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Ganoderic acid D

$572

  • Brand : BIOFRON

  • Catalogue Number : BD-P0080

  • Specification : 98.0%(HPLC)

  • CAS number : 108340-60-9

  • PUBCHEM ID : 14109405

  • Volume : 25mg

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Catalogue Number

BD-P0080

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

Appearance

Powder

Botanical Source

Ganodermalucidum(Leyss.exFr.)Karst.

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(CC(=O)CC(C)C(=O)O)C1CC(=O)C2(C1(CC(=O)C3=C2C(CC4C3(CCC(=O)C4(C)C)C)O)C)C

Synonyms

Ganoderic-acid-D/Lanost-8-en-26-oic acid, 7-hydroxy-3,11,15,23-tetraoxo-, (7β)-/GanodericacidD/(7β)-7-Hydroxy-3,11,15,23-tetraoxolanost-8-en-26-oic acid

IUPAC Name

6-(7-hydroxy-4,4,10,13,14-pentamethyl-3,11,15-trioxo-1,2,5,6,7,12,16,17-octahydrocyclopenta[a]phenanthren-17-yl)-2-methyl-4-oxoheptanoic acid

Applications

Ganoderic acid D, a highly oxygenated tetracyclic triterpenoid, is the major active component of Ganoderma lucidum. Ganoderic acid D upregulates the protein expression of SIRT3 and induces the deacetylated cyclophilin D (CypD) by SIRT3. Ganoderic acid D inhibits the energy reprogramming of colon cancer cells including glucose uptake, lactate production, pyruvate and acetyl-coenzyme production in colon cancer cells[1]. Ganoderic acid D can inhibit the growth of numerous cancer cell lines and it inhibits HeLa human cervical carcinoma cells with an IC50 of 17.3 mM[2].

Density

1.2±0.1 g/cm3

Solubility

Methanol

Flash Point

384.1±28.0 °C

Boiling Point

688.3±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C30H42O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h15-16,18-19,21,32H,8-14H2,1-7H3,(H,36,37)/t15-,16?,18-,19+,21?,28+,29-,30+/m1/s1

InChl Key

YTVGSCZIHGRVAV-FTRKVESOSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:108340-60-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

22942320

Abstract

Ganoderic acid D (GD) is the major active triterpenoid in Ganoderma lucidum, a medicinal fungus used daily. However, the metabolic fate of GD remains unknown. To know whether GD is extensively metabolized, we first investigated the metabolism of GD in vitro and in vivo. The metabolic profiles of the bile samples obtained from rats in vivo were almost the same as those obtained in vitro. Using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry, a total of 25 metabolites were identified from the bile sample. Few metabolites were found in the urine samples. These results indicated that biliary rather than renal clearance was the major route of excretion. The major metabolites were identified by comparison with the standard reference compounds. Metabolites at low concentrations were identified by interpreting the mass spectra. Both phase I and phase II metabolites were observed. The metabolic transformation included reduction, monohydroxylation, dihydroxylation, trihydroxylation, oxidation, desaturation, sulfation, and glucuronidation. The main metabolic soft spots in the chemical structure of GD were the 3-carbonyl group, angular methyl groups, the 7-hydroxy group, and the 26-carboxylic acid moiety. Overall, this study gives us an insight into the metabolism of GD, an active oxygenated tetracyclic triterpenoid.

Title

Identification of Metabolites of Ganoderic Acid D by Ultra-Performance Liquid Chromatography/Quadrupole Time-Of-Flight Mass Spectrometry

Author

Chunru Cheng 1 , Min Yang, Kate Yu, Shuhong Guan, Sijia Tao, Alan Millar, Xiaoyan Pang, Dean Guo

Publish date

2012 Dec

PMID

29374515

Abstract

Ganoderic acid D (GAD) is a highly oxygenated tetracyclic triterpenoid. This study aims to assess the effects of GAD on the energy metabolism of colon cancer through the regulation of SIRT3 expression and whether this effect is related to acetylated cyclophilin D. The results demonstrated that GAD inhibits the energy reprogramming of colon cancer cells including glucose uptake, lactate production, pyruvate and acetyl-coenzyme production in colon cancer cells. Meanwhile, GAD upregulated the protein expression of SIRT3. Furthermore, the interruption of SIRT3 expression significantly reversed all the effects of SIRT3 on the energy reprogramming of colon cancer. In addition, GAD induced the deacetylated cyclophilin D (CypD) by SIRT3, whereas SIRT3-shRNA inhibited its combining effect on CypD. The energy reprogramming effects of GAD on colon cancer seem to be mediated by SIRT3 upregulation via acetylated CypD inhibition.

KEYWORDS

Colon cancer; Cyclophilin D; Ganoderic acid D; Glucose metabolism; SIRT3; Warburg effect.

Title

Effect of Ganoderic Acid D on Colon Cancer Warburg Effect: Role of SIRT3/cyclophilin D

Author

Zhendong Liu 1 , Liang Li 1 , Bei Xue 2

Publish date

2018 Apr 5

PMID

23692850

Abstract

The present study aims to investigate the pharmacokinetics of ganoderic acid D (GD), a representative active triterpenoid from Ganoderma lucidum. A sensitive and selective liquid chromatography-tandem mass spectrometry method was developed for the simultaneous determination of the concentrations of GD and its main metabolite (ganoderic acid B) in rat plasma. Following protein precipitation, the analytes were separated on a reversed-phase C18 column. Acetonitrile-water-acetic acid (40:60:0.01) was used at a flow-rate of 0.2ml/min. A triple quadrupole mass spectrometer equipped with an electrospray ionization source was used as the detector and was operated in the negative ion mode. Multiple reaction monitoring using the characteristic transitions was performed to quantify the analytes. The method had a lower limit of quantification of 8.19ng/ml for GD, and 8.59ng/ml for ganoderic acid B (GB). The calibration curves were demonstrated to be linear over the concentration range of 8.19-4096ng/ml and 8.59-2149ng/ml, respectively. Variations within- and between-batch were less than 6.4% and 4.6%, respectively. The extraction recovery rates ranged from 98.8 to 105.2% and 100.7 to 113.6%, respectively. The validated method was successfully applied to the quantification of GD and GB concentrations in rat plasma after oral administration (or intravenous administration) of GD preparations at a dose of 15mg/kg. The data showed that the absolute bioavailability increased from 22% to 70% after the GD suspension was changed to GD loaded solid lipid nanoparticles. In the meantime, the Cmax increased from 107.2 to 1555.6ng/ml; the tmax changed from 2.0h to 0.3h. These results are very helpful in the further studies.
Copyright © 2013 Elsevier B.V. All rights reserved.

Title

Pharmacokinetics of Ganoderic Acid D and Its Main Metabolite by Liquid Chromatography-Tandem Mass Spectrometry

Author

Chun-Ru Cheng 1 , Min Yang, Shu-Hong Guan, Xiao-Hui Wu, Xiao-Yan Pang, Yang Wang, Yi Yang, Jie Ding, De-An Guo

Publish date

2013 Jul 1