A Review for Discovering Bioactive Minor Saponins and Biotransformative Metabolites in L

Overview

Journal Front Pharmacol

Date 2022 Aug 18

PMID 35979234

Authors

Zhiyou Yang

Jiahang Deng

Mingxin Liu

Chuantong He

Xinyue Feng

Shucheng Liu

Shuai Wei

Affiliations

Soon will be listed here.

Abstract

L. has attracted extensive attention worldwide because of its prominent pharmacological properties on type 2 diabetes, cancers, central nervous system, and cardiovascular diseases. Ginsenosides are active phytochemicals of , which can be classified as propanaxdiol (PPD)-type, propanaxtriol (PPT)-type, oleanane-type, and ocotillol-type oligo-glycosides depending on the skeleton of aglycone. Recently, advanced analytical and isolated methods including ultra-performance liquid chromatography tandem with mass detector, preparative high-performance liquid chromatography, and high speed counter-current chromatography have been used to isolate and identify minor components in , which accelerates the clarification of the material basis. However, the poor bioavailability and undetermined bio-metabolism of most saponins have greatly hindered both the development of medicines and the identification of their real active constituents. Thus, it is essential to consider the bio-metabolism of constituents before and after absorption. In this review, we described the structures of minor ginsenosides in , including naturally occurring protype compounds and their metabolites. The preclinical and clinical pharmacological studies of the ginsenosides in the past few years were also summarized. The review will promote the reacquaint of minor saponins on the growing appreciation of their biological role in .

Citing Articles

Comprehensive Investigation of Ginsenosides in the Steamed with Different Processing Conditions Using LC-MS.

Fan J, Liu F, Ji W, Wang X, Li L Molecules. 2024; 29(3).

PMID: 38338369 PMC: 10856252. DOI: 10.3390/molecules29030623.

References

Shin K, Guo H, Cha Y, Ban Y, Seo D, Choi Y . Cereboost™, an American ginseng extract, improves cognitive function via up-regulation of choline acetyltransferase expression and neuroprotection. Regul Toxicol Pharmacol. 2016; 78:53-8. DOI: 10.1016/j.yrtph.2016.04.006. View

Wan J, Liu P, Wang H, Qi L, Wang C, Li P . Biotransformation and metabolic profile of American ginseng saponins with human intestinal microflora by liquid chromatography quadrupole time-of-flight mass spectrometry. J Chromatogr A. 2013; 1286:83-92. DOI: 10.1016/j.chroma.2013.02.053. View

Gao J, Lv G, He B, Zhang B, Zhang H, Wang N . Ginseng saponin metabolite 20(S)-protopanaxadiol inhibits tumor growth by targeting multiple cancer signaling pathways. Oncol Rep. 2013; 30(1):292-8. PMC: 3729206. DOI: 10.3892/or.2013.2438. View

Kim J, Oh J, Chun S, Park H, Im W . Enzymatic Biotransformation of Ginsenoside Rb into Rd by Recombinant α-L-Arabinopyranosidase from Blastococcus saxobsidens. J Microbiol Biotechnol. 2020; 30(3):391-397. PMC: 9728169. DOI: 10.4014/jmb.1910.10065. View

Xu X, Hu J, Liu Z, Zhang R, He Y, Hou W . Saponins (Ginsenosides) from the Leaves of Panax quinquefolius Ameliorated Acetaminophen-Induced Hepatotoxicity in Mice. J Agric Food Chem. 2017; 65(18):3684-3692. DOI: 10.1021/acs.jafc.7b00610. View

Lu D, Li P, Liu J . Quinquenoside F₆, a new triterpenoid saponin from the fruits of Panax quinquefolium L. Nat Prod Res. 2011; 26(15):1395-401. DOI: 10.1080/14786419.2011.592833. View

Quan L, Min J, Jin Y, Wang C, Kim Y, Yang D . Enzymatic biotransformation of ginsenoside Rb1 to compound K by recombinant β-glucosidase from Microbacterium esteraromaticum. J Agric Food Chem. 2012; 60(14):3776-81. DOI: 10.1021/jf300186a. View

Wang J, Yau L, Tong T, Feng Q, Bai L, Ma J . Characterization of oxygenated metabolites of ginsenoside Rb1 in plasma and urine of rat. J Agric Food Chem. 2015; 63(10):2689-700. DOI: 10.1021/acs.jafc.5b00710. View

Quan L, Jin Y, Wang C, Min J, Kim Y, Yang D . Enzymatic transformation of the major ginsenoside Rb2 to minor compound Y and compound K by a ginsenoside-hydrolyzing β-glycosidase from Microbacterium esteraromaticum. J Ind Microbiol Biotechnol. 2012; 39(10):1557-62. DOI: 10.1007/s10295-012-1158-1. View

10.

Qian T, Cai Z . Biotransformation of ginsenosides Rb1, Rg3 and Rh2 in rat gastrointestinal tracts. Chin Med. 2010; 5:19. PMC: 2887866. DOI: 10.1186/1749-8546-5-19. View

11.

Xie J, Zhao D, Zhao L, Pei J, Xiao W, Ding G . Characterization of a novel arabinose-tolerant α-L-arabinofuranosidase with high ginsenoside Rc to ginsenoside Rd bioconversion productivity. J Appl Microbiol. 2016; 120(3):647-60. DOI: 10.1111/jam.13040. View

12.

Xiang Z, Lv J, Zhou Z, Li Y, Dou D, Zhao J . Two new dammarane-type saponins from leaves of Panax quinquefolium. Nat Prod Res. 2012; 27(14):1271-6. DOI: 10.1080/14786419.2012.730045. View

13.

Wu L, Jin Y, Yin C, Bai L . Co-transformation of Panax major ginsenosides Rb₁ and Rg₁ to minor ginsenosides C-K and F₁ by Cladosporium cladosporioides. J Ind Microbiol Biotechnol. 2012; 39(4):521-7. DOI: 10.1007/s10295-011-1058-9. View

14.

Wang H, Zhang C, Zuo T, Li W, Jia L, Wang X . In-depth profiling, characterization, and comparison of the ginsenosides among three different parts (the root, stem leaf, and flower bud) of Panax quinquefolius L. by ultra-high performance liquid chromatography/quadrupole-Orbitrap mass spectrometry. Anal Bioanal Chem. 2019; 411(29):7817-7829. DOI: 10.1007/s00216-019-02180-8. View

15.

Liu L, Gu L, Zhang D, Wang Z, Wang C, Li Z . Microbial conversion of rare ginsenoside Rf to 20(S)-protopanaxatriol by Aspergillus niger. Biosci Biotechnol Biochem. 2010; 74(1):96-100. DOI: 10.1271/bbb.90596. View

16.

Kang A, Zhang S, Zhu D, Dong Y, Shan J, Xie T . Gut microbiota in the pharmacokinetics and colonic deglycosylation metabolism of ginsenoside Rb1 in rats: Contrary effects of antimicrobials treatment and restraint stress. Chem Biol Interact. 2016; 258:187-96. DOI: 10.1016/j.cbi.2016.09.005. View

17.

Wang L, Liu Q, Sung B, An D, Lee H, Kim S . Bioconversion of ginsenosides Rb(1), Rb(2), Rc and Rd by novel β-glucosidase hydrolyzing outer 3-O glycoside from Sphingomonas sp. 2F2: cloning, expression, and enzyme characterization. J Biotechnol. 2011; 156(2):125-33. DOI: 10.1016/j.jbiotec.2011.07.024. View

18.

Shen L, Li X, Meng X, Wu J, Tang H, Huang L . Prediction of the globally ecological suitability of Panax quinquefolius by the geographic information system for global medicinal plants (GMPGIS). Chin J Nat Med. 2019; 17(7):481-489. DOI: 10.1016/S1875-5364(19)30069-X. View

19.

Vuksan V, Xu Z, Jovanovski E, Jenkins A, Beljan-Zdravkovic U, Sievenpiper J . Efficacy and safety of American ginseng (Panax quinquefolius L.) extract on glycemic control and cardiovascular risk factors in individuals with type 2 diabetes: a double-blind, randomized, cross-over clinical trial. Eur J Nutr. 2018; 58(3):1237-1245. DOI: 10.1007/s00394-018-1642-0. View

20.

Kim M, Upadhyaya J, Yoon M, Ryu N, Song Y, Park H . Highly regioselective biotransformation of ginsenoside Rb2 into compound Y and compound K by β-glycosidase purified from mycelia. J Ginseng Res. 2018; 42(4):504-511. PMC: 6187093. DOI: 10.1016/j.jgr.2017.07.001. View