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Procyanidin A1

$572

  • Brand : BIOFRON

  • Catalogue Number : BD-P0296

  • Specification : 98.0%(HPLC)

  • CAS number : 103883-03-0

  • Formula : C30H24O12

  • Molecular Weight : 576.51

  • PUBCHEM ID : 134715108

  • Volume : 25mg

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Catalogue Number

BD-P0296

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

576.51

Appearance

Powder

Botanical Source

Structure Type

Anthocyanins/Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(OC2=C1C(=CC3=C2C4C(C(O3)(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O)C7=CC(=C(C=C7)O)O)O

Synonyms

procyanidin A1/Proanthocyanidin A-1/epicatechin-(4β-->8, 2β-->O-->7)-catechin/PROANTHOCYANIDIN A/proanthocyanidin A1

IUPAC Name

(1R,5R,6S,13S,21S)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol

Applications

Procyanidin A1 (Proanthocyanidin A1) is a procyanidin dimer, which inhibits degranulation downstream of protein kinase C activation or Ca2+ influx from an internal store in RBL-213 cells. Procyanidin A1 has antiallergic effects[1].

Density

Solubility

Methanol

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26+,27+,29-,30-/m0/s1

InChl Key

NSEWTSAADLNHNH-LQBIBLAPSA-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#:103883-03-0) 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

17473436

Abstract

In this study, we investigated the effects of an aqueous extract of peanut (Arachis hypogaea L.) seed skin (PSE) and its main constituent procyanidin A1 (PA) on the allergic response to allergen ovalbumin (OVA) in a mouse model. Mice immunized interaperitoneally with OVA dramatically increased anti-OVA IgE and total IgG1 levels in serum compared with non-treated control mice. Oral injection of PSE at doses ranging from 10 to 100 mg/kg/d (for 21 consecutive days) decreased anti-OVA IgE and IgG1 levels 21 d after OVA-immunization. OVA-induced increments in spleen weight and peripheral white blood cell count were also suppressed by this PSE administration. Polyphenol-enriched fractions from apple (30 mg/kg) and grape seed (30 mg/kg) also decreased anti-OVA IgE level but did not affect total IgG1 levels. Oral injection of PA (1 to 10 mg/kg/d) purified from PSE resulted in a suppression of IgE and total IgG1 levels in serum. An increment of serum interleukin-4 level in mice that were immunized with OVA was reduced by all tested samples, whereas PSE and PA were the only compounds that could reverse the reduced interferon-gamma level by OVA. These findings suggest that intake of PSE or its main active constituent PA may prevent an allergic reaction by inhibiting immunoglobulin synthesis, and the mechanism of this action of PSE and PA is in part due to their regulation of T helper cytokine production.

Title

Aqueous Extract of Peanut Skin and Its Main Constituent Procyanidin A1 Suppress Serum IgE and IgG1 Levels in Mice-Immunized With Ovalbumin

Author

Fumihide Takano 1 , Takanobu Takata, Akio Yoshihara, Yuka Nakamura, Yukiko Arima, Tomihisa Ohta

Publish date

2007 May

PMID

21897038

Abstract

Peanut skin contains large amounts of polyphenols having antiallergic effects. We found that a peanut-skin extract (PSE) inhibits the degranulation induced by antigen stimulation of rat basophilic leukemia (RBL-2H3) cells. A low-molecular-weight fraction from PSE, PSEL, also had inhibitory activity against allergic degranulation. A main polyphenol in PSEL was purified by gel chromatography and fractionated by YMC-gel ODS-AQ 120S50 column. Electrospray ionization mass spectrometry (ESI-MS) analysis of the purified polyphenol gave m/z 599 [M+Na]⁺. Based on the results of ¹H-NMR, ¹³C-NMR spectra, and optical rotation analysis, the polyphenol was identified as procyanidin A1. It inhibited the degranulation caused by antigen stimulation at the IC₅₀ of 20.3 µM. Phorbol-12-myristate-13-acetate (PMA) and 2,5,-di(tert-butyl)-1,4-hydroquinone (DTBHQ)-induced processes of degranulation were also inhibited by procyanidin A1. These results indicate that peanut-skin procyanidin A1 inhibits degranulation downstream of protein kinase C activation or Ca²⁺ influx from an internal store in RBL-2H3 cells.

Title

Effects of Peanut-Skin Procyanidin A1 on Degranulation of RBL-2H3 Cells

Author

Keisuke Tomochika 1 , Akiko Shimizu-Ibuka, Tomoko Tamura, Kiyoshi Mura, Naoki Abe, Jun-Ichi Onose, Soichi Arai

Publish date

2011

PMID

31636354

Abstract

Inflammation is a complex physiological process that poses a serious threat to people’s health. However, the potential molecular mechanisms of inflammation are still not clear. Moreover, there is lack of effective anti-inflammatory drugs that meet the clinical requirement. Procyanidin A1 (PCA1) is a monomer component isolated from Procyanidin and shows various pharmacological activities. This study further demonstrated the regulatory role of PCA1 on lipopolysaccharide (LPS)-stimulated inflammatory response and oxidative stress in RAW264.7 cells. Our data showed that PCA1 dramatically attenuated the production of pro-inflammatory cytokines such as NO, iNOS, IL-6, and TNF-α in RAW264.7 cells administrated with LPS. PCA1 blocked IκB-α degradation, inhibited IKKα/β and IκBα phosphorylation, and suppressed nuclear translocation of p65 in RAW264.7 cells induced by LPS. PCA1 also suppressed the phosphorylation of JNK1/2, p38, and ERK1/2 in LPS-stimulated RAW264.7 cells. In addition, PCA1 increased the expression of HO-1, reduced the expression of Keap1, and promoted Nrf2 into the nuclear in LPS-stimulated RAW264.7 cells. Cellular thermal shift assay indicated that PCA1 bond to TLR4. Meanwhile, PCA1 inhibited the production of intracellular ROS and alleviated the depletion of mitochondrial membrane potential in vitro. Collectively, our data indicated that PCA1 exhibited a significant anti-inflammatory effect, suggesting that it is a potential agent for the treatment of inflammatory diseases.

Title

Procyanidin A1 Alleviates Inflammatory Response Induced by LPS Through NF-κB, MAPK, and Nrf2/HO-1 Pathways in RAW264.7 Cells

Author

Shan Han 1 2 , Hongwei Gao 1 2 , Shaoru Chen 3 , Qinqin Wang 1 2 , Xinxing Li 1 2 , Li-Jun Du 4 , Jun Li 5 , Ying-Ying Luo 5 , Jun-Xiu Li 1 2 , Li-Chun Zhao 6 7 , Jianfang Feng 8 9 , Shilin Yang 1 2

Publish date

2019 Oct 21