Ангидронотоптол

Substance identification

Anhydronotoptol (Anhydro notoptol, also spelled Anhydronotoptol) is a natural alkaloid-phenolic component of plant materials. CAS number 88206-51-3, additional identifiers MFCD30828772, AKOS037515357.

Physico-chemical characteristics

• Chemical formula: C21H22O4
• Molecular Weight: 336.3811
• Exact weight: 336.136
• PSA specifications: 48.7
• XLogP3: 5.8

Plant source

Anhydronotoptol was found in the rhizomes and roots of the plant Notopterygium incisum (Qianghu, Qianhu) - a raw material of traditional Chinese medicine from the Apiaceae family. The compound belongs to the derivatives of natural phenolic substances of this plant.

Substance class

According to its chemical structure, it belongs to furanocoumarins - a class of oxygen-containing heterocyclic compounds that are widespread in plants of the Apiaceae family and are characterized by a condensed furan ring at the coumarin core. The prefix "anhydro-" indicates the dehydrated form of the related compound notoptol. Along with anhydronotoptol, the rhizome of Notopterygium incisum also contains other coumarins and furanocoumarins - notopterol, isoimperatorin, nodakenetin and notopterygine, which together determine the pharmacological profile of the raw material.

Traditional use of raw materials

The rhizome of Notopterygium incisum (Qianghu) is classified in traditional Chinese medicine as a "wind and damp expeller" and is used for colds with chills, headaches, and rheumatic pain in the joints and muscles of the upper body. The pharmacological properties of the raw material are associated primarily with the coumarins and essential oils it contains.

Biological activity

Published studies have demonstrated anti-inflammatory and antidiabetic activity of the compound in vitro: anhydronotoptol suppresses nitric oxide (NO) production in cells with an IC50 of 36.6 μM, and also inhibits monoamine oxidase, which is considered a potentially useful property in the development of treatments for diabetic neuropathy. Inhibition of monoamine oxidase is an activity characteristic of other furanocoumarins from plants of the Apiaceae family.

Scope of application

It is used as an analytical standard and an object for pharmacological studies of natural compounds from the rhizome of Notopterygium incisum. It is not produced on an industrial scale; it is supplied as a reagent for scientific laboratories.

General properties of furanocoumarins

Linear and angular furanocoumarins of plants of the Apiaceae family, the structural series of which includes anhydronotoptol, are known for their photosensitizing effect upon UV irradiation of the skin (due to the ability to integrate into DNA and form adducts under the influence of ultraviolet radiation), as well as inhibition of cytochrome P450 enzymes and monoamine oxidase - these properties common to the class explain the interest in anhydronotoptol as a model compound for studying the structure-activity relationships of furanocoumarins.

Storage

As a natural phenolic compound, sensitive to oxidation and light, it is stored in sealed containers protected from light at low temperatures.