Flavonoids PDF

FLAVONOIDS B O 2 A C 4 O  FLAVONOIDS ❑ Universal plant pigments ❑ Responsible for the color of the flowers, fruits, and sometimes leaves: Yellow flavonoids; chalcones, aurones Red, blu...

FLAVONOIDS B O 2 A C 4 O  FLAVONOIDS ❑ Universal plant pigments ❑ Responsible for the color of the flowers, fruits, and sometimes leaves: Yellow flavonoids; chalcones, aurones Red, blue or purple; anthocyanins Sometimes contribute to the color by acting as copigments (protect anthocyanins)  FLAVONOIDS Role in plants; ❑ Attract insects by absorbing near-UV radiation ❑ Protect tissue against the UV radiation in the leaf cuticle and epidermal cells Occurrence ❑ Widespread in plant kingdom except for Algae ❑ Structural diversity is maximal in Angiosperms ❑ The glycosidic forms of flavonoids are H2O- Remember that soluble and accumulate in vacuoles glycos d cforms are more polar h b l ty ❑ Free aglycones are located in the leaf cuticle s aᵗhay  FLAVONOIDS CHEMISTRY and CLASSIFICATION EEEtnen.noman ❑ Possess "2-phenylchromane" skeleton ❑ Fall into several classes depending on the degree of oxidation of the "pyran" ring no 2-phenylchromones; * Flavones, flavonols and dimers * Flavanones and dihydroflavonols 2-phenylchromanes: * Flavans * Flavan-3-ols and flavan-3,4-diols  FLAVONOIDS CHEMISTRY and CLASSIFICATION 3-phenylchromones: * Isoflavones 2 phenyl ones are flavones themselves * Isoflavanones carbon results Phenyl nat sfafferent Chalcones and dihydrochalcones (pyran ring open) 2-benzylidene coumaranones (= Aurones) 2-phenylbenzopyriliums: anthocyanins B double bond O atone 2 9511g A C 3 f ne 4 O 2-phenylchromone  FLAVONOIDS CHEMISTRY and CLASSIFICATION 2-Phenylchromones (Flavones and Flavonols) R R 3' OH OH 2 4' 8 1 1' B HO 9 O HO O 7 2 5 A C 6 3 4 3 6 10 OH 5 OH O OH O Favored flavonen R: H Apigenin R: H Kaempferol R: OH Luteolin R: OH Quercetin te  FLAVONOIDS CHEMISTRY and CLASSIFICATION 2-Phenylchromones (Flavones and Flavonols) ❖ Constitute 80% of known flavonoids ❖ Mostly universally distributed ❖ Some are restricted to a particular family and have chemotaxonomic importance; 6-O-substituted flavonoids are common in Lamiaceae, Rutaceae, Asteraceae 5-deoxyflavones in Fabaceae and Myrtales 2'-O-substituted flavonols in Lamiaceae and Solanaceae  FLAVONOIDS CHEMISTRY and CLASSIFICATION 2-Phenylchromones (Flavones and Flavonols) ❖ Structural Diversity; Substitution at C-5 and C-7 by -OH groups (90%) - Free - Etherified (-OMe) - Engaged in glycosidic linkage (O-glc…) Substitutions at C-6 and C-8; - Free or etherified -OH groups - Isoprenylation - Methylation - C-glycosylation  FLAVONOIDS CHEMISTRY and CLASSIFICATION III thromone 2-Phenylchromones (Flavones and Flavonols) ❖ Structural Diversity; EIII.tn Substitution at B ring; 3tavonee - C-4'-OH (OMe) IF - 3',4'-di OH (OMe) flavonet - 3',4',5'-tri OH (less cases)  FLAVONOIDS CHEMISTRY and CLASSIFICATION 2-Phenylchromones (Flavanones & Dihydroflavonols) an means no double bond ❖ Characterized by the absence of a 2,3-double bond ❖ At least one asymmetric center is present ❖ C-2 is normally in the S configuration R R OH OH HO O HO O 2 H H OH H OH O OH O R: H Naringenin R: H Dihydrokaempferol R: OH Eriodictyol R: OH Dihydroquercetin  FLAVONOIDS CHEMISTRY and CLASSIFICATION 2-Phenylchromanes (Flavan-3-ol & Flavan-3,4-diols) OH OH OH OH HO O HO O H H OH OH H H H OH OH OH Catechin Leucocyanidin  FLAVONOIDS CHEMISTRY and CLASSIFICATION 3-Phenylchromones (Isoflavonoids) Is O O 3 O O ISOFLAVONE ISOFLAVANONE  FLAVONOIDS CHEMISTRY and CLASSIFICATION Chalcones t c t ❖ C-ring is opened ❖ Characterized by the presence of a "3C-chain" with a ketone function and an ,-unsaturation R 3 OH 4 1 HO 4'  1'  R: H Isoliquritigenin 2' R: OH Butein O  FLAVONOIDS CHEMISTRY and CLASSIFICATION 2-Benzylidenecoumaranone (AURONES) OH 1 HO O 2 O Hispidol  FLAVONOIDS CHEMISTRY and CLASSIFICATION Biflavonoids I tw tteredtostatmother HO I 8 6 O 2 4' OH 1' HO 3 O OH 4' II 8 HO O 2 1' 6 3 O OH Amentoflavone  FLAVONOIDS CHEMISTRY and CLASSIFICATION 2-phenylbenzopyriliums (ANTHOCYANIDINS) R OH HO O + OH OH R: H Pelargonidin R: OH Cyanidin  FLAVONOIDS CHEMISTRY and CLASSIFICATION Biflavonoids ❖ Flavonoids can also bond to one another (C-6 or C-8) ❖ The interflavonoid linkage can be; * C-C type (e.g. amentoflavon) * C-O-C type (e.g. hinokiflavone) ❖ Two flavonoid units of the biflavonoid may or may not be of the same type; * Biflavone * Biflavanone double bond no * Flavone-flavanone  Eh tht FLAVONOIDS CHEMISTRY and CLASSIFICATION Flavonoid Glycosides (O-glycosides) ❖ Mono-,di-, and trisaccharides (according to sugar numbers) ❖ Sugars: * Hexoses; D-glc, D-galactose, D-allose * Pentoses; D-apiose, L-ara, L-rha, D-xyl * Uronic acid: D-glucuronic acid, D-galacturonic acid ❖ Glycosation point is most often; * C-7(OH) in flavones or * C-3(OH) in flavonols  FLAVONOIDS CHEMISTRY and CLASSIFICATION Flavonoid Glycosides (O-glycosides) ❖ Any OH group of sugar units may be esterified with; * Aliphatic acids (Acetic, malonic, tiglic, etc.) * Aromatic acids ( Gallic, benzoic, cinnamic acids and other derivatives of cinnamic acid) OH O OH OH O O O 8 O1 HO 7 OH 2 HO 6 OH 43 O  FLAVONOIDS CHEMISTRY and CLASSIFICATION Flavonoid Glycosides (C-glycosides) ❖ The glycosidation bond occurs between anomeric carbon of the sugar unit and the C-6 or C-8 of the aglycone (C-C) ❖ The sugars are generally; glc, gal and xyl glucose 2 xyl tol ❖ Several types; galactose Mono-C-glycosidic flavonoids Di-C-glycosidic flavonoids C-glycosyl-O-flavonoid glycosides  FLAVONOIDS CHEMISTRY and CLASSIFICATION Flavonoid Glycosides (C-glycosides) OH OH OH HO OH O OH OH OH HO O O HO 08 O1 2 HO OH OH O 2 7 HO O 3 65OH 4 O HO OH 4 O OH Orientin Saponarin Biosynthetic origin of flavonoids FLAVONOIDS OH O + - O 3x CoAS CoAS O O Isoflavone 3 phenyl chromone OH OH HO OH HO 1 O 2 Aurone OH O OH O Flavone Biosynthetic origin of flavonoids FLAVONOIDS OH have s ngutty OH P af hamakes HO O HO O great OH 31h9 OH OH O OH O OH OH HO O HO O OH OH OH OH OH OH HO O + Proanthocyanidins OH OH  FLAVONOIDS PHYSICO-CHEMICAL PROPERTIES Solubilities and Extraction 53 ns T5opn1 solvents ❖ Generally, flavonoid glycosides are soluble in H2O and alcohols (EtOH, MeOH) Exception: Rutin and hesperidin sparingly soluble Tyhavahydroxyl group ❖ Aglycones are soluble in apolar solvents ❖ If at least one free phenolic group exists, dissolve in alkaline hydroxide solutions ❖ Glycosides are extracted by acetone or EtOH (or MeOH):H2O mixtures (20-50%)  FLAVONOIDS PHYSICO-CHEMICAL PROPERTIES Solubilities and Extraction ❖ Fractionation: - Liquid-liquid extraction with H2O and H2O- immiscible solvents; * Petroleum ether; to remove chlorophyll and lipids * Et2O / CH2Cl2; to separate aglycones * EtOAc; to extract majority of flavonoid glycosides * Free saccharides and most polar glycosides remained in the aqueous phase  FLAVONOIDS PHYSICO-CHEMICAL PROPERTIES Solubilities and Extraction F rst we elute non phenol c ❖ Separation and Purification: group Chromatographic techniques; - Polyamide - Sephadex - Silica gel - RP-MPLC and RP-HPLC reverse phase C 18column ❖ Structure Elucidation: NMR: 1D- and 2D-NMR mass spectrometry MS: Fragmentation UV: Chromophore groups  FLAVONOIDS PHYSICO-CHEMICAL PROPERTIES Qualitative Analysis ❖ TLC th n layer chromatography Chalcones and aurones are; - Usually visible - Turn orange (chalcones) and red (aurones) when exposed to NH3 Examination under UV light for fluorescent; - Before and after spraying reagents (AlCl3, Vanilin/H2SO4)  FLAVONOIDS Rut n s also 7 conta n t presey.to g nnswortmuchmpMar  P FLAVONOIDS PHYSICO-CHEMICAL PROPERTIES Qualitative Analysis ❖ TLC Th n Layer chromatography By spraying 2-aminoethanol / diphenylboric acid (1%), "Naturstoff Reagenz A" Spraying phenol reagents: FeCl3, Anisaldehyde… ❖ Specific chemical reactions: Mg++/HCl; red-orange color (Shibato reaction)  FLAVONOIDS PHYSICO-CHEMICAL PROPERTIES Quantitative Analysis 1) Colorimetric 2) Spectrofotometric 3) HPLC-DAD  FLAVONOIDS BIOLOGICAL PROPERTIES Common properties and uses 1) Decreasing effect on capillary fragility and permeability; * Vitamin P or "P factor" nterstood that theyagra ty v tam ns they are not * Venous tonic so changed * Vascular protective the proffer * Topical agents in phlebology ❖ Used alone or in combination formulations;  FLAVONOIDS BIOLOGICAL PROPERTIES Common properties and uses * To treat symptoms of venous and lymphatic insufficiency; -Tiredness or fullness in the legs - Paresthesias - Cramps - Pains - Edemas  FLAVONOIDS BIOLOGICAL PROPERTIES Common properties and uses * Treatment of dysfunctions linked to the acute attack of piles ❖ Metrorrhagias linked to intra-uterine contraceptive devices ❖ Treatment of lymphedema of the arm subsequent to breast cancer radiation therapy and chemotherapy ❖ Circulatory disorders of the retina and choroid  FLAVONOIDS BIOLOGICAL PROPERTIES Common properties and uses 2) Free radical scavenging activity; ❖ Structural requirements: For opt mal act v ty - 2 ortho-hydroxyl groups on the B ring - Ketone function at C-4 OH ortho - 2,3-unsaturation OH B O Pyranr ng s R ng C A C 2 3 unsaturat on Flavan no unsaturat on a O  FLAVONOIDS BIOLOGICAL PROPERTIES Common properties and uses 3) Effects on Enzymes; ❖ Several flavonoids may inhibit or stimulate some enzymes A) Enzyme inhibition; catalyze hydrolys s of CALIP Inhibition of cAMP phosphodiesterase Aldose-reductase inhibition Lipooxygenase and cyclooxygenase B) Enzyme stimulation; Proline hydroxylase (reinforce collagen strength and stability)  FLAVONOIDS BIOLOGICAL PROPERTIES Other properties S lybum mar anum when Marflavonal gnan ❖ Anti-inflammatory ❖ Antiallergic ❖ Hepatoprotective (flavonolignans) ❖ Antispasmodic ❖ Decrease blood cholesterol ❖ Diuretic ❖ Antibacterial and antiviral ❖ Cytostatic (in vitro)  FLAVONOIDS CHIEF FLAVONOIDS ON THE MARKET Citroflavonoids (Flavonoids from the fruits of they were f rst obta ned from C trus various citrus) fru ts Rutaceae fam ly ❖ Citrus (Rutaceae) species are widely used for their essential oils ❖ They are also a source of pectins and FLAVONOIDS ❖ Flavonoids are abundant in the pericarp; on the outer layerof the fru t * Hesperidin (= hesperetin 7-O-rutinoside) * Neohesperidin  FLAVONOIDS CHIEF FLAVONOIDS ON THE MARKET OH Citroflavonoids OCH3 * Naringenin HO O * Eriodyctin * Diosmin OH O * Rutin OH OH Hesperetin OH O OH O OCH3 HO O O O flavanone structure HO Ketone OH Hesperidin d glycos d form OH O of hesperet n  FLAVONOIDS CHIEF FLAVONOIDS ON THE MARKET Dafton conta ns Citroflavonoids D ogg nnesper d ng ❖ Citroflavonoids are extracted from pericarps and pulps as Ca, and Mg derivatives ❖ Some pharmaceutical companies prepare pure products: Diosmin (semisyntheticly) used for Pentotho Hesperidin Naringin Mixtures (titrated for diosmin and hesperidin)  FLAVONOIDS CHIEF FLAVONOIDS ON THE MARKET Citroflavonoids OH OH OH OH OH OH O O OH OH O OCH3 O OCH3 O O HO O O HO HO O O HO OH 2 OH dehydrogenation 3 OH O OH O thaturat on Diosmin flaveone (diosmetin 7-rutinoside) Hesperidin an suff x nd cates that flavone the_ unsaturat on  FLAVONOIDS CHIEF FLAVONOIDS ON THE MARKET Citroflavonoids ❖ Citroflavonoids are used pure or in various combinations; - With ascorbic acid - Methylaesculetin - Rutin - Ruscosides Top cally for hemorrho ds - Vincamine - Papaverine  FLAVONOIDS CHIEF FLAVONOIDS ON THE MARKET Uses of Citroflavonoids nes EEE.EE ❖ In the treatment of the leg symptoms of chronic functional and organic venous insufficiency kvenotyetmezl l ❖ Daily administration of high doses (1 g/day) for a fairly long time (8 weeks) makes the symptoms disappear or regress ❖ Higher doses (2 g/day) are proposed to treat the functional symptoms of the acute attack of piles  FLAVONOIDS CHIEF FLAVONOIDS ON THE MARKET RUTIN (quercetin 3-O-rutinoside) ❖ Although abundant in plants, only a small number of drugs contain quantities sufficient for industrial extraction OH OH OH OH HO O OH O O O O OH HO OH O OH rutinose  FLAVONOIDS CHIEF FLAVONOIDS ON THE MARKET Uses of rutin ❖ Used alone or in combination (with aesculin, citroflavonoids, or ascorbic acid) ❖ Due to its low solubility, more soluble derivatives are prepared; - Morpholinylethylrutin - 3',4',7-tris-(hydroxyethyl)-rutin - Na rutosylpropylsulfonate  FLAVONOIDS RUTIN-CONTAINING DRUGS Japanese Pagoda Tree Sophora japonica (Fabaceae) Flower buds…..15-20% rutin  FLAVONOIDS RUTIN-CONTAINING DRUGS Buckwheat, Karabuğday Cel ac d sease Fagopyrum esculentum (Polygonaceae) Leaves…..2-8% rutin  FLAVONOIDS RUTIN-CONTAINING DRUGS Eucalyptus macrorrhyncha (Myrtaceae) we Leaves…..10% rutin  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Maidenhair Tree, Gingko Ginkgo biloba (Ginkgoaceae) Leaves contagguff of flavono d  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Maidenhair Tree, Gingko, Mabet ağacı Ginkgo biloba (Ginkgoaceae) ❑ Cultivated in Korea, France and USA Chemical composition the pharmacolog cal effect amount s because of h gh ❖ Flavonoids (20 flavonol glycosides) of flayedes OH OH - Quercetin 3-glycosides HO O - Kaempferol 3-glycosides O OH O - p-coumaric acid esters of HO O O O HO O kaempferol and quercetin glycosides O OH HO OH - Biflavonoids (amentoflavone)  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Maidenhair Tree, Ginko, Mabet ağacı Ginkgo biloba (Ginkgoaceae) ❑ Cultivated in Korea, France and USA Chemical composition ❖ Terpenic trilactones the for heathy - Ginkgolides - Bilobalides was ❖ Proanthocyanidins Ol de suff x means lactone structure s present  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Maidenhair Tree, Japon eriği Ginkgo biloba (Ginkgoaceae) Pharmacological Activity ✓ Ginkgolide B inhibits PAF ✓ Extract is a vasoregulating agent ✓ Arteriol vasodilator ✓ Improves tissue irrigation ✓ Activates cell metabolism, particularly in the cortex (by increasing glucose and O2 uptake)  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Maidenhair Tree, Japon eriği Ginkgo biloba (Ginkgoaceae) Uses ✓ Leaves are used to produce the extracts ✓ Standardized extract should contain; - 24% Flavonoids - 6% Ginkgolides ✓ Mainly used to enhance cognitive functions ✓ Used to treat the symptoms of senile cerebral insufficiency, Vertigo, tinnitus and hearing loss  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Maidenhair Tree, Japon eriği Ginkgo biloba (Ginkgoaceae) Uses I ✓ In the treatment of intermittent claudication due to chronic occlusive arterial disease of the lower limbs and of Raynaud's disease Extreme stress or cold causes G ngko helps blood nto arter es goand ✓ Venous and lymphatic vessel insufficiency cap llar es ✓ Functional symptoms of the acute attack of piles ✓ Against Alzheimer’s disease ? Itdoesn't treat but slows down  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Passion Flower, Çarkıfelek Native to USA Passiflora incarnata (Passifloraceae) and Mexico Aerial parts cult vated paft  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Passion Flower, Çarkıfelek Passiflora incarnata (Passifloraceae) Chemical composition ❖ Flavonoids (Flavon-C-glycosides) Must be > 1.5% - Shaftoside - Saponarin - Isovitexin - Isoorientin - 2''-glycosides of isovitexin and isoorientin ❖ Phenolic acids  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Passion Flower, Çarkıfelek Passiflora incarnata (Passifloraceae) R4 OH R3 R2O O R1 R2 R3 R4 R1 Vitexin H H Glc H OH O Isovitexin Glc H H H EE.EE Isoorientin Glc H H OH Schaftoside Glc H Ara H Saponarin Glc Glc H H  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Passion Flower, Çarkıfelek Passiflora incarnata (Passifloraceae) Chemical composition ❖ Indole alkaloids (< 0.03%) - Harman - Harmin - Harmol ❖ Coumarins ❖ Cyanogenic glycosides ❖ Phytosterols ❖ Maltol  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Passion Flower, Çarkıfelek Passiflora incarnata (Passifloraceae) Pharmacological activity and uses ✓ Sedative and anxiolytic - In minor sleep disturbances - To treat the symptoms of nervousness; * Alone (Passiflora syrup) theelsafghts detogether * Combination: Hawthorn, valerian and other sedatives - Passiflora shows its activity via modulation of the GABA system hed ota ✓ Antispasmodic Valer an  calls be the on FLAVONOIDS FLAVONOID-CONTAINING DRUGS Thyme, Kekik Thymus vulgaris , T. spec.(Lamiaceae) Aerial parts  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Thyme, Kekik Thymus vulgaris, T. spec. (Lamiaceae) Chemical composition OH ❖ Essential oil OH ❖ Flavonoids Glc-O O - Apigenin HO 6 - Luteolin OH O - 6-hydroxyluteolin glycosides ❖ Phenolic acids ❖ Triterpenes  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Thyme, Kekik Thymus vulgaris, T. spec. (Lamiaceae) Pharmacological activity and uses ❖ Thyme essential oil is antifungal and antibacterial ❖ The spasmolytic activity of thyme is most often V s t ❖ Traditionally used for; ng attributed to the phenols contract ons - Gastrointestinal disturbances Kek k - Cough - Disorders of the oral cavity  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Field Horsetail, Atkuyruğu Equisetum arvense (Equisetaceae) Aerial parts  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Field Horsetail, Atkuyruğu Equisetum arvense (Equisetaceae) Chemical composition ❖ Minerals (15-20%) - SiO2 (5-10%) Equ setum genal usually has po sonous plants ❖ Flavonoids - Quercetin 3-O-glucoside - Isovitexin - Flavone 5-glucosides  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Field Horsetail, Atkuyruğu Equisetum arvense (Equisetaceae) Pharmacological activity and uses ❖ Traditionally used as diuretic ❖ Recent experimental data support this activity ❖ Hemostatic ❖ Remineralizing agent helps Yhf tooth repa r ng ❖ Widely used in cosmetology; * Prevention of wrinkles, vibex and cellulites ❖ Its phytopharmaceuticals are used as an adjunct in weigh loss programs  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Equisetum palustre (Equisetaceae) Marsh horsetail TOXICITY ❖ Equisetum palustre is known for its toxicity particularly for livestock a tt kmay29thfusesan n ❖ It has been shown to contain some alkaloids ❖ May also show intoxications in humans? ❖ Sometimes E. arvense is adulterated with E. palustre ❖ The absence of this toxic species should be confirmed in the preparations of E. arvense  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Roman Camomile, Romen papatyası Chamaemelum nobile (Asteraceae) Flowers  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Roman Camomile, Romen papatyası Chamaemelum nobile (Asteraceae) Chemical composition s m lar flavono ds ❖ Sesquiterpene lactones (0.6%) also present n Matr car a rec t ta - Germacranolides (bitter taste) ❖ Essential oil Cor nne Asteraceae fam ly ❖ Phenolic acids usually has sesqu terpene lactones ❖ Flavonoids - Apigenin and luteolin glycosides  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Roman Camomile, Romen papatyası Chamaemelum nobile (Asteraceae) Pharmacological activity and uses ❖ Antiinflammatory: Essential oils and flavonoids ❖ Antispasmodic: Flavonoids ❖ Traditionally used for GIS disorders gastro ntest nal ❖ Topically; emollient, itch-relieving adjunct in the treatment of skin disorders ❖ Antalgic for oral cavity and oropharynx ❖ Cosmetology; ingredients of color-lightening shampoos  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Yarrow, Çivanperçemi Paportyag ller Achillea millefolium (Asteraceae) Flowers ATraceTs fam ly onvery large  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Yarrow, Çivanperçemi Achillea millefolium (Asteraceae) Flowers Chemical composition Mostly known for ts ❖ Essential oil fragrance has a lot of essent al o ls ❖ Sesquiterpene lactones ❖ Flavonoids - 6-methoxylated flavones  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Yarrow, Çivanperçemi Achillea millefolium (Asteraceae) Pharmacological activity and uses ❖ Antiinflammatory Ach llus I ❖ Antispasmodic ❖ Traditionally used; * For GIS disorders * To enhance renal and digestive elimination function ❖ Topically; emollient, itch-relieving adjunct in the treatment of skin disorders  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Immortelle flower, Ölmez çiçek, altın otu Helichrysum plicatum (Asteraceae) Flowers Very mportant spec es  FLAVONOIDS FLAVONOID-CONTAINING DRUGS Immortelle flower, Ölmez çiçek, altın otu Helichrysum plicatum (Asteraceae) Flowers Chemical composition called mmortal flower because when you pluck t they don't w lt ❖ Essential oil for 1 2 years ❖ Flavonoids Yellow color - Apigenin-7-glucoside - Kaempferol and quercetin glycosides ❖ Phenolic acids Caffe s ac d der vat ve - Chlorogenic acid Abundant n many plant spec es  we FLAVONOIDS FLAVONOID-CONTAINING DRUGS Immortelle flower, Ölmez çiçek, altın otu Helichrysum plicatum (Asteraceae) Flowers Bobrell toklan atmak a n Traditional use and pharmacological activity ❖ In Anatolian folk medicine, it is used for the treatment of wounds, burns, otitis, nephritis, to pass kidney stones as well as against stomach ulcer and diabetes É t cat on ❖ Its extracts have been shown to exert antimicrobial, hypoglycaemic, antioxidant activities ant theft's ❖ The extract was shown to possess preventive role in experimentally induced urolithiasis model in rats drol th as s s