Периглауцин B

Description

Periglaucine B is a hasubanan-type alkaloid isolated from the aerial parts of the plant Pericampylus glaucus of the moonseed family (Menispermaceae). Together with it, periglaucines A, C and D, as well as the well-known alkaloids norrufscine, (−)-8-oxotetrahydropalmatine and (−)-8-oxocanadine, were obtained from the same raw materials. The group's first description was published in the Journal of Natural Products in May 2008.

Biological activity

• suppression of the secretion of hepatitis B virus surface antigen (HBsAg) in Hep G2.2.15 cells - the effect is shown for all four periglaucines A–D

Basic Attributes

• CAS No: 1025023-05-5
• Chemical formula: C20H23NO6
• Molecular Weight: 373.405
• Exact weight: 373.153
• PSA: 66.5
• XLogP3: 0.7

Structure and synthesis

Full structural name: (7beta,8beta,10beta)-8,10-epoxy-7,8-dimethoxy-17-methyl-2,3-[methylenebis(oxy)]hasubanan-6-one. Hasubanan's backbone is a characteristic tetracyclic skeleton with a quaternary carbon center, making the compound a challenging synthetic target. The first enantioselective total synthesis of (+)-periglaucine B was performed by the Herzon group and published in Angewandte Chemie International Edition in 2011 in a single paper with the syntheses of (−)-hasubanonine, (−)-runanine and (−)-delavaine.

Purpose

• reference standard for chromatographic and spectral analysis of Pericampylus glaucus extracts
• test compound in studies of antiviral activity against hepatitis B virus
• object of work on the total synthesis of alkaloids of the hasubanan series

Storage and handling

Supplied as a high purity sample for scientific research. Keep the container tightly closed, in the cold, away from light and moisture. Wear gloves and safety glasses. The GHS hazard classification for the compound is not given in the original data sheet, so it is treated as a substance with an unknown hazard profile.