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Prostratin

$832

  • Brand : BIOFRON

  • Catalogue Number : BN-O1776

  • Specification : 98%(HPLC)

  • CAS number : 60857-08-1

  • Formula : C22H30O6

  • Molecular Weight : 390.476

  • Volume : 1mg

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Catalogue Number

BN-O1776

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

390.476

Appearance

Botanical Source

Structure Type

Category

SMILES

CC1CC2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)CO)O)C)O)OC(=O)C

Synonyms

(1aR,1bS,4aR,7aS,7bR,8R,9aS)-4a,7b-Dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl acetate/13-O-Acetyl-12-deoxyphorbol/12-Deoxyphorbol-13-acetate/Stillingia Facto/5H-Cyclopropa[3,4]benz[1,2-e]azulen-5-one, 9a-(acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1aR,1bS,4aR,7aS,7bR,8R,9aS)-/12-Deoxyphorbol 13-Acetate,dPAc/13-O-Acetylphorbol/Stillingia factor S7/SA 101A/prostratin/12-deoxyphorbal-13-acetate

IUPAC Name

Density

1.3±0.1 g/cm3

Solubility

Flash Point

188.7±23.6 °C

Boiling Point

550.5±50.0 °C at 760 mmHg

Melting Point

216-219℃

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:60857-08-1) 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

25963564

Abstract

Terpenoid class of molecules possesses a diverse therapeutic properties and potentials owing to their specific structural features. Prostratin and its derivatives are exemplified in this context to exhibit a variety of biological activities. In this review we discuss in detail the role of prostratin as potential therapeutic and underlying molecular mechanisms by which it accomplishes these activities. Prostratin [13-O-acetyl-12-deoxyphorbol] is a phorbol ester that was first isolated from Strathmore weed Pimelea prostrate, a small endemic New Zealand shrub, and characterized by Hecker in 1976. Structurally, prostratin contains four rings designated as A, B, C and D. Ring A is trans linked to the 7-membered ring B while Ring C is a 6 membered and is cis linked to the cyclopentane ring D. Chemical synthesis of this compound initiated with acidic hydrolysis of phorbol, a tigliane diterpene isolated from croton oil. Prostratin-containing extracts have been used by the Samoan healers to treat individuals with certain medical conditions such as jaundice. Importantly, these treatments are not associated with any significant side effect. Prostratin inhibits HIV-1 infections by down regulating HIV-1 cellular receptors through the activation of protein kinase C (PKC) pathway and reduces the HIV-1 latency. Unlike other phorbol esters that induce carcinogenesis by activating PKC, prostratin does not induce tumors rather has shown tumor suppressing activity. Its ability to induce lytic gene expression supports a role for phorbol-ester regulated signaling pathways in Kaposi’s sarcoma associated herpes-virus reactivation.

Title

Prostratin: An Overview.

Author

Miana GA, Riaz M1, Shahzad-ul-Hussan S, Paracha RZ, Paracha UZ.

Publish date

2015

PMID

29435066

Abstract

Prostratin, a phorbol ester natural plant compound, has been demonstrated to exert an anti-retroviral effect through activation of latent cluster of differentiation (CD)4+T lymphocytes and inhibition of viral entry into the cell through downregulation of chemokine receptor type 4 (CXCR4) expression. However, the potential effect of prostratin on cancer is yet to be defined. As CXCR4 is well known to induce cancer migration, it was hypothesized that prostratin induces an anti-cancer effect through inhibition of CXCR4 expression. The authors previously demonstrated that high stimulating conditions (sub-minimal IL-17, 0.1 ng/ml, synergized with high salt, Δ0.05 M NaCl) promote breast cancer cell proliferation and CXCR4 expression through upregulation of salt-inducible kinase (SIK)-3. The present study demonstrated that prostratin selectively exerted increased cytotoxicity (IC50 of 7 µM) when breast cancer cells were cultured in high stimulating conditions, compared with regular basal culture conditions (IC50 of 35 µM). Furthermore, the cytotoxic potential of prostratin was increased seven-fold in the four breast cancer cell lines (MCF-7, MDA-MB-231, BT-20 and AU-565) compared with the non-malignant MCF10A breast epithelial cell line. This suggested that prostratin specifically targets cancer cells over normal cells. Mechanistic studies revealed that prostratin inhibited CXCR4 expression in breast cancer cells through downregulation of SIK3 expression. Overall, the data suggest that prostratin is a novel drug target for the pro-oncogenic factor SIK3. These studies could form a basis for further research to evaluate the anticancer effect of prostratin in a combinatorial chemotherapeutic regimen.

KEYWORDS

breast cancer; chemokine; inflammation; interleukin-17; prostratin; salt inducible kinase-3

Title

Potential anticancer effect of prostratin through SIK3 inhibition.

Author

Alotaibi D1, Amara S2, Johnson TL1, Tiriveedhi V1,3.

Publish date

2018 Mar

PMID

16391719

Abstract

The persistence of latent reservoirs of human immunodeficiency virus type 1 (HIV-1) represents a major barrier to virus eradication in patients on combination antiretroviral therapy. It has been suggested that treating infected individuals simultaneously with highly active antiretroviral therapy (HAART) and agents that activate cells to express HIV-1 might eliminate these latent reservoirs. The phorbol ester prostratin, used in Western Samoa as an ethno-botanical treatment for viral hepatitis, was isolated at the National Cancer Institute in 1992. Prostratin represents a distinct subclass of protein kinase C activators, since unlike other phorbol esters it does not induce tumor formation. Prostratin upregulates expression of viral products from latently infected cells such as U1, ACH-2 and peripheral blood mononuclear cells from patients on HAART with undetectable plasma viremia. It also inhibits HIV infection and viral spread at the entry/fusion step of viral life cycle. The lack of tumor promotion of prostratin coupled with its ability to upregulate latent HIV-1 provirus expression and inhibition of viral infection are important features that could be exploited as effective therapy to eliminate latent reservoirs.

(c) 2005 Prous Science. All rights reserved.

Title

Prostratin as a new therapeutic agent targeting HIV viral reservoirs.

Author

Hezareh M1.

Publish date

2005 Oct


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