SIRT1 activator isolated from artificial gastric juice incubate of total saponins in stems and leaves of Panax ginseng.

Panax ginseng as a traditional Chinese medicine has been extensively used for the treatment of many diseases, especially in prolonging life and anti-tumor. Dammarane-type triterpenoids from P. ginseng have diverse beneficial effects and their chemical structures can be modified in the gastrointestinal tract after oral administration. In this paper, the dammarane-type triterpenoids were isolated from artificial gastric juice incubate of total saponins in the stems and leaves of P. ginseng through column chromatographic methods and their chemical structures were determined based on spectral data. Two new dammarane-type triterpenoids named ginsenotransmetins B (1) and C (2), along with twenty-nine known compounds (3-31), were obtained. All 31 compounds isolated were investigated for their activities of SIRT1 using SIRT1 fluorometric drug discovery assay kit. Among them, compounds 11, 17, 18, 20, 23, 24, 28, and 29, which were found to be potential as SIRT1 activators, exhibited significant stimulation of SIRT1 activity. The results showed that these compounds may be considered to be a useful medicinal resource for prolonging life and anti-tumor. In addition, the results were helpful to explain the longevity effect of ginseng from the new field of view.

A green protocol for efficient discovery of novel natural compounds: characterization of new ginsenosides from the stems and leaves of Panax ginseng as a case study.

Exploration of new natural compounds is of vital significance for drug discovery and development. The conventional approaches by systematic phytochemical isolation are low-efficiency and consume masses of organic solvent. This study presents an integrated strategy that combines offline comprehensive two-dimensional liquid chromatography, hybrid linear ion-trap/Orbitrap mass spectrometry, and NMR analysis (2D LC/LTQ-Orbitrap-MS/NMR), aimed to establish a green protocol for the efficient discovery of new natural molecules. A comprehensive chemical analysis of the total ginsenosides of stems and leaves of Panax ginseng (SLP), a cardiovascular disease medicine, was performed following this strategy. An offline 2D LC system was constructed with an orthogonality of 0.79 and a practical peak capacity of 11,000. The much greener UHPLC separation and LTQ-Orbitrap-MS detection by data-dependent high-energy C-trap dissociation (HCD)/dynamic exclusion were employed for separation and characterization of ginsenosides from thirteen fractionated SLP samples. Consequently, a total of 646 ginsenosides were characterized, and 427 have not been isolated from the genus of Panax L. The ginsenosides identified from SLP exhibited distinct sapogenin diversity and molecular isomerism. NMR analysis was finally employed to verify and offer complementary structural information to MS-oriented characterization. The established 2D LC/LTQ-Orbitrap-MS/NMR approach outperforms the conventional approaches in respect of significantly improved efficiency, much less use of drug materials and organic solvent. The integrated strategy enables a deep investigation on the therapeutic basis of an herbal medicine, and facilitates new compounds discovery in an efficient and environmentally friendly manner as well.

A new triterpene natural product from stems and leaves of Panax ginseng / 中草药

Objective: To study the chemical constituents of saponins in the stems and leaves of Panax ginseng. Methods: The chemical constituents were isolated and purified by various chromatographic methods, and their structures were identified by NMR and MS data analysis. Results: Nine compounds were isolated and identified as 3β,6α,12β,25-tetrahydroxy-dammar-E-20(22)-ene-6-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (1), sanchinoside B1 (2), 3β,6α,12β-dammar-E-20(22)-ene-3,6,12,25-tetraol (3), ginsenoside Rk3 (4), ginsenoside Rh4 (5), notoginsenoside T2 (6), 3β,6α,12β-dammar-20(21),24-diene-3,6,12-triol (7), ginsenoside Rk1 (8), and ginsenoside Rg5 (9). Conclusion: Compound 1 is a new natural product and the other eight compounds are all isolated from the stems and leaves of P. ginseng for the first time.

Chemical constituents in acid hydrolysates of total saponins from stems and leaves of Panax ginseng / 中草药

Objective: To study the chemical constituents in the acid hydrolysates of total saponins from the stems and leaves of Panax ginseng. Methods: The chemical constituents were isolated and purified by various chromatographic methods, and their structures were identified by NMR and MS data analysis. Results: Thirty-four compounds were isolated and identified as 3β-acetoxy-12β-hydroxy-20(R), 25-epoxydammarane (1), 3β, 6α-diacetoxy-12β-hydroxy-20(R), 25-epoxydammarane (2), 3β-acetoxy-6α, 12β-dihydroxy-20(R), 25-epoxydammarane (3), 20(R)-panaxadiol (4), isodehydroprotopanaxatriol (5), 3-oxo-6α, 12β-dihydroxy-20(R), 25-epoxydammarane (6), dammar-(E)-20(22)-ene-3β, 12β, 25-triol (7), 6α-acetoxy-3β, 12β-dihydroxy-20(R), 25-epoxydammarane (8), 20(S)-protopanaxadiol (9), 20(R)-protopanaxadiol (10), 20(S)-25-ethoxyl-dammarane-3β, 12β, 20-triol (11), 20(R)-panaxatriol (12), dammar-(E)-20(22), 24-diene-3β, 6α, 12β-triol (13), 27-demethyl-(E, E)-20(22), 23-dien-3β, 12β-dihydroxydammar-25-one (14), 3β, 12β-dihydroxy-22, 23, 24, 25, 26, 27-hexanordamaran-20-one (15), 3β-acetoxy-6α, 12β, 25-trihydroxy-20(S), 24(R)-epoxy-dammarane (16), 20(S)-25-ethoxyl-dammarane-3β, 12β, 20-triol (17), dammar-(E)-20(22)-ene-3β, 6α, 12β, 25-tetrol (18), dammar-(Z)-20(22)-ene-3β, 6α, 12β, 25-tetrol (19), 20(S)-dammarane-3β, 12β, 20, 25-tetrol (20), 20(R)-dammarane-3β, 12β, 20, 25-tetrol (21), 20(S)-protopanaxatriol (22), 20(R)-protopanaxatriol (23), (20S, 24S)-dammarane-20, 24-epoxy-3β, 6α, 12β, 25-tetraol (24), (20S, 24R)-dammarane-20, 24-epoxy-3β, 6α, 12β, 25-tetraol (25), (20R, 24R)-dammarane-20, 24-epoxy-3β, 6α, 12β, 25-tetraol (26), 3β, 6α, 12β-trihydroxy-22, 23, 24, 25, 26, 27-hexanordamaran-20-one (27), 12β-hydroxy-20(R), 25-epoxydammarane-3β-O-β-D-glucopyranoside (28), 20(S)-dammarane-3β, 6α, 12β, 20, 25-pentol (29), 20(R)-dammarane-3β, 6α, 12β, 20, 25-pentol (30), 20(R)-dammarane-3β, 6α, 12β-trihydroxy-20, 25-epoxy-6-O-β-D-glucopyranoside (31), pseudo-ginsenoside-Rh2 (32), 20(S)-ginsenoside-Rh1 (33), and 20(R)-ginsenoside-Rh1 (34). Conclusion: Compounds 1-3, 6, 8, 11, 17, 24-26, and 32 are ginseng triterpenoids isolated from the acid hydrolysates of total saponins from the stems and leaves of P. ginseng for the first time. Pseudo-ginsenoside-Rh2 is a potent antiproliferative agent against human cancer cells.

20(S)-Ginsenoside-Rf2, a novel triterpenoid saponin from stems and leaves of Panax ginseng / 中草药

Objective: To study the chemical constituents of saponins in the stems and leaves of Panax ginseng. Methods: The chemical constituents were isolated and purified by various chromatographic methods, and the chemical structures were identified by NMR and MS data analyses. Results: A total of 39 compounds were isolated and identified. Among them, 17 compounds were determined as ginsenoside Re (1), 20(S)-ginsenoside Rh1 (2), 20(R)-ginsenoside Rh1 (3), ginsenoside Rh5 (4), 20(E)-ginsenoside F4 (5), ginsenoside F2 (6), 20(S)-ginsenoside Rg3 (7), 20(R)-ginsenoside Rg3 (8), 20(S)-ginsenoside Rf2 (9), 20(R)-ginsenoside Rf2 (10), 20(S)- protopanaxadiol (11), 20(R)-protopanaxadiol (12), 20(S)-ginsenoside Rh2 (13), 20(R)-ginsenoside Rh2 (14), 20(S)-protopanaxatriol (15), 20(R)-protopanaxatriol (16), and ginsenoside Rd (17). Conclusion: Compound 9 is a new saponin. Compounds 2-10, 13, and 14 are rare ginsenosides.