Друпацин

Description

Drupacin is a natural alkaloid of the Cephalotaxus series, isolated from plants of the genus Cephalotaxus (plume-shaped yew), in particular from the branches and leaves of Cephalotaxus fortunei. The systematic name is cephalotaxin, 2,11-epoxy-1,2-dihydro-, (2alpha,11alpha)-.

Basic Attributes

• CAS No.: 49686-57-9
• English name: Drupacine
• Chemical formula: C18H21NO5
• Molecular weight: 331.4 g/mol (by dump; calculated molar mass using the formula C18H21NO5 is 331.37 g/mol)
• Exact mass: 331.14197277 g/mol
• NSC Number: 142198
• PSA specifications: 60.4 Ų

Synonyms

Drupacin; Cephalotaxin, 2,11-epoxy-1,2-dihydro-, (2alpha,11alpha)-.

Structural classification

Refers to cephalotaxus alkaloids - nitrogen-containing secondary metabolites of plants of the genus Cephalotaxus, built on a cephalotaxin (spirocyclopentane) core; drupacin is distinguished by the presence of an epoxy bridge between positions 2 and 11 of this core.

Source and biological activity

Isolated from the branches and leaves of Cephalotaxus fortunei by bioanalysis-directed fractionation, carried out in the search for nematicidal compounds. Drupacin and the total alkaloid extract of Cephalotaxus suppress the hatching of nematodes, activity at mixed stages of development, and the number of populations on plant roots. The ED50 value of drupacin for the pine stem nematode Bursaphelenchus xylophilus is 27.1 µg/ml, for the root-knot nematode Meloidogyne incognita - 76.3 µg/ml. Additionally, the compound has been described to have an antitumor effect.

Scope of application

It is being studied as a research object for natural nematicides to protect plants from parasitic nematodes (including the causative agent of pine wilt Bursaphelenchus xylophilus and the root-knot nematode Meloidogyne incognita), as well as as a reference standard in the phytochemical analysis of Cephalotaxus alkaloids and in screening the antitumor activity of natural compounds. Not intended for medical or agricultural use without additional testing.

Storage and transportation

Store in a dry place, protected from direct light, in a hermetically sealed container, at a low temperature - cephalotaxus alkaloids are sensitive to oxidation and hydrolysis of the epoxy group during long-term storage. According to available data, transport codes and established hazard classes are not provided.

Significance in the Cephalotaxus alkaloid family

In addition to drupacin, a number of related alkaloids have been isolated from plants of the genus Cephalotaxus - cephalotaxin, hainanolide, garringtonine and deoxygarringtonine, some of which (in particular, homogarringtonine) are used in clinical oncohematology. Drupacin, distinguished by an epoxide group at positions 2,11, is of interest as an intermediate in studies of structure-activity relationships within this alkaloid family, primarily in relation to nematocidal and cytotoxic effects.

Practical significance of nematicidal activity

The activity of drupacin against the pine stem nematode Bursaphelenchus xylophilus is of practical interest in the context of combating pine dieback, a disease caused by this parasite that causes significant damage to coniferous forests in East Asia; Natural Cephalotaxus alkaloids are considered as a potential alternative to synthetic nematicides for the protection of forest plantations.