Ergot Alkaloid: Naturally occurring in Rivea corymbosa and Ipomoea

violacea, Family: Convolvulaeae.

Ergot is a fungal disease commonly found on many wild and cultivated
grasses, and it is caused by Claviceps purpurea. The disease is eventually
characterized by the formation of hard, seed like ergot, called sclerotia.
(Resting stage of fungus)

Synonym: Ergot of rye and Ergot of wheat

Biological source: Dried sclerotium of the fungus Claviceps purpurea

(Family: Clavipitaceae), arising in the ovary of rye plant Secale cereale
(Family: Gramineae).

Geographical distribution: N-W Spain, Russia, Germany, Hungary,

Switzerland, and India.

Cultivation & Collection:

 Systematic field cultivation on rye is the main source of crude drug.

 Rye plant is first raise and the field is utilized to inoculate the flowers
of the plant artificially with conidiospores of Claviceps purpurea
through inoculating media.
 The inoculum is prepared through the utilization of conidiospores
culture.
 After three weeks from inoculation time, the mature sclerotia are
harvested by hand picking.
 Ergot can be harvested along with grains and can be separated by
thrashing and sieving.
 Alternatively they can be separated from the grains by throwing the
grains in to 25% of common salt solution, wherein the ergot float
while the rye sinks.
 Ergot after collection must be dried immediately and stored carefully
to avoid deterioration.

Life cycle of Ergot:

Life cycle of ergot is completed in three stages:
 Honeydew stage or Sphacelia
 Sclerotium stage or Resting Stage
 Ascospore stage
Honeydew stage or Sphacelia: During the flowering period spores of the
fungus from Ascospore stage are carried by insects or wind currents, reach
to the flowers of the rye plant and deposited at the base of the ovary of the
flowers. Spores germinate and form hyphal strands which penetrate the wall
of ovary by enzymatic action and form a soft white mass on the surface of
ovary known as Sphacelia. This Sphacelia secretes sweet saccharine
yellowish coloured liquid called honeydew. Insects are attracted to
honeydew because of sweet taste and asexual spores are carrying them to
other plants and spread the disease.

Sclerotium stage: In the first stage hyphae penetrates only the walls of
ovary. Gradually it penetrates deeper and deeper into the ovary and develops
further feeding itself on the mass of the ovary and in the end replaces the
entire mass of ovary by a new hard compact dark purple
pseudoparenchymatous mass, known as ergot or Sclerotium.

Ascospore stage: Some Sclerotia are not collected and fall on the ground
and these sclerotia produce stromata after germination. These stromata have
a stalk and a round head. The head contains flask shaped pockets known as
perithesia. A number of asci are found in perithesia and each ascus contains
eight filamentous Ascospore. This Ascospore is carried by insects or wind
and life cycle is completed.
Morphology of Ergot:
Size: 1-4cm long, 2-7mm wide
Shape: slightly curved, fusiform, tapering at both ends.
Surface: black to purplish brown, longitudinally furrowed with occasional
transverse cracks.
Odour: characteristic. It should possess neither rancid nor ammoniacal
odour.
Taste: unpleasant.

Microscopic Character: Microscopically ergot is characterized by presence

of tightly packed purple coloured rectangular cells at outer zone and inner
pseudoparenchymatous oval or rounded cells. They contain fixed oil and
protein.

Chemistry of Ergot alkaloid:

Ergot alkaloids belong to the large class of indole alkaloids, in which the
indole group is built into tetra cyclic ring system: Ergoline
(octahydroindoloquinoline)
Basic ring is:

There are three main classes of Ergoline derivatives:

1. Water soluble amide of lysergic acid: Lysergic acid amide. E.g.
Ergine, Ergonovine, Methergine, Methysergide, LSD.
Name R1 R2 R3
Ergine H H H
Ergonovine H H

Methergine H H

Methysergide CH3 H

LSD H C2H5 C2H5

2. Water insoluble peptide alkaloids: Ergopeptide; these compounds

have a tripeptide structure attached to the basic Ergoline ring, in the
same location as the amide group of the lysergic acid derivatives. E.g.
Ergotamine, Ergocristine, Ergocornine, Ergocryptine,Bromocryptine,
Ergovaline.

Name R1 R2 R3
Ergotamine - CH3 Benzyl
Ergocristine - CH(CH3)2 Benzyl
Ergocornine - CH(CH3)2 CH(CH3)2
Ergocryptine - CH(CH3)2 CH2CH(CH3)2
Bromocryptine Br CH(CH3)2 CH2CH(CH3)2
Ergovaline - CH3 CH(CH3)2

3. Clavines: derivatives of dimethyl Ergoline. E.g. Agroclavine,

Elymoclavine, Lysergol.
Biosynthesis of ergot alkaloid:
These alkaloids are derived from (+)- Lysergic acid, which includes
ergometrine and ergotamine. The building blocks for lysergic acid are
Tryptophan and an isoprene unit. Alkylation of Tryptophan with DMAPP
gives 4-methyl-allyl-L-tryptophan, which then undergoes N-methylation,
form tetra cyclic ring system of lysergic acid.