Amygdalin

Description

Amygdalin is a cyanogenic glycoside that has been found in seeds from plants of the Rosaceae family and has diverse biological activities. It induces cell cycle arrest at the G₀/G₁ phase, decreases cyclin A and Cdk2 levels, and inhibits cell growth in UMUC-3, RT112, and TCCSUP bladder cancer cells when used at concentrations ranging from 1.25 to 10 mg/ml. Amygdalin (3 mg/kg) reduces the number of primary microtubules and microvessels in aortic rings isolated from rats with diabetes induced by streptozotocin . In vivo, amygdalin reduces triglyceride, total cholesterol, and LDL levels and aortic sinus plaque area in an LDLR^-/- mouse model of atherosclerosis. It also reduces production of TNF-α, IL-1β, and IL-6, as well as neutrophil and macrophage infiltration, in bronchoalveolar lavage fluid (BALF) in a mouse model of LPS-induced acute lung injury.

Chemical properties

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The Uses of Amygdalin

Amygdalin, a cyanide containing glycoside, may be used as a substrate to identify, differentiate and characterize enzymes such as maltase(s), emulsin(s) and β-glucosidase(s).

The Uses of Amygdalin

antiinflammatory, experimental antineoplastic

The Uses of Amygdalin

A cyanogenic glycoside occurring in seeds of Rosaceae, principally in bitter almonds and peach and apricot pits. Some time ago it was said to be effective in the treatment of cancer, but controlled clinical trials repeatedly failed to confirm such claims.

What are the applications of Application

Amygdalin is cyanide containing glycoside used to characterize a variety of enzymes

Definition

ChEBI: An amygdalin in which the stereocentre on the cyanohydrin function has R-configuration.

World Health Organization (WHO)

Laetrile, which consists mainly of amydgalin, a glycoside extracted from the kernels of apricots, peaches and other fruits, has been available for over 30 years in preparations purporting to be beneficial in the treatment of cancer. Although there is no evidence that these are efficacious, preparations continued to be widely used and, until the late 1970s, they were considered to be harmless. However, oral dosage forms, which may be broken down in the gut to hydrogen cyanide, have subsequently been shown to be potentially lethal. This has resulted in restrictive regulatory measures in several countries.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Cyanogenic glycoside that is a component of bitter almonds and apricot pits. There is no scientific evidence that amygdalin itself is an effective anti-cancer agent. Recent studies using β?glucoside linked to a tumor-associated monoclonal antibody to release cyanide at the tumor cell has shown significant cytotoxicity.

Safety Profile

Human poison by ingestion(infant data). Poison experimentally by ingestion. Anexperimental teratogen. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

Purification Methods

D-Amygdalin recrystallises from water as the trihydrate, or from EtOH. It is present in bitter almonds. [Smith Chem Ber 64 1115 1931, Beilstein 17/8 V 188.]