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Prosaikogenin G Sale

(Synonyms: 柴胡次皂苷G) 目录号 : GC61210

ProsaikogeninG是从柴胡的根中分离出的,对AngII诱导的大鼠系膜细胞增殖具有明显的抑制作用。ProsaikogeninG对肾脏有保护作用。ProsaikogeninG是Saikosaponind在胃肠道中的衍生物。

Prosaikogenin G Chemical Structure

Cas No.:99365-23-8

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产品描述

Prosaikogenin G, isolated from the roots of Buleurum bicaule Helm (Apiaceae), exhibits significant inhibitory effects on rat mesangial cell proliferation induced by Ang II. Prosaikogenin G has protective action on the kidney[1]. Prosaikogenin G is a derivative of Saikosaponin d in the gastrointestinal tract[2].

Prosaikogenin G (25, 50 μM) has protective action on the kidney for their down-regulated activity to the rat mesangial cell line (MC) proliferation induced by Ang II (1 μM), and does not exhibit injury to the normal MC[1].

[1]. Nan Xu, et al. A new saikogenin from the roots of Bupleurum bicaule. Chin J Nat Med. 2014 Apr;12(4):305-8. [2]. Pei Yu, et al. In vitro metabolism study of saikosaponin d and its derivatives in rat liver microsomes. Xenobiotica. 2017 Jan;47(1):11-19.

Chemical Properties

Cas No. 99365-23-8 SDF
别名 柴胡次皂苷G
Canonical SMILES O[C@H]([C@H]([C@H]([C@@H](C)O1)O)O)[C@@H]1O[C@@H]2CC[C@]3(C)[C@@]4([H])C=C[C@]56[C@]7([H])CC(C)(C)CC[C@@](CO6)7[C@@H](O)C[C@](C)5[C@@](C)4CC[C@]([H])3[C@@]2(C)CO
分子式 C36H58O8 分子量 618.84
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Research Update

Production of Prosaikogenin F, Prosaikogenin G, Saikogenin F and Saikogenin G by the Recombinant Enzymatic Hydrolysis of Saikosaponin and their Anti-Cancer Effect

Molecules 2022 May 19;27(10):3255.PMID:35630731DOI:10.3390/molecules27103255.

The saponins of Bupleurum falcatum L., saikosaponins, are the major components responsible for its pharmacological and biological activities. However, the anti-cancer effects of prosaikogenin and saikogenin, which are glycoside hydrolyzed saikosaponins, are still unknown due to its rarity in plants. In this study, we applied two recombinant glycoside hydrolases that exhibit glycoside cleavage activity with saikosaponins. The two enzymes, BglPm and BglLk, were cloned from Paenibacillus mucilaginosus and Lactobacillus koreensis, and exhibited good activity between 30-37 °C and pH 6.5-7.0. Saikosaponin A and D were purified and obtained from the crude B. falcatum L. extract using preparative high performance liquid chromatography technique. Saikosaponin A and D were converted into saikogenin F via prosaikogenin F, and saikogenin G via Prosaikogenin G using enzyme transformation with high β-glycosidase activity. The two saikogenin and two prosaikogenin compounds were purified using a silica column to obtain 78.1, 62.4, 8.3, and 7.5 mg of prosaikogenin F, Prosaikogenin G, saikogenin F, and saikogenin G, respectively, each with 98% purity. The anti-cancer effect of the six highly purified saikosaponins was investigated in the human colon cancer cell line HCT 116. The results suggested that saikosaponins and prosaikogenins markedly inhibit the growth of the cancer cell line. Thus, this enzymatic technology could significantly improve the production of saponin metabolites of B. falcatum L.

A new saikogenin from the roots of Bupleurum bicaule

Chin J Nat Med 2014 Apr;12(4):305-8.PMID:24863358DOI:10.1016/S1875-5364(14)60060-1.

Aim: To study the chemical constituents from the roots of Buleurum bicaule Helm (Apiaceae). Method: Silica gel, Sephadex LH-20, MPLC Rp-C18 column chromatography, and HPLC were used for isolation of compounds. The structures were elucidated on the basis of 1D- and 2D-NMR technology and HRESI-MS. Compounds were evaluated in vitro for their inhibitory ability against the proliferation of rat mesangial cells by the MTT method. Results: Twelve compounds were isolated, and their structures were identified on the basis of their spectroscopic and physico-chemical properties as 13, 28-epoxy-olean-11-en-3-one (1), saikogenin E (2), saikogenin G (3), 11α-methoxy-3β, 16β, 23, 28-tetrahydroxyolean-12-ene (4), saikogenin D (5), prosaikogenin F (6), prosaikogenin A (7), Prosaikogenin G (8), prosaikogenin D (9), laccaic acid (10b), methyl gallate (11), and ethyl gallate (12). Compounds 1, 2, 7, 8, and 10 were observed to have inhibitory activity against mesangial cell proliferationin to different degrees. Conclusion: Compound 1, 8, and 10 exhibit significant inhibitory effects on rat mesangial cell proliferation induced by Ang II.

Corticosterone secretion-inducing activity of saikosaponin metabolites formed in the alimentary tract

Chem Pharm Bull (Tokyo) 1989 Oct;37(10):2736-40.PMID:2611932DOI:10.1248/cpb.37.2736.

The corticosterone secretion-inducing activities of saikosaponin a, saikosaponin c and saikosaponin d, isolated from the root of Bupleurum falcatum L., and 27 metabolites formed in the murine alimentary tract were studied in mice. Serum corticosterone was determined by high-performance liquid chromatography (HPLC). Intraperitoneal administration of saikosaponin a and its intestinal metabolite, prosaikogenin F, showed corticosterone secretion-inducing activity at a dose of 0.1 mmol/kg, and maximally increased it at a dose of 0.4 mmol/kg. On the other hand, the genuine sapogenin, saikogenin F, was inactive. Saikosaponin b1 and saikosaponin g, gastric metabolites of saikosaponin a, and their intestinal metabolites, prosaikogenin A, prosaikogenin H, saikogenin A and saikogenin H, were also inactive. Serum corticosterone was increased by the administration of saikosaponin d and its intestinal metabolite, Prosaikogenin G, at a dose of 0.04 mmol/kg, and it reached the maximal level at the dose of 0.1 mmol/kg. Saikogenin G also showed a slight activity. A gastric metabolite of saikosaponin d, saikosaponin b2, and its intestinal metabolites, prosaikogenin D and saikogenin D, were inactive. In the experiments on saikosaponin c and its metabolites, saikosaponin c was inactive but its intestinal metabolites, especially prosaikogenin E-2, showed activity almost equal to that of saikosaponin a. Saikosaponin h and saikosaponin i, gastric metabolites of saikosaponin c, were also inactive, but their prosaikogenins showed slight activities. When these compounds were orally administered, their corticosterone secretion-inducing activities were similar to those obtained in the intraperitoneal experiment. These results suggest that a proper polar balance between the sugar moiety and the aglycone is important for the corticosterone secretion-inducing activity of saikosaponins and their metabolites.

Saikosaponin derivatives from Bupleurum wenchuanense

Phytochemistry 1993 Jul;33(5):1197-1205.PMID:7764030DOI:10.1016/0031-9422(93)85049-w.

From the roots of Bupleurum wenchuanense 14 derivatives of saikosaponin were isolated and identified as 2"-O-beta-D-xylopyranosylsaikosaponin b2, 3",6"-O O-diacetylsaikosaponin b2, 2"-O-beta-D-glucopyranosylsaikosaponin b2, saikosaponin b2, 6"-O-acetylsaikosaponin b2, saikosaponin d, 2"-O-acetylsaikosaponin d, 3"-O-acetylsaikosaponin d,6"-O-acetylsaikosaponin d, 16-epichikusaikoside, Prosaikogenin G, saikosaponin a,2"-O-acetylsaikosaponin a and 3"-O-acetylsaikosaponin a. The first two compounds are new derivatives of saikosaponin and this is the first isolation of Prosaikogenin G from a plant. Their complete 1H and 13C NMR assignments were made by using a combination of 2D NMR techniques (DQF-COSY, HOHAHA, ROESY, HETCOR, HMQC and HMBC). Some of the compounds showed cytotoxic activity against the P-388 cell line.

In vitro metabolism study of saikosaponin d and its derivatives in rat liver microsomes

Xenobiotica 2017 Jan;47(1):11-19.PMID:27052332DOI:10.3109/00498254.2016.1163753.

1. Saikosaponins, one of the representative bioactive ingredients in Radix Bupleuri, possess hepatoprotective, anti-inflammatory, antiviral, antitumor, and other pharmacological activities. Up to now, few studies focused on the further metabolism of saikosaponins and their secondary metabolites absorbed into the circulatory system. 2. To understand the in vivo efficacy of saikosaponin d, the in vitro metabolism of saikosaponin d, and its two derivatives formed in the gastrointestinal tract, Prosaikogenin G and saikogenin G was investigated in rat liver microsomes, respectively. 3. Fifteen metabolites were detected using high-performance liquid chromatography hybrid ion trap and time-of-flight mass spectrometry and triple-quadrupole mass spectrometry, and the predominant metabolic reactions were hydroxylation, carboxylation and combinations of these steps on the aglycone moiety. 4. The metabolic pathways of saikosaponin d, Prosaikogenin G, and saikogenin G were proposed in vitro and the results contribute to the understanding of saikosaponins in vivo metabolism.