Chemotaxonomy of Medicinal plant

CHEMOTAXONOMY:
Definition:-The approach of taxonomy in which chemical nature of plants are used in developing classification or in solving taxonomical problems is called chemotaxonomy ,chemosystematics, chemical taxonomy ,chemical plant taxonomy or plant chemo taxonomy are the common names of chemotaxonomy. It gives the close relationship between chemical constituents of plants and their taxonomical status. Chemotaxonomy establishes relationship between the position of the plant and exact understanding of biological evaluation and natural relation ship. Depending upon chemical evidence, plants are classified accurately as alkaloids, flavonoids, carotenoids, polysaccharides, terpenoids, fatty acids (proteins). Purpose of chemotaxonomy:Chemotaxonomy has been used in all levels of classification. Chemical evidences have been used in all the groups of the plant kingdom starting from simple organism like fungi and bacteria up to the most highly advanced and specialized group of Angiosperms. The evidence is used in classification of plants into 2 main purposes. 1. To improve the existing system of plants differentiation. 2. To develop the present day knowledge of natural relationship of plants. o Chemical characters and their use in taxonomy: - Naik divided the chemical characters into 3 categories. 1. Directly visible characters:-Starch grains, raphides, silica ,gypsum ,etc 2. chemical test characters:-phenolic ,betalins, oil fats, waxes ,alkaloids 3. Proteins o On the other hand in 1987 some authors divided the natural chemicals plants products into 2 groups on the basis of molecular weight. 1. Low molecular weight compounds:- That is a molecular weight of 1000 or less than 1000 called as Micromolecules. Ex:-Amino acids, alkaloids, fatty acids, terpenoids, flavonoids. 2. High molecular weight compounds:- with a molecular weight of more than 1000 called as Macromoecules. Ex:-proteins, DNA, RNA complex , Polysaccharides. History of Chemotaxonomy: • The concept of classification of plant based on chemical character is not new. it is started in 15th &16th centuries by anatomist Newmann, Grew & James petitver. They recognized similar chemicals or medicinal effects of umbelliferous plants. (carminative)

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chemical convergence and divergence in the plant. Dyanamic taxonomy is based on biosynthetic pathway. develop paper chromatography. By: Anukul . on their molecular characteristics. showed that paper chromatography applied to analysis of plant pigments. 2. suggested that chemical characters should be included in natural classification. Different plants sometimes contain secondary constituents belonging to different classes of compound but biosynthetically appear to be same. Beale and coworkers in 1940. Clasification of Chemotaxonomy: based on the taxonomical and chemical knowledge: Descriptive taxonomy Dynamic taxonomy Serotaxonomy Descriptive taxonomy deals with the classification of plant and secondary metabolite and other products like sugar & amino acid.Chemotaxonomy of Medicinal plant • • • • • • Greshoff in 1909.al. DNA. Bat & smith in 1948. surveyed 32 species of Tulip for anthocyanin contents and distribution of group of compounds in genus as a taxonomic characters. i. worked on single genus Eucalyptus (176)-collected morphological and chemical data and finally concluded on the morphological basis the feather contended leaves having more pinene in their volatile oil. Serotaxonomy or semantics is based on pathway of specific proteins and amino acids sequencing in proteins. in 1944. 1.primary semantics RNA-secondary semantics Proteins-tertiary semantics Principle of chemotaxonomy Chemical classification of plants is based on their chemical constitutions. says that ‘more closely related taxas produce more similar chemical products’. 3. Baker and Smith in 1920. Mc Nair in 1935. The same type of metabolites can be the product of two quite different pathways. It is further classified as.e. It is also concerned with evolutionary change. Conden et.

Such integrated investigations are necessary in order to obtain really convincing evidence for the relationship of plants. Before any important conclusions are drawn about the presence or absence of a particular compound adequate sampling of a large number of members of the species at different stages of development and growing in different environment should be made. The collection of plant sample done: By the help of professional plant collector From national garden and national herbarium From professional plant sellers Personal travel & collection Modification of suitable chemical techniques: Depending upon the choice of investigator. cuticles and seed. wood. and spectroscopy. chromatography. Intraspecific chemical variation Qualitative and quantitative variation between different parts of same plant Variation due to Seasonal and environmental fluctuation Analysis of the material: qualitative and quantitative analysis is done by phytochemical screening. taxonomic survey and sound sampling modification of suitable chemical techniques Analysis of all material interpretation of data and its comparison from all other sources According to the interest of investigation the relative stages may vary (for taxonomy. All the spectra obtained from different technique should be analyses. 3.Chemotaxonomy of Medicinal plant Chemotaxonomic studies include the investigation of the pattern of compound occurring in the plant and preferentially in all various individual parts of plant such as the bark . By: Anukul . what class of material is likely to exhibit useful variation at the taxonomic level. 2. 4. phylogenetic & chemistry) Sound sampling: an understanding of natural variation within a group and phylogenies are helpful in good sampling. root. Different stages of Chemotaxonomic investigation: 1. Choice of group. leaves . electrophoresis. finger print.

characteristic of family rosaceae and gentianaceae respectively. It is reported that sorbitol is present in all species belong to subfamily of rosaceae like spiraeoidae. L-oleandrose. 6-Deoxy hexose: It occurs in the form of methyl ether that is restricted to certain family. 1. phylogenetic and taxonomy is interpreted & depending upon the evidence the classification of plant should be reconsidered. 2. 3. Example. most of them are of universal occurrence and is utilized by the plant itself for growth and development. Polyols: Among monosaccharide derivatives eg. Eg. carbohydrate is having little chemotaxonomic significance. If only a minor change occurs in the match of chemical and other variation then the classification is essentially confirmed. but in species of ulmaria genus belong to By: Anukul . Primary metabolites. 2. • • • • 6-Deoxy hexose. D-sorbitol. and rosoidae. are parts of vital metabolic pathways. Thus. but some of the rare sugars having chemotaxonomic significance. starch.. citric acid. CARBOHYDRATES IN CHEMOTAXONOMY: Carbohydrates are universal constituents of living organism and widely distributed in the plant. Gentiobiose & Gentianose.Chemotaxonomy of Medicinal plant Interpretation and comparison of data: All the data obtained from chemistry. 6-Dideoxy hexose. L-thevetose and D-digitalose are used as cardiotonic. D-cyamarose sugars are particularly abundant in family apocynaceae and asclepiadaceae (both are group of unrelated family). aleurone grain. So the presence or absence of such sugars is help in the study of phylogenetic relationship. 6-Dideoxy hexose: Cardinolides containing D-digitoxose. Primary metabolites 2. prunoidae. Ex. Polyols and polysaccharides. The presence or absence of these sugar alcohol in rosaceae can be utilized to identify subfamily. Secondary metabolites. etc. Three broad categories of compounds are used in Chemotaxonomy:. Semantices. D-mannitol and mesoxylitol. aconitic acid. pomoidae. D-sorbitol occurs naturally in fruits of various rosaceae family. Gentiobiose and gentianose: These are uncommon sugar in amygdalin. chlorophyll.

while temperate grasses accumulate fructans. dextran. cellulose. while the fructan is present in family graminae. moringaceae. They are found in some plants containing anthraquinone derivatives eg. capparaceae. By: Anukul . S-glycoside. So. Distribution of O-glycosides is widespread.Chemotaxonomy of Medicinal plant rosoidae. About 25 C-glycosides of flavonoid group are known more are flavone and few iso-flavone and flavanone. Starch. cascaroside in cascara-rhamnaceae. Aloin in aloe-liliaceae. Eg. Rhein. Polysaccharides: It is condensation of large number of monosaccharide molecules. alkaloid. These compounds are characteristic of the family cruciferae. D-digitalose. is used for protection and defence. Secondary metabolites present in plant. Among these polysaccharides inulin is characteristic of family compositae. but studied in C-glycosides. eg. Dcymarose. Adenosine. N-glycoside. eg. S-glycosides are examplified by those produce isothiocyanate on hydrolysis. polysaccharide is also utilized in confirming phylogenetic relationship. So these family having phylogenetic relationship. Aloin. Glycoside. eg. Eg. which possess a direct carbon linkage between sugar and non-sugar are rare in nature. cascaroside. and inulin. eg. L-thevetose. volatile oil. so it is having little chemotaxonomic value. Glycosides in chemotaxonomy: Glycosides are compounds in which one or more sugars are combined with non-sugar components by glycosidic linkage or by hemiacetal linkage involving oxygen (Oglycoside). these are plant phenol. That is universal in the energy storage forms eg. Tropical and subtropical species of grasses accumulate starch in their leaves. Thus. C-glycoside. Eg. fructan. Depending upon the linkage the glycoside may be classified as: • • • • O-glycoside. sorbitol is absent. the absence of this chemotaxonomy marker confirms the removal of ulmaria from spiraeoidae to rosoidae. Sinigrine. flavonoid and plant phenol. The nature of sugar moiety and its position of attachment to aglycone maybe characteristics of cardiac glycosides.L-oleandrose (cardiotonic) C-glycosides.

but same compound synthesized from amino acid valine or isoleucine is restricted to Leguminosae.Most of them derived from. On the basis of amino acid precursors some conclusion may be derived. The accumulation of cyanogenetic glycoside is also significant in confirming the position of certain family. Different amino acid like phenyl alanine. On the basis of alkyl component of glucosinolate compound. but lack a heterocyclic ring. ephedrine . Passifloraceae. brassica species can be differentiated eg. ALKALOID IN CHEMOTAXONOMY Alkaloids are compounds. Natural protoalkaloids are usually simple amines e. Leguminosae. because that is hybrid of B. By: Anukul . Such compounds are restricted to plant kingdom. and isoleucine are precursor for the biosynthesis of cyanogenetic glycosides. containing heterocyclic nitrogen. mescaline. leucine. o Pseudo alkaloids biologically unrelated to amino acids. tyrosine. o Proto alkaloids – derived from amino acids. but they are restricted to particular family. valine.terpenes. Capparidaceae. Tropaeolaceae and Resedaceae. Gramineae. restricted rosaceae. nigra (allyl glucosinate) and B. sterols .g. nicotinic acid or purines. basic character and complex molecular structure. Thioglucoside in chemotaxonomy: These are responsible for the characteristic flavors of various plants or family brassicaceae and few related family like. o True alkaloids have a nitrogen-containing nucleus derived from biogenetic amine. Example: Leucine-Leguminosae and sapindaceae. Brassica juncea (mustard) from Indian subcontinent contain 3-butenyl glucosinate and allyl glucosinate while those from Asiatic country contain only allyl compound. So ancestry of Indian species is doubtful. at family level cyanogenetic glycoside amygdaline synthesized from phenyl alanine.Chemotaxonomy of Medicinal plant Cyanogenetic glycoside in chemotaxonomy: Plant species having ability to produce hydrogen cyanide by enzymatic hydrolysis are common in family Rosaceae.Some times they may be precursor of true alkaloids. compestris (3-butenyl glucosinate).

E. alkaloids. A few alkaloids occur as glycoside of sugars like glucose. Biological amines like Ephedrine . both are usually classified as alkaloids. They are of limited distribution in plant kingdom.g. alkaloids of solanum and veratrum groups as amides (Piperine). but less frequent in lower plants and fungi.Hardenine. Criteria for using Alkaloids in taxonomy: Definition of alkaloids Definition of alkaloid plants The type of alkaloids that can be distinguished Homologous and analogous characters Definition: Alkaloids are more or less toxic substances having physiological action. tartaric acid. steroids.Cholin.Chemotaxonomy of Medicinal plant Occurrence and Distribution: Higher plants particularly in the dicotyledons. purines. nicotinic acid. Muscarine. as esters (Atropine. Rubiaceae. contain heterocyclic nitrogen. due to their basic nature.” But such definition excludes a number of nitrogen containing plant constituents. These can also be classified according to precursor on which they are based and collectively called as pseudo alkaloids. Solanaceae. Papaveraceae. citric acid. and galactose. In plants.g.di-terpenes. Ex. Mescaline in cactaceae family. Another group of nitrogen compounds that fall outside our definition of alkaloids are mono. Caffeine. Rutaceae. E. They are basic in nature. malic acid. rhamnose.g . Ranculaceae. sesqui. By: Anukul . Conessine. All such alkaloids are separately referred as protoalkaloids or biological amines or amino alkaloids. tannic acid etc.. But when protoalkaloids and true alkaloids occur in same genus or family. which are normally thought as alkaloids. and are synthesized in plants from amino acid and or their intermediate derivatives. E. – Hardenine. generally exist as a salt of organic acid like. abundance in the Angiosperms families Apocynaceae. Some alkaloids like narceine and nicotine are occurring free in nature. oxalic acid. Cocaine) of organic acid.Betain .

Morphine group. Papaverine group. that’s why these two bases have been kept outside the class of true alkaloids. histidine. Homologous and analogous chemical characters: Two similar substances or even same substance may be isolated from two different plants and are taxonomically important if the compounds are derived from exactly same metabolically process.Ajamaline. we can define lower limit as 0. Ecgonine etc . ornithine. By: Anukul .Chemotaxonomy of Medicinal plant Definition of alkaloid plants: There is no sharp dividing line between alkaloids containing plants and alkaloids free plants. E. Type of alkaloids that can be distinguished: – It has been found that amino acids phenylalanine. Lysine family . Each of this amino acid can be regarded as starting point for synthesis of one or more types of alkaloids. Anthranilic acid are primary precursors of alkaloids in plants. E. Anabasine etc. There are also numbers of alkaloids which can be regarded as hybrids. But same compounds or similar compounds are produced by different metabolic pathways in different plants. From practical point of view. Anahaline group. lysine. Ornithine family . tryptophan.Hygrine.01% of dry weight. vinblastine etc. Ephedrine. Yohimbine. Phenylalanine family –Hardenine.Coniine. Ricinine is only alkaloid in Ricinus communis and Genitianine only alkaloid in Gentianaceae.g. Another characteristic of true alkaloid is that it always contains more than one alkaloid. Atropine. Tryptophan family .g. Therefore we may put the alkaloids into families corresponding to six amino acids mentioned above.

Some alkaloids are restricted to only very certain plants e. they should be treated as one unit from chemotaxonomic point of view. In the legume and chenopod species where Anabasine also occurs. The quinoline alkaloids of cinchona bark are obviously quite different structurally from yohimbine alkaloids from yohimbe bark but they are closely related biosynthetically and this points to a close relation between the plants in which they occur. Evidences from basic moiety: Pyridine and Piperidine The parent base pyridine occurs in some plants as Lobeline obtained from Lobelia inflata family Lobeliaceae. E. Therefore. Anabasine occurs in tobacco. Both families accumulate Isoquinoline alkaloids.Chemotaxonomy of Medicinal plant E. Strychnine is restricted to strychnos species Accumulation of Isoquinoline alkaloids in families Fumariaceae and Papaveraceae. it can be synthesized from two molecules of lysine. somniferum family Papaveraceae By: Anukul .g. where it is formed from lysine and nicotinic acid. Papaverine is obtained from P. Nicotine obtained from Nicotiana tobaccum family Solanaceae Anabasine obtained from Nicotiana gluaca family chenopodiaceae. Similarly quinine has been isolated from several unrelated genera.g. Anabasine in Nicotiana genus (Solanaceae family) is formed from one molecule of lysine on the other hand in Leguminosae family two molecules of lysine are involved. There are instances where alkaloid biosynthesis can be helpful to chemotaxomist for arranging the species within genus according to their alkaloid content. Generally ornithine and lysine families of alkaloids are closely related. and always contain Protopine. Isoquinoline Alkaloids Isoquinoline alkaloids are obtained from following plants.g. somniferum Coniine is restricted to Umbeliferous sp. Thus it seems that Anabasine of Solanaceae is not equivalent (homologous) to that in Leguminosae. indicate that there is close relationship between two families. Morphine is restricted to P.

but in case of Astilbe genus. Tryptamine (Loganiaceae). In erythroxylum. cocaine alkaloids are found which are same in nucleus but do not occur in the solanacae. Hydrastine which is found in Berberidaceae and Rannunculaceae. gymnosperm and monocotyledon. 4-hydroxy benzoic acid and 4-hydroxy phenyl acetic acid have been reported in eight genera of family saxifragaceae. It is useful chemotaxonomic marker in subfamily rosoidae (tribe-kerrieae)-rosaceae. Plant Phenol in chemotaxonomy: Most commonly occurred phenolic compound is mono or Dihydroxy derivatives of benzoic and cinnamic acid. Physostigmine obtained from Physostigma venonsum family Leguminosae. Atropine and Hyoscyamine serve as example. Ornithine is the precursor Indole Alkaloids Indole alkaloids are found in following plants. By: Anukul . Trihydroxy derivatives of benzoic acid and cinnamic acid. which are very characteristic of the solanaceae. Tropane alkaloids Among the best-known members of the group are the solanaceae alkaloids. Eg: Ellagic acid is absent in fern. Vinblastine obtained from Catharanthus roseus family Apocyanaeae. Phenolic compounds having restricted occurrence may have chemotaxonomic value eg. Indole alkaloids origination from Phenylalanine as in Erythria alkaloids (Leguminosae) such as Erysopine.g.Chemotaxonomy of Medicinal plant Berberine is obtained from Hydrastis canadensis family Berberidaceae The amino acid phenylalanine and tyrosine act as precursor for isoquinoline nucleus. yohimbine (Apocyanaceae) and strychnine (Loganiaceae) the parent compound is tryptophan. 4-hydroxy phenyl acetic acid is replaced by 2-hydroxy phenyl acetic acid. In most cases e. but it is infrequently found in dicotyledon family. Yohimbine obtained from Rauwolfia serpentina family Apocyanaceae.

Flavone & flavanols and their glycosides are universally distributed but some of the substitution patterns are restricted to certain family.g. flavanol. e. having chemotaxonomic importance.g. 2-phenyl benzo pyrilium: anthocyanin & 2-phenyl chromone: flavone. These are rare in gymnosperm but mostly occurs in angiosperm. blue. Different classes of flavanoids: • Flavones • Flavanone • Isoflavanone • Isoflavonoids • Anthocyanidin • Chalcone All flavonoids have common biosynthetic origin and therefore it posses the same basic structural element.g.Chemotaxonomy of Medicinal plant Coumarin derivatives are common volatile constituent responsible for odour in many plants. • E. They are mostly found in the vacuole of higher plant and absent in lower plant. e. pink. isoflavone. water soluble pigments responsible for red.violet colours to flower and fruit. Umbelliferone occurs widely in Umbelliferae while in Compositae it is characteristic of genus Hieracium (hawkweed).Rutaceae. Asteraceae. Anthocyanidins. Except in Caryophyllales. 2-phenylchromone skeleton. The hydroxylated derivative are having restricted distribution can be utilized as chemotaxonomic marker eg. purple.these pigments occurs as glycoside anthocynidins and their aglycones anthocyanidins. They may be present in many classes depending on degree of oxidation of pyran ring which may be open and cyclize into furan ring. By: Anukul . Solanaceae. 6-o-substituted flavonoids in family: Laminaceae. • 5-deoxy flavone in family: Fabaceae • 2-o-substitueted flavonols in family: Laminaceae. Flavonoids are largest group of phenolic compounds.