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Dehydropachymic acid

$896

  • Brand : BIOFRON

  • Catalogue Number : BD-P0826

  • Specification : 98.5%(HPLC)

  • CAS number : 77012-31-8

  • PUBCHEM ID : 15226717

  • Volume : 25mg

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Catalogue Number

BD-P0826

Analysis Method

HPLC,NMR,MS

Specification

98.5%(HPLC)

Storage

-20℃

Molecular Weight

Appearance

White crystalline powder

Botanical Source

Poria cocos./ Poria cocos and other fungi

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(C)C(=C)CCC(C1C(CC2(C1(CC=C3C2=CCC4C3(CCC(C4(C)C)OC(=O)C)C)C)C)O)C(=O)O

Synonyms

Lanosta-7,9(11)-dien-21-oic acid, 3-(acetyloxy)-16-hydroxy-24-methylene-, (3β,16α)-/(3β,16α)-3-Acetoxy-16-hydroxy-24-methylenelanosta-7,9(11)-dien-21-oic acid/9-Dehydropachymic acid

IUPAC Name

(2R)-2-[(3S,5R,10S,13R,14R,16R,17R)-3-acetyloxy-16-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid

Applications

Dehydropachymic acid is one of the major triterpenes isolated from Poria cocos. Dehydropachymic acid is more effective in autophagy-lysosome pathway (ALP) impaired cells rather than normal cells[1].

Density

1.1±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

192.1±25.0 °C

Boiling Point

629.3±55.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C33H50O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h12,14,19,22,25-28,35H,3,10-11,13,15-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1

InChl Key

RWIALJIVPUCERT-DRCQUEPLSA-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

provides coniferyl ferulate(CAS#:77012-31-8) 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

30987348

Abstract

As an edible sclerotia-forming fungus, Poria cocos is widely used as a food supplement and as a tonic in China. High-performance liquid chromatography-quadrupole/time-of-flight mass spectrometry (HPLC-QTOF-MS/MS) was applied to identify triterpene acids in fermented mycelia of P. cocos, as well as the epidermis and inner part of natural sclerotia. A total of 19 triterpene acids were identified in fermented mycelia, whereas 31 were identified in the epidermis and 24 in the inner part. Nine triterpene acids were quantitatively determined, and the concentrations of two valuable triterpenes, dehydropachymic acid and pachymic acid, reached 1.07 mg/g and 0.61 mg/g in the fermented mycelia part, respectively, and were both significantly higher than the concentration in the two natural parts. The fermented mycelia could be a good choice for producing some target triterpene compounds and functional foods through fermentation thanks to the high concentration of some triterpene acids.

KEYWORDS

fungi, mycelium, sclerotium, triterpene, HPLC-QTOF-MS/MS

Title

Insights into Triterpene Acids in Fermented Mycelia of Edible Fungus Poria cocos by a Comparative Study

Author

Jian Jin,1,† Rongrong Zhou,2,3,† Jing Xie,1 Huixuan Ye,4 Xuejuan Liang,1 Can Zhong,1 Bingbing Shen,1 You Qin,1 Shuihan Zhang,1,5,* and Luqi Huang2,3,*

Publish date

2019 Apr;

PMID

28077330

Abstract

ETHNOPHARMACOLOGICAL RELEVANCE:
Fuling, the sclerotium of Poria cocos, was frequently used in traditional Chinese medicine (TCM) formulae for Alzheimer’s disease (AD) intervention over the past 10 centuries. And its extracts exhibited significant effects in both cellular and animal models of AD in previous studies. However, its mechanisms on prevention and treatment of AD have not been well elucidated yet.

AIM OF THE STUDY:
To investigate the effect and corresponding mechanisms of dehydropachymic acid, which is one of the major triterpenes in P. cocos, on the clearance of β-amyloid accumulation in bafilomycin A1 induced PC12 cells.

MATERIALS AND METHODS:
MTT assay was used to examine the DPA effect on the viability of PC12 cells stable transfected with pCB6-APP (PC12-APP). PC12-APP cells were treated with DPA at the concentration of 6.25, 12.5, 25μg/mL for 4h, and then co-treated with 50nmol/L bafilomycin A1 for 48h except the controls. The Aβ1-42 content in culture medium was determined by ELISA. The intracellular amount of APP, Aβ1-42, LC3, cathepsin D was measured by Western blotting and normalized to GAPDH loading control. The PC12 cells stable transfected with pSelect-LC3-GFP (PC12-LC3-GFP) was used in the fluorescence microscopy estimation of autophagosomes accumulation. The internal pH in lysosome was detected by LysoTracker Red staining.

RESULTS:
DPA had no significant effect on the cell viability but could significantly decrease Aβ1-42 content in culture medium and eliminate the intracellular accumulation of APP and Aβ1-42 in bafilomycin A1 induced PC12-APP cells. Furthermore, DPA lowered the LC3-II/LC3-I ratio and reduced the GFP-labeled LC3 puncta which were elevated by bafilomycin A1. And the increase in internal pH of lysosome and decrease in mCatD amount in Bafilomycin A1 induced PC12-APP cells were restored by DPA treatment. These results indicated that DPA could restore the lysosomal acidification and recover the autophgic flux which is impaired by bafilomycin A1.

CONCLUSIONS:
DPA could effectively clear the accumulation of Aβ1-42 in bafilomycin A1 impaired PC12 cells through restoring the lysosomal acidification and recovering the autophgic flux. And these results highlight its therapeutic potential for AD treatment.

Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

KEYWORDS

Alzheimer's disease; Autophagy; Bafilomycin A1; Bafilomycin A1 (PubChem CID: 6436223); Dehydropachymic acid; Dehydropachymic acid (PubChem CID: 15226717); Lysosome; β-amyloid

Title

Dehydropachymic acid decreases bafilomycin A1 induced β-Amyloid accumulation in PC12 cells.

Author

Yu M1, Xu X1, Jiang N1, Wei W1, Li F1, He L1, Luo X2.

Publish date

2017 Feb 23

PMID

27808511

Abstract

Six new and 16 known lanostanoids were isolated from the sclerotia of Poria cocos. The structures of the new isolates were elucidated to be 16α-hydroxy-3-oxo-24-methyllanosta-5,7,9(11),24(31)-tetraen-21-oic acid (1), 3β,16α,29-trihydroxy-24-methyllanosta-7,9(11),24(31)-trien-21-oic acid (2), 3β,16α,30-trihydroxy-24-methyllanosta-7,9(11),24(31)-trien-21-oic acid (3), 3β-acetoxy-16α,24β-dihydroxylanosta-7,9(11),25-trien-21-oic acid (4), 3β,16α-dihydroxy-7-oxo-24-methyllanosta-8,24(31)-dien-21-oic acid (5), and 3α,16α-dihydroxy-7-oxo-24-methyllanosta-8,24(31)-dien-21-oic acid (6), based on extensive spectroscopic analyses. The absolute configuration of 4 was determined using Mosher’s method. The antiproliferative activity of the isolated compounds (except 3 and 4) was evaluated against four leukemic cell lines (Molt 4, CCRF-CEM, HL 60, and K562). Dehydropachymic acid (9), dehydroeburicoic acid (12), pachymic acid (14), and lanosta-7,9(11),24-trien-21-oic acid (20) exhibited an antiproliferative effect on the CCRF-CEM cancer cell line with IC50 values of 2.7, 6.3, 4.9, and 13.1 μM, respectively. Both dehydropachymic acid (9) and dehydroeburicoic acid (12) showed antiproliferative effects against Molt 4 (IC50 13.8 and 14.3 μM) and HL 60 (IC50 7.3 and 6.0 μM) leukemic cell lines. Primary computational analysis using a chemical global positioning system for natural products (ChemGPS-NP) on the active lanostanoids from P. cocos suggested that targets other than topoisomerases may be involved in the antiproliferative activity.

Title

Cytotoxic Lanostanoids from Poria cocos.

Author

Lai KH1,2, Lu MC3,4, Du YC1, El-Shazly M1,5, Wu TY1, Hsu YM1, Henz A2, Yang JC6,7, Backlund A2, Chang FR1,8,9, Wu YC1,6,7,10.

Publish date

2016 Nov 23