Ангелоилгомизин H

Substance identification

Angeloylgomisin H is a dibenzocyclooctadiene lignan from Schisandra chinensis. CAS number 66056-22-2, formula C28H36O8, UNII Y16R9MI4T6. Synonyms: (+)-angeloylgomisin H; dibenzo[a,c]cyclooctene, a derivative of 2-butenoic acid; 2-Butenoic acid, 2-methyl-, (6S,7S,12aR)-5,6,7,8-tetrahydro-7-hydroxy-2,3,10,11,12-pentamethoxy-6,7-dimethyldibenzo[a,c]cycloocten-1-yl ester, (2Z)-.

Physico-chemical characteristics

• Molecular Weight: 500.58064
• Exact weight: 500.58
• Density: 1.1±0.1 g/cm3
• Boiling point: 656.3±55.0 °C at 760 mm Hg. Art.
• Flash point: 212.3±25.0 °C
• Refractive index: 1.539
• PSA Specifications: 92.68
• XLogP3: 4.92

Plant source and substance class

One of the major dibenzocyclooctadiene lignans of leaf extracts of Schisandra chinensis (Schisandra chinensis) - according to published data, is contained in the leaves in a concentration of about 31.4 mg per 100 g of dry weight. Structurally, it is an ester of (2Z)-2-methylbut-2-enoic (angelic) acid at the hydroxyl group of the pentamethoxylated dibenzocyclooctadiene skeleton with the absolute configuration (6S,7S,12aR).

Biological activity

Angeloylgomisin H in the concentration range of 10, 50 and 100 µmol/l significantly induces the activity of quinone reductase, the enzyme of the second phase of xenobiotic detoxification, which is considered as one of the mechanisms of the hepatoprotective effect of Schisandra lignans. Dibenzocyclooctadiene lignans from Schisandra chinensis have been generally studied as compounds with antitumor, antioxidant, and anti-inflammatory activities that can prevent hepato- and nephrotoxicity.

Traditional use and group nomenclature

Schisandra fruits (wu-wei-tzu, “berry of five tastes”) in traditional Chinese medicine are classified as adaptogens used for fatigue and liver diseases; The Pharmacopoeia of the People's Republic of China standardizes Fructus Schisandrae raw materials according to the content of marker lignans, primarily schisandrin. The designations of dibenzocyclooctadiene lignans from Schisandra have historically evolved from several parallel systems - gomisins, schisandrins, deoxyschisandrin; acylation of hydroxyl groups with residues of various organic acids (angelic, tiglic, benzoic) determines individual structural variants of the group’s compounds, including angeloylgomisin H. Biosynthetically, such lignans are formed by oxidative radical dimerization of two molecules of a phenylpropanoid precursor with the formation of a central eight-membered ring connecting two aromatic fragments.

Scope of application

Used as an analytical standard in the standardization of leaf and fruit extracts of Schisandra chinensis and in pharmacological studies of detoxification mechanisms induced by natural lignans.

Storage

Store in a sealed container protected from light at a low temperature.