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PHARMACOGNOSY II PHAR306 6th Semester 5th Lecture Prof. Dr. Müberra Koşar Ass. Prof. Dr. Aybike Yektaoğlu Eastern Mediterranean University Faculty of Pharmacy Department of Pharmacognosy PHARMACEUTICAL FIXED OILS AND ANIMAL FATS FIXED OILS & ANIMAL FATS Amygdalae oleum • “Almond oil” • obtained by crushing of the seeds of two varieties Prunus dulcis var. dulcis or P. dulcis var. amara (Rosaceae) in the cold • Almond oil is obtained in the Mediterranean countries (Italy, France, Spain and North Africa) where its culture is obtained • The only difference between the two varieties is the cyanogenic glycoside content of the var. amara FIXED OILS&ANIMAL FATS Amygdalae oleum • seeds carries 40-55% fixed oil • the refined oil mainly contains oleic acid (62-86%), linoleic (20- 30%), palmitic (4-9%) • Amydalae oleum raffinatum (Almond oil, refined) (Eur.Pu.) • Amydalae oleum virginale (Almond oil, virgin) (Eur.Ph.) • major used in cosmetology and dermatology • used as a carrier in oily injectable preparations FIXED OILS&ANIMAL FATS Arachidis oleum • “Arachis oil, Peanut oil” – “Peanut butter” • Arachis hypogaea (Fabaceae) • cultivated in South America, China, India, Australia, and West Africa • due to various genotypes they vary in fatty acid content • the seeds are cold-pressed • they have similar properties as olive oil • most suitable oil for added for embedding purposes into other oils (e.g. olive oil) FIXED OILS&ANIMAL FATS Arachidis oleum - content • seeds carries 40-50% fixed oil • 50-65% oleic acid • 18-30% linoleic acid • 8-10% palmitic acid • stearic acid, arachidic acid • Arachidis oleum raffinatum (Arachis oil, refined) (Eur.Ph.) • Arachidis oleum hydrogenatum (Arachis oil, hydrogenated) (Eur.Ph.) FIXED OILS&ANIMAL FATS Arachidis oleum - application • is one of the most consumed oil in the world • controlled release in IM (intramascular) injectable preparation as solvent • in topical preparations vehicle • solvents for hormones and vitamins • in nutrition products for preparations of emulsions • liniment, ointment bases, at enema • in ear drops • in the food industry (margarine, cooking oil) FIXED OILS&ANIMAL FATS Coconut oil • “Coconut oil„ • Cocos nucifera (Palmae) • A drupe having fibrous fruit mesocarp and a hard endocarp • solid part of the endosperm of seeds is dried and squeezed where "coconut oil" is obtained • Coconut oil refined (Eur.Ph.) • A semi-solid fat, melts at 24 ᵒ C FIXED OILS&ANIMAL FATS Coconut oil • large amount of the composition is formed predominantly of unsaturated fatty acids (90%); lauric and myristic acid • lesser amounts of caproic, caprylic, oleic, palmitic and stearic acids • in particular, it contains high rates of medium chain fatty acid that is readily absorbed from the GIS (gastro intestinal system). Therefore the oil is used in the diet of patients with absorption problems FIXED OILS&ANIMAL FATS Coconut oil Fractionated coconut oil: • endosperm oil of fractionated and purified C. Nucifera • carries short and medium chain fatty acids (octanoic, decanoic acid, etc..) • its low viscosity continous until coming close to the melting point (0 °C). Therefore, it is used to create a nonacuse environment in certain oral drugs • Medium-chain triglycerides (Eur.Ph.) FIXED OILS&ANIMAL FATS Palm kernel oil • Elaeis guineensis (Palmae) is obtained from the dried endosperm of seeds • used in the preparation of Medium-chain triglycerides (Eur.Ph.) • caprylic (50-80%), capric (20-50%), caprylic, lauric, myristic acid mp. 31-36 °C • used in the preparation of suppository as a base FIXED OILS&ANIMAL FATS Palm oil • Elaeis guineensis (Palma) is prepared by squeezing of the mesocarp of the fruit • major compounds palmitic and oleic acid • mp. 30 °C • margarine preparation and soap industry FIXED OILS&ANIMAL FATS Gossypii oleum • “Cottonseed oil„ • is obtained from several Gossypium (Malvaceae) by squeezing from the seeds • after removal of seed testae the inner part is kept hot • used refined • semi-dry oil (depending on the absorbtion of oxygen from air) • the hydrogenated oil is offisinal FIXED OILS&ANIMAL FATS Gossypii oleum- content • seeds carries 15% fixed oil • 45% linoleic acid • 30% oleic acid • 20% palmitic acid • 3% myristic acid • 1% stearic acid, 1% arachidic acid • gossypol has a polyphenolic structure that are toxic FIXED OILS&ANIMAL FATS Gossypii oleum- application • used as a solvent in IM injection • in nutrition products in the preparation of IV (intravenous) emulsions • Gossypol, during administration of the IV emulsions mild bradycardia, may cause drop in blood pressure • as a cooking oil in the food industry and in margarine preparation FIXED OILS&ANIMAL FATS Lini oleum • “Linseed oil„ • is obtained from Linum usitatissimum (Linaceae) by squeezing the seeds in hot medium • seeds carries 30-40% fixed oil 36-50% α-linolenic acid 23-24% linoleic acid 10-18% oleic acid 5-11% unsaturated fatty acid (myristic, stearic, palmitic acid) • in contact with air, the oxygen absorbent is dried and forms a thin film on the surface • paint industry FIXED OILS&ANIMAL FATS Lini oleum • Linseed oil, virgin (Eur.Ph.) • is used in the preparation of liniment • hydrolysed linseed oil; is effective against strains of antibiotic-resistant Staphyllococcus aureus. Due to this effect it is used in the topical preparations for its antibacterial effect FIXED OILS&ANIMAL FATS Olivae oleum • “Olive oil„ • Olea europae (Oleaceae) • it is cultivated in the Mediterranean countries and in the south-western United States and also in other subtropical countries • is obtained by extraction from the mature fruit • the residue is named "pomace" • Olivae oleum raffinatum (Eur.Ph.) • Olivae oleum virginale (Eur. Ph.) FIXED OILS&ANIMAL FATS Olivae oleum- content • the composition of the oil obtained from different sources is different • Fruit carries 15% fixed oil; 65-75% oleic acid 9-15% linoleic acid 10-15% palmitic and stearic acid • cholagogue and has a laxative effect • externally emollient • in parenteral preparations solvent, carrier • liniments, ointments, plasters and soap making • as topical emollients in eczema and psoriasis • used as edible oils in the food industry FIXED OILS&ANIMAL FATS Brassicae oleum • “Rapeseed oil„ • its fixed oil is obtained from the seeds of Brassica napus and B. campestris (Brassicaceae) by extraction or mechanic expression (40%) • in the composition; oleic (61%), linoleic (21%), α-linolenic (11%), erucic (0.2-2%) acid, saturated fatty acid (7%) • is normally obtained from seeds. It contains 20-40% erucic acid FIXED OILS&ANIMAL FATS Brassicae oleum • animal experiments have shown that erucic acid has myocardial toxicity • erucic acid content more than 2% in cooking oil is undesirable • Thus, oil from genetically modified varieties are prepared • used in the preparation of biodiesel FIXED OILS&ANIMAL FATS Sesami oleum • “Sesame oil, gingelly oil, teel oil” • its fixed oil is obtained from the seeds of Sesamum indicum (Pedaliaceae) by extraction or squeezing • is cultivated in India, China, Japan, and also in many tropical countries • Sesami oleum raffinatum (Eur.Ph.) FIXED OILS&ANIMAL FATS Sesami oleum- content • it contains 50% of oil in its seeds • Refined sesame oil: 43% oleic acid, 43% linoleic acid 9% palmitic acid, 4% stearic acid 0.8% arachidic acid • In very small amounts; in 1% lignan structure the hydrolysis product phenolic compound SESAMOL of sesamin and sesamolin FIXED OILS&ANIMAL FATS Sesami oleum • Sesamol is determined by Baudouin test • 1% sucrose in conc. HCl is added to sesame oil and shaken where a formation of pink color sesami oil presence proves (sesamol hydroxymethyl furfural) • This reaction allows the determination of sesame oil among all oils sesamol FIXED OILS&ANIMAL FATS Sesami oleum- application • in oral or rectal capsules • in ophthalmic preparations • in suspension and emulsion formulations • as liniments, ointment bases and porous-pflaster bases • expecially in controlled release IM preparations as a solvent (steroids: estradiol valerate, hydroxyprogesterone caproate, testosterone enanthate, nandrolone decanoate and other fat-soluble pharmaceutical crude materials- like fluphenazine decanoate and enanthate esters) • in subcutaneous injectable preparations as a solvent FIXED OILS&ANIMAL FATS Sojae oleum • “Soya oil” • its fixed oil is obtained from the seeds of Glycine soja ve G. max (Fabaceae) • homeland East Asia • cultivated in U.S.A., South America, in India • its seeds carries 20% fixed oil • mainly linoleic (50%), oleic (30%), linolenic (7%) and saturated fatty acids (14%) FIXED OILS&ANIMAL FATS Sojae oleum-application • refined soybean oil; • as a source of fat in parenteral nutritional products, in the preparation of emulsions • as a carrier in oral and IV preparations • in the preparation vitamins, steroids that are poorly water soluble, diazepam, emulsions of fluorocarbons • in the formulations of liposomes FIXED OILS&ANIMAL FATS Sojae oleum-application • is an important source of proteins. Sediment carries 45-65% protein • after oil is obtained from seeds, lecithin is obtained from the residue • regulates lecithin lipid and cholesterol metabolism • stigmasterol in seeds are used in the semi-synthesis of steroidal hormones • cultivated in Marmara and the East Black Sea in Turkey FIXED OILS&ANIMAL FATS Helianthi oleum • “Sunflower oil” • its fixed oil is obtained from the seeds of Helianthus annuus (Compositae) • major: linoleic (48-74%), oleic acid (10-14%) • carrier in injectable preparations • nutritional support • in cosmetics FIXED OILS&ANIMAL
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    cancers Review Androgen Receptor-Dependent Mechanisms Mediating Drug Resistance in Prostate Cancer Marzieh Ehsani, Faith Oluwakemi David and Aria Baniahmad * Institute of Human Genetics, Jena University Hospital, Am Klinikum 1, 07740 Jena, Germany; [email protected] (M.E.); [email protected] (F.O.D.) * Correspondence: [email protected]; Tel.: +49-3641-9396820 Simple Summary: Prostate cancer can develop under hormone treatment and chemotherapy from a castration-sensitive towards a castration-resistant into a drug resistant-tumor. The main hormonal drug target is the androgen receptor (AR). Androgen deprivation therapy reduces body-own andro- gen production and AR antagonists inhibit androgen-mediated activation of AR. Here, molecular mechanisms are described that review knowledge about tumor cells escape therapy by developing bypass mechanisms of AR-signaling. This includes genomic and non-genomic signaling. Deciphering the involved molecules that mediate castration and drug resistance will provide the basis of potential novel drug targets that may be used in addition to AR inhibition as combinatory treatment. Abstract: Androgen receptor (AR) is a main driver of prostate cancer (PCa) growth and progression as well as the key drug target. Appropriate PCa treatments differ depending on the stage of cancer at diagnosis. Although androgen deprivation therapy (ADT) of PCa is initially effective, eventually tumors develop resistance to the drug within 2–3 years of treatment onset leading to castration resistant PCa (CRPC). Castration resistance is usually mediated by reactivation of AR signaling. Citation: Ehsani, M.; David, F.O.; Eventually, PCa develops additional resistance towards treatment with AR antagonists that occur Baniahmad, A.