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INTRODUCTION TO  PHYTOCHEMICALS SAIFUL IRWAN ZUBAIRI   PMIFT, Grad B.E.M.   B. Eng. (Chemical-Bioprocess) (Hons.), UTM M. ...
PHYTOCHEMICALS Phytochemicals Phyto  comes from the Greek word means plant.  Chemicals  Chemicals present naturally in pla...
PLANT LIPIDS <ul><li>Defined as substances that can be extracted from cells & tissues by nonpolar organic solvents.  </li>...
<ul><li>Simple lipids </li></ul><ul><li>1) Steroids </li></ul><ul><li>2) Prostaglandins </li></ul><ul><li>3) Terpenoids </...
Steroids Cholesterol <ul><li>Common biological intermediate </li></ul><ul><li>Believed to be the biosynthetic precursor to...
Prostaglandins PGE 1 <ul><li>Prostaglandins – first isolated from secretion of prostate gland </li></ul><ul><li>regulate d...
Complex lipids <ul><li>Those that easily hydrolysed to simple constituents </li></ul><ul><li>Mostly esters of long-chain c...
Trigliseride <ul><li>Esters of gliserol </li></ul><ul><li>Liquid (oil) </li></ul><ul><li>Solid (fat) </li></ul>Tristearin ...
Waxes <ul><li>Esters of long chain fatty acids with long chain alcohols </li></ul><ul><li>Serve a number of purposes in pl...
BIOSYNTHESIS OF PHYTOCHEMICALS CO 2  + H 2 O Carbohydrates CH 3 COCOOH Pyruvic acid CH 3 COOH Acetic acid Fatty Acids & Po...
ESSENTIAL OILS <ul><li>Volatile aromatic compounds obtained  </li></ul><ul><li>via  steam or hydrodistillation </li></ul><...
Concretes <ul><li>Solvent extracted product contains volatile & </li></ul><ul><li>non volatile components </li></ul>Absolu...
TERPENOIDS <ul><li>Natural products derived from mevalonic acid </li></ul><ul><li>Consist of isoprene units - C 5 </li></u...
CLASSIFICATION OF TERPENOIDS MONOTERPENOIDS SESQUITERPENOIDS DITERPENOIDS C 10  Skeleton C 15  Skeleton C 20  Skeleton Ess...
ESSENTIAL OILS Source Components Anethole Linalool Myrcene Curcuma mangga Mango flavour Coriander seed Oil of Coriander An...
CONSTITUENTS OF ESSENTIAL OILS & ESSENTIAL OIL DRUGS MONOTERPENOIDS - ALCOHOL (-)- β -citronellol (-)- linalool geraniol (...
(+)- camphor KETONES (+)- limonene (+)- carvone Used in liniments against rheumatic pains ~ 3% solution in ethanol sooth i...
PHENOLS  Thymol Carvacrol Thymi   herba The extract is used in cough mixture as an expectorant PHYRETROIDS  <ul><li>Flower...
<ul><li>ALKALOIDS </li></ul><ul><li>Contain nitrogen, N – usually derived from amino acids </li></ul><ul><li>Bitter tastin...
AlKALOIDS Nicotine – alkaloid from tobacco Cocaine – local anaestatic Morphine – Analgesic Codeine – Analgesic, antitussiv...
GLYCOSIDES <ul><li>Glycosides are compounds containing carbohydrates and noncarbohydrate residue in the same molecule  </l...
Example Methyl glucoside will be formed when a solution of glucose in boiling methyl alcohol is treated with 0.5 % HCl as ...
CLASSIFICATION OF GLYCOSIDES   GLYCOSIDES Alcohol group Saponin group Anthraquinone group Aldehyde group Carboxylic group ...
SAPONIN Glycone Aglycone Sugar Sapogenin -  Glucose - Arabinose - xylose - glucronic acid - Neutral Saponin - Steroids - S...
PHENOLIC <ul><li>Most phenolic compounds belong to the flavonoids. </li></ul><ul><li>Lignin the primary substances of wood...
<ul><li>The flavonoids are polyphenolic compounds possessing 15 carbon atoms; two benzene rings joined by a linear three c...
FLAVONOID <ul><li>Chalcones </li></ul><ul><li>- can be found in cinnamon </li></ul>
<ul><li>Flavones </li></ul><ul><li>  - generally in herbaceous families,  </li></ul><ul><li>e.g. Labiatae, Umbelliferae, C...
<ul><li>Flavonol </li></ul><ul><li>-  generally in woody angiosperms </li></ul><ul><li>- kaemferol ( Sambucus nigra, Cassi...
<ul><li>Flavones </li></ul><ul><li>-  Can be found in genus  Citrus. </li></ul><ul><li>such as lemon, orange etc. </li></u...
<ul><li>Antocyanins </li></ul><ul><li>- Occur in the form of salt </li></ul><ul><li>- Can be found in fruits such as oil p...
<ul><li>Isoflavonoids </li></ul><ul><li>- Most commonly found in soya bean </li></ul><ul><li>-Roots of Leguminosae </li></...
<ul><li>Aurone </li></ul>FLAVONOID <ul><li>Special class of flavonoid </li></ul><ul><li>It has five membered ring in the 2...
Lignins Catecholmelanine (Condensed tannins) (C 6 - C 3 )n (C 6 )n (C 6 - C 3 - C 6 )n n biflavonoids (C 6 - C 3 - C 6 ) 2...
Estrogen effect, toxic for fungi 15 Isoflavonoids Gingko 65 Biflavonoids Some have properties like those of tannins 40 Cat...
Juglon in  Juglans regia Hyroquinone in  Arctostaphylos Sialic acid in  Quercus falcate Ferulic acid in  Adenostoma Quinon...
Juglone in  Carya ovata Gallotannine in  Quercus robur Quercitine-glycosids in Gossypium Quinones Tannines Flavonols Prote...
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Phytochemicals

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  1. 1. INTRODUCTION TO PHYTOCHEMICALS SAIFUL IRWAN ZUBAIRI PMIFT, Grad B.E.M. B. Eng. (Chemical-Bioprocess) (Hons.), UTM M. Eng. (Bioprocess), UTM ROOM NO.: 2166, CHEMISTRY BUILDING, TEL. (OFF.): 03-89215828, FOOD SCIENCE PROGRAMME, CENTRE OF CHEMICAL SCIENCES AND FOOD TECHNOLOGY, UKM BANGI, SELANGOR
  2. 2. PHYTOCHEMICALS Phytochemicals Phyto comes from the Greek word means plant. Chemicals Chemicals present naturally in plants Phytochemicals include secondary plant metabolites: Essential oils Oleoresin Phenolic compounds-flavonoids Glycosides Alkaloids Bioactive compounds
  3. 3. PLANT LIPIDS <ul><li>Defined as substances that can be extracted from cells & tissues by nonpolar organic solvents. </li></ul><ul><li>Devided into two major classses: </li></ul><ul><li>1) Simple lipids </li></ul><ul><li>2) Complex lipids </li></ul>
  4. 4. <ul><li>Simple lipids </li></ul><ul><li>1) Steroids </li></ul><ul><li>2) Prostaglandins </li></ul><ul><li>3) Terpenoids </li></ul><ul><li>4) Fat-soluble vitamins </li></ul><ul><li>Those that are not easily hydrolysed by aqueous acid or base </li></ul><ul><li>Seem inappropriate because many so-called “simple” lipids are quite complex molecules </li></ul>
  5. 5. Steroids Cholesterol <ul><li>Common biological intermediate </li></ul><ul><li>Believed to be the biosynthetic precursor to other steroids </li></ul>
  6. 6. Prostaglandins PGE 1 <ul><li>Prostaglandins – first isolated from secretion of prostate gland </li></ul><ul><li>regulate diverse functions </li></ul><ul><li>eg: blood pressure, blood clotting, allergic, inflammatory etc. </li></ul>
  7. 7. Complex lipids <ul><li>Those that easily hydrolysed to simple constituents </li></ul><ul><li>Mostly esters of long-chain carboxylic acids called fatty acids </li></ul>Triglicerides Waxes
  8. 8. Trigliseride <ul><li>Esters of gliserol </li></ul><ul><li>Liquid (oil) </li></ul><ul><li>Solid (fat) </li></ul>Tristearin (a fat)
  9. 9. Waxes <ul><li>Esters of long chain fatty acids with long chain alcohols </li></ul><ul><li>Serve a number of purposes in plants & animals </li></ul><ul><li>eg: Beeswax – a mixture of waxes that bees use to </li></ul><ul><li>form their honeycomb </li></ul>(a component of beeswax) <ul><li>Carnuba waxes – secreted by carnuba plant to coat its leaves to prevent excessive loss of water by evaporation </li></ul>
  10. 10. BIOSYNTHESIS OF PHYTOCHEMICALS CO 2 + H 2 O Carbohydrates CH 3 COCOOH Pyruvic acid CH 3 COOH Acetic acid Fatty Acids & Polyketides Mevalonic acid Terpenes Steroids Purines Protein Peptides Alkaloids Aromatic Amino Acids Phenylpropanoids Flavonoids Nucleic Acid PO 4 3- Shikimic Acid Amino Acid Tannin N 2 Photosynthesis Chorismic Acid CH 3 CCH 2 COOH OH CH 2 CH 2 OH
  11. 11. ESSENTIAL OILS <ul><li>Volatile aromatic compounds obtained </li></ul><ul><li>via steam or hydrodistillation </li></ul><ul><li>Mainly terpenes and terpenoids </li></ul><ul><li>(mono and sesqui) </li></ul><ul><li>Some esters and alcohols </li></ul>
  12. 12. Concretes <ul><li>Solvent extracted product contains volatile & </li></ul><ul><li>non volatile components </li></ul>Absolutes <ul><li>Ethanol soluble concretes </li></ul>Oleoresin <ul><li>Solvent extracted product </li></ul>Tincture <ul><li>Product obtained by soaking dry plant materials </li></ul><ul><li>in 50-95% ethanol in a ratio of 1:5 </li></ul><ul><li>(herbs material : solvent) </li></ul>
  13. 13. TERPENOIDS <ul><li>Natural products derived from mevalonic acid </li></ul><ul><li>Consist of isoprene units - C 5 </li></ul><ul><li>Contain oxygen in variety of functional groups </li></ul><ul><li>Alcohol </li></ul><ul><li>Ketone/ aldehyde </li></ul><ul><li>Ester </li></ul><ul><li>Ether </li></ul><ul><li>Carboxylic acids </li></ul><ul><li>Subdivided/ classified according to the number of carbons </li></ul><ul><li>mono, sesqui, di, tri, tetra, etc. </li></ul>
  14. 14. CLASSIFICATION OF TERPENOIDS MONOTERPENOIDS SESQUITERPENOIDS DITERPENOIDS C 10 Skeleton C 15 Skeleton C 20 Skeleton Essential Oils (aroma) TRITERPENOIDS C 30 Skeleton (Steroids skeleton) TETRATERPENOIDS C 40 Skeleton ß -carotene  pigment in carrot  Vitamin A Lycopene  pigment in tomato
  15. 15. ESSENTIAL OILS Source Components Anethole Linalool Myrcene Curcuma mangga Mango flavour Coriander seed Oil of Coriander Anise Seed Oil of anise β - Selinene Celery Oil of Celery Mixture of Terpenes & Terpenoids Flowers Perfumes & Flavours
  16. 16. CONSTITUENTS OF ESSENTIAL OILS & ESSENTIAL OIL DRUGS MONOTERPENOIDS - ALCOHOL (-)- β -citronellol (-)- linalool geraniol (+)- α -terpineol (-)- β -menthol (+)-Borneol
  17. 17. (+)- camphor KETONES (+)- limonene (+)- carvone Used in liniments against rheumatic pains ~ 3% solution in ethanol sooth itching <ul><li>From caraway </li></ul><ul><li>used as spice </li></ul><ul><li>From lemon, orange, grape fruit </li></ul><ul><li>For flavouring </li></ul><ul><li>Food & perfumery industries </li></ul>Citral <ul><li>from ginger </li></ul><ul><li>For flavouring </li></ul>
  18. 18. PHENOLS Thymol Carvacrol Thymi herba The extract is used in cough mixture as an expectorant PHYRETROIDS <ul><li>Flower of Chrysanthimum sp. </li></ul><ul><li>Insecticides </li></ul>O Pyrethrin
  19. 19. <ul><li>ALKALOIDS </li></ul><ul><li>Contain nitrogen, N – usually derived from amino acids </li></ul><ul><li>Bitter tasting, usually in the forms of solids/ crystals </li></ul><ul><li>Precipitate with heavy metal iodides. </li></ul><ul><li>Testing the presence of alkaloids. </li></ul><ul><li>- Mayer’s reagent ( Potassiomercuric iodide solution). </li></ul><ul><li>Cream coloured precipitate. </li></ul><ul><li>- Dragendoff’s reagent (solution of potassium bismuth iodide). </li></ul><ul><li>Orange coloured precipitate. </li></ul><ul><li>Alkaloids are basic-form water-soluble salts.Most alkaloids are well defined crystalline substances, which react with acids to form salts. In plants, they may exist : </li></ul><ul><li>- as free state </li></ul><ul><li>- as salts </li></ul><ul><li>- as N-oxides </li></ul>
  20. 20. AlKALOIDS Nicotine – alkaloid from tobacco Cocaine – local anaestatic Morphine – Analgesic Codeine – Analgesic, antitussive Vincristine & vinblastine – anticancer From Catharanthus roseus (Kemunting Cina) Terpenes/ steroids also build into final alkaloid skeleton Morphine, R=H Codeine, R=CH 3
  21. 21. GLYCOSIDES <ul><li>Glycosides are compounds containing carbohydrates and noncarbohydrate residue in the same molecule </li></ul><ul><li>The carbohydrate residue is attached by an acetyl linkage at carbon atom 1 to a noncarbohydrate residue or AGLYCONE </li></ul><ul><li>The nonsugar component is known as the AGLYCONE . The sugar component is called GLYCONE </li></ul><ul><li>If the carbohydrate portion is glucose, the resulting compound is a glucosides </li></ul>
  22. 22. Example Methyl glucoside will be formed when a solution of glucose in boiling methyl alcohol is treated with 0.5 % HCl as catalyst  or   or 
  23. 23. CLASSIFICATION OF GLYCOSIDES GLYCOSIDES Alcohol group Saponin group Anthraquinone group Aldehyde group Carboxylic group Tannin Lactone group Cyanate group Isothiocyanate group Phenol group Flavonol group <ul><li>SAPONIN GLYCOSIDES </li></ul><ul><li>Saponin glycosides are devided into 2 types based on the chemical structure of </li></ul><ul><li>their aglycones (sapogenins) </li></ul><ul><li>E.g. : Dried rhizome and root Glycyrrhiza glabra (licorice) from Leguminosae family. </li></ul>
  24. 24. SAPONIN Glycone Aglycone Sugar Sapogenin - Glucose - Arabinose - xylose - glucronic acid - Neutral Saponin - Steroids - Saponin Acid - Triterpenoids <ul><li>The main pathway leading to both types of sapogenins is similar and involves the head to tail coupling units. However, a branch occurs, after the formation of the triterpenoids hydrocarbon, squalene, that leads the steroids in one direction and to cyclic triterpenoids in the other. </li></ul>
  25. 25. PHENOLIC <ul><li>Most phenolic compounds belong to the flavonoids. </li></ul><ul><li>Lignin the primary substances of wood is the most </li></ul><ul><li>common member of this group </li></ul>
  26. 26. <ul><li>The flavonoids are polyphenolic compounds possessing 15 carbon atoms; two benzene rings joined by a linear three carbon chain. </li></ul>FLAVONOIDS <ul><li>The skeleton can be represented as C6 – C3 – C6 </li></ul><ul><li>Many flavonoids are easily recognized as flower pigments in most angiosperm families (flowering plants) </li></ul><ul><li>Most characteristic compounds in plants </li></ul>
  27. 27. FLAVONOID <ul><li>Chalcones </li></ul><ul><li>- can be found in cinnamon </li></ul>
  28. 28. <ul><li>Flavones </li></ul><ul><li> - generally in herbaceous families, </li></ul><ul><li>e.g. Labiatae, Umbelliferae, Compositae </li></ul>FLAVONOID
  29. 29. <ul><li>Flavonol </li></ul><ul><li>- generally in woody angiosperms </li></ul><ul><li>- kaemferol ( Sambucus nigra, Cassia Senna, </li></ul><ul><li> Equisetum arvense, Lamium album ) </li></ul>FLAVONOID
  30. 30. <ul><li>Flavones </li></ul><ul><li>- Can be found in genus Citrus. </li></ul><ul><li>such as lemon, orange etc. </li></ul>FLAVONOID
  31. 31. <ul><li>Antocyanins </li></ul><ul><li>- Occur in the form of salt </li></ul><ul><li>- Can be found in fruits such as oil palm, </li></ul><ul><li>bilberry flowers eg: Roselle, Hibiscus </li></ul><ul><li>- Give different colour in different media </li></ul><ul><li>(pH) </li></ul>FLAVONOID
  32. 32. <ul><li>Isoflavonoids </li></ul><ul><li>- Most commonly found in soya bean </li></ul><ul><li>-Roots of Leguminosae </li></ul>FLAVONOID
  33. 33. <ul><li>Aurone </li></ul>FLAVONOID <ul><li>Special class of flavonoid </li></ul><ul><li>It has five membered ring in the 2 nd ring </li></ul>
  34. 34. Lignins Catecholmelanine (Condensed tannins) (C 6 - C 3 )n (C 6 )n (C 6 - C 3 - C 6 )n n biflavonoids (C 6 - C 3 - C 6 ) 2 30 Flavonoids,isoflavonoids (C 6 - C 3 ) 2 18 xanthone C 6 - C 3 - C 6 15 Stilbene,anthrachinone C 6 - C 2 - C 6 14 Xanthone C 6 - C 1 - C 6 13 Naphtoquinone C 6 - C 4 10 Hydroycinnamic acid,polypropene,coumarin, isocoumarin C 6 - C 3 9 Acetophenone,phenylacetic acids C 6 - C 2 8 Phenolic acids C 6 - C 1 7 Simple phenols,benzoquinones C 6 6 Class Basic skeleton Number of C-atoms The Most Important Classes of Phenolic Compounds in Plants
  35. 35. Estrogen effect, toxic for fungi 15 Isoflavonoids Gingko 65 Biflavonoids Some have properties like those of tannins 40 Catechins Astringent substances 50 Proanthocyanidins Some taste bitter 10 Dihydrochalcones Feeding repellents in leaves 350 Flavonols Cream-colored pigments of flower 350 Flavones Yellow pigments 20 Aurones Yellow pigments 60 Chalcones Red and blue pigments 250 Anthocyanins Biological significance Number of known members Class The Most Important Classes of Flavonoids and their Biological Significance
  36. 36. Juglon in Juglans regia Hyroquinone in Arctostaphylos Sialic acid in Quercus falcate Ferulic acid in Adenostoma Quinones Phenols Phenolcarboxylic acids Hydrocinnamic acids Allelopathic substances Petunidin glucoside in Atropa belladonna Osajin in Maclura pomifera Ocanin in Kyllingi breviofolia Antocyanines Isoflavones Chalcones Fruit pigments Cyanidins-3, 5-diglucoside in Rosa Coreopsin in Coreopsis tinstoria Aureusin in Anthirrhinum majus Gossypetine-7-glucoside in Gossypium Apegenin-7-glucoside in Bellis Perennis Anthocyanes Chalcones Aurones Yellow flavonoids Flavones Flower pigments Example(s) and plant species where the effect was studied Group Function The Ecological Meaning of Some Phenolic Compounds for Plants
  37. 37. Juglone in Carya ovata Gallotannine in Quercus robur Quercitine-glycosids in Gossypium Quinones Tannines Flavonols Protection against pests Luteon in Lupinus Protocatechunic acid in Allium Phloridcine in Malus pumila Isoflavones Phenolcarboxylic acids Dihydrochalcones Fungicides Reservatrol in Arachis hypogaea Orchinol in Orchis militaris Vestitol in Lotus corniculatus Pisatin in Pisum sativum Coniferyl alcohol in Linum usitiltissimum Psoralen in Petroselinum crispum Stilbens Phenylanthrenes Isoflavanes Pterocarpens Phenylpropanoids Fucocoumarins Phytoalexines Example(s) and plant species where the effect was studied Group Function The Ecological Meaning of Some Phenolic Compounds for Plants
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