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Shikimate Pathway) (Acetate Pathways) 47 Biosynthesis of Flavonoids Cinnamoyl-CoA (shikimate pathway) (acetate pathways) 1000 times sweeter Bitter 48 than table sugar Anthocyanidins • The hydroxyl groups are usually found on positions 5, 7 of ring A or at 4-, (3-, 4-), on ring B and sometimes they maybe in the form of methoxy or alkoxy, and the sugar is usually attached to the OH groups to form the glycosides. • Anthocyanins are glycosides of anthocyanidins. Either (-) or (+)- catechin • They could be found in different parts of the plant specially in cell sap (the watery fluid within the central vacuole of a plant cell). • Many of them are diuretic, diaphoretic and some have the ability to decrease the bleeding tendency of blood vessels and to affect the permeability of the capillaries like Rutin and Hesperidin which decrease the capillary fragility. • In plants, in addition to being flower pigments and attracting pollinating birds and insects, other suggested roles e.g. control of plant growth, inhibiting and activating plants enzymes, some have fungicidal effect and protect plant against attack by parasites. 49 Drugs containing anthocynidins 1. Pelargonin • This anthocyanin glycoside is found in the flowers of Pelargonium (Family: Geraniaceae). • It is the 3,5-O-diglucoside of pelargonidin, and it contains one hydroxyl group on the benzene ring B. Pelargonidin Pelargonin 50 2. Cyanidin • Is found in cornflowers and it has 2 hydroxyl groups on benzene ring B. 51 3. Delphinidin • It occurs in the plants Delphinium and Viola species. • This glycoside contains 3 hydroxyl group on benzene ring B. 52 4. Malvidin : Blue Berry, Bilberry, European Berry (Vaccinium myrtillus ) • Blue berry is rich in phenolic acids, flavonoids (hyperin, quercitin) and anthocynin 0.5 % such as cyanidin, delphinidin and malvidin. Malvidin Vaccinium myrtillus 53 Pharmacological activity: Blue berry anthocyanins have: 1. Vascular protection. 2. Antiedemic effect. 3. Anti-inflammatory effect. 4. Clinically, it is used for eye disease such as retina bleeding risk. 5. It has a free radical-scavenging activity (Anti-oxidant). 6. It alleviates the cognitive decline occurring in Alzheimer disease and other conditions of aging. 7. It prevents urinary tract infection. 8. It lowers cholesterol and total lipid levels. 54 : كركديه (Roselle (Hibiscus subdariffa • The part used is the calyx (cup) of flowers, which is widely used for the treatment of hypertension. • This is due to angiotensin-converting enzyme activity (ACE Inhibitor) due to delphinidin-3-O-sambubioside and cyanidin-3-O- sambubioside. Delphinidin-3-o-sambubioside 55 Leucoanthocyanidins Leucoanthocynidins are a group of water-soluble plant pigments, very closely related to anthocynidins. They are converted to the related anthocynidins when boiled with aqueous or alcoholic HCl acid. Chemically, they are flavan-3,4-diols like melacacidin from Acacia species. Melacacidin 56 Catechins • Catechins are flavan-3-ol deravatives. • Catechin itself is 3,5,7,3’,4’ pentahydroxyflavan. Catechin • FlavAnols (with an "a") are not to be confused with flavOnols (with an "o"), a class of flavonoids containing a ketone group. • Catechin is found in tea {Thea senesis}. • It has heart-protective effect. 57 Phytoalexins • They are antibiotics produced by plants that act as toxins against the attacking organisms. 1. Pterocarpans: • Pterocarpans are derivatives of isoflavonoids • found in the Fabaceae family. • Like medicarpin and pisatin. 2. Rotenone: Medicarpin • Is an odorless, colorless, crystalline derivatives of isoflavone used as a broad- and ,مبيد لﻷسماك spectrum insecticide, piscicide pesticide. • Found in Derris and Lonchocarpus species of Derris • They are insecticide. • Roots from both plants contain 3-5 % of rotenone, and are also used as fish poisoning material. • They are not toxic to humans as they are metabolized rapidly after ingestion. 58 Lonchocarpus Derris 59 60 Cyanogenic/Cyanophore Glycosides Cyanogenic glycosides (or Cyanophore Glycosides) are O-glycosides yielding HCN gas on hydrolysis . Cyanogenesis is the ability of some plants to synthesize cyanogenic glycosides. They are condensation products of HCN to a carbonyl compounds producing Cyanohydrin (unstable) which upon glycosylation gives Cyanogenic glycosides (stable). CN R R R CN HCN Glycosylation C O C C R R OH R O-Sug Cyanohydrine Cyanogenic glycoside (Unstable) (Stable) Cyanogenesis is one of the mechanisms of plant as a protective device against predators such as the herbivores. Cyanogenic glycosides or cyanoglycosides account for approximately 90% of the wider group of plant toxins known as cyanogens. 61 Cyanogenic/Cyanophore Glycosides Cyanogenic glycosides when enzymically hydrolyzed, release cyanohydric acid (HCN). In most cases, hydrolysis is accomplished by the β-glucosidase, producing sugars and a cyanohydrin that spontaneously decomposes to HCN and a ketone or aldehyde. The second step can also be catalysed by the hydroxynitrile lyase, which is widespread in cyanogenic plants. In the intact plant, the enzyme and the cyanogenic glycoside remain separated, but if the plant tissue is damaged both are put in contact and cyanohydric acid is released. 62 Cyanogenic/Cyanophore Glycosides Cyanohydric acid is extremely toxic to a wide spectrum of organisms, due to its ability of linking with metals (Fe++, Mn++ and Cu++) that are functional groups of many enzymes, inhibiting the reduction of oxygen in the cytochrome respiratory chain inhibiting the electron transport in the photosynthesis, and inhibiting the activity of enzymes like catalase, oxidase. The level of cyanogenic glycosides produced is dependent upon the age and variety of the plant, as well as environmental factors. Cyanogenic glycosides are widely distributed among 100 families of flowering plants. They are also found in some species of ferns, fungi and bacteria. There are many economical important plants highly cyanogenic, including white clover, linum, almond, sorghum, the rubber tree and cassava. 63 Cyanogenic/Cyanophore Glycosides The best known drugs derived from such glycosides are volatile oils of bitter almond and wild cherry, both are used as sedatives, specially in various cough syrups and similar preparations. Wild cherry 64 Amygdalin This glycoside is found in bitter almond and in the kernels (nuclei) of fruits like apricot, cherries, peaches, plums. Family: Rosaceae. Amygdalin Peaches Plums 65 Hydrolysis of Amygdalin The enzyme emulsin (obtained from almond kernals), consists of a mixture of 2 enzymes, amygdalase responsible for the first step and prunase for the second step. O H HCN + CHO CH CN Mandilonitril 1-6 linkage O glc glc O glc CH CH Amygdalase Prunase CN CN Amygdalin Prunasin (Mandelonitrile glucoside) Since one of the products is benzaldehyde, thus amygdalin containing drugs are classified with aldehyde glycoside group. 66 Amygdalin We have 2 types of mandelonitrile: D & L relative configurations in relation to mandelic acid which is used for aromatic and not for aliphatic compounds. The group of cyanophore glycosides are represented by amygdalin which is found in large quantities in bitter almond, and also by prunasin which is found in Prunus padus (Bird cherry) Mandelic acid Prunus padus 67 Wild Cherry: Dried stem bark of Prunus serotina Family: Rosaceae The plant is indigenous to USA and Canada. The plant was used by the red Indians as a domestic medicine and it contains: D-mandelonitrile glucoside (prunasin) Emulsin β-methyl aesculetin (methylether of dihydroxy coumarin). It also contains L-mandelic acid and p-coumaric acid, trimethylgallic acid. The HCN acid liberated from this plant is between 0.23 - 0.32% from the inner bark and 0.03% from the outer bark. Uses: most important uses as syrup, flavoring agent, sedative expectorant. 68 Cyanogenic/Cyanophore Glycosides Typical levels for some plant materials consumed by humans are: 70 71 Isothiocyanate Glycosides . This group of glycosides are sometimes called thiocyanate or sulphurated glycosides where the aglycones are thiocyanates. Thioglycosides are particularly abundant in the families Brassicaceae (also called Cruciferae) and Capparidaceae . It is believed that these glycosides protect plants against parasites. Biosynthesis . The biosynthesis of these glycosides was proven to be from shikimic acid for the aromatic glycosides like sinalbin, while the acetate units are the precursors for the sinigrin which are found in the white and black mustard respectively. Sinalbin in seeds of white mustard . Sinigrin in seeds of black mustard 72 73 O K O S O M y r o s i n a s e N C H 2 O H N O S C O S C H 2 C C C H 2 O H H C C C H 2 H O H 2 H O H M u s t e r e d o i l 74 S i n i s r i n ( a l l y l i s o t h i o c y a n a t e ) 75 76 77 78 79 Simple phenolic/aldehyde glycosides . This group of glycosides contains phenolic, alcoholic, or aldehyde, group as an aglycone part of glycosides. All are derived from shikimic acid pathway. 80 81 ALCOHOL GLYCOSIDES 1. Salicin It is O-hydroxy benzoylglucoside. It is found in different species of :like the following صفصاف Willow bark 1. Salix purpurea Family: Salicaceae 2. Salix fragilis Family: Salicaceae 3. Populus species. Usually it is hydrolyzed by the enzyme emulsin to D-glucose and saligenin. Act as an analgesic, antipyretic and anti-inflammatory agent in human body. 82 S. purpurea S. fragilis الصفصاف الهش الصفصاف اﻻرجواني 83 2. Populin: It is benzoyl salicin and is a phenolic alcoholic glucoside. It is found in the bark and leaves of Populus species and Family: Salicaceae. Hydrolysis: 1. By alkali : it gives benzoic acid and salicin. 2. By acid: it gives benzoic acid, saligenin (salicyl alcohol) and glucose. 84 P o p u l i n Populus deltoides 85 3.Coniferin: It is m-methoxy-p-hydroxy cinnamyl alcohol glycoside . النباتات الصنوبرية This is found in most coniferous plants Is used for preparation of vanillin. 86 Phenol Glycosides Arbutin Extracted from the dried leaf of Arctostaphylos uva-ursi .الخلنجية Family Ericaceae USES 1.
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