Ganodermanondiol

CAS# 107900-76-5

Ganodermanondiol

2D Structure

Catalog No. BCN5879----Order now to get a substantial discount!

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Quality Control of Ganodermanondiol

3D structure

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Ganodermanondiol

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Chemical Properties of Ganodermanondiol

Cas No. 107900-76-5 SDF Download SDF
PubChem ID 73294 Appearance Powder
Formula C30H48O3 M.Wt 456.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (5R,10S,13R,14R,17R)-17-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-3-one
SMILES CC(CCC(C(C)(C)O)O)C1CCC2(C1(CC=C3C2=CCC4C3(CCC(=O)C4(C)C)C)C)C
Standard InChIKey AAJIHHYEPHRIET-XEFAKFPISA-N
Standard InChI InChI=1S/C30H48O3/c1-19(9-12-25(32)27(4,5)33)20-13-17-30(8)22-10-11-23-26(2,3)24(31)15-16-28(23,6)21(22)14-18-29(20,30)7/h10,14,19-20,23,25,32-33H,9,11-13,15-18H2,1-8H3/t19-,20-,23+,25+,28-,29-,30+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Ganodermanondiol

The fruit body of Ganoderma lucidum

Biological Activity of Ganodermanondiol

DescriptionGanodermanondiol exhibits potent cytoprotective effects on t-BHP-induced hepatotoxicity in human liver-derived HepG2 cells, presumably through Nrf2-mediated antioxidant enzymes and AMPK. It also can significantly inhibit the proliferation of leukemic cancer cells, and it could be one of the antileukemie active constituents of Ganoderma lucidum. Ganodermanondiol shows a strong anticomplement activity against the classical pathway (CP) of the complement system with IC(50) values of 41.7 microM. It shows significant anti-human immunodeficiency virus (anti-HIV)-1 protease activity with IC50 values of 20-90 microM.
TargetsNrf2 | HIV | AMPK
In vitro

Protective effect of ganodermanondiol isolated from the Lingzhi mushroom against tert-butyl hydroperoxide-induced hepatotoxicity through Nrf2-mediated antioxidant enzymes.[Pubmed: 23266269]

Food Chem Toxicol. 2013 Mar;53:317-24.

Ganodermanondiol, a biologically active compound, was isolated from the Lingzhi mushroom (Ganoderma lucidum). The present study examined the protective effects of Ganodermanondiol against tert-butyl hydroperoxide (t-BHP)-induced hepatotoxicity.
METHODS AND RESULTS:
Ganodermanondiol protected human liver-derived HepG2 cells through nuclear factor-E2-related factor 2 (Nrf2) pathway-dependent heme oxygenase-1 expressions. Moreover, Ganodermanondiol increased cellular glutathione levels and the expression of the glutamine-cysteine ligase gene in a dose-dependent manner. Furthermore, Ganodermanondiol exposure enhanced the phosphorylation of adenosine monophosphate-activated protein kinase (AMPK) and its upstream kinase activators, LKB1 and Ca(2+)/calmodulin-dependent protein kinase-II (CaMKII).
CONCLUSIONS:
This study indicates that Ganodermanondiol exhibits potent cytoprotective effects on t-BHP-induced hepatotoxicity in human liver-derived HepG2 cells, presumably through Nrf2-mediated antioxidant enzymes and AMPK.

Anticomplement activity of terpenoids from the spores of Ganoderma lucidum.[Pubmed: 11745016]

Planta Med. 2001 Dec;67(9):811-4.

A new lanostane-type terpenoid, lucidenic acid SP1 (1), was isolated from a CHCl(3)-soluble fraction of Ganoderma lucidum spores together with four other known compounds (2 - 5). The structure of lucidenic acid SP1 was determined to be 3 beta,7 beta-dihydroxy-4,4,14 alpha-trimethyl-11,15-dioxo-5 alpha-chol-8-en-24-oic acid by spectroscopic means including 2D-NMR.
METHODS AND RESULTS:
Twelve triterpenes (1-12) isolated from G. lucidum spores were investigated in vitro for their anticomplementary activity. Compounds 1 - 5 were inactive, whereas ganoderiol F (8), Ganodermanondiol (9) and ganodermanontriol (10) showed a strong anticomplement activity against the classical pathway (CP) of the complement system with IC(50) values of 4.8, 41.7, and 17.2 microM, respectively. The potency of these triterpene alcohols (8-10) in inhibiting CP activity was improved when the number of hydroxymethyl groups on the side chain moiety is increased. On the other hand, the ganoderic acids 1-7, which contain a carboxyl group in the side chain, and lucidumols A and B (11, 12) had little activity on this system.

Protocol of Ganodermanondiol

Kinase Assay

Triterpenes from the spores of Ganoderma lucidum and their inhibitory activity against HIV-1 protease.[Pubmed: 9810695]

Chem Pharm Bull (Tokyo). 1998 Oct;46(10):1607-12.

Two new lanostane-type triterpenes, lucidumol A and ganoderic acid beta, were isolated from the spores of Ganoderma (G.) lucidum, together with a new natural one and seven that were known. The structures of the new triterpenes were determined as (24S)-24,25-dihydroxylanost-8-ene-3,7-dione and 3 beta,7 beta-dihydroxy-11,15-dioxolanosta-8,24(E)-dien-26-oic acid, respectively, by chemical and spectroscopic means.
METHODS AND RESULTS:
The quantitative analyses of 5 fruiting bodies, antlered form and spores of G. lucidum were performed by high performance liquid chromatography and demonstrated that ganoderic alcohol and acid contents were quite high in the spore. Of the compound isolated, ganoderic acid beta, (24S)-lanosta-7,9(11)-diene-3 beta,24,25-triol (called lucidumol B), Ganodermanondiol, ganodermanontriol and ganolucidic acid A showed significant anti-human immunodeficiency virus (anti-HIV)-1 protease activity with IC50 values of 20-90 microM.

Ganodermanondiol Dilution Calculator

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Ganodermanondiol Molarity Calculator

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Preparing Stock Solutions of Ganodermanondiol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1896 mL 10.9481 mL 21.8962 mL 43.7924 mL 54.7405 mL
5 mM 0.4379 mL 2.1896 mL 4.3792 mL 8.7585 mL 10.9481 mL
10 mM 0.219 mL 1.0948 mL 2.1896 mL 4.3792 mL 5.4741 mL
50 mM 0.0438 mL 0.219 mL 0.4379 mL 0.8758 mL 1.0948 mL
100 mM 0.0219 mL 0.1095 mL 0.219 mL 0.4379 mL 0.5474 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Ganodermanondiol

Protective effect of ganodermanondiol isolated from the Lingzhi mushroom against tert-butyl hydroperoxide-induced hepatotoxicity through Nrf2-mediated antioxidant enzymes.[Pubmed:23266269]

Food Chem Toxicol. 2013 Mar;53:317-24.

Ganodermanondiol, a biologically active compound, was isolated from the Lingzhi mushroom (Ganoderma lucidum). The present study examined the protective effects of Ganodermanondiol against tert-butyl hydroperoxide (t-BHP)-induced hepatotoxicity. Ganodermanondiol protected human liver-derived HepG2 cells through nuclear factor-E2-related factor 2 (Nrf2) pathway-dependent heme oxygenase-1 expressions. Moreover, Ganodermanondiol increased cellular glutathione levels and the expression of the glutamine-cysteine ligase gene in a dose-dependent manner. Furthermore, Ganodermanondiol exposure enhanced the phosphorylation of adenosine monophosphate-activated protein kinase (AMPK) and its upstream kinase activators, LKB1 and Ca(2+)/calmodulin-dependent protein kinase-II (CaMKII). This study indicates that Ganodermanondiol exhibits potent cytoprotective effects on t-BHP-induced hepatotoxicity in human liver-derived HepG2 cells, presumably through Nrf2-mediated antioxidant enzymes and AMPK.

Anticomplement activity of terpenoids from the spores of Ganoderma lucidum.[Pubmed:11745016]

Planta Med. 2001 Dec;67(9):811-4.

A new lanostane-type terpenoid, lucidenic acid SP1 (1), was isolated from a CHCl(3)-soluble fraction of Ganoderma lucidum spores together with four other known compounds (2 - 5). The structure of lucidenic acid SP1 was determined to be 3 beta,7 beta-dihydroxy-4,4,14 alpha-trimethyl-11,15-dioxo-5 alpha-chol-8-en-24-oic acid by spectroscopic means including 2D-NMR. Twelve triterpenes (1-12) isolated from G. lucidum spores were investigated in vitro for their anticomplementary activity. Compounds 1 - 5 were inactive, whereas ganoderiol F (8), Ganodermanondiol (9) and ganodermanontriol (10) showed a strong anticomplement activity against the classical pathway (CP) of the complement system with IC(50) values of 4.8, 41.7, and 17.2 microM, respectively. The potency of these triterpene alcohols (8-10) in inhibiting CP activity was improved when the number of hydroxymethyl groups on the side chain moiety is increased. On the other hand, the ganoderic acids 1-7, which contain a carboxyl group in the side chain, and lucidumols A and B (11, 12) had little activity on this system.

Triterpenes from the spores of Ganoderma lucidum and their inhibitory activity against HIV-1 protease.[Pubmed:9810695]

Chem Pharm Bull (Tokyo). 1998 Oct;46(10):1607-12.

Two new lanostane-type triterpenes, lucidumol A and ganoderic acid beta, were isolated from the spores of Ganoderma (G.) lucidum, together with a new natural one and seven that were known. The structures of the new triterpenes were determined as (24S)-24,25-dihydroxylanost-8-ene-3,7-dione and 3 beta,7 beta-dihydroxy-11,15-dioxolanosta-8,24(E)-dien-26-oic acid, respectively, by chemical and spectroscopic means. The quantitative analyses of 5 fruiting bodies, antlered form and spores of G. lucidum were performed by high performance liquid chromatography and demonstrated that ganoderic alcohol and acid contents were quite high in the spore. Of the compound isolated, ganoderic acid beta, (24S)-lanosta-7,9(11)-diene-3 beta,24,25-triol (called lucidumol B), Ganodermanondiol, ganodermanontriol and ganolucidic acid A showed significant anti-human immunodeficiency virus (anti-HIV)-1 protease activity with IC50 values of 20-90 microM.

Description

Ganodermanondiol is a melanogenesis inhibitor isolated from the Ganoderma lucidum.Ganodermanondiol exhibits potent cytoprotective effects on tert-butyl hydroperoxide-induced hepatotoxicity. Ganodermanondiol shows significant anti-HIV-1 protease activity with an IC50 of 90 μM. Ganodermanondiol exhibits a strong anticomplement activity against the classical pathway of the complement system with an IC50 of 41.7μM.

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