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Polyporenic acid C

$1,344

  • Brand : BIOFRON

  • Catalogue Number : BD-P0822

  • Specification : 98.0%(HPLC)

  • CAS number : 465-18-9

  • Formula : C31H46O4

  • Molecular Weight : 482.69

  • PUBCHEM ID : 9805290

  • Volume : 25mg

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Catalogue Number

BD-P0822

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

482.69

Appearance

White crystalline powder

Botanical Source

Poria cocos

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

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

Synonyms

Polyporenic acid C

IUPAC Name

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

Applications

Bioactivity-guided isolation of anti-inflammatory triterpenoids from the sclerotia of Poria cocos using LPS-stimulated Raw264.7 cells. PUMID/DOI:DOI: 10.1016/j.bioorg.2016.11.012 Bioorg Chem. 2017 Feb;70:94-99. Poria cocos Wolf (Polyporaceae) has been used as a medicinal fungus to treat various diseases since ancient times. This study aimed to investigate the anti-inflammatory chemical constituents of the sclerotia of P. cocos. Based on bioassay-guided fractionation using lipopolysaccharide (LPS)-stimulated Raw264.7 cells, chemical investigation of the EtOH extract of the sclerotia of P. cocos resulted in the isolation and identification of eight compounds including six triterpenoids, namely poricoic acid A (1), 3-O-acetyl-16a-hydroxydehydrotrametenolic acid (2), polyporenic acid C (3), 3?hydroxylanosta-7,9(11),24-trien-21-oic acid (4), trametenolic acid (5), and dehydroeburicoic acid (6), as well as (-)-pinoresinol (7) and protocatechualdehyde (8). The structures of the isolated compounds were determined by spectroscopic analysis, including 1H and 13C NMR spectra, and LC/MS analysis. The anti-inflammatory activities of the isolates were evaluated by estimating their effect on the production of nitric oxide (NO) and prostaglandin E2 (PGE2) in LPS-stimulated Raw264.7 as well as on the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Compounds 1-5 inhibited NO production and iNOS expression in LPS-stimulated Raw264.7 cells. Among them, compound 1 exerted the highest anti-inhibitory activity and reduced PGE2 levels via downregulation of COX-2 protein expression. The findings of this study provide experimental evidence that the sclerotia of P. cocos are a potential source of natural anti-inflammatory agents for use in pharmaceuticals and functional foods. Furthermore, the most active compound 1, seco-lanostane triterpenoid, could be a promising lead compound for the development of novel anti-inflammatory agents. Lanostane Triterpenes Isolated from Antrodia heteromorpha and Their Inhibitory Effects on RANKL-Induced Osteoclastogenesis. PUMID/DOI:DOI: 10.1021/acs.jnatprod.6b00207 J Nat Prod. 2016 Jun 24;79(6):1689-93. Two new spiro-lanostane triterpenoids, antrolactones A and B (1 and 2), along with polyporenic acid C (3), were isolated from an EtOAc-soluble extract of Antrodia heteromorpha culture medium, and the chemical structures of the new compounds were elucidated by application of NMR, MS, and ECD spectroscopic techniques. All isolated compounds exhibited inhibitory effects on receptor activator of nuclear factor-kappaB ligand-induced osteoclastogenesis. Bioactive Triterpenes from the Fungus Piptoporus betulinus PUMID/DOI: Alresly Z, Lindequist U, Lalk M, et al. Bioactive triterpenes from the fungus Piptoporus betulinus[J]. Records of Natural Products, 2016, 10(1):103-108. Phytochemical investigation of the ethyl acetate extract of the fruiting bodies from the basidiomycete Piptoporus betulinus led to the isolation of a new bioactive lanostane triterpene identified as 3 beta-acetoxy-16-hydroxy-24-oxo-5 alpha-lanosta-8-ene-21-oic acid (1). In addition, ten known triterpenes, polyporenic acid A (5), polyporenic acid C (4), three derivatives of polyporenic acid A (8, 10, 11), betulinic acid (3), betulin (2), ergosterol peroxide (6), 9,11-dehydroergosterol peroxide (7), and fomefficinic acid (9), were also isolated from the fungus. All isolated compounds were tested for antimicrobial activity against some Gram-positive and Gram-negative bacteria as well as against a fungal strain. The new triterpene and some of the other compounds showed antimicrobial activity against Gram-positive bacteria. Diuretic activity of aqueous and ethanol extracts fromPoria cocos and Cortex Poriae and active component identification PUMID/DOI: Tian T, Chen H, Yin L, et al. Diuretic activity of aqueous and ethanol extracts from Poria cocos and Cortex Poriae and active component identification[J]. Chinese Journal of Pharmacology & Toxicology, 2014, 28(1):57-62. OBJECTIVE: To evaluate the main chemical components in active fractions and diuretic activities of Poria cocos and Cortex Poriae in saline-loaded rats through chemical component extraction and separation. METHODS The extracts were orally administered to rats at different doses. Urinary volume, pH and electrolyte excretion were measured in the urine of saline-loaded rats in 6 h. The chemical components were isolated from the active fractions and their structures were identified using different chromatographic and spectroscopic techniques. RESULTS The urine output of the ethanol extract of Cortex Poriae150,300 and 600 mg·kg~(-1) groups was increased by 29%,21% and 42% respectively (P <0. 01), which had a remarkable effect on K ~+ retention (18%,22% and 27% respectively,P <0. 01),but induced notable excretion of Na ~+. Each Na ~+ /K ~+ ratio was also enhanced by the ethanol extract of Cortex Poriae. The aqueous extracts of P. cocos (50,100 and 200 mg·kg~(-1)) and Cortex Poriae (75,150 and300 mg·kg~(-1)) as well as the ethanol extract of P. cocos (62. 5,125 and 250 mg·kg~(-1)) showed no diuretic activity. The separation experiment results showed that tetracyclic triterpenoid components,such as pachymic acid,polyporenic acid C,dehydroeburicoic acid,3-epidehydrotumulosic acid,dehydrotumulosic acid,eburicoic acid and dehydroeburiconic acid were the main components of the ethanol extract of Cortex Poriae. CONCLUSION The ethanol extract of Cortex Poriae displays remarkable diuretic activity and its main components are the tetracyclic triterpenoid compounds. Triterpenes from Poria cocos suppress growth and invasiveness of pancreatic cancer cells through the downregulation of MMP-7 PUMID/DOI:DOI: 10.3892/ijo.2013.1902 Int J Oncol. 2013 Jun;42(6):1869-74. Poria cocos is a medicinal mushroom that is widely used in traditional Asian medicine. Here, we show that a characterized mixture of triterpenes extracted from P. cocos (PTE) and three purified triterpenes: pachymic acid (PA), dehydropachymic acid (DPA) and polyporenic acid C (PPAC) suppress the proliferation of the human pancreatic cancer cell lines Panc-1, MiaPaca-2, AsPc-1 and BxPc-3. Moreover, the most effective compound, PA, only slightly affects the proliferation of HPDE-6 normal pancreatic duct epithelial cells. The anti-proliferative effects of PTE on BxPc-3 cells are mediated by the cell cycle arrest at G0/G1 phase. DNA microarray analysis demonstrated that PTE significantly downregulates the expression of KRAS and matrix metalloproteinase-7 (MMP-7) in BxPc-3 cells. In addition, PTE and PA suppress the invasive behavior of BxPc-3 cells. The inhibition of invasiveness by PTE and PA was associated with the reduction of MMP-7 at the protein level and the role of MMP-7 further confirmed by the gene silencing of MMP-7 which also suppressed the invasiveness of BxPc-3 cells. In conclusion, triterpenes from P. cocos demonstrate anticancer and anti-invasive effects on human pancreatic cancer cells and can be considered as new therapeutic agents in the treatment of pancreatic cancer. Polyporenic acid C induces caspase-8-mediated apoptosis in human lung cancer A549 cells. PUMID/DOI:DOI: 10.1002/mc.20487 Mol Carcinog. 2009 Jun;48(6):498-507. Lung cancer continues to be the leading cause of cancer-related mortality worldwide. This warrants the search for new and effective agents against lung cancer. We and others have recently shown that lanostane-type triterpenoids isolated from the fungal species Poria coco

Density

Solubility

Methanol

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C31H46O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h11,13,18,20,23-24,26,32H,3,9-10,12,14-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24+,26+,29-,30-,31+/m1/s1

InChl Key

KPKYWYZPIVAHKU-WMNQUVFJSA-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

30042340

Abstract

Wolfiporia cocos is a fungus containing triterpenoids and is widely used as an herbal medicine. However, it is unknown whether its main triterpenoid contents differ in different tissues. In this study, we identified dehydrotumulosic acid, polyporenic acid C, pachymic acid, dehydrotrametenolic acid, and dehydroeburicoic acid as the five main triterpenoids in W. cocos. We also systematically profiled the contents and distribution of these main triterpenoids in different tissues of W. cocos. High contents of all five triterpenoids were found in the surface layer of W. cocos. Intriguingly, we noted that the highest contents of the five triterpenoids were found in the surface layer of the sclerotium grown under pollution-controlled cultivation; the second-highest contents were found in the surface layer of the natural sclerotium. These results indicate that environmentally friendly cultivation of the sclerotium of W. cocos is a practical way to increase the productivity of W. cocos. In addition, our findings suggest that the triterpenoids may contribute to the pharmacological activity of W. cocos, and the surface layer of sclerotium in W. cocos might be a promising raw material for applications in health care and the development of functional medical products.

KEYWORDS

Wolfiporia cocos; fruiting body; pollution-controlled cultivation; sclerotium; triterpenoids

Title

Determination of the Five Main Terpenoids in Different Tissues of Wolfiporia cocos.

Author

Fu M1,2, Wang L3, Wang X4, Deng B5, Hu X6,7, Zou J8,9.

Publish date

2018 Jul 24

PMID

27266877

Abstract

Two new spiro-lanostane triterpenoids, antrolactones A and B (1 and 2), along with polyporenic acid C (3), were isolated from an EtOAc-soluble extract of Antrodia heteromorpha culture medium, and the chemical structures of the new compounds were elucidated by application of NMR, MS, and ECD spectroscopic techniques. All isolated compounds exhibited inhibitory effects on receptor activator of nuclear factor-kappaB ligand-induced osteoclastogenesis.

Title

Lanostane Triterpenes Isolated from Antrodia heteromorpha and Their Inhibitory Effects on RANKL-Induced Osteoclastogenesis.

Author

Kwon J, Lee H, Yoon YD1, Hwang BY2, Guo Y3, Kang JS1, Kim JJ, Lee D.

Publish date

2016 Jun 24;

PMID

23944068

Abstract

OBJECTIVE:
To study the dymamic accumulation of triterpenic acids production in submerged cultivation mycelium of Poria cocos.

METHOD:
Liquid culture method of P. cocos was established and RP-HPLC was applied to determine the contents of three main triterpenic acids dehydrotumulosic acid (DTA), 3-epi-dehydrotumulosic acid (eDTA) and polyporenic acid C (PAC) in submerged cultivation mycelium P. cocos at different culture stages and the contents were compared with cultivated P. cocos. The HPLC method is as follows, column: Plastisil ODS (4.6 mm x 250 mm, 5 microm); mobile phase: ACN/0.5% phosphate (80:20); flow rate: 1.0 mL . min-1; detective wavelength: 242 nm.

RESULT:
The maximum biomass occurred at the 8th d after inoluctation, however, the contents and yield of three compounds increased till the 17th day. The contents of three compounds were 1. 2% (DTA), 0. 42% (eDTA) and 1.0% (PAC) at the 17th day after inoculation, which were significantly higher than that in cultivated material [0.2% (DTA), 0. 12(eDTA) and 0. 16% (PAC) ]. Furthermore, a correlation analysis between the content ratios of three independent compounds was carried out. The results showed that DTA negatively correlated with eDTA and PAC, with R2 of 0. 857 6 and 0. 971 7, respectively, which suggested the role of DTA as an important intermediate in the biosynthesis of triterpenic acids in P. cocos.

CONCLUSION:
The sum content of three main terpenoids in submerged cultivation mycelium P. cocos was 5. 55 times as that in cultivated material, which strongly suggested the possibility of fermentation in the production of medicinally important triterpenic acids in the future.

Title

[Dynamic accumulation of three main triterpenic acids in submerged cultivation mycelium of Poria cocos].

Author

Zhang Y1, Hu GS, Han ZF, Xiao W, Wang ZD, Bi YA, Jia JM.

Publish date

2013 May