastragalosides I (4) and II (8) and cycloastragenol $3-O-{\beta}-D-xyloside$ (5), together with the known saponins. This is the first report of these saponins (4, 5, and 8) from the intact plant. Although the occurrence of the oleanane-type triterpene saponin, azukisaponin V methyl ester (15), in Astragalus plants has been demonstrated by others, this is the first report of the azukisaponin V methyl ester (15) from the Astragalus plants.

• Bulletin of the Korean Chemical Society
• /
• v.30 no.8
• /
• pp.1811-1816
• /
• 2009

An extensive phytochemical investigation of the polar fractions of a methanolic extract of Egyptian medicinal food, black cumin (seeds of Nigella sativa L.) led to the isolation of two new triterpene saponins, named sativosides A and B (1-2), along with four known saponins (3-6). Sativoside A (1) is the first example of saponins containing 18-ene triterpene aglycon not only in this Nigella genus but also in the family Ranunculaceae. The structure of the new saponins was elucidated mainly by a combination of 1D and 2D NMR data, together with HRFABMS and acid hydrolysis. Three compounds (1-3) showed the significant inhibition effect of phorbol 12-myristate 13-acetate (PMA) plus calcium ionophore A23187-induced production of IL-6 in a human mast cell (HMC-1) line.

• YAKHAK HOEJI
• /
• v.36 no.2
• /
• pp.129-136
• /
• 1992

The effects of ginseng saponins, gypsophila saponin, sodium dodecyl sulfate(SDS), and Triton X-100 on membrane $K^+-dependent$ phosphatase activity which is lipid dependent and represents dephosphorylation step of the complete Na+, $K^+-ATPase$ reaction were investigated in this study to elucidate whether the effects of ginseng saponins are due to the detergent action, using sarcolemma enriched preparation isolated from dog ventricle. $Na^+$, $K^+-ATPase$ and $K^+-dependent$ phosphatase activities of cardiac sarcolemma were about $143\;{\mu}mol$ Pi/mg protein/hr and $34\;{\mu}mol$ p-nitrophenol/mg protein/hr, respectively. While ginseng saponins (triol>total>diol) inhibited $K^+-dependent$ phosphatase activity, gypsophila saponin, and low dose of SDS($0.4\;{\mu}g/{\mu}g$ protein), and Triton X-100 ($0.6\;{\mu}g/{\mu}g$ protein) increased the enzyme activity, indicating disruptive effect of detergents on membrane barriers. The activating effect of low doses of Triton X-100 on membrane $K^+-dependent$ phosphatase appeared at concentration decreasing light scattering. However, the inhibitory effect of ginseng saponin appeared before a decrease in light scattering. These results suggest that low concentrations of ginseng saponins inhibit the membrane $K^+-dependent$ phosphatase by interacting directly with enzyme before membrane disruption.

• Archives of Pharmacal Research
• /
• v.12 no.1
• /
• pp.42-47
• /
• 1989

From the roots of Puisatiila koreana, three monodesmosides(pulsatilla saponins A, B and D) and two bisdesmosides(pulsatilla saponins F and H) were isolated. The structure of these saponins have been determined as hederagenin 3-O-${\beta}$-L-rhamnopyranosyl($1{\to}2$)- ${\alpha}$-L-arabinopyranoside(A), hederagenin 3-O-${\beta}$-D-glucopyrano syl($1{\to}4$) - ${\alpha}$-L-arabinopyranoside(B), hederagenin 3-O- ${\alpha}$-L-rhamnopyranosyl ($1{\to}2$)-[${\beta}$-D-glucopyranosyl($1{\to}4$]-${\alpha}$-L-arabinopyranoside(D), 3-O-${\alpha}$-L-rhamnopyranosyl($1{\to}2$)-{${\alpha}$-L-arabinopyranosyl hederagenin 28-O-${\alpha}$-L-rhamnopyrano syl($1{\to}4$)-${\beta}$-D-glucopyrano syl($1{\to}6$)-${\beta}$-D-glucopyranosyI ester (F) and 3-O-${\alpha}$-L-rhamnopyranosyl($1{\to}2$)-[${\beta}$-D-glucopyranosyl($1{\to}4$)]- ${\alpha}$-L-arabinopyranosyl hederagenin 28-O-${\alpha}$-L-lharnnopyranosyl($1{\to}4$)-${\beta}$-D-glucopyranosyl($1{\to}6$)-${\beta}$-D-glucop yranosyl ester(H) on the basis of chemical and spectral studies. Pulsatilla saponin B is the first report of its presence in plants but saponins A, D, F, and H have recently been isolated from the same genus p. cernua.