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. 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

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

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. 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. CONSTITUENTS OF ESSENTIAL OILS & ESSENTIAL OIL DRUGS MONOTERPENOIDS - ALCOHOL (-)- β -citronellol (-)- linalool geraniol (+)- α -terpineol (-)- β -menthol (+)-Borneol

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

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 

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. 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. 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. 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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