Ginsenoside Rb1 Chemical Properties

Melting point:

197.5°C

Boiling point:

766.35°C (rough estimate)

Density 

1.0971 (rough estimate)

refractive index 

1.6500 (estimate)

storage temp. 

2-8°C

solubility 

methanol: soluble9.80 - 10.20 mg/mL, clear, colorless to faintly yellow

form 

Solid

pka

12.85±0.70(Predicted)

color 

Off-White to Pale Beige

Stability:

Hygroscopic

InChI

InChI=1/C54H92O23/c1-23(2)10-9-14-54(8,77-48-44(69)40(65)37(62)29(74-48)22-70-46-42(67)38(63)34(59)26(19-55)71-46)24-11-16-53(7)33(24)25(58)18-31-51(5)15-13-32(50(3,4)30(51)12-17-52(31,53)6)75-49-45(41(66)36(61)28(21-57)73-49)76-47-43(68)39(64)35(60)27(20-56)72-47/h10,24-49,55-69H,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-,49-,51-,52+,53+,54-/s3

InChIKey

GZYPWOGIYAIIPV-VOKNSFSUNA-N

SMILES

[C@]12([H])C[C@H]([C@]3([H])[C@]([H])(CC[C@@]3(C)[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O[C@H]3[C@H](O)[C@H]([C@H](O)[C@@H](CO)O3)O)CO)CC[C@]21C)[C@](C)(CC/C=C(\C)/C)O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO[C@H]2[C@H](O)[C@H]([C@H](O)[C@@H](CO)O2)O)O1)O)O |&1:0,3,4,6,10,12,16,21,23,25,26,28,30,32,33,35,36,38,47,49,58,59,61,62,64,67,68,70,71,73,r|

LogP

2.900 (est)

CAS DataBase Reference

41753-43-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi,T,F

Risk Statements 

20/21/22-39/23/24/25-23/24/25-11

Safety Statements 

26-36-45-36/37-16-7

WGK Germany 

3

RTECS 

LZ5856000

HS Code 

29389090

Toxicity

oms-rat-ipr 50 mg/kg CPBTAL 24,2400,76

MSDS

• Language:English Provider:SigmaAldrich

Ginsenoside Rb1 Usage And Synthesis

Description

Ginsenoside Rb1, a glycosylated PPD type ginsenoside with two sugars linked to C-3 and two sugars linked to C-20, is the major active constituent of American ginseng. Studies have demonstrated the anti-aging effects of ginsenoside Rb1 at both animal and cell levels. 20-O-β-D-glucopyranosyl-20(S)-protopanaxadiol (20GPPD) is the major ingredient of ginsenoside Rb1, which has been shown to increase HAS2 expression by phosphorylating ERK and AKT signaling in human keratinocytes in a dose-dependent manner in vitro.

Uses

A major bioactive component of panax ginseng that promotes neurotransmitter release by modulating phosphorylation of synapsins through a cAMP-dependent protein kinase pathway. It has been reported to display immunostimulatory and anticancer effects.

Uses

Reference standard in the analysis of herbal medicinal products.

Definition

ChEBI: Ginsenoside Rb1 is a ginsenoside found in Panax ginseng and Panax japonicus var. major that is ginsenoside Rd in which the beta-D-glucopyranoside group at position 20 is replaced by a beta-D-glucopyranosyl-beta-D-glucopyranoside group. It has a role as a neuroprotective agent, an anti-obesity agent, an anti-inflammatory drug, an apoptosis inhibitor, a radical scavenger and a plant metabolite. It is a ginsenoside, a glycoside and a tetracyclic triterpenoid. It is functionally related to a ginsenoside Rd.

benefits

Ginsenoside Rb1 (G-Rb1) is a tetracyclic triterpenoid mainly obtained from the roots or stems of Panax notoginseng and ginseng by extraction and purification. It is one of the main bioactive compounds of ginseng with minimal toxicity and neurotrophic and neuroprotective effects on brain injury. G-Rb1 promotes hippocampal nerve regeneration, enhances learning and memory, and has anti-aging and anti-fatigue effects. In addition, it activates antioxidants, stimulates the immune system, has anti-apoptotic activity, and maintains cell adenosine triphosphate (ATP) levels[1].

General Description

Ginsenoside Rb1 (Gypenoside Ⅲ) is a protopanaxadiol that has diverse in vitro and in vivo effects, including neuroprotective, anti-inflammatory, and anti-obesity actions. Ginsenoside Rb1, a main constituent of the root of Panax ginseng, inhibits Na+, K+-ATPase activity with IC50 of 6.3±1.0 μM. Ginsenoside also inhibits IRAK-1 activation and phosphorylation of NF-κB p65. Ginsenoside Rb1 reduces the expressions of TLR3, TLR4 and TRAF-6, and down-regulates the levels of TNF-α, IFN-β and iNOS.

Biochem/physiol Actions

Triterpene saponin found in ginseng.

Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal route. Mutation data reported. Whenheated to decomposition it emits acrid smoke and irritating fumes.

target

p38MAPK | JNK | GLUT | Akt | IFN-γ | IL Receptor | GSK-3 | HO-1 | PKA | Estrogen receptor | Progestogen receptor

References

[1] Shan Wen. “Ginsenoside Rb1 improves energy metabolism after spinal cord injury.” Neural Regeneration Research 18 6 (2023): 1332–1338.

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