Калицифиллин А

Substance identification

Calyciphylline A is an alkaloid of the Daphniphyllum series, a rare C22-containing hexacyclic nor-daphniphyllum structure, which gives the name to the whole structural type of daphniphyllum alkaloids (calyciphylline A-type).

• CAS No: 596799-30-3
• Chemical Formula: C23H31NO4
• Molecular weight: 385.5
• Exact weight: 385.22530847

Substance class and biosynthesis

Caliciphylline A-type alkaloids are one of four structurally related groups of daphniphyllum alkaloids (along with macrodaphniphyllamine, daphnilongeranine A- and daphnicycladine D-types). They are formed by cleavage of the C1–N bond of the yuzurimine-type alkaloid precursor and the formation of a new bond between C4 and nitrogen, resulting in the characteristic hexacyclic ring system 6/5/5/7/5/6 with an oxo group at C1.

Biological activity type

A wide range of biological activities have been documented for the Daphniphyllum alkaloid family, caliciphylline A-type: inhibition of tubulin polymerization, antiviral action against HIV, anticancer, vasodilator, cytotoxic and neurotrophic activity. These properties make the structural type the object of active synthetic and pharmacological study, including the development of methods for the complete chemical synthesis of representatives of the group.

Application

It is used as an object for phytochemical and synthetic studies of Daphniphyllum alkaloids, and also as a model structure for the development of methods for the asymmetric synthesis of complex polycyclic alkaloid frameworks. Confirmed data on the industrial or clinical use of caliciphyllin A specifically have not been established in available sources.

Molecule structure

The formula C23H31NO4, with four oxygen atoms and one nitrogen atom in the hexacyclic framework, reflects the high degree of structural complexity typical of Daphniphyllum alkaloids - this complexity is the main reason for the active interest of synthetic chemists in developing efficient routes for the complete synthesis of such molecules.

Storage and transportation

As a polycyclic alkaloid with an oxo group, the substance can be sensitive to hydrolytic and oxidative processes if improperly stored. It is recommended to store in an airtight container in a cool, dry place. UN transport codes and GHS classification for CAS 596799-30-3 are not included in the source data.

Synthetic interest

The compact but highly saturated ring system of calyciphylline A-type has been repeatedly the target of total chemical synthesis in academic groups working on methodologies for constructing complex polycyclic scaffolds: strategies based on the construction of C4–N and C1–C8 bonds using substrates and reactions recapitulating the putative biogenetic pathway have been published. Such work serves the purpose of obtaining the alkaloid itself and the development of general methods for the asymmetric synthesis of natural compounds.

Related structural types

In addition to the A-type calyciphylline, the genus Daphniphyllum contains macrodaphniphyllamine, daphnilongeranine A- and daphnicycladine D-type alkaloids - all derived from a common biogenetic precursor, but differing in the details of cyclization and rearrangement of the carbon skeleton, which explains the structural diversity of this plant genus.