Неотуберостемонин

Description

Neotuberostemonin is an alkaloid from the roots of Stemona tuberosa Lour., one of the main species of the genus Stemona used in traditional medicine in East Asia. Belongs to the tuberostemonine type of stemone alkaloids; the core of the molecule is a saturated tricyclic pyrrolo[3,2,1-jk][1]benzazepine with a butyrolactone fragment. The commercial form is a reference standard of plant origin.

Basic Attributes

• CAS No: 143120-46-1
• Chemical formula: C22H33NO4
• Molecular Weight: 375.509
• Exact weight: 375.50
• PSA specifications: 55.8
• XLogP3: 2.28
• Density: 1.2 ± 0.1 g/cm³
• Boiling point: 554.2 ± 50.0 °C at 760 mm Hg. Art.
• Flash point: 289.0 ± 30.1 °C
• Refractive index: 1.556

Activity studied

Neotuberostemonin is one of the main antitussive alkaloids of the Stemona tuberosa root. Fractionation of the extract with control for biological activity identified it among the compounds with reliable suppression of cough in guinea pigs during the citrate test. The point of application of the substance differs from croomin: neotuberostemonin, tuberostemonin and stemonin act on the peripheral part of the cough reflex, while croomin acts on the central part. A separate area of ​​work is pulmonary fibrosis: the compound attenuated bleomycin-induced pulmonary fibrosis in mice by suppressing the recruitment and activation of macrophages.

Structural-functional connection

The key element for the antitussive effect is the saturated tricyclic nucleus of pyrrolo[3,2,1-jk][1]benzazepine; A completely cis-configuration of ring articulation is considered optimal. Synonyms in catalogs: stemonin LG, tuberostemonin LG, (+)-neotuberostemonin.

Scope of application

• standard sample for standardization of Stemona (百部) raw materials by HPLC and LC-MS methods
• pharmacological studies of the cough reflex and pulmonary fibrosis
• works on the structural and functional patterns of stemone alkaloids

Storage and handling

Toxicological data and transport classification are not given in the card. Handle as a pharmacologically active alkaloid of an unknown hazard class: gloves, glasses, hanging in a fume hood, tightly closed containers, protection from light and moisture.