Ginsenoside Rf

Names

[ Name ]:
Ginsenoside Rf

[Synonym ]:
(3β,6α,12β)-3,12,20-Trihydroxydammar-24-en-6-yl 2-O-β-D-glucopyranosyl-β-D-glucopyranoside
Ginsenoside Rf
GinsenosideRf
β-D-Glucopyranoside, (3β,6α,12β)-3,12,20-trihydroxydammar-24-en-6-yl 2-O-β-D-glucopyranosyl-
PANAXOSIDE RF
ginsinoside Rf

Biological Activity

[Description]:

Ginsenoside Rf is a trace component of ginseng root. Ginsenoside Rf inhibits N-type Ca2+ channel.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Neurological Disease

Natural Products >> Terpenoids and Glycosides

Research Areas >> Cancer

[Target]

N-Type Ca2+ Channel

[In Vitro]

Ginsenoside Rf is a saponin, which is present in only trace amounts within ginseng. At saturating concentrations, Ginsenoside Rf rapidly and reversibly inhibits N-type, and other high-threshold, Ca2+ channels in rat sensory neurons to the same degree as a maximal dose of opioids. The effect is dose-dependent (half-maximal inhibition: 40 μM) and it is virtually eliminated by pretreatment of the neurons with pertussis toxin, an inhibitor of G(o) and Gi GTP-binding proteins. Ginsenoside Rf also inhibits Ca2+ channels in the hybrid F-11 cell line[1].

[In Vivo]

Since inhibition of Ca2+ channels in sensory neurons contributes to antinociception by opioids, analgesic actions of Ginsenoside Rf are tested. Dose-dependent antinociception is found by systemic administration of Ginsenoside Rf in mice using two separate assays of tonic pain: in the acetic acid abdominal constriction test, the ED50 is 56±9 mg/kg, a concentration similar to those reported for aspirin and acetaminophen in the same assay; in the tonic phase of the biphasic formalin test, the ED50 is 129±32 mg/kg[2].

[Animal admin]

Mice[2] Naive, adult (7-12 week old) mice of outbred Swiss-Webster stock are used in all in vivo experiments. Mice are brought to a quiet testing room, and acclimated to table-top Plexiglas observation chambers (30 cm high; 30 cm diameter) for 30 min. They are then weighed and injected with Ginsenoside Rf (25, 50, or 75 mg/kg) or vehicle (preceded by naloxone or saline in one experiment). Twenty min later, a 0.9% solution of glacial acetic acid is injected intraperitoneally (i.p.) in a volume of 10 mL/kg. For the next 30 min, the number of constrictions (writhes)-strong contractions of the abdominal musculature accompanied by dorsoflexion of the back and extension of the hindlimbs-are counted and recorded in 5-min blocks. Four mice (one per chamber) are observed simultaneously by a single, experienced experimenter. To control for the considerable circadian and other environmental variance accompanying this nociceptive assay, two vehicle controls are tested alongside two Ginsenoside Rf-administered mice in every experimental session[2].

[References]

[1]. Nah SY, et al. A trace component of ginseng that inhibits Ca²⁺ channels through a pertussis toxin-sensitive G protein. Proc Natl Acad Sci U S A. 1995 Sep 12;92(19):8739-43.

[2]. Mogil JS, et al. Ginsenoside Rf, a trace component of ginseng root, produces antinociception in mice. Brain Res. 1998 May 11;792(2):218-28.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
912.3±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₂H₇₂O₁₄

[ Molecular Weight ]:
801.013

[ Flash Point ]:
505.5±34.3 °C

[ Exact Mass ]:
800.492188

[ PSA ]:
239.22000

[ LogP ]:
3.51

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.602

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LY9536900

CHEMICAL NAME :: Ginsenoside RF

CAS REGISTRY NUMBER :: 52286-58-5

LAST UPDATED :: 199312

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C42-H72-O14

MOLECULAR WEIGHT :: 801.14

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1340 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 25,539,1975

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ Safety Phrases ]:
2-45

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
LY9536900

[ HS Code ]:
29389090

Precursor & DownStream

Precursor

DownStream

Articles

Determination of ginsenoside Rf and Rg2 from Panax ginseng using enzyme immunoassay.

Chem. Pharm. Bull. 46(7) , 1144-7, (1998)

We have developed an enzyme immunoassay (EIA) to quantify trace amounts of ginsenoside Rf (Rf), one of the glycosides of protopanaxatriol from Panax ginseng. A carrier protein of bovine serum albumin ...

[Practical optimization of the two-dimensional thin-layer chromatographic separation of ginsenosides].

Se Pu 18(6) , 546-9, (2000)

A computer-assisted method is presented for optimization of mobile phase selection for separation of the mixture of ginsenosides in two-dimensional TLC. This method bases on the correlation between th...

Microbial conversion of rare ginsenoside Rf to 20(S)-protopanaxatriol by Aspergillus niger.

Biosci. Biotechnol. Biochem. 74(1) , 96-100, (2010)

In this study, rare ginsenoside Rf was transformed into 20(S)-protopanaxatriol (PPT(S)) by glycosidase from Aspergillus niger. By investing the reaction conditions, the optimal conditions were obtaine...