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Ganoderol B

$516

  • Brand : BIOFRON

  • Catalogue Number : BD-P0077

  • Specification : 95.0%(HPLC)

  • CAS number : 104700-96-1

  • PUBCHEM ID : 13934286

  • Volume : 10mg

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Catalogue Number

BD-P0077

Analysis Method

HPLC,NMR,MS

Specification

95.0%(HPLC)

Storage

2-8°C

Molecular Weight

Appearance

White crystalline powder

Botanical Source

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(CCC=C(C)CO)C1CCC2(C1(CC=C3C2=CCC4C3(CCC(C4(C)C)O)C)C)C

Synonyms

ganoderol B/Lanosta-7,9(11),24-triene-3,26-diol, (3β,24E)-/(3β,24E)-Lanosta-7,9(11),24-triene-3,26-diol/Ganodermadiol

IUPAC Name

(3S,5R,10S,13R,14R,17R)-17-[(E,2R)-7-hydroxy-6-methylhept-5-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-ol

Applications

Triterpenoids from Ganoderma lucidum inhibit the activation of EBV antigens as telomerase inhibitors PUMID/DOI:DOI: 10.3892/etm.2017.4883 Exp Ther Med. 2017 Oct;14(4):3273-3278. Nasopharyngeal carcinoma (NPC) is a malignant disease that threatens the health of humans. To find effective agents for the inhibition of Epstein-Barr virus (EBV) infection, which is associated with NPC, a phytochemical investigation of Ganoderma lucidum was carried out in the present study. Five triterpenoids were identified, including ganoderic acid A (compound 1), ganoderic acid B (compound 2), ganoderol B (compound 3), ganodermanontriol (compound 4), and gano-dermanondiol (compound 5), on the basis of spectroscopic analysis. An inhibition of EBV antigens activation assay was implemented to elucidate the triterpenoids from G. lucidum and potentially prevent NPC. All the triterpenoids showed significant inhibitory effects on both EBV EA and CA activation at 16 nmol. At 3.2 nmol, all the compounds moderately inhibited the activation of the two antigens. The activity of telomerase was inhibited by these triterpenoids at 10 mu M. Molecular docking demonstrated that compound 1 was able to inhibit telomerase as a ligand. In addition, the physicochemical properties of these compounds were calculated to elucidate their drug-like properties. These results provided evidence for the application of these triterpenoids and whole G. lucidum in the treatment of NPC. Protective effects of triterpenoids from Ganoderma resinaceum on H2O2-induced toxicity in HepG2 cells PUMID/DOI:DOI: 10.1016/j.foodchem.2013.03.071 Food Chem. 2013 Nov 15;141(2):920-6. Ganoderma resinaceum Boud. (Polyporeseae) has long been used for antioxidant, immunoregulation and liver protection. From the fruiting bodies of G. resinaceum, eight new lanostanoids, lucidones D-G (1-4), 7-oxo-ganoderic acid Z(2) (5), 7-oxo-ganoderic acid Z(3) (6), ganoderesin A (7), and ganoderesin B (8), together with six known lanostanoids (9-14) were isolated. The structures of new compounds were elucidated through extensive spectroscopic analysis. In an in vitro model, ganoderesin B (8), ganoderol B (10) and lucidone A (11) showed inhibitory effects against the increase of ALT and AST levels in HepG2 cells induced by H2O2 compared to a control group in the range of their maximum non-toxic concentration (MNTC). However, compounds 8, 10 and 11 displayed no anti-oxidant activities by DPPH assay. Mean-while, activation for PXR (Pregnane X Receptor) of ganoderesin B (8), ganoderol B (10) and lucidone A (11) was evaluated; ganoderol (10) exhibited a vital activation for PXR-induced CYP3A4 expression. These results suggested that GTs (Ganoderma triterpenoids) exhibited hepatoprotective activities by lowering ALT and AST levels. (C) 2013 Elsevier Ltd. All rights reserved. Ganoderol B: A potent alpha-glucosidase inhibitor isolated from the fruiting body of Ganoderma lucidum PUMID/DOI:DOI: 10.1016/j.phymed.2011.03.011 Phytomedicine. 2011 Sep 15;18(12):1053-5. alpha-Glucosidase inhibitor has considerable potential as a diabetes mellitus type 2 drug because it prevents the digestion of carbohydrates. The search for the constituents reducing alpha-glucosidase activity led to the finding of active compounds in the fruiting body of Ganoderma lucidum. The CHCl3 extract of the fruiting body of G. lucidum was found to show inhibitory activity on alpha-glucosidase in vitro. The neutral fraction, with an IC50 of 88.7 mu g/ml, had stronger inhibition than a positive control, acarbose, with an IC50 of 336.7 mu g/ml (521.5 mu M). The neutral fraction was subjected to silica gel column chromatography and repeated p-HPLC to provide an active compound, (3 beta,24E)-lanosta-7,9(11),24-trien-3,26-diol (ganoderol B). It was found to have high alpha-glucosidase inhibition, with an IC50 of 48.5 mu g/ml (119.8 mu M). (C) 2011 Elsevier GmbH. All rights reserved. The anti-androgen effect of ganoderol B isolated from the fruiting body of Ganoderma lucidum PUMID/DOI:DOI: 10.1016/j.bmc.2007.04.036 Bioorg Med Chem. 2007 Jul 15;15(14):4966-72. The anti-androgenic activity of the ethanol extract of the fruiting body of Ganoderma lucidum has been previously reported. Ganoderol B with 5 alpha-reductase inhibitory activity and the ability to bind to androgen receptor (AR) can inhibit androgen-induced LNCaP cell growth and suppress regrowth of the ventral prostate induced by testosterone in rats. The down-regulation of AR signaling by ganoderol B provides an important mechanism for its anti-androgenic activity. In view of the fact that PSA (prostatic specific antigen, a well-accepted prognostic indicator of prostate cancer) is down-regulated, an important implication of this study is that ganoderol B intervention strategy aimed at toning down the amplitude of androgen signaling could be helpful in controlling morbidity of prostate cancer. In conclusion, our result suggests that ganoderol B might be useful in prostate cancer and benign prostatic hyperplasia (BPH) therapy through suppressing the function of androgen and its receptor. (c) 2007 Elsevier Ltd. All rights reserved.

Density

1.0±0.1 g/cm3

Solubility

Methanol; Chloroform; Ethyl Acetate

Flash Point

226.1±24.7 °C

Boiling Point

552.7±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C30H48O2/c1-20(19-31)9-8-10-21(2)22-13-17-30(7)24-11-12-25-27(3,4)26(32)15-16-28(25,5)23(24)14-18-29(22,30)6/h9,11,14,21-22,25-26,31-32H,8,10,12-13,15-19H2,1-7H3/b20-9+/t21-,22+,25?,26+,28-,29-,30+/m1/s1

InChl Key

AOXXVRDKZLRGTJ-CUJMEZSJSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

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No Technical Documents Available For This Product.

PMID

29748985

Abstract

Ganoderic acid S, ganoderic acid T and ganoderal B are the main bioactive triterpenes of Ganoderma lucidum. In this study, mycelia of G. lucidum were obtained by two-stage fermentation and then extracted by ethanol and petroleum ether sequentially to obtain crude triterpenes. The crude sample was further purified by recycling high-speed counter-current chromatography with n-hexane-ethyl acetate-methanol-water (7:12:11:5, v/v/v/v) as the optimized two-phase solvent system. A 16.4 mg aliquot of ganoderol B with a purity of 90.4% was separated from 300 mg of the crude sample in a single run. After employing the recycling elution mode of HSCCC with n-hexane-ethyl acetate-methanol-water (6:10:8:4.5, v/v/v/v) for five cycles, 25.7 mg ganoderic acid T and 3.7 mg ganoderic acid S with purities of 97.8 and 83.0%, respectively, were obtained. The purities of three compounds were determined by high-performance liquid chromatography and their chemical structures were identified by NMR and MS data.

Copyright © 2018 John Wiley & Sons, Ltd.

KEYWORDS

Ganoderma lucidum; bioactive triterpenes; high-performance liquid chromatography; high-speed counter-current chromatography

Title

Preparative isolation of ganoderic acid S, ganoderic acid T and ganoderol B from Ganoderma lucidum mycelia by high-speed counter-current chromatography.

Author

Feng N1, Wei Y2, Feng J1, Tang Q1, Zhang Z1, Zhang J1, Han W2.

Publish date

2018 Oct;

PMID

21596546

Abstract

α-Glucosidase inhibitor has considerable potential as a diabetes mellitus type 2 drug because it prevents the digestion of carbohydrates. The search for the constituents reducing α-glucosidase activity led to the finding of active compounds in the fruiting body of Ganoderma lucidum. The CHCl(3) extract of the fruiting body of G. lucidum was found to show inhibitory activity on α-glucosidase in vitro. The neutral fraction, with an IC(50) of 88.7 μg/ml, had stronger inhibition than a positive control, acarbose, with an IC(50) of 336.7 μg/ml (521.5 μM). The neutral fraction was subjected to silica gel column chromatography and repeated p-HPLC to provide an active compound, (3β,24E)-lanosta-7,9(11),24-trien-3,26-diol (ganoderol B). It was found to have high α-glucosidase inhibition, with an IC(50) of 48.5 μg/ml (119.8 μM).

Copyright © 2011 Elsevier GmbH. All rights reserved.

Title

Ganoderol B: a potent α-glucosidase inhibitor isolated from the fruiting body of Ganoderma lucidum.

Author

Fatmawati S1, Shimizu K, Kondo R.

Publish date

2011 Sep 15;

PMID

17499997

Abstract

The anti-androgenic activity of the ethanol extract of the fruiting body of Ganoderma lucidum has been previously reported. Ganoderol B with 5alpha-reductase inhibitory activity and the ability to bind to androgen receptor (AR) can inhibit androgen-induced LNCaP cell growth and suppress regrowth of the ventral prostate induced by testosterone in rats. The down-regulation of AR signaling by ganoderol B provides an important mechanism for its anti-androgenic activity. In view of the fact that PSA (prostatic specific antigen, a well-accepted prognostic indicator of prostate cancer) is down-regulated, an important implication of this study is that ganoderol B intervention strategy aimed at toning down the amplitude of androgen signaling could be helpful in controlling morbidity of prostate cancer. In conclusion, our result suggests that ganoderol B might be useful in prostate cancer and benign prostatic hyperplasia (BPH) therapy through suppressing the function of androgen and its receptor.

Title

The anti-androgen effect of ganoderol B isolated from the fruiting body of Ganoderma lucidum.

Author

Liu J1, Shimizu K, Konishi F, Kumamoto S, Kondo R.

Publish date

2007 Jul 15;