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CHEMOSYSTEMATICS
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Chemical features of plants are used in
developing classifications or in solving
taxonomic problems
Chemotaxonomy
Chemosystematics
Chemical Taxonomy
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
MARKERS
Alkaloids
Flavonoids
Carotenoi
ds
Polysaccha
rides
Terpenoid
s
Fatty acids
Amino
acids
Aromatic
Compoun
ds
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Evidences of SUCCESS
Aromatic plants in Juglandales
Betalins in Caryophyllales
Aromatic compounds in Lamiaceae
Alkaloids in Solanaceae
Tannifeorus materials in Sapindaceae
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
WHERE we can APPLY?
Starting from the rank of ‘variety’ up to the rank of
‘division’
Starting from simple organisms to highly
specialized group of angiosperms
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
PURPOSES
To develop taxonomic
character which may
improve the existing
system
To develop the present
day knowledge of
phylogeny
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
HISTORY
HEMLOCK (Conium
maculatum)
SOCRATES
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
DIOSCORIDES
1st Century
AD
Aromatic
Mints
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Modern phase of Chemotaxonomy began with
the work of Abbott (1886) in Botanical Gazette
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
McNair published a series of papers from
1917 to 1945
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Taxonomically significant phytochemicals
1. Directly visible- starch grains; raphides; crystals
2. Chemical test characters- phenolics; betalins;oils;
fats; waxes; alkaloids
3. Proteins
 Micromolecules
 Macromolecules
 Sematides
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Flavonoids
Phenolic glycosides having two benzene rings
linked together through a heterocyclic pyrane
ring
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Why flavonoids became significant in
taxonomy?
Wide spread distribution
chemical complexity
physiological stability
quick and easy identification
structural variation
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Classes of Flavonoids with systematic
significance
Anthocyanidins Cyanidin, Delphinidin
Flavones Apigenin, Levtolin
Biflavonyls Amentoflavone
Flavanols Kaempferol, Quercetin
Flavonones Naringenin
Isoflavones Orobol
Isoflavonoids Ferreirin
Chalcones Butein
Aurones Sulphuretin
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Betalins
Nitrogeneous
anthocyanins
Include red to violet
betacyanins and
yellow betaxanthins
Aizoaceae, Amaranthaceae,
Basellaceae, Caryophyllaceae,
Chenopodiaceae, Didieraceae,
Molluginaceae, Nyctaginaceae,
Phytoalecaceae and Portulacaceae
produce betalins and are placed
together in a single order
Caryophyllales
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
• Also called isoprenoids
• Polymers of isoprene units
• Mevalonic acid is the precursor
• Used extensively in chemosystematics of Mints,
Umbellifers, Citrus plants and Gymnosperms
Terpenoids
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Terpenoids and systematics
Volatile
monoterpenoids and
sesquiterpenoids
Major components of
essential oils
Magnoliales, Laurales,
Austrobaileyales,
Piperales
Sesquiterpene Asteraceae, Apiaceae, Magnoliaceae, Lauraceae
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Triterpenoid ‘Betulin’ Seen in the bark of Betula papyrifera and
relatives
Triterpene saponins Apiaceae and Pittospraceae
Triterpenoid derivatives ‘limonoids’ &
‘Quassinoids’
Limited to Rutaceae, Meliaceae and
Simaroubaceae (of Sapindales)
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
• Triterpene derivative
• Alcohols or esters having two methyl groups
• Located in plant cutins
• Perform the function of water proofing
• Helpful for the taxonomy of the genera of
tribe Veratreae of family Liliaceae
Steroids
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Iridoids
Monoterpenoid cyclopentanoid lactones
Found in many families of the Asterid clade
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Seco-iridoids Gentianales, Dipsales, and many
families of Cornales and
Carbocyclic iridoids Lamiales, except for Oleaceae,
Tetrachondraceae and
Gesneriaceae
Alkaloids
Basic nitrogen-containing organic compounds, with
heterocyclic ring
Derived from different amino acids or mevalonic
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Secologanin-type indole alkaloids Apocyanaceae, Gelsemiaceae,
Loganiaceae and Rubiaceae
Tropane alkaloids Solanaceae & Convolvulaceae
Benzylisoquinoline alkaloids Magnoliales, Laurales, Ranunculales
Isopremoid alkaloids Scattered distribution
Less systematic interestPyrrolizidine alkaloids
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Glocosinolates
Thioglucosides which on hydrolysis form a glucose
and a corresponding isothiocyanate
Mustard oil glucosides
Synapomorphic for Brassicales
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Cyanogenic Glycosides
Defensive compounds
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
Cyclopentanoid cyanogenic
glycosides
Restricted to Achariaceae,
Passifloraceae, Turneraceae &
Malesherbiaceae
CG from leucine Rosaceae
CG from tyrosine Magnoliales and Laurales
Polyacetylenes
Non-nitrogeneous secondary metabolites
Asterid families-Asteraceae, Apiaceae,
Pittosporaceae, Campanulaceae, Goodeniaceae
and Caprifoliaceae
Falcarinone polyacetylenes restricted to
Araliaceae and Pittosporaceae
SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1

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Chemosystematics

  • 2. Chemical features of plants are used in developing classifications or in solving taxonomic problems Chemotaxonomy Chemosystematics Chemical Taxonomy SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 4. Evidences of SUCCESS Aromatic plants in Juglandales Betalins in Caryophyllales Aromatic compounds in Lamiaceae Alkaloids in Solanaceae Tannifeorus materials in Sapindaceae SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 5. WHERE we can APPLY? Starting from the rank of ‘variety’ up to the rank of ‘division’ Starting from simple organisms to highly specialized group of angiosperms SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 6. PURPOSES To develop taxonomic character which may improve the existing system To develop the present day knowledge of phylogeny SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 9. Modern phase of Chemotaxonomy began with the work of Abbott (1886) in Botanical Gazette SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 10. McNair published a series of papers from 1917 to 1945 SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 11. Taxonomically significant phytochemicals 1. Directly visible- starch grains; raphides; crystals 2. Chemical test characters- phenolics; betalins;oils; fats; waxes; alkaloids 3. Proteins  Micromolecules  Macromolecules  Sematides SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 12. Flavonoids Phenolic glycosides having two benzene rings linked together through a heterocyclic pyrane ring SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 13. Why flavonoids became significant in taxonomy? Wide spread distribution chemical complexity physiological stability quick and easy identification structural variation SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 14. Classes of Flavonoids with systematic significance Anthocyanidins Cyanidin, Delphinidin Flavones Apigenin, Levtolin Biflavonyls Amentoflavone Flavanols Kaempferol, Quercetin Flavonones Naringenin Isoflavones Orobol Isoflavonoids Ferreirin Chalcones Butein Aurones Sulphuretin SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 15. Betalins Nitrogeneous anthocyanins Include red to violet betacyanins and yellow betaxanthins Aizoaceae, Amaranthaceae, Basellaceae, Caryophyllaceae, Chenopodiaceae, Didieraceae, Molluginaceae, Nyctaginaceae, Phytoalecaceae and Portulacaceae produce betalins and are placed together in a single order Caryophyllales SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 16. • Also called isoprenoids • Polymers of isoprene units • Mevalonic acid is the precursor • Used extensively in chemosystematics of Mints, Umbellifers, Citrus plants and Gymnosperms Terpenoids SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 17. Terpenoids and systematics Volatile monoterpenoids and sesquiterpenoids Major components of essential oils Magnoliales, Laurales, Austrobaileyales, Piperales Sesquiterpene Asteraceae, Apiaceae, Magnoliaceae, Lauraceae SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1 Triterpenoid ‘Betulin’ Seen in the bark of Betula papyrifera and relatives
  • 18. Triterpene saponins Apiaceae and Pittospraceae Triterpenoid derivatives ‘limonoids’ & ‘Quassinoids’ Limited to Rutaceae, Meliaceae and Simaroubaceae (of Sapindales) SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 19. • Triterpene derivative • Alcohols or esters having two methyl groups • Located in plant cutins • Perform the function of water proofing • Helpful for the taxonomy of the genera of tribe Veratreae of family Liliaceae Steroids SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 20. Iridoids Monoterpenoid cyclopentanoid lactones Found in many families of the Asterid clade SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1 Seco-iridoids Gentianales, Dipsales, and many families of Cornales and Carbocyclic iridoids Lamiales, except for Oleaceae, Tetrachondraceae and Gesneriaceae
  • 21. Alkaloids Basic nitrogen-containing organic compounds, with heterocyclic ring Derived from different amino acids or mevalonic SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 22. Secologanin-type indole alkaloids Apocyanaceae, Gelsemiaceae, Loganiaceae and Rubiaceae Tropane alkaloids Solanaceae & Convolvulaceae Benzylisoquinoline alkaloids Magnoliales, Laurales, Ranunculales Isopremoid alkaloids Scattered distribution Less systematic interestPyrrolizidine alkaloids SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 23. Glocosinolates Thioglucosides which on hydrolysis form a glucose and a corresponding isothiocyanate Mustard oil glucosides Synapomorphic for Brassicales SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1
  • 24. Cyanogenic Glycosides Defensive compounds SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1 Cyclopentanoid cyanogenic glycosides Restricted to Achariaceae, Passifloraceae, Turneraceae & Malesherbiaceae CG from leucine Rosaceae CG from tyrosine Magnoliales and Laurales
  • 25. Polyacetylenes Non-nitrogeneous secondary metabolites Asterid families-Asteraceae, Apiaceae, Pittosporaceae, Campanulaceae, Goodeniaceae and Caprifoliaceae Falcarinone polyacetylenes restricted to Araliaceae and Pittosporaceae SHAIJU PUSHPANGADAN, FMNC, KOLLAM-1