548-19-6

Basic information

• Product Name: ISOGINKGETIN
• Synonyms: ISOGINKGETIN;2-(4-Methoxyphenyl)-5,7-dihydroxy-8-[2-methoxy-5-(4-oxo-5,7-dihydroxy-4H-1-benzopyran-2-yl)phenyl]-4H-1-benzopyran-4-one;2-(4-Methoxyphenyl)-8-[6-methoxy-3-(4-oxo-5,7-dihydroxy-4H-1-benzopyran-2-yl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one;4',4'''-Dimethoxyamentoflavone;8-[5-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one;3''',8-Biflavone, 5,5'',7,7''-tetrahydroxy-4',4'''-dimethoxy-;4',4'''-Dimethylamentoflavone;ISOGINKGETIN(RG)(PLEASE CALL)
• CAS NO: 548-19-6
• Molecular Formula: C₃₂H₂₂O₁₀
• Molecular Weight: 566.51
• Mol File: 548-19-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 355℃
• Boiling Point: 843.6°Cat760mmHg
• Flash Point: 280.2°C
• Appearance: /
• Density: 1.506
• Vapor Pressure: 8.5E-30mmHg at 25°C
• Refractive Index: 1.714
• Storage Temp.: 2-8°C(protect from light)
• PKA: 6.16±0.40(Predicted)
• CAS DataBase Reference: ISOGINKGETIN(CAS DataBase Reference)
• NIST Chemistry Reference: ISOGINKGETIN(548-19-6)
• EPA Substance Registry System: ISOGINKGETIN(548-19-6)

Safety Data

• Hazardous Substances Data: 548-19-6(Hazardous Substances Data)

Usage

Description

Isoginkgetin is a biflavonoid that has been found in G. biloba and is an inhibitor of pre-mRNA splicing. Isoginkgetin (33 μM) reduces the activity of an mRNA-dependent luciferase reporter by 5-fold, shifts the composition of total RNA extract from predominantly mRNA to pre-mRNA, and arrests cell growth in HEK293 cells. Isoginkgetin (10 μM) suppresses mouse lymphocyte proliferation induced by concanavalin A (Con A; ) and LPS by approximately 87 and 90%, respectively. It also suppresses arachidonic acid release induced by phorbol 12-myristate 13-acetate (PMA; ) and the calcium ionophore A23187 by 32.5 and 48.4%, respectively, in rat peritoneal macrophages when used at a concentration of 10 μM. Isoginkgetin (5-20 μM) reduces matrix metalloproteinase-9 (MMP-9) activity, expression, and mRNA levels in and decreases cell invasion by HT1080 fibrosarcoma cells in a concentration-dependent manner.

Definition

ChEBI: A biflavonoid resulting from the formal oxidative dimerisation between position 8 of one molecule of 5,7-dihydroxy-4'-methoxyflavone and the 3' position of another. Found in the leaves of Ginkgo biloba, it is a potent inhibitor of matrix metal oproteinase 9 (MMP-9).

General Description

A cell-permeable, naturally isolated Ginkgo biloba biflavanoid that acts as a general pre-mRNA splicing inhibitor (ICmax = 50 μM in splicing assays using HeLa nuclear extract) by blocking the spliceosome-meidated splicing process at the prespliceosome/A complex stage. Isoginkgetin treatment is shown to result in growth arrest in HEK293-derived cultures in a reversible manner without affecting cell viability (33 μM for 24 h).

InChI:InChI=1/C32H22O10/c1-39-18-6-3-15(4-7-18)26-14-24(38)31-22(36)12-21(35)29(32(31)42-26)19-9-16(5-8-25(19)40-2)27-13-23(37)30-20(34)10-17(33)11-28(30)41-27/h3-14,33-36H,1-2H3

Upstream product

• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 108-73-6 3,5-dihydroxyphenol 

Downstream Products

• 2206-43-1 4-methoxyisophthalic acid 
• 100-09-4 4-methoxybenzoic acid 
• 1617-53-4 amentoflavone 
• 3778-26-5 Amentoflavon 
• 3778-25-4 7,4',7'',4'''-tetra-O-methylamentoflavone 

Relevant articles and documents

Biological Investigation of a Water-Soluble Isoginkgetin-Phosphate Analogue, Targeting the Spliceosome with In Vivo Antitumor Activity

The first total synthesis of the natural product Isoginkgetin as well as four water-soluble Isoginkgetin-phosphate analogues is reported herein. Moreover, the full study of the IP2 phosphate analogue with respect to pharmacological properties (metabolic and plasmatic stabilities, pharmacokinetic, off-target, etc.) as well as in vitro and in vivo biological activities are disclosed herein.