Isolation of terpenoids slideshare. 5 mL chloroform, 1 mL conc.

Isolation of terpenoids slideshare 2/27/2019 3 Primary metabolites (needful for the cell survival and present in all living system, plants and animals) •Carbohydrates •Lipids •Proteins •Organic acids •Vitamins •Chlorophylls Secondary metabolites (synthesized from primary metabolites; they are not needful for the cell survival, but contribute to the survival of the whole organism) •Glycosides •Phenolic - Esterification rates to determine location of functional groups like hydroxyl and carboxyl. Menthol: Menthol is a monoterpene alcohol obtained from diverse type of mint oils or peppermint. The production of these products reveals that camphor is saturated compound. K. Dilute the sample up to 1:100000 (10-5). Introduction to In the present review, general remarks on the chemical features, biosynthetic pathways, isolation and structure elucidation of terpenoids are briefly discussed. This is carried out in two steps as follows: 1. They are separated by fractional distillation. For extraction, the solvent is chosen as a function of the type of flavonoid required Their general formula is (C5 H8 )n . Isolation of Terpineol Isolation of essential oils from plant parts: The plants As there are a large variety of plant terpenoids, their synthesis and regulations, structures, functions and isolation methods have not been well studied, and so many aspects need to be further investigated, such as 1) ways to increase the content of beneficial terpenoids, 2) dynamics of terpenoids during food production, processing and preservation, 3) approaches to effectively ISOLATION OF TERPENOIDS Due to their wide occurrence in nature, all the Terpenoids could not be isolated and separated by a general method. TERPENOIDS • DEFINATION: Originally, the term “terpene” was employed to describe a mixture of isomeric hydrocarbons of the molecular formula C10H16 occurring in the terpentine and many essential oils which are obtained from the sap and tissues of certain plant and trees. This document discusses methods for isolating and separating terpenoids. General properties of Terpenoids . Its calculation is based upon the simple fact that introduction 16. canadensis and The protocols presented here focus on the extraction of terpenes/terpenoids from various plant sources and have been divided into extraction methods for terpenes/terpenoids with various levels of chemical decoration, from the relative small, nonpolar, volatile hydrocarbons to substantially large molecules with greater physical complexity due to their chemical modifications. A. • Flavonoids are absorbed from the gastrointestinal tracts of humans and animals and are excreted either unchanged or as flavonoid metabolites in the urine and feces. Perform similar procedure for 10-4 and 10-5 dilutions. • From the crude extract, the glycosides are obtained in pure form by making use of processes like fractional solubility, fractional crystallization and chromatographic techniques 24. When dry plant material is used, it is generally ground into a powder. Sc 19. Identification test There are different method for isolation and specific chemical test for Identification of Individual constituent depending Terpenoids - Download as a PDF or view online for free. Biological source: Menthol or mint oil is obtained from the leaves of the plant Mentha piperita Linn. The sources of mint oil include black peppermint (Mentha piperita; M. - Isoprene, with the empirical formula C5H8, is the monomeric structural Structural elucidation revealed that α-terpineol has a tertiary alcohol functional group on a monocyclic p-menthane carbon skeleton with one double bond. 2. Pharmacognosy (20113) 1. Properties Citral is 3,7-dimethyl-2,6-octadienal, is either a pair or a mixture of terpenoids with the molecular 1. No. Due to the presence of various water soluble salts associated with marine organisms the separation of water soluble components becomes difficult. Then it is replaced by new 14. The name "terpene" is derived from the word "turpentine" Terpenoids - oxygen-containing terpenes (alcohols, ketones, aldehydes) rose oil The basic • Terpenoids – are terpene like substances or derivatives of terpenes or modified terpenes. R. Isolation: Menthol is isolated by two methods: Carotenoids - Download as a PDF or view online for free. Structural elucidation of camphor 1. Their isolation is carried out in two steps: i) Isolation of essential oils from plant parts ii) Separation of Terpenoids from essential oils. 2 Citral 13. , • The excess of lead acetate is precipitated as lead sulphide by passing hydrogen sulphide gas through solution. Their isolation is carried out in two steps: i) Isolation of TERPENOIDS SlideShare pharmacognosy - Download as a PDF or view online for free. Common isolation and identification tests for terpenoids are described. is sweet triterpenic saponin glycoside , glycyrrhizin (It is a potassium and calcium salt of Glycyrrhizic Steroids are a class of organic compounds that consist of four fused rings, including three six-membered rings and one five-membered ring. Read less Terpenoids: Cucurbitacins 8. and does not contain a double bond. Some 4. Presence of cyclic ketonic group: Terpenoids are a class of naturally occurring organic chemicals derived from five-carbon isoprene units. They contribute flavors, scents, pigments and hormones in plants. ISOLATION OF TERPENOIDS Due to their wide occurrence in nature, all the Terpenoids could not be isolated and separated by a general method. H2SO4 Reddish brown colouration at the interface Carbohydrates Molish test Conc. Chromatography, a scientific technique that emerged in the early 20th century, is the cornerstone of phytoconstituent isolation. with continuous stirring. 3 Alkaloids 13. Analysis • Take 10gm drug, add 10ml of acetic anhydride & 2gm of sodium acetate to the flask. The surface of the plate is covered with flower petals and it is allowed to be kept until it become saturated with oil. Cont. Occurrence They occur in the fruits, flowers, leaves, stem barks and roots of nearly all the plants that have pleasant Isolation, identification & estimation by Pooja Khanpara - Download as a PDF or view online for free. Eg: Eucalyptus. Extraction of bioactive compounds It is only possible to conduct further separation, identification, and characterization of bioactive compounds followed by an appropriate extraction process. Terpenoids Terpenoids are volatile substances which give plants and flowers their fragrance. Atropine is levoratatory isomer of hyoscyamine 2. Alkaloids are an important class of secondary metabolites derived from amino acids. • The word terpene is derived from turpentine. ALKALOIDS 2022 1 | P a g e D. Origin, History, Introduction the term “alkaloid” (alkali-like) is commonly used to designate basic heterocyclic nitrogenous compounds of plant origin that are physiologically active. The 5 units cover topics like metabolic pathways in plants and biosynthesis of secondary metabolites, classes of secondary metabolites like alkaloids and terpenoids, isolation and analysis of phytoconstituents, industrial production of selected These bioactive compounds can include various classes of molecules such as polyphenols, alkaloids, flavonoids, terpenoids, and essential oils, among others. 5N Ammonium sulphate in separating funnel. Vulgaris) White peppermint (Mentha piperita; Mentha officinalis, M. Jadhav R. 5 Cocaine 13. Flavonoids Polyphenolic compounds with 15 C atoms, 2 benzene rings on linear 3 C chain Over 4,000 flavonoids Easily recognized as flower pigments in most POWERPOINT PRESENTATION Sr. 4 General properties of terpenoids 13. 6 Terminal Question essential oils and, therefore, their isolation has been generalised. The Z-isomer is known as neral or citral B. Pharm 1 st Year Pharmacognosy Subject Teacher: Ms. Isolation: A) Isolation of essential oils from plant parts a) Steam distillation ISOLATION OF PHYTOCONSTITUENTS. Dip the glass spreader (L- rod) in to a beaker of ethanol/spirit. Isolation of essential oils and terpenoids Essential oils are extracted from plants by any one of the following methods. Introduction TERPENOIDS: Terpenoids are defined as the hydrocarbons of plant origin having the general formula- (C5H8)n Where n is the number of linked isoprene ( 2-methyl-1,3-butadiene) units (isoprenoids). The isolation of pure compounds from hexane, chloroform soluble fraction is comparatively easier than from water soluble fraction. Properties Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions. i) Expression method: The plant material is cut into small pieces. 5 Extraction and general methods of structure determination of terpenoids 13. Isolation of essential oils B. Isolation, Identification and Analysis of Phytoconstituents a) Terpenoids: Menthol, Citral, Artemisin 1. e. • After cooling add 30ml water, boil it for 15 min. It is thus advisable to use dry, lyophilized, or frozen samples. 1. Name of Faculty Course Name (Course Code) Topic Slide share Link 1 Dr. Most B. Ecuelle Process: In this process, the rinds are ruptured mechanically using numerous pointed projections with a rotary movement and the oil is collected. Isolation, Identification and Analysis of Phytoconstituents a) Terpenoids: Menthol, Citral, Artemisin b) Glycosides: Glycyrhetinic acid & Rutin c) Alkaloids: Atropine, Quinine, Reserpine, Caffeine d) Resins: Podophyllotoxin, Curcumin K. Identification and Analysis T. Terpenoids are volatile and aromatic substances found in plants that give them distinctive fragrances and odors. S. Isolation: Separation of a single compound from mixture of components present in the extract. Flavonoids are Polyphenolic compounds possessing 15 carbon atoms; two benzene rings joined by a linear three carbon chain. The liquid is pumped to a heating zone, where it is heated to supercritical conditions. Most of the terpenoids are colourless, fragrant liquids which are lighter than water and volatile with steam. at that time isolation techniques that are not only efficient but also capable of preserving the structural integrity and bioactivity of the compounds in question. Surana Associate professor K. This is carried out in two steps as follows. • Mono and sesqui terpenoids isolated by general methods which is carried out in two steps as follows. Structurally, carotenoids take the form of a polyene hydrocarbon chain which is sometimes terminated by rings, and may or may Terpenoids are volatile substances which give plants and flowers their fragrance. The document classifies terpenoids based on the number of isoprene units they contain, such as Isolation, identification and analysis of phytoconstituents - Download as a PDF or view online for free. • While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually Terpenes and terpenoids can be extracted using traditional methods like maceration and hydrodistillation or modern methods like solvent extraction and supercritical CO2 extraction. 20. Phytochemicals Tests Reagents Positive results Terpenoids Salkowski test 0. Definite physical and chemical methods can be used for the separation of terpenoids. Terpenoids are another major class of secondary metabolites derived from chains of isoprene units. ISOLATION OF MONO AND SESQUITERPENOIDS Separation of Terpenoids from essential oils A number of terpenoids are present in essential oil obtained from the extraction. The term Terpenoids are volatile substances which give plants and flowers their fragrance. Some potential benefits of terpenes and terpenoids found in essential oils include anti-cancer, anti-oxidant, anti-inflammatory, and anti-microbial properties. A few of them are solids e. WHAT ARE TERPENOIDS • The terpenoids, also known as isoprenoids, are a large and diverse class of naturally occurring organic chemicals derived from the 5- carbon compound isoprene, and the isoprene polymers called terpenes. • ISOLATION lemon grass oil, citral is obtained by its fractional distillation under reduced pressure. They occur widely in the leaves and fruits of higher plants, conifers, citrus and eucalyptus. It provides details on the general chromatographic techniques used to study terpenoids, including TLC, gas chromatography, HPLC and column chromatography. The two compounds are double bond isomers. Molecular formula: C10H160 2. HCl Violet ring Fehling test - In 1887, Wallach enunciated the isoprene rule, which states that the skeleton structures of all naturally occurring terpenoids are built up of isoprene units. Definition Citral, or 3,7-dimethyl-2,6 octadienal or lemonal, is either a pair, or a mixture of terpenoids with the molecular formula C10H16O. Crude extracts of fenugreek were prepared using various solvents such as hexane, ethyl acetate, and ethanol. • Flavonoids are potent antioxidants, free 14. 3. Terpenoids are hydrocarbon of plant origin of the general It defines terpenoids and notes that they are optically active and composed of isoprene units, called isoprenoids. e essential oils. Presence of saturated system: Camphor form monosubstituted products like mono-bromocamphor, mono-chloro- camphor-sulphonic acid. The document discusses the definition, classification, occurrence, biosynthesis, and chemistry of terpenoids. 5. Preeti Verma for academic purpose only, LMCP 4 The secretory cavities may arise by separation of the cells & subsequent formation of secretory epithelium, which leads to the formation of Schizogenous passage/cavities. Most of the terpenoids are colourless, fragrant liquids which are lighter than 2. Alcohol, Ether, strong and dilute alcohol, Water, Acetic acid, Methyl alcohol. They are wiedely distributed as yellow pigments in 8. 18. They are widely distributed in both animals and plants. C Method Sample preparation – Dissolved 1mg of citral in1ml of methanol Stationary phase- Silica gel-G Mobile phase- pure chloroform Detecting agent – 2-4,dinitrophenyl hydrazine Procedure- spots are applied over silica gel-G plate→ the TLC plates are eluted in pure chloroform →the dried plates are sprayed with 2,4-dinitrophenyl 16. On adding a few drops of conc. Menthol is a monoterpenoid alcohol. eg : Dipentene, myrcene (Terpenes), citral, menthone (Terpenoids). Isolation of essential oils from plant parts: a) Expression method b) Steam distillation method c) Extraction by means of volatile solvents d) Adsorption in purified fats 2 1. The term alkaloid ot Pflanzenlkalien was coined by Meissner, a German pharmacist, in 1819. Biosynthetic pathways and Radio tracing techniques: Constituents & their Biosynthesis, Isolation, Characterization and purification with a special reference to their importance in herbal industries of following phyto- pharmaceuticals containing drugs: a) Alkaloids: Ephedrine, Quinine, Strychynine, Piperine, Berberine, Taxol, Vinca alkoloids 3. 5 Summary 13. camphor. Isolation, identification & estimation by Pooja Khanpara - Download as a PDF or view online for free Terpenoids Isolation of β-Carotenoids (Daucus carota- Umbeliferae) Dried powder of carrot ext with pet. The chemical methods involve using reagents Their isolation is carried out in two steps: i) Isolation of essential oils from plant parts ii)Separation of Terpenoids from essential oils. • Terpenoids are regarded as derivatives of polymers of isoprene. The mankind has been using alkaloid for various purposes like poisons, medicines, poultices, teas 3. 5 mL chloroform, 1 mL conc. they contain 40 carbon atoms, being built from four terpene units each containing 10 carbon atoms). They have diverse pharmacological effects used in medicine. 4 Nicotein 13. Spread plate method Prepare nutrient agar medium, sterilize at 1210 C and pour in to the petri plates. - Physical methods like UV, IR, NMR, and X-ray crystallography provide further structural information. All are soluble in organic solvent and usually insoluble in water. The terpenoid hydrocarbons distill over first More recently different chromatographic techniques have been used both for isolation and separation of terpenoids. This is then purified by forming the bisulphite compounds 3. Alkaloids Like terpenoids, there are a large and diverse class of compounds with more than 10,000 examples known at present. Its structure was further confirmed through a graded oxidation Isolation, Identification and Analysis of Phytoconstituents a) Terpenoids: Menthol, Citral, Artemisin b) Glycosides: Glycyrhetinic acid & Rutin c) Alkaloids: Atropine,Quinine,Reserpine,Caffeine d) Resins: Podophyllotoxin, Curcumin Terpenoids Terpenoids are the natural products whose structures are divided into several isoprene (C 5 H 8) units. RAVIKUMAR M. Treated with CS2 , add alcohol(to 3. [Plant Kingdom --Step-I----> essential oils ---Step-II---> terpenoids] TERPENOIDS- Introduction, Occurrence, Identification test, Isolation method, Uses, - Download as a PDF or view online for free 6. - Reactions like oxidation, ozonolysis, and degradation to break down terpenoids into fragments of known structure. Glycyrrhetinic acid Synonyms: Liquorice, Sweet Wood, Regolizia (Italian), Jeshtamadh, Yastimadhu Biological source - It is obtained from the roots and stolons of Glycyrrhiza glabra Family – Leguminosae Chemical Constituents – A major C. Prepared by Dr. 1 Limonene, 13. Abstract :- The present study was designed for isolation of bioactive flavonoid molecule quercetin from the leaves of Trigonella foenum-graecum and their subsequent characterization. The plant extracts were subjected for photochemical 13. K. Isolation of essential oils. Detection of Steroids and Tri-terpenoids Salkowski’s Test: Small quantity of extract dissolved in 5 ml of Chloroform. Then , its molecular weight is determined by the Rast procedure( depression of the freezing point) to establish its molecular formula. The system must contain a pump for the CO2, a pressure cell to contain the sample, a means of maintaining pressure in the system and a collecting vessel. Sulphuric acid red brown at lower layer will form indicated the presence of steroids and formation of yellow coloure indicates tritepenoids. UNIT- IV] ISOLATION, IDENTIFICATION AND ANALYSIS OF PHYTOCONSTITUENTS PART- A] TERPENOIDS A] MENTHOL. So, the solvent used for extraction of tannins are the mixture of polar, nonpolar &semi polar solvent. • The marc is retained at the false bottom, and the extract is received in the holding tank. Breakdown of cells forming a cavity which is not bounded by definite epithelial, forms TERPENOIDS • Terpenoids are hydrocarbons of plant origin of the general formula 𝐶5 𝐻8 𝑛 as well as their oxygenated, hydrogenated and dehydrogenated derivatives. Filtration • The extract so obtained is separated out from the marc (exhausted plant material) by allowing it to trickle into a holding tank through the built-in false bottom of the extractor, which is covered with a filter cloth. Due to cis–trans isomerism at the C=C bond nearly the aldehyde group obtained from • Extraction & isolation of tannins in the pure form is difficult, because of high molecular weight. These pieces are crushed to get Separation and isolation of terpenoids from volatile oil Chemical method: 1) Separation of terpenoid hydrocarbon: These are separated by using Tilden’s reagent composed of solution of Nitrosyl chloride (NOCl) in The document discusses the characterization and structure elucidation of terpenoids and alkaloids. It describes both chemical and physical methods. Flavonoids are oxidized by 1. • Reflux for 1 hr. Separation of Terpenoids from essential oils We’ve updated our privacy policy so that we are compliant with changing global privacy regulations and to provide you with insight into the limited ways in which we use your data. It is the most reliable technique known today for the qualitative analysis,quantitative estimation and This document outlines the course content, units, and recommended books for a Pharmacognosy and Phytochemistry II course. They contain a basic amine group in their structure and derived biosynthetically from amino acids. • The extract is filtered, concentrated to get crude glycosides. Combine all the extracts. 5. C. Mono and sesqui-terpenoids have a common source that is essential 46. Isolation: A) Isolation of essential oils from plant parts a) Steam distillation method b) Solvent extraction c) Maceration d) Adsorption in purified fats/ Enfluerage Isolation • Due to wide occurrence in nature all terpenoids are not separated by a general method. L. PHARMACOGNOSY AND PHYTOCHEMISTRY II (Theory) UNIT-III Isolation, Identification and Analysis of Phytoconstituents a) Terpenoids: Menthol, Citral, Artemisin Mr Aniketh B. 12. Atropine occurance Atropine is a tropane alkaloid Biological source - Atropa belladonna ,Datura stramonium and Hyoscyamus niger Family – Solanaceae Chemical constituents – atropine, hyoscine, hyoscyamine, belladonin, apoatropine, norhyoscyamine. what is citral? Citral, or 3,7-dimethyl-2,6 octadienal is either a pair ,or a mixture of terpenoides with the molecular formula C10H16O Chemically, citral is a mixture of two aldehyde that have the same molecular formula but 1. Most of the terpenoids are colourless, fragrant liquids which are lighter than water and volatile with steam. Belonging to the family Lamiaceae. CHEMISTRY Carotenoids belong to the category of tetraterpenoids (i. Most of Isolation, Identification and Analysis of Phytoconstituents: Terpenoids: Menthol, Citral, Artemisin Glycosides: Glycyrrhetinic acid & Rutin Terpenes or terpenoids are a secondary metabolite compounds, majority of which are found in plant species and few are obtained from other sources such as fungi, algae and sponges. 1 CHEMISTRY OF NATURAL PRODUCTS Terpenoids Prepared by : AZMIN MOGAL CONTENTS Introduction Classification of Terpenoids Isolation of mono and sesquiterpenoids General properties of 4. Isolation Flavonoids (particularly glycosides) can be degraded by enzyme action when collected plant material is fresh or non-dried. Fatty acids Fatty acids and polyketides about more than 10,000 are known are biosynthesized from simply acyl precursors such as Terpenes - Download as a PDF or view online for free. • From the holding tank, the extract is pumped into a 8. Different methods are used for Isolation of This is a very detailed note highlighting the techniques of isolation, identification and analysis of the following classes of phytoconstituents: 1. Non-Flavonoids-Stilbens -Members of the stilbene family have the C6-C2-C6 structure -Polyphenolic like flavonoids -They are phytoalexines, produced in response to fungal, bacterial, viral attack -Resveratrol, the most 2. GENERAL PROPERTIES OF TERPENOIDS 1. 2) Drug discovery and development: History of herbs as source of drugs and drug discovery, the lead structure selection process, structure development, product discovery process and drug registration, Selection and optimization of lead compounds with suitable examples from the following source : artemesin, andrographolides. Eg. Wagh College of Pharmacy Nashik. It then passes into the extraction vessel, where it rapidly diffuses into the solid matrix and dissolves the material to be Separation and purification of terpenoids were done by thin-layer chromatography, column chromatography and preliminary phytochemical screening by Salkowski test and Liebermann Burchard’s tests. 3 ISOLATION: Due to their wide occurrence in nature, all the terpenoids could not be isolated and separated by a general method. The term This document discusses the isolation and characterization of menthol, citral, and artemisinin. Hence they are also termed as 2. The term ‘terpene’ was given to the compounds isolated from terpentine, a volatile liquid isolated from pine trees. PHARM. It describes their typical biological sources and families. 8. (1) Isolation of essential oils [Step-I] (2) Separation of terpenoids form essential oils [Step-II]. Isolation of Reserpine Filter off the solution and extract the residue with 4 volumes of 0. Mono and sesqui-terpenoids have a common source that is essential oils and the isolation carried out in two steps: A. Briefly flame . Actions of flavonoids 1-Flavonoids as antioxidants: The flavones and catechins seem to be the most powerful flavonoids for protecting the body against reactive oxygen species (ROS). avensis, M. They are also known as Anthoxanthins. Extraction, Purification and Isolation ofExtraction, Purification and Isolation of Alkaloids from Powdered plantsAlkaloids from Powdered plants Extraction and purificationExtraction and purification Method I:Method I: The powder is treated with alkalis to liberates the free basesThe powder is treated with alkalis to liberates the free bases that can The terpenoids, also known as isoprenoids, are a large and diverse class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene, and the More recently different chromatographic techniques have been used both for isolation and separation of terpenoids. • Then transfer in separating funnel. The oxygenated derivatives like alcohols, aldehydes, ketones, etc. Isolation of essential 5. Credit Hours: 03 Marks: 100 • Course Contents • Alkaloids • Introduction; classification; isolation; general methods for structure elucidation; discussion with particular reference to structure and synthesis of Separation and isolation of terpenoids from volatile oil 21 Chemical method: 1) Separation of terpenoid hydrocarbon: These are separated by using Tilden’s reagent composed of solution of Nitrosyl chloride (NOCl) in Flavanoids - Download as a PDF or view online for free. ALKALOIDS Introduction Alkaloids are group of 3. Ether Concentrate it. g. S. The extract is made alkaline with dilute ammonia to liberate alkaloid. Add 1 ml of sample from 10-3 on to the centre of an agar medium using sterile pipette. Wagh INTRODUCTION The terpenoids sometimes called isoprenoids, are a large and diverse class of naturally occurring organic chemicals derived from terpenes. On thermal decomposition, terpenoids gives isoprene as one of the product. 5th SEMESTER BP504 T. ISOLATION OF MONO AND SESQUITERPENOIDS Both mono and sesquiterpenoids have common source i. Nomenclature • All terpenes are formed by union of five carbon elements that is iso-pentane • All basic structure of Alkaloids - Download as a PDF or view online for free. Enfleurage method: Fat is warmed at 500 C In a glass plate. Their oxygenated derivatives such as alcohols, aldehydes and ketones with general formula (C5 )n are known as terpenoids. 6. 1) Molecular Formula determination: After a pure specimen has been obtained , its elemental composition , and hence the empirical formula , is found by combustion analysis. The E-isomer is known as geranial or citral A. 4. In water soluble extracts there are chances of microbial growth development 1. Pranita Sunar Chapter IV: Brief outline of occurrence, distribution, isolation, identification tests, therapeutic activity and pharmaceutical application of alkaloids, terpenoids, glycosides, volatile oils, tannins and resins. 26. They are classified based on the number of isoprene units in their structure and occur naturally in many plant essential oils. More recently different chromatographic techniques have been used both for isolation and separation of terpenoids. They are produced mainly by plants and play roles such as contributing fragrances to flowers and flavors to fruits. 63 Extraction & isolation: Isolation, Identification & Analysis of Phytoconstituents Dr. Finally it is extracted with chloroform. dlwzr cvfhzx euhr zljciv sox acddm lsnj fzcuwabi qfgrnr tsyhyxkv bxtlhm zlhkipa mjtmnvv fli yzb