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Pachypodol

$986

  • Brand : BIOFRON

  • Catalogue Number : BD-P0745

  • Specification : 99.0%(HPLC&TLC)

  • CAS number : 33708-72-4

  • Formula : C18H16O7

  • Molecular Weight : 344.3

  • PUBCHEM ID : 5281677

  • Volume : 25mg

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Catalogue Number

BD-P0745

Analysis Method

HPLC,NMR,MS

Specification

99.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

344.3

Appearance

Yellow powder

Botanical Source

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC(=C2C(=C1)OC(=C(C2=O)OC)C3=CC(=C(C=C3)O)OC)O

Synonyms

5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one/5,4'-dihydroxy-3,3',7-trimethoxyflavone/quercetin 3,3',7-trimethyl ether/4',5-Dihydroxy-3,3',7-trimethoxyflavone/Pachypodol/5,4'-dihydroxy-3,7,3'-trimethoxyflavone/Quercetin 3,7,3'-trimethyl ether/4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-/5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxychromen-4-one

IUPAC Name

5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxychromen-4-one

Applications

Density

1.5±0.1 g/cm3

Solubility

Methanol; Acetontrile; DMSO

Flash Point

220.7±23.6 °C

Boiling Point

598.8±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-11(19)13(6-9)23-2/h4-8,19-20H,1-3H3

InChl Key

KQFUXLQBMQGNRT-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2914500000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:33708-72-4) 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

31438541

Abstract

Oxidative stress has been implicated in the pathogenesis of many diseases including chronic liver diseases. Nrf2 is a master transcriptional factor regulating the induction of cellular antioxidant defense systems. Here, the Nrf2-activating effect of the crude methanol extract of dried leaves of Pogostemon cablin Bentham was demonstrated by measuring the antioxidant response element (ARE)-driven luciferase activity and pachypodol, 4′,5-dihydroxy-3,3′,7-trimethoxyflavone, was isolated by bioactivity-guided fractionation and further separation using chromatographic techniques. To our knowledge, this is the first study to evaluate the antioxidant and cytoprotective effects of pachypodol in HepG2 cells as well as the underlying molecular mechanisms. Indeed, pachypodol protected HepG2 cells from cell death caused by tert-butylhydroperoxide-induced oxidative stress and also attenuated ROS production. The ability of pachypodol to activate Nrf2/ARE pathway was further confirmed by observing Nrf2 expression in nuclear fraction, mRNA levels of Nrf2 target antioxidants, and cellular glutathione content in HepG2 cells. Extracellular signal-regulated kinase (ERK) is one of the important kinases involved in Nrf2 activation. Pachypodol increased ERK phosphorylation and ERK inhibition by PD98059 totally abrogated the increase in ARE luciferase activity, nuclear Nrf2 accumulation and mRNA levels of antioxidant enzymes by pachypodol. In conclusion, pachypodol isolated from P. cablin can protect hepatocytes from oxidative injury, possibly mediated by enhancing endogenous antioxidant defense system through ERK-dependent Nrf2 activation.

KEYWORDS

ERK; Nrf2; Pogostemon cablin; antioxidants; hepatocyte protection; pachypodol.

Title

Pachypodol, a Methoxyflavonoid Isolated From Pogostemon cablin Bentham Exerts Antioxidant and Cytoprotective Effects in HepG2 Cells: Possible Role of ERK-Dependent Nrf2 Activation

Author

Eun Kyung Kim 1, Ji Hoon Kim 1, Soyeon Jeong 1, Yong Won Choi 1, Hyun Jung Choi 1, Chul Young Kim 2, Young-Mi Kim 3

Publish date

2019 Aug 21

PMID

26322527

Abstract

Flavonoids retusin (5-hydroxy-3,7,3′,4′-tetramethoxyflavone) (1) and pachypodol (5,4′-dihydroxy-3,7,3′-trimethoxyflavone) (2) were isolated from Croton ciliatoglanduliferus Ort. Pachypodol acts as a Hill reaction inhibitor with its target on the water splitting enzyme located in PSII. In the search for new herbicides from natural compounds, flavonoids 1 and 2 and flavonoid analogues quercetin (3), apigenin (4), genistein (5), and eupatorin (6) were assessed for their effect in vitro on the photosynthetic electron transport chain and in vivo on the germination and growth of the plants Physalis ixocarpa, Trifolium alexandrinum and Lolium perenne. Flavonoid 3 was the most active inhibitor of the photosynthetic uncoupled electron flow (I50 = 114 μM) with a lower log P value (1.37). Results in vivo suggest that 1, 2, 3, and 5 behave as pre- and postemergent herbicides, with 3 and 5 being more active.

KEYWORDS

apigenin; eupatorin; genistein; pachypodol; photophosphorylation; quercetin; retusin.

Title

Flavonoids Affect the Light Reaction of Photosynthesis in Vitro and in Vivo as Well as the Growth of Plants

Author

Felix Morales-Flores 1, Karen Susana Olivares-Palomares 1, Maria Isabel Aguilar-Laurents 1, Jose Fausto Rivero-Cruz 1, Blas Lotina-Hennsen 1, Beatriz King-Diaz 1

Publish date

2015 Sep 23;

PMID

25891300

Abstract

In recent years, phosphatidylinositol 4-kinase III beta (PI4KB) has emerged as a conserved target of anti-picornavirus compounds. In the present study, PI4KB was identified as the direct target of the plant-derived anti-picornavirus compounds, oxoglaucine and pachypodol (also known as Ro 09-0179). PI4KB was also identified as the target via which pachypodol interferes with brefeldin A (BFA)-induced Golgi disassembly in non-infected cells. Oxysterol-binding protein (OSBP) inhibitor also has interfering activity against BFA. It seems that this interference is not essential for the anti-poliovirus (PV) activities of BFA and PI4KB/OSBP inhibitors. BFA inhibited early to late phase PV replication (0 to 6 hr postinfection) as well as PI4KB inhibitor, but with some delay compared to guanidine hydrochloride treatment. In contrast with PI4KB/OSBP inhibitors, BFA inhibited viral nascent RNA synthesis, suggesting that BFA targets some step of viral RNA synthesis located downstream of the PI4KB/OSBP pathway in PV replication. Our results suggest that PI4KB is a major target of anti-picornavirus compounds identified in vitro for their anti-picornavirus activities and for some uncharacterized biological phenomena caused by these compounds, and that BFA and PI4KB/OSBP inhibitors synergistically repress PV replication by targeting distinct steps in viral RNA replication.

KEYWORDS

oxoglaucine; pachypodol (Ro 09-0179); phosphatidylinositol 4-kinase III beta; poliovirus.

Title

Phosphatidylinositol 4-kinase III Beta Is the Target of Oxoglaucine and Pachypodol (Ro 09-0179) for Their Anti-Poliovirus Activities, and Is Located at Upstream of the Target Step of Brefeldin A

Author

Minetaro Arita 1, Stefan Philipov 2, Angel S Galabov 3

Publish date

2015 Jun;