Борапетозид Е

Substance identification

Borapetoside E is a clerodane-type furanoditerpene glycoside from the plant Tinospora crispa. Chemical formula C27H36O11, CAS number 151200-49-6.

Basic Attributes

• Molecular weight: 536.6
• Exact weight: 536.22576196

Physico-chemical characteristics

• Density: 1.41±0.1 g/cm3 (predicted value)
• Boiling point: 711.1±60.0 °C (predicted value)

Substance class and biological activity

Borapetoside E belongs to the group of clerodane furanoditerpenoids and their glycosides from Tinospora crispa (Tinospora, family Menispermaceae), a plant widely used in traditional medicine in Southeast Asia for diabetes mellitus. The group's related compounds, borapetosides A and C, at a dose of 5 mg/kg, significantly reduced blood glucose levels in normal and type 1 diabetic mice, comparable to the effect of metformin at a dose of 200 mg/kg; Borapetoside C at a dose of 3 mg/kg exhibited activity against type 2 diabetes due to an insulin-secretagogue effect comparable to glibenclamide (5 mg/kg), realized through enhanced glucose uptake by peripheral tissues and suppression of hepatic gluconeogenesis. The mechanisms of the antidiabetic action of clerodane glycosides from Tinospora crispa include stimulation of insulin secretion, increased glycogen synthesis in skeletal muscles and inhibition of the enzymes alpha-glucosidase and alpha-amylase, while among the studied glycosides of the group, borapetoside C shows the most pronounced inhibition of both enzymes.

Source plant

Tinospora crispa (tinospora) is a liana of the Menispermaceae family, common in Southeast Asia; In folk medicine of the region, the plant is traditionally used for diabetes and fever and as a general tonic. Clerodane furanoditerpenoids and their glycosides are considered to be the main active compounds of plant stem extracts.

Storage and transportation

Store in a cool, dry place in a tightly closed container, protected from light, taking into account the relatively high calculated density and the tendency of glycosides to oxidize during storage. Protect from overheating and direct sunlight during transportation, as well as from prolonged contact with air, which accelerates the oxidative degradation of the glycoside and the loss of biological activity.

Place among related compounds

The molecular weight of 536.6 and the calculated density of 1.41 g/cm3 are close to those of its structurally neighboring borapetoside F (534.6), which reflects the similarity of the skeleton of the clerodane diterpene in this pair of compounds and only minor differences in the degree of saturation or glycosylation, common for natural series of related metabolites of the same plant and typical for the biosynthetic pathways of clerodane diterpenoids in general, which is confirmed similar molecular formula C27H36O11, differing from borapetoside F by only two hydrogen atoms. This relationship is typical for a series of natural metabolites synthesized along the common biochemical pathway of one plant.