DITERPENE ALKALOIDS_F inal

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DITERPENE ALKALOIDS:

DITERPENE ALKALOIDS DR. HARISH KAKRANI & PURVI KAKRANI

DITERPENE ALKALOIDS:

DITERPENE ALKALOIDS Diterpene alkaloids are a group of alkaloids with a structure similar to terpenes . Diterpene alkaloids are usually derived from kaurene . They are best known from the Ranunculaceae ( Aconitum and Delphinium ) and Garryaceae . These compounds are similar in structure to kaurene and other diterpenes of this series, but contain a nitrogen atom, usually of obscure origin. 2 Diterpene Alkaloids, Dr. Harish & Purvi Kakrani

DITERPENE ALKALOIDS:

DITERPENE ALKALOIDS Kaurene Other similar diterpene alkaloids are found in Inula royaleana ( Asteraceae ) and in Spiraea japonica ( Rosaceae ). 3 Diterpene Alkaloids, Dr. Harish & Purvi Kakrani

DITERPENE ALKALOIDS:

Two main structural types are found. One: Series of comparatively simple and relatively non- toxic Amino alcohols and esters Modelled on a C 20 skeleton. The second group Based on a C 19 skeleton. More heavily substituted and much more toxic. The best known compound, aconitine , is exceedingly toxic. DITERPENE ALKALOIDS 4 Diterpene Alkaloids, Dr. Harish & Purvi Kakrani

DITERPENE ALKALOIDS:

These alkaloids are exceedingly toxic. As little as 2-5 mg of some is enough to kill an adult human. Many of these plants have been used as traditional and other medicine, but their toxicity limits their usefulness. They are responsible for numerous cases of livestock poisoning. DITERPENE ALKALOIDS 5 Diterpene Alkaloids, Dr. Harish & Purvi Kakrani

DITERPENE ALKALOIDS:

Mechanism by which they are toxic is they hold sodium channels open: Na channels are transmembrane proteins which are fundamental for cellular communication. These proteins form pores in the plasma membrane allowing passive ionic movements to occur. Their opening and closing are controlled by gating systems which depend on both membrane potential and time. Neurotoxins bind to the receptor sites on these Na channels produce alterations in channel inactivation activate channels at membrane potentials more negative than do unmodified channels changes in action potential duration DITERPENE ALKALOIDS 6 Diterpene Alkaloids, Dr. Harish & Purvi Kakrani

ACONITE:

ACONITE 7 Diterpene Alkaloids, Dr. Harish & Purvi Kakrani

ACONITE:

Synonyms : Aconite root, Bachnag , Monk’s hood Biological source : It is dried root of Aconitum napellus Linn., belonging to family Ranunculaceae . Should contain not less than 0.6% of alkaloids of aconite, of which not less than 30% should be aconitine . Geographical source : Hungary, Germany, Spain & Switzerland Cultivated in England In India, it collected from wild or cultivated from A. chasmanthum or A. ferox . Diterpene Alkaloids, Dr. Harish & Purvi Kakrani 8 ACONITE

ACONITE:

Macroscopical Characters : Color: Dark brown Odour : Slight Taste: slight that causes tingling sensation followed by numbness of tongue Dimensions: 4-10cm in length; 1-3.5cm in width Shape: Broad towards the crown, tapering towards the distal end Fracture: Short & horny Surface: Deeply wrinkled; broad end bears numerous rootlets & scars Diterpene Alkaloids, Dr. Harish & Purvi Kakrani 9 ACONITE

ACONITE:

Chemical constituents : Diterpene alkaloids: aconitine , hypaconitine , neopelline , napelline , neoline Aconitine - Chief constituent Ether soluble Vary in different species of aconite Other constituents: aconitic acid, succinic acid, starch, traces of sparteine & ephedrine Aconitine (Acetyl benzoyl aconine ) Benzoyl aconine + Acetic acid Benzoyl aconine Aconine + Benzoic acid Diterpene Alkaloids, Dr. Harish & Purvi Kakrani 10 ACONITE Hydrolysis Hydrolysis

ACONITE:

Diterpene Alkaloids, Dr. Harish & Purvi Kakrani 11 ACONITE Aconitine Aconine

ACONITE:

Standards : Ash: Not more than 5% Acid insoluble ash: Not more than 1% Aerial stem: Not more than 5% Foreign organic matter: Not more than 2% Uses : Highly poisonous Used externally (liniment) in treatment of neuralgia, sciatica, rheumatism & inflammation Analgesic & cardiac depressant Restricted to homeopathic system of medicine only Diterpene Alkaloids, Dr. Harish & Purvi Kakrani 12 ACONITE

ACONITE:

Substitutes: Japanese aconite: Aconitum unicinatum Indian aconite: A. chasmanthum Diterpene Alkaloids, Dr. Harish & Purvi Kakrani 13 ACONITE

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