Хлорантолид С

Substance identification

Chlorantholide C is a sesquiterpene lactone of the eudesmane type from the series of chlorantholides A–F isolated from the aerial part of Chloranthus elatior (chloranthaceae). The systematic name for the naphtho[2,3-b]furan skeleton is (4aR,8aS,9aR)-4,4a,8,8a,9,9a-hexahydro-3,5,8a-trimethylnaphtho[2,3-b]furan-2,7-dione. The synonym “8-epichlorantholide B” indicates a stereoisomeric relationship with chlorantholide B—the compounds differ in the configuration of one stereocenter. Formally, it belongs to the same class of natural lactones as chlorantholides A, B, D, E, F, found in the same plant source and published in a single phytochemical work on the composition of Chloranthus elatior.

Basic Attributes

• CAS No: 1372558-35-4
• Chemical formula: C15H18O3
• English name: ChlorantholideC
• Molecular Weight: 246.30162
• Exact weight: 246.30
• Synonyms: Chlorantholide C; 8-epichlorantholide B

Class and structure

In terms of the number of oxygen atoms (three versus four for chlorantholide D and five for chlorantholide E), the chlorantholide C molecule is the least oxidized member of the series: it contains a naphthofuran-type lactone ring without an additional hydroxy group characteristic of chlorantholides D and E. The C15 eudesmane skeleton is typical of sesquiterpenoids of the genus Chloranthus.

Botanical source and series of compounds

Isolated from the same ethanolic extract of Chloranthus elatior as chlorantholides A, B, D, E, F - all six lactones are described in one phytochemical work as a structurally related series of eudesmanolides. The genus Chloranthus also contains lindenanolides and dimeric lindanes, which is used in the chemotaxonomy of the family.

Biological activity

No direct published data on the activity of chlorantholide C specifically have been found. Antibacterial and anti-inflammatory activity has been described for structurally related members of the series (chlorantholide D) - this creates a context for further study of chlorantholide C, but is not a confirmed fact about it itself.

Application

Reference and analytical standard for phytochemical studies of Chloranthus extracts: confirmation of the structure of related metabolites by NMR and mass spectrometry, comparison of chromatographic behavior in the separation of complex mixtures of terpenoids.

Missing data

Density, melting, boiling and flash points, refractive index, solubility, vapor pressure, toxicological parameters (LD50), GHS phrases and UN transport codes are not published by the supplier and are deliberately not given - substitution of estimated values ​​by analogy with related lactones is prohibited by the description rules.

Storage and transportation

Specific storage temperature and transportation conditions are not specified by the manufacturer. As a lactone without a free hydroxyl group, chlorantholide C is generally more resistant to hydrolysis than chlorantholide D, but numerical storage parameters (temperature, shelf life) are not available in open sources and are therefore not given.