Natural Products From Acetate Pathway (Lipids) PDF

NATURAL PRODUCTS FROM ACETATE PATHWAY (LIPIDS) Assoc. Prof. Dr. Juriyati Jalil Faculty of Pharmacy Universiti Kebangsaan Malaysia LIPIDS Fatty acids Fixed oils Fat Waxes LIPIDS Lipids Long chain fatty acids and alcohols Fixed oil, fats & waxes Fatty a...

NATURAL PRODUCTS FROM ACETATE PATHWAY (LIPIDS) Assoc. Prof. Dr. Juriyati Jalil Faculty of Pharmacy Universiti Kebangsaan Malaysia LIPIDS Fatty acids Fixed oils Fat Waxes LIPIDS Lipids Long chain fatty acids and alcohols Fixed oil, fats & waxes Fatty acids (alkanoic acid) Straight chain, saturated or unsaturated monocarboxylic acid FATTY ACIDS Biosynthesis of Fatty Acids Fatty Acids Abbreviations Common Naturally Occuring Fatty Acids Common Naturally Occuring Fatty Acids FIXED OILS & FATS Fixed oils and Fats Esters of fatty acid with glycerides At room temperature Fixed oils : non-volatile, thick, viscous, yellow liquid Fats (more saturated acids) : semi-solid or solid Non-aromatic & greasy Permanent translucent stain on paper Rancid on prolong storage Lighter than water Fixed oils and Fats Solubility Soluble in organic solvents Insoluble in H2O Uses: Food value Pharmaceutical uses Emollient Demulcent WAXES Waxes Esters of fatty acids with high MW monohydric alcohols. At room temperature, viscous solid mass with waxy lustre. Similar to fats but only saponified by alcoholic alkali. Waxes Sources Animals: Beeswax, Wool fat Plants: Carnauba wax, Sesame wax Mineral: Paraffin Protective covering against penetration & water loss Pharmaceutical uses Ointments, creams, etc LIPIDS IN PHARMACY Lipids in Pharmacy Carnauba wax Leaves of Copernicia prunifera (Palmae) Used as polish of coated tablet Jojoba oil Seeds of Simmondsia chinensis (Buxaceae) Used as non-greasy lubricant in creams & lotions Lipids in Pharmacy White & Yellow Beeswax Honeycomb made by the honey-bee (Apis mellifera) Pharmaceutical aid Wool fat Wool of sheep (Ovis aries) Pharmaceutical excipient OTHER IMPORTANT FATTY ACIDS Acetylenic Fatty Acids Unsaturated fatty acids with acetylenic bonds Highly unstable but detectable under UV Some are toxic & allergenic Cicutoxin from water hemlock (Cicuta virosa, Umbelliferae) Oenanthotoxin from hemlock water dropwort (Oenanthe crocata, Umbelliferae) Acetylenic Fatty Acids Some are biologically active Wyerone from broad bean (Vicia faba, Leguminosae) Examples of Acetylenic Fatty Acids Branched-chain Fatty Acids Derived from mammals Wool fat & butter fat Some from plants: Chemical Source Species Effect Sterculic acid Seed Sterculia Alter membrane foetida permeability & inhibit reproduction Chaulmoorgric Seed Hydnocarpus Bactericidal against & hydnocarpic wightiana leprosy infection acids Prostaglandins Cyclized C20 fatty acids containing Cyclopentane ring, COOH at C7 & C8 side chain with terminal CH3 Biosynthesized from fatty acids E.g. dihomo--linolenic acid, arachidonic acid & eicosapentaenoic acid) Mainly derived from mammals Soft coral sea whip (Plexaura homomalla) Prostaglandin esters (2-3%) & PGA2 (1-2%)