10267-15-9

Basic information

• Product Name: (+)-Polyalthic acid methyl ester
• Synonyms: (+)-Polyalthic acid methyl ester;(1R,8aα)-5β-[2-(3-Furanyl)ethyl]decahydro-1,4aβ-dimethyl-6-methylene-1α-naphthalenecarboxylic acid methyl ester
• CAS NO: 10267-15-9
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.4611
• Mol File: 10267-15-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Polyalthic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Polyalthic acid methyl ester(10267-15-9)
• EPA Substance Registry System: (+)-Polyalthic acid methyl ester(10267-15-9)

Safety Data

• Hazardous Substances Data: 10267-15-9(Hazardous Substances Data)

Usage

General Description

The chemical (+)-Polyalthic acid methyl ester is a natural product isolated from the tree Polyalthia. It is a member of the annonaceous acetogenin family, which are known for their potential anticancer and pesticidal activities. (+)-Polyalthic acid methyl ester has been the subject of research for its biological properties and potential applications in medicine and agriculture. Studies have shown its cytotoxicity against various cancer cell lines and its insecticidal activity against agricultural pests. Its chemical structure and unique biological properties make it a promising candidate for the development of new drugs and pesticides.

Upstream product

• 186581-53-3 diazomethane 
• 1235-76-3 lambertiainic acid 
• 31685-80-0 Pinusolide 

Downstream Products

• 31685-80-0 Pinusolide 
• 933046-23-2 methyl 5-{2-[1-(2-aminophenyl)-2-oxo-2,5-dihdyro-1H-pyrrol-3-yl]ethyl}-1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylate 

Relevant articles and documents

Gram-scale synthesis of pinusolide and evaluation of its antileukemic potential

Pinusolide (1), a known platelet-activating factor (PAF) receptor binding antagonist, was synthesized from lambertianic acid (2), a labdane-type diterpene readily accessible in multigram quantities from the Siberian pine tree. It was shown that 1 not only decreases the proliferation activity of tumor cells at relatively low concentrations but specifically induces apoptosis at 100 μM via the mitochondrial pathway in the Burkitt lymphoma cell line BJAB. Also, using primary lymphoblasts and leukemic cells from children with acute lymphoblastic leukemia (ALL) and acute myeloid leukemia (AML), a significant DNA fragmentation in pinusolide-treated cells could be detected in an ex vivo apoptosis assay.

In vitro platelet-activating factor receptor binding inhibitory activity of pinusolide derivatives: A structure-activity study

Pinusolide, a labdane-type diterpene lactone isolated from Biota orientalis, was found to be a potent platelet-activating factor (PAF) receptor binding antagonist. To investigate the structure-activity relationship and find derivatives with improved pharmacological profiles, 17 pinusolide derivatives were prepared and tested for their ability to inhibit the PAF receptor binding. The results demonstrated that the carboxymethyl ester group at C-19, the integrity of the α,β-unsaturated butenolide ring, and the exocyclic olefinic function of pinusolide are all necessary for its maximum PAF receptor binding inhibitory activity. Among the derivatives, the 17-nor-8-oxo derivative 8 was found to be as potent as pinusolide. The results also suggested that several derivatives warrant further pharmaceutical and pharmacological studies due to their improved water solubility (8 and 11) and apparent lack of susceptibility to Michael-type nucleophilic addition (13 and 18).