Dammarane-type Triterpene Saponins Research Articles

Two new triterpene saponins from Gynostemma pentaphyllum

Two new dammarane-type triterpene saponins, gypenbiosides A (1) and B (2), were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Their structural elucidations were accomplished mainly on the basis of the interrelation of spectroscopic methods, such as IR, HR-TOF-MS, and NMR. The cytotoxic activity was evaluated against one human cancer cell line HL-60 using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.

New triterpenoids from the stems and leaves of Panax ginseng

Three new dammarane-type triterpene saponins ginsenosides Rh18 (1), Rh19 (3) and Rh20 (4), along with two new triterpene sapogenins 12β,23(R)-epoxydammara-24-ene-3β,6α,20(S)-triol (2) and dammara-(20E)22,25-diene-3β,6α,12β,24S-tetrol (5) were isolated from the stems and leaves of Panax ginseng C. A. Mey. Their structures were elucidated on the basis of spectral evidence and comparisons with literature data.

A new triterpenoid saponin from Gynostemma pentaphyllum

A new dammarane-type triterpene saponin was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Its structural elucidation was accomplished mainly on the basis of the interpretation of spectroscopic data, such as IR, HR–TOF–MS and NMR. Its cytotoxic activity was evaluated against one human cancer cell line HL-60 using MTT assay.

Acylated Protopanaxadiol‐Type Ginsenosides from the Root of Panax ginseng

Six new protopanaxadiol-type ginsenosides, named ginsenosides Ra(4) -Ra(9) (1-6, resp.), along with 14 known dammarane-type triterpene saponins, were isolated from the root of Panax ginseng, one of the most important Chinese medicinal herbs. The structures of the new compounds were determined by spectroscopic methods, including 1D- and 2D-NMR, HR-MS, and chemical transformation as (20S)- 3-O-{β-D-6-O-[(E)-but-2-enoyl]glucopyranosyl-(1→2)-β-D-glucopyranosyl}-20-O-[β-D-xylopyranosyl-(1→4)-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]protopanaxadiol (1), (20S)-3-O-[β-D-6-O-acetylglucopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-[β-D-xylopyranosyl-(1→4)-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]protopanaxadiol (2), (20S)-3-O-{β-D-6-O-[(E)-but-2-enoyl]glucopyranosyl-(1→2)-β-D-glucopyranosyl}-20-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]protopanaxadiol (3), (20S)-3-O-{β-D-6-O-[(E)-but-2-enoyl]glucopyranosyl-(1→2)-β-D-glucopyranosyl}-20-O-[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]protopanaxadiol (4), (20S)-3-O-{β-D-4-O-[(E)-but-2-enoyl]glucopyranosyl-(1→2)-β-D-glucopyranosyl}-20-O-[α-L-arabinofuranosyl-(1→6)-β-D-glucopyranosyl]protopanaxadiol (5), (20S)-3-O-{β-D-6-O-[(E)-but-2-enoyl]glucopyranosyl-(1→2)-β-D-glucopyranosyl}-20-O-[α-L-arabinofuranosyl-(1→6)-β-D-glucopyranosyl]protopanaxadiol (6). The sugar moiety at C(3) of the aglycone of each new ginsenoside is butenoylated or acetylated.

Two new dammarane-type triterpene saponins from red American ginseng

Two new dammarane-type triterpene saponins were isolated from the red American ginseng. The new saponins were named as pseudoginsenoside G1 (1) and pseudoginsenoside G2 (2). Their structures were elucidated by the combined analysis of NMR and mass spectrometry as 3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl]-dammar-12-one-20S,24R-epoxy-3β,25-diol (pseudoginsenoside G1) (1) and 3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl]-dammar-12-one-20S,24S-epoxy-3β,25-diol (pseudoginsenoside G2) (2).

Triterpenoid saponins from Gynostemma pentaphyllum

Four new dammarane-type triterpene saponins, 1–4, were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Their structural elucidations were accomplished mainly on the basis of spectroscopic methods, such as IR, HR-TOF-MS, and NMR. Compounds 1–4 showed moderate cytotoxic activities against cancer cell lines HL-60, Colon205, and Du145 in vitro.

Three new dammarane-type triterpene saponins from the leaves of Panax ginseng C.A. Meyer

Three new dammarane-type triterpene ginsenosides, together with six known ginsenosides, were isolated from the leaves of Panax ginseng C.A. Meyer. The new saponins were named as ginsenoside Rh11, ginsenoside Rh12, and ginsenoside Rh13. Their structures were elucidated as (20S)-3β,6α,12β,20-tetrahydroxydammara-25-ene-24-one 20-O-β-d-glucopyranoside (1), (20S)-3β,12β,20,24,25-pentahydroxydammarane 20-O-β-d-glucopyranoside (2), and (20S,23E)-3β,12β,20,25-tetrahydroxydammara-23-ene 20-O-β-d-glucopyranoside (3) on the basis of 1D and 2D NMR experiments and mass spectra. The known ginsenosides were identified as ginsenoside M7cd, ginsenoside Rg6, ginsenoside Rb3, gypenoside XVII, gypenoside IX, and 20-(E)-ginsenoside F4.

Three New Triterpene Saponins from Gynostemma pentaphyllum

AbstractThree new dammarane‐type triterpene saponins, 1–3, together with three known compounds, 4–6, were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. By means of chemical and spectroscopic methods, their structures were established as (20S)‐3β,20,21‐trihydroxydammara‐23,25‐diene 3‐O‐[α‐L‐rhamnopyranosyl‐(1→2)] [β‐D‐xylopyranosyl‐(1→3)]‐β‐D‐glucopyranosyl‐21‐O‐β‐D‐glucopyranoside (1), (20R,23R)‐3β,20‐dihydroxy‐19‐oxodammar‐24‐en‐21‐oic acid 21,23‐lactone 3‐O‐[α‐L‐rhamnopyranosyl‐(1→2)] [β‐D‐xylopyranosyl‐(1→3)]‐α‐L‐arabinopyranoside (2), and (21S,23S)‐3β,20ξ,21,26‐tetrahydroxy‐19‐oxo‐21,23‐epoxydammar‐24‐ene 3‐O‐[α‐L‐rhamnopyranosyl‐(1→2)] [β‐D‐xylopyranosyl‐(1→3)]‐α‐L‐arabinopyranoside (3).

A new dammarane-type triterpene saponin from Gynostemma pentaphyllum

One new dammarane-type triterpene saponin, named (20 S)-3β,20,21-trihydroxydammar-24-ene 3- O-[α- l- rhamnopyranosyl(1 → 2)][β- d-xylopyranosyl(1 → 3)]-β- d-glucopyranoside ( 1), was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino. Its structural elucidation was accomplished mainly on the basis of the interrelation of spectroscopic methods, such as IR, HR-TOF-MS, NMR.

Dammarane-type triterpene saponins from the flowers of Panax notoginseng.

Four new dammarane-type triterpene saponins named floranotoginsenosides A (1), B (2), C (3) and D (4), together with five known triterpene saponins, were isolated from the flowers of Panax notoginseng. Their structures were elucidated on the basis of spectral and chemical evidence.

Structures of new dammarane-type Triterpene Saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal Ginseng Saponins.

The saponin fraction from the flower buds of Panax notoginseng exhibited protective effect on liver injury induced by d-galactosamine and lipopolysaccharide. From the saponin fraction with hepatoprotective effect, five new dammarane-type triterpene saponins, notoginsenosides-O (1), -P (2), -Q (3), -S (4), and -T (5), were isolated together with nine known protopanaxadiol oligoglycosides. The structures of the new saponins were elucidated on the basis of chemical and physicochemical evidence. The principal dammarane-type triterpene saponins from the roots and flower buds of Panax notoginseng were found to show potent hepatoprotective effects.

Triterpene saponins from Vietnamese ginseng (Panax vietnamensis) and their hepatocytoprotective activity.

The methanol extract of Vietnamese ginseng (Panax vietnamensis) was found to possess hepatocytoprotective effects on D-galactosamine (D-GalN)/tumor necrosis factor-alpha (TNF-alpha)-induced cell death in primary cultured mouse hepatocytes. Further chemical investigation of the extract afforded two new dammarane-type triterpene saponins, ginsenoside Rh(5) (1) and vina-ginsenoside R(25) (2), as well as eight known dammarane-type triterpene saponins, majonoside R(2) (3), pseudo-ginsenoside RT(4) (4), vina-ginsenosides R(1) (5), R(2) (6), and R(10) (7), ginsenosides Rg(1) (8), Rh(1) (9), and Rh(4) (10), and a known sapogenin protopanaxatriol oxide II (11). Their structures were elucidated on the basis of spectral analysis. In addition, by the using LC-electrospray ionization (ESI)-MS method, five known saponins, ginsenosides Rb(1), Rb(2), Rc, Rd, and Re (12--16), were also identified in the extract. Among the compounds isolated, majonoside R(2) (3), the main saponin in Vietnamese ginseng, showed strong protective activity against D-GalN/TNF-alpha-induced cell death in primary cultured mouse hepatocytes. This demonstrates that the hepatocytoprotective effect of Vietnamese ginseng is due to dammarane-type triterpene saponins that have an ocotillol-type side chain, a characteristic constituent of Vietnamese ginseng.

Six new dammarane-type triterpene saponins from the leaves of Panax ginseng.

Six new minor saponins, together with known ginsenosides, were isolated from the leaves of Panax ginseng. The new saponins were named as ginsenoside-Rh5, -Rh6, -Rh7 -Rh8, -Rh9 and -Rg7, and their structures were elucidated on the basis of chemical and physicochemical evidence to be as follows: ginsenoside-Rh5: 3beta,6alpha,12beta,24zeta-tetrahydroxy-dammar-20(22),25-diene 6-O-beta-D-glucopyranoside (1), -Rh6: 3beta,6alpha12beta,20(S)-tetrahydroxy-25-hydroperoxy-dammar-23-ene 20-O-beta-D-glucopyranoside (2), -Rh7: 3beta,7beta,12beta,20(S)-tetrahydroxy-dammar-5,24-diene 20-O-beta-D-glucopyranoside (3), -Rh8: 3beta,6alpha,20(S)-trihydroxy-dammar-24-ene-12-one 20-O-beta-D-glucopyranoside (4), -Rh9: 3beta,6alpha,20(S)-trihydroxy-12beta,23-epoxy-dammar-24-ene 20-O-beta-D-glucopyranoside (5) and -Rg7: 3-O-beta-D-glucopyranosyl 3beta,12beta,20(S),24(R)-tetrahydroxy-dammar-25-ene 20-O-beta-D-glucopyranoside (6).

Bioactive saponins and glycosides. XIX. Notoginseng (3): immunological adjuvant activity of notoginsenosides and related saponins: structures of notoginsenosides-L, -M, and -N from the roots of Panax notoginseng (Burk.) F. H. Chen.

New dammarane-type triterpene saponins, notoginsenosides-L, -M, and -N, were isolated from the glycosidic fraction of the dried roots of Panax notoginseng (Burk.) F. H. Chen. Their structures were elucidated on the basis of chemical and physicochemical evidence. Immunological adjuvant activities of the principal notoginsenosides and related dammarane-type triterpene saponins were examined and notoginsenosides-D, -G, -H, and -K were found to increase the serum IgG level in mice sensitized with ovalbumin.

Studies on Dammarane-Type Saponins in the Flower-Buds of Panax ginseng C.A. Meyer

From the dried flower-buds of Panax ginseng C.A. Meyer, a new minor dammarane-type triterpene saponin named ginsenoside III together with nine known saponins was isolated. On the basis of spectral and chemical evidence, the structure of the new saponin was elucidated as 3-O-[β-D-glucopyranosyl(1 → 2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranosyl-3β,12β,20(S)-trihydroxy-dammar-25-en-24-one.