PHYTOCHEMISTRY Flashcards
study of composition of plant principle, their extraction, biosynthesis and identification
PHYTOCHEMISTRY
HISTORY
- slow progress
- era of pure compounds
- know how to prepare crude drugs (thru incineration)
- has difficulty in differentiating poisonous vs. non-poisonous plants
19th century
responsible for contact dermatitis due to poison oak, ivy
urushiol
sugar was isolated from sugar cane by using
alcohol
who isolated sugar from sugar cane
Nicholas Lemery
- disposed aristotle’s theory of 4 elements
- didnt isolate or purify an alkaloid
- used potassium carbonate and alcohol to purify but wasnt able to finish
Robert Boyle
isolated sugar from sugar beet
A.S. Marggraf
- Father of Modern Phytochemistry
- isolated many organic or plant acids such as citric acid from citrus, malic acid, gallic acid, oxlic acid, tartaric acid, prussic acid
K.W. Scheele
malic acid is from
apple
oxalic acid is from
kamias
tartaric acid is from
grapes
- first alkaloid
- all has nitrogen in their structure
Narcotine
elucidated the chemical nature of fats (margaric acid) and fixed oils
Mitchel Eugene Chevreul
era of structure determination
middle 20th century
EXTRACTION PROCEDURE
dried plants
powdered before extraction
EXTRACTION PROCEDURE
Fresh plants
homogenized / macerated w/ alohol
general solvent
alcohol (80%)
solvent for essential & fixed oils
light petroleum
solvent for alkaloids, quinones
ether & chloroform
solvent for basification (water-immsicible)
alkaloids
solvent for aromatic acids & phenols
acidification
EXTRACTION
repeated maceration with agitation, percolation or continuous using a hot solvent
EXTRACTION
EXTRACTION
utilize unscented fat in the preparation of pomade
enfleurage
EXTRACTION
sound waves - can damage hearing
sonification
EXTRACTION
part of rotavapor where the material is placed
thimble
EXTRACTION
- also known as ball mill
- uses tumbling motility
spouted bed extraction
temperature where the solid & liquid mixes
supercritical fluid
EXTRACTION
- extraction of herbal medicines, flavorant, cosmetics
Supercritical fluid extraction
EXTRACTION
reported that supercriticial fluid extraction can be used in research and medicine
Cagniard de la Tour
EXTRACTION
suitable for volatile oil containing drugs
solid phase microextraction
EXTRACTION
oppostie of absorption; release
desorption
the most difficult operation in phytochemistry
Separation & isolation
bcs time consuming
method of choice in isolation and purification of caffeine
solid to gas
SUBLIMATION
used in isolation of volatile oils
distillation
DISTILLATION
- for volatile oils
- using mixtures with varying boiling points
fractional distillation
DISTILLATION
useful in isolating volatile oils and HCN
steam distillation
employed in isolation and purification of alkaloids (weakest to strongest base)
fractional liberation
- a method used in **traditional isolations **and still valuable for the resolution of often otherwise intractable mixtures
- frequently derivatives of the particular components are employed (picrates of alkaloids, osazones of sugars)
fractional crystallization
substance to be separated during chromatography
analyte
visual output
chromatogram
mobile phase leaving the column (solvent); solution obtained
eluate
solvent that carry the analyte
eluent
process of desorption
elution
moves in definite direction
mobile phase
fixed place for the chromatographic procedure
stationary phase
reagent used for visualization
ninhydrin
CHROMATOGRAPHY
- one of the oldest and most useful
- utilizes a mobile liquid or gaseous phase that is adsobed onto the surface of a stationary phase
- ex: light petroleum extract of green leaves
Adsorption chormatography
- Martin & Synge (1941): acetylated amino acids
- Evans & Partridge (1948): alkaloids
- replaced by HPLC
- inexpensive, easy to set-up & operate
Partition chromatography / Paper chromatography
CHROMATOGRAPHY
method of choice for fractionation
partition chromatography on paper
CHROMATOGRAPHY
- highly improved form of column chromatography
- expensive
- use narrow columns
- temperature of 200C and use of high pressure
- employ small pre-column containing a cartridge
HPLC / High-speed LC
CHROMATOGRAPHY
- both qualitative and quantitative analysis and purification of low to moderate molecular weight, thermolabile molecules
- it can also be used for the separation of chiral compounds
Supercriticial fluid chromatog
CHROMATOGRAPHY
- uses Craig apparatus
- consists of a series of glass tubes that are designed and arranged such that the lighter liquid phase is transferred from one tube to the next
- liquid-liquid extractions are taking place simultaneously in all tubes which are driven electromechanically
COUNTER-CURRENT EXTRACTION
apparatus used in counter-current extraction
Craig apparatus
perfromed on a sheet of glass, plastic, or aluminum foil, which is coated with a thin layer of adsorbent material, usually silica gel, aluminum oxide, or cellulose (blotter paper)
thin layer chromatog
- common type of chromatog used in analytic chemistry for separating and analyzing compounds that can be vaporized without decomposition
- stationary phase: liquid
gas-liquid chromatography
- capillary bore columns are used rather than the standard columns
- speed of analysis is much greater compared to GC
cAPILLARY-COLUMN GAS CHROMATOG
- lacks an attractive interaction between the staionary phase and solute
- the liquid or gaseous phase passes through a porous gel which separates the molecules according to its molecular size
gel filtration chromatog
gel permeation chromatog
- is a chemical separation technique used to resolve and separate mostly large biomolecules such as proteins
- it is a combination of size exclusion chromatog andd gel electrophoresis
- molecules are separated by size due to the gel filtration mechanism and by electrophoretic mobility due to the gel electrophoresis mechanism
electrochromatography
the most selective type of chromatography
affinity chromatography
the penultimate stage in biogenetic study is the ____ involved in the pathways under consideration and the in vitro demonstration of their properties
isolation of enzymes
- a process of fusing plant material from two different plants
- important in determining the site of primary and secondary metabolite production
graft
MUTANT STRAINS
utilizes “brewer’s soluble” → mevalonic acid
Lactobacillus acidophilus
MUTANT STRAINS
induced mutant of ergot auxotrophic
UV