19667-13-1Relevant articles and documents
Synthesis of Ocotillol-Type Ginsenosides
Shen, Renzeng,Cao, Xin,Laval, Stephane,Sun, Jiansong,Yu, Biao
, p. 10279 - 10294 (2016)
A total of 14 ocotillol-type ginsenosides were conveniently synthesized employing glycosylation of ocotillol sapogenin derivatives with glucosyl ortho-alkynylbenzoate donors under the promotion of a gold(I) catalyst as the key step. Relying on a rational protecting group strategy and the unexpected regioselectivity of the glycosylation of the 3,25-diol sapogenins (2a/2b, 5a/5b) for the tertiary 25-OH, mono 3-O-glucosyl ocotillol-PPD, 6-O-glucosyl ocotillol-PPT, 25-O-glucosyl ocotillol-PPD/PPT and 3,25-di-O-glucosyl ocotillol-PPD/PPT ginsenosides were prepared in which the configuration at the C-24 is either R or S.
Dammarane saponins of leaves of Panax pseudo-ginseng subsp. himalaicus
Tanaka, Osamu,Yahara, Shoji
, p. 1353 - 1358 (1978)
From dried leaves of Panax pseudo-ginseng subsp. himalaicus collected in Eastern Himalaya, new dammarane saponins, named pseudo-ginsenosides-F11 and -F8 were isolated along with the known Ginseng-root saponins, ginsenosides-Rb3, Rd and -Re. Pseudo-ginsenoside-F8 was proved to be a mono-acetyl-ginsenoside-Rb3 and the location of its acetyl group was established mainly by 13C NMR spectroscopy. Pseudo-ginsenoside-F11, was identified as the 6-O-α-rhamnopyransyl(1 → 2)-β-glucopyranoside of 3β,6α,12β,25-tetrahydoxy-(20S,24R)-epoxy-dammarane. The C-24 configuration of ocotillone and its related triterpenes was confirmed to be 24R excluding the recent comment by Lavie et al.
Stereoselective oxidation metabolism of 20(S)-protopanaxatriol in human liver microsomes and in rats
Wang, Wenyan,Ni, Yingying,Wang, Li,Che, Xin,Liu, Wanhui,Meng, Qingguo
, p. 385 - 395 (2015)
1. In this study, the oxidative metabolites of 20(S)-protopanaxatriol (PPT) were identified in human liver microsomes (HLMs) and in rats using liquid chromatography-electrospray ionization tandem mass spectrometry. 2. Twelve oxidative metabolites were found in HLM, eight of which have not been previously reported. Twenty-four oxidative metabolites were found in rat feces after oral administration and 20 of these, including six found in HLM, were first reported. The results indicated PPT was more extensively metabolized in rats than in HLM. C20-24 epoxides, a pair of epimers (namely, M1-1 and M1-2) were the major metabolites, and other metabolites were derived from their further metabolism. 3. Enzyme kinetics experiments showed that the apparent formation Vmax of M1-1 was 10.4 folds and 2.4 folds higher than that of M1-2 in HLM and in rat liver microsomes (RLMs), respectively. The depletion rate of M1-2 was 11.0 folds faster than M1-1 in HLM, and was similar in RLM. Hence, the remarkable species differences of PPT metabolism mainly resulted from the stereoselective formation and further metabolic elimination of M1-1 and M1-2. 4. Chemical inhibition study and recombinant human P450 isoforms analysis showed that CYP3A4 was the predominant isoform involved in the oxidative metabolism of M1-1 and M1-2.
With antibacterial activity (20 S, 24 R) - ocotillol-type Ginseng saponin derivatives, their preparation and use
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Paragraph 0082-0084; 0089, (2017/09/01)
The invention relates to the fields of organic synthesis and pharmaceutical chemistry, in particular to a (20S, 24R)-ocotillol type ginsenoside derivative having represented in a structural formula (I). The invention further discloses a reparation method of the (20S, 24R)-ocotillol type ginsenoside derivative, pharmaceutical compositions containing the derivative and anti-bacterial and anti-infection application.
Biotransformation of 20(S)-protopanaxatriol by Aspergillus niger and the cytotoxicity of the resulting metabolites
Chen, Guangtong,Song, Yan,Ge, Hongjuan,Ren, Jie,Yang, Xue,Li, Jianlin
, p. 111 - 115 (2015/02/05)
The microbial transformation of 20(S)-protopanaxatriol by cell suspension cultures of Aspergillus niger AS 3.1858 yielded metabolites 1-13. The chemical structures of these transformed products were elucidated based on various spectroscopic analyses, incl
Synthesis, structural determination of a new ocotillol derivative and its epimer
Meng, Qingguo,Bi, Yi,Wang, Liang,Jiang, Naicaiv,Jiang, Yongtao,Zhang, Jiangfeng,Yi, Songtao,Sun, Haijun
, p. 682 - 685 (2012/06/01)
Epimeric 20S, 24-epoxy-dammarane-3β, 6α, 12β, 25-tetraol acetic ester was synthesized from 20(S)-protopanaxatriol in the presence of acetic anhydride and the product oxidated by m-CPBA. 20S, 24R-epoxy dammarane-3β, 6α, 12β, 25-tetraol (ocotillol derivative) and its epimer were synthesized by saponification in the presence of sodium hydroxide in 1:1 molar ratio. The structures of the two compounds were characterized by X-ray diffraction method. The results showed the configuration of C-24 of two epimers as S-form (4, ocotillol derivative) and R-form (3, epimer), respectively.
