Аллосекуринин

Description

Allosecurinine (Phyllochrysine, 2-Allosecurinine) is an alkaloid of the Securinega group, a diastereomer of securinine, built on the same tricyclic securinan framework: a lactone condensed with an indolizidine fragment (the substance belongs to the class of indolizines). Isolated from plants of the genus Margaritaria (M. indica, M. discoidea), traditionally studied as a source of securinan alkaloids. The source data dump for the product was limited to molecular weight; the description is supplemented with verified literature information based on the CAS number.

Basic Attributes

• CAS No.: 884-68-4
• Chemical formula: C13H15NO2
• Molecular weight: 217.2637

Physico-chemical characteristics

• Melting point: 136-138 °C

Synonyms

Allosecurinin; Phyllochrysine; 2-Allosecurinine; (2α)-Securinan-11-one; (2S)-Securinan-11-one; Securinan-11-one, (2,alpha,)-; NSC 107415.

Scope of application

Like other securinane alkaloids, allosecurinine is studied primarily as an object of pharmacological and phytochemical research, and not as a commercial reagent for general use. The antifungal activity of the compound has been described. In comparative studies of cytotoxicity on HeLa cervical cancer cells, the activity of allosecurinin and plant extracts based on it turned out to be noticeably lower than the activity of securinin, the closest structural analogue and a more well-known representative of the same alkaloid series. Securinane alkaloids are generally considered to be GABA receptor modulators and targets for compounds with CNS activity; allosecurinin is used for research purposes as a reference compound in the study of structure-activity relationships within this group. The closest analogue, securinine, has historically been used in medical practice as an analeptic - a stimulant of the central nervous system with a milder effect than strychnine, therefore diastereomeric securinane alkaloids, including allosecurinine, are of interest for the comparative pharmacology of this structural class.

Class and origin

Natural source - plants of the genus Margaritaria (Phyllanthaceae): M. indica and M. discoidea. The compound belongs to bicyclic lactone-indolizidine alkaloids (indolizines), stereochemically differing from securinine in the configuration of one of the asymmetric centers, which is reflected in the name (“allo-” indicates a diastereomeric relationship to securinine).

Appeal

Supplied as a research reagent; data on acute toxicity, transport codes and GHS phrases for the product form were not found in open sources and are not given in order to avoid introducing unreliable values. When working with an alkaloid as a poorly studied biologically active substance, it is recommended to use standard personal protective equipment for an organic synthesis laboratory - gloves, goggles, a fume hood.

Delivery form

Supplied as an analytical or research reagent in small packages, usually in the form of a powder or crystalline substance with a specified degree of purity; a certificate of analysis accompanies the batch, since there is no pharmacopoeial standard for allosecurinin.

Storage

Store in a tightly closed container, in a dry place at room temperature or below, away from direct light and heat sources: the lactone moiety of the securinan framework is sensitive to prolonged heat, and opening of the lactone ring is possible upon hydrolysis in the presence of moisture and alkaline impurities.