ДАРУТИГЕНОЛ

Description

Darutigenol (Darutigel) is a diterpene aglycone, a product of hydrolysis of the glycoside darutoside: the cleavage of the sugar residue from darutoside gives darutigenol as the aglycone part of the molecule. Belongs to the same class of diterpenes from plants of the genus Siegesbeckia (Cocklebur, Asteraceae family) as kirrenol and darutoside - these three compounds together form the main complex of anti-inflammatory and analgesic components of plant raw materials.

Basic Attributes

• CAS No: 5940-00-1
• Chemical formula: C20H34O3
• Synonyms: Darutigel, (1R)-1-[(2S,4aa,8aa)-2,3,4,4a,4b,5,6,7,8,8a,9,10-Dodecahydro-7β-hydroxy-2,4bß,8,8-tetramethylphenanthren-2-yl]-1,2-ethanediol
• Molecular weight: 322.48; exact mass: 322.250793
• NSC number: 310619
• PSA: 60.69000; XLogP3: 3.50

Physico-chemical characteristics

• Density: 1.1 ± 0.1 g/cm3
• Boiling point: 471.2 ± 45.0 °C at 760 mm Hg. Art.
• Flash point: 210.7 ± 23.3 °C
• Refractive index: 1.552

Biological activity and applications

Kirrenol, darutoside and darutigenol are diterpene components of the genus Siegesbeckia, which have been studied in recent years for their pronounced analgesic and anti-inflammatory effects. As an aglycone of darutoside, darutigenol is formed in the body or during the extraction process by cleavage of the glycosidic moiety, remaining structurally related by its mechanism of action to the parent glycoside: suppression of COX-2 expression and inflammatory cell migration underlies the anti-inflammatory effect of this entire group of Siegesbeckia plant diterpenes.

Storage

Store in a sealed container, protected from light, at a low temperature, in a dry place - unsaturated and hydroxylated fragments of the diterpene skeleton are sensitive to oxidation.

Source plant

Siegesbeckia (Cocklebur, Sigesbeckia, Asteraceae family) are herbaceous plants of Asia, traditionally used in Chinese medicine under the general name Xi-Hsien-Cao for rheumatism, arthritis and skin diseases. Darutigenol is formed as an aglycone during the hydrolysis of the glycoside darutoside - the cleavage of the sugar residue from darutoside releases this particular molecule. Kirrenol, darutoside and darutigenol together constitute the main complex of diterpenes that determine the analgesic and anti-inflammatory activity of Siegesbeckia plant materials.

Connection class

Darutigenol, like darutoside, belongs to the diterpenoids of the erth-pimarane series, a structural class widely represented in the genus Siegesbeckia: phytochemistry of Siegesbeckia pubescens revealed seventeen diterpenoids, among which twelve have an erth-pimarane skeleton, three more have an erth-kauran skeleton, and two have an acyclic structure. The absolute configuration of such compounds is determined by X-ray diffraction analysis and circular dichroism spectroscopy. CAS 5940-00-1, NSC number 310619, molecular weight 322.48.