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Details

Stereochemistry ABSOLUTE
Molecular Formula C53H90O22
Molecular Weight 1079.2685
Optical Activity UNSPECIFIED
Defined Stereocenters 29 / 29
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GINSENOSIDE C

SMILES

[H][C@@]1(CC[C@]2(C)[C@]1([H])[C@H](O)C[C@]3([H])[C@@]4(C)CC[C@H](O[C@]5([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@]6([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@]4([H])CC[C@@]23C)[C@](C)(CCC=C(C)C)O[C@@H]7O[C@H](CO[C@]8([H])OC[C@H](O)[C@H](O)[C@H]8O)[C@@H](O)[C@H](O)[C@H]7O

InChI

InChIKey=NODILNFGTFIURN-GZPRDHCNSA-N
InChI=1S/C53H90O22/c1-23(2)10-9-14-53(8,75-47-43(67)39(63)37(61)29(72-47)22-69-45-41(65)34(58)26(57)21-68-45)24-11-16-52(7)33(24)25(56)18-31-50(5)15-13-32(49(3,4)30(50)12-17-51(31,52)6)73-48-44(40(64)36(60)28(20-55)71-48)74-46-42(66)38(62)35(59)27(19-54)70-46/h10,24-48,54-67H,9,11-22H2,1-8H3/t24-,25+,26-,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39-,40-,41+,42+,43+,44+,45-,46-,47-,48-,50-,51+,52+,53-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.lktlabs.com/product/ginsenoside-rb2/ https://www.ncbi.nlm.nih.gov/pubmed/23717160

Ginsenoside C is a triterpene saponin originally found in species of Panax (ginseng) that exhibits anti-osteoporotic, antioxidative, antiviral, anti-hyperlipidemic, anti-metastatic, anti-angiogenic, and anticancer chemotherapeutic activities. In vivo, ginsenoside C decreases levels of malondialdehyde and increases levels of glutathione, improving bone microarchitecture and bone mineral density. In other animal models, this compound decreases virus titers and protects against infection of hemagglutinating virus of Japan. In adipocytes, ginsenoside C decreases levels of cholesterol and triglycerides and increases expression of SREBP. In uterine endometrial cancer cells, ginsenoside C decrease expression of matrix metalloproteinase 2 (MMP2), suppressive cellular invasion; this compound also inhibits neovascularization and tumor growth in animal models of melanoma. Ginsenoside C is a component of Korean Red Ginseng, marketed in Korea. Korean ginseng (Panax ginseng Meyer, Araliaceae) is traditionally used as an important herbal medicine in Far East Asia. Korean Red Ginseng is possibly effective for: • Alzheimer's disease. Evidence shows that taking Panax ginseng root daily for 12 weeks can improve mental performance in people with Alzheimer's disease. • Lung disease called chronic obstructive pulmonary disease (COPD). Taking Panax ginseng by mouth seems to improve lung function and some symptoms of COPD. • Mental function. Taking Panax ginseng by mouth might improve abstract thinking, mental arithmetic skills, and reaction times in healthy, middle-aged people but not in young adults. Panax ginseng alone does not seem to improve memory. But there is some evidence that a combination of Panax ginseng and ginkgo leaf extract can improve memory in otherwise healthy people between the ages of 38 and 66. • Erectile dysfunction (ED). Taking Panax ginseng by mouth seems to improve sexual function in men with erectile dysfunction. • Flu. Taking a specific Panax ginseng by mouth appears to reduce the risk of getting a cold or the flu. But, taking Panax ginseng does not seem to reduce flu symptoms or the length of the illness. • Multiple sclerosis-related fatigue. Taking Panax ginseng daily for 3 months reduces feelings of tiredness and improves quality of life in females with MS. • Premature ejaculation. Applying a cream containing Panax ginseng, angelica root, Cistanches deserticola, Zanthoxyl species, torlidis seed, clover flower, asiasari root, cinnamon bark, and toad venom (SS Cream) to the penis one hour before intercourse and washing off immediately before intercourse seems to help prevent premature ejaculation.

CNS Activity

Curator's Comment: has depressing effect on the central nervous system

Approval Year

PubMed

PubMed

TitleDatePubMed
Ginsenosides increase secretion of lipoprotein lipase by 3T3-L1 adipocytes.
1996 Dec
Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I.
2007 Feb
Effects of ginsenosides on the expression of cytochrome P450s and transporters involved in cholesterol metabolism.
2014 Apr
Patents

Sample Use Guides

KRG extract contained 1.62mg/g Ginsenoside C, as well as ginsenoside-Rb1: 4.26mg/g, -B2: 1.71 mg/g, -Rc: 1.80mg/g, -Rd: 0.29mg/g, -Rf: 0.67mg/g, -Rg1: 2.61mg/g, -Rg2: 0.20mg/g, -Rg3: 0.13mg/g, and other minor ginsenosides. During the study period, three capsules (500 mg/dose) were taken daily for 12 weeks
Route of Administration: Oral
Treatment of 0.1 to 10uM Ginsenoside C promoted the proliferation of MC3T3-E1 cells, improved alkaline phosphatase (ALP) expression, elevated calcium mineralization and mRNA expressions of Alp, Col1a1, osteocalcin (Ocn) and osteopontin (Opn) against oxidative damage induced by H2O2.
Name Type Language
GINSENOSIDE C
Common Name English
GINSENOSIDE RB2
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,12.BETA.)-20-((6-O-.ALPHA.-L-ARABINOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-12-HYDROXYDAMMAR-24-EN-3-YL 2-O-.BETA.-D-GLUCOPYRANOSYL-
Common Name English
GINSENOSIDE RB2 (CONSTITUENT OF AMERICAN GINSENG, ASIAN GINSENG, AND TIENCHI GINSENG) [DSC]
Common Name English
NSC-308878
Code English
Code System Code Type Description
NSC
308878
Created by admin on Sat Dec 16 03:08:24 GMT 2023 , Edited by admin on Sat Dec 16 03:08:24 GMT 2023
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CHEBI
77151
Created by admin on Sat Dec 16 03:08:24 GMT 2023 , Edited by admin on Sat Dec 16 03:08:24 GMT 2023
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ECHA (EC/EINECS)
234-251-4
Created by admin on Sat Dec 16 03:08:24 GMT 2023 , Edited by admin on Sat Dec 16 03:08:24 GMT 2023
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DRUG BANK
DB06748
Created by admin on Sat Dec 16 03:08:24 GMT 2023 , Edited by admin on Sat Dec 16 03:08:24 GMT 2023
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CHEBI
77152
Created by admin on Sat Dec 16 03:08:24 GMT 2023 , Edited by admin on Sat Dec 16 03:08:24 GMT 2023
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PUBCHEM
6917976
Created by admin on Sat Dec 16 03:08:24 GMT 2023 , Edited by admin on Sat Dec 16 03:08:24 GMT 2023
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CAS
11021-13-9
Created by admin on Sat Dec 16 03:08:24 GMT 2023 , Edited by admin on Sat Dec 16 03:08:24 GMT 2023
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EPA CompTox
DTXSID00911541
Created by admin on Sat Dec 16 03:08:24 GMT 2023 , Edited by admin on Sat Dec 16 03:08:24 GMT 2023
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FDA UNII
N219O0L31C
Created by admin on Sat Dec 16 03:08:24 GMT 2023 , Edited by admin on Sat Dec 16 03:08:24 GMT 2023
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