Page 1 of 12 Pharmacognosy Department-College of Pharmacy TANTA UNIVERSITY FACULTY OF PHARMACY DEPARTMENT OF PHARMACOGNOSY "FINAL EXAM FOR SECOND VEAR STUDENTS" try of Crude Drugs | COURSE CoD! TOTAL ASSESMENT TIME ALLOWEI 2 HOURS, | Che The exam consists of 2 questions in 12 pages + separate answer sheet for electron’ ' * Question 1 . 37.5 marks, 30 minutes) Question 2 -----...85 MCQs (2.5 * 85 = 212.5 marks, 90 minutes). * ~All questions must be answered in the specified places. - In MCQs, mark the correct answer in the separate answer sheet prov ided. - Use blue pen only. Answers using pencils will not be accepted.Page 2 of 12 Pharmacognosy Department-College of Pharmacy Question I (37.5 marks. 30 min) ‘A-Draw the chemical structure and name the following (24 marks, 15 min) a-A morphinan alkaloid b-A water soluble ergoline c-An indoline alkaloid with with cyclohexadiene ring alkaloid carbamate functionality d-A terpenoid indole alkaloid e-A sesquiterpene with fA tetrahydroxy used as aphrodisiac quinolizidine nucleus indolizidine alkaloidPage 3 of 12 Pharmacognosy Department-College of Pharmacy B: Identify the names of the following structures; give also the chemical and biosynthetic classes also precursors & intermediates whenever applicable. Answers should be listed in Table 1 (13.5 marks,15 min) « Nae, i Cosi MeO 6, N H (@) (b) © oO N. N o HOO (@) R=OH (0) © Table () No. [Name Chemical class Biosynthetic class/ precursors & intermediate | a 6 | 3 | a e - = LPage 4 of 12 Pharmacognosy Department-College of Pharmacy Question 2 (212.5 marks, 90 minutes). You are provided with 85 MCQs. Select only one answer and mark your choice in answer sheet for electronic correction machine. A- From Q. No. 1-35......Alkaloids (87.5 marks, 35 minutes) B- From Q. No. 36-85.... Volatile oils (125 marks, 55 minutes) Az Alkaloi 1- Double Mannich reaction of benzoyl acetic acid and A'-piperidine produces: A-Lobeline B-Lobelanidine _C- Lobelanine D-Norlobelanine E- Norlobeline 2. Full reduction of lobelanine produces: A-Lobeline B+ Lobelanidine C-Norlobelanidine D- Norlobelanine E- Norlobeline 3 Crystallization from ether is used to separate pseudopelletierine from: A; Pelletierine B- Methyl pelletierine C-Isopelletierine D- Inflatine E- Norlobeline 4- Salts of coniine can be cleaved by: A-KOH B- NaHCO; C- NaxCOs D- NH,OH E=CaCOs 5- A solid non-volatile tobacco alkaloid is A-Nocotine —_B- Nornicotine C- Anabasine D- telline —_E- Nicoteine 6- Vanilline HCl produces red color with: A-Nocotine —_B- Nornicotine C- Anabasine D-Nicotelline E+ Nicoteine 7- N-demethylation of trigonelline in acidic medium produces: A-Benzene —_B- Nicotinic acid. C- Benzaldehyde —_D- Pyridine E- Benzoie acid 8- Dragendorff’s reagent is used to isolate the alkaloids of: A- Pomegranate B- Lobelia C- Tobacco D-Conium E- Areca 9- Tropine f-tropate can be obtained by the optical resolution of: A-Hyocine —B- Cocaine C- Atropine D- Hyoscyamine E- Ecgonine 10- Curare like activity of tropan alkaloids is obtained by: A: Hydrolysis of ester B- Presence of OH C- N-demethylation D- Quaternization with methyl group E- Quaternization with higher alkyl group 11- One of the tropane alkaloids more soluble in ether: A-Hyocine — B- Cocaine C- Atropine D- Hyoscyamine _E- Ecgonine 12- Scopine is one product of the hydrolysis of hyoscine by: A-Heating Be Alkai C Acid D- Enzyme E- Water 13- €-Tropie acid is the rearrangement product of: Ae Pr B- Phenylalanine C- Lysine D- Omithine E- Tyrosine 14- Ephedrine acts through the action of endogenous: A- Amphetamine B- Acetylcholine C- Epinephrine D- Pseudoephedrine E- Catecholamines 15- Cathinone acts by inducing the release of: A- Amphetamine B- Acetylcholine C- Epinephrine D- Pseudoephedrine E- CatecholaminesPage 5 of 12 Pharmacognosy Department-College of Pharmacy 16- N-Methyl pyroplynium salt is an intermediate for the biosynthesis of: A-Tropine —B- Aropic acid C-Cinnamic acid D- Benzoic acid E- Atropic acid For 17-20 choose from: A- The principle CNS stimulant from fresh leaves of khat, B- Can be converted directly to (++) pseudoephedrine by methylation using SAM C- Is responsible for the optical activity of solanaceous alkaloids D- Atropic acid E+ Cinnamic acid OH ‘CO;H 21- d-Tubocurarine HCI lacks the following character: A- Alcohol and water solubility. B- Contraction of smooth muscle, C- Reaction with ammonium rheineckate D- Antidote to atropine toxicity E- Possessing a quaternary nitrogen 22- The following alkaloid does not contain a weakly basic amido nitrogen: A- Strychnine B- Capsaicin C- Colchicine D- Camptotheein E- Yohimbine 23. Van Urk reagent gives a positive reaction with: A- Protoveratrine A B- Strychnine C- Ergot alkaloids. D- Quinine E+ Tropie acid esters 24- Quinidine can be: A- Used in treatment of cardiac arrhythmia B- Used in treatment of nocturnal recumbence leg cramps C- Differentiated from quinine by fluorescence test with HSOz D- Has the same stereochemistry like cinchonidine at 9°, 8 positions E- Isolated from a mixture with quinine by extraction with ether 25- Isoquinoline alkaloids are: ‘A- Abundant in family Umbelliferae B- Rare in nature C- Biosynthesized from phenylalanine and tyrosine D- Exemplified by ergot alkaloids E- Lacking in Papaveraceae 1 test used for detection of both psychotrine and cephaline but not emetine is: A- Reaction with Ca hypochlorite/HCl reagent B- Mandalin's test C- Test with Frochde’s reagent D- Coupling with p-nitrodiazobenzene E- Cherry red color with Erdman’s testPage 6 of 12, Pharmacognosy Department-College of Pharmacy 27- The narcotic analgesic activity of morphine is increased by: A- Opening the oxide ring B- Fission of heterocyclic ring C- Introduction of C-14 hydroxyl D- Quaternization of nitrogen E- Methylation of the phenolic hydroxyl group 28- d-Tubocurarine is: ‘Ac Obtained from calabash curare (Menispermaceae) B- Convertible to a better muscle relaxant by reaction with methyl iodide called di-O-methyl-d- tubocurarine iodide C-Contains two quaternary nitrogens separated by ten carbons or fourteen Angstrom. D. Formed of two units of R-N-methyl coclaurine. E- Soluble in organic solvents. 29. Reserpine is not: A: A B-carboline alkaloid B- Antihypertensive and tranquillizer. C- Assayed by acid/base titration. D- A terpenoid indole. E- Detectable by vanillin/suliuric acid reagent 30- Comparing vinblastine and vincristine, A- Vinblastine is superior to vincristine therapeutically. B- Vincristine is present in higher amount in the plant. C- The two alkaloids have similar antitumor activity. D- Vinblastine can be converted to vincristine using controlled chromic acid oxidation. E- N-demethylation of vinblastine cannot be achieved chemically or microbiologically. 31- Theobromine A- Soluble in benzene B-Amphoteric and form salts with silver nitrate C- Present mainly in coffee D- Dissolves in ammonium hydroxide E- Strongly basic 32- Pilocarpine is not: A- An example of glyoxaline group B- Obtained from jaborandi C- Non volatile liquid alkaloid. D- Resistant to treatment with KMnO, E- Used to treat mouth dryness due to cancer radiotherapy 33- Aconitine is not: A; Obtained from Delphenium species family Ranunculaceae B- Neurotoxic used as arrow poison in India C- Example of sesquiterpene alkaloids D- Ether soluble ester alkaloid E- Example of pseudo alkaloid. 34- Gluco alkaloids exist in family Ac Apocyanaceae B- Solanaceae C- Buxaceae D- Liliacea E- Euphorbiaceae 35- Colehicine is A- Biosynthesized from tyrosine, intermediate is autumnaline B- Strongly basic alkaloid C- Present only in Colchicum autumnale D- Gives a red color with HCI E- Produces allocolchicine by reaction with mineral acidsPage 7 of 12 Pharmacognosy Department-College of Pharmacy B- Volatile oils (from Q 36-85) (125 marks, 55 minutes) 36- Some theories of aromatherapy suggest: A- Stimulation the body to produce pain-fighting substances B- The oils are thought to interact with some receptors C- The aromatic substances from a flower inhibit the olfactory bulb D- Therapeutic benefit through oral application E- Improve cognitive function through inhalation 37- Clary Sage oil: ‘A- Treats respiratory problems B- Balances hormones C- Treats wounds D- Is anti-inflammatory E- Treats head and muscle aches 38- Rosemary (Rosmarinus officinalis) oil: ‘A- Is antidepressant B- Balances hormones in women C- Is one of NAHA’S top ten essential oils D- Is naturally antifungal E- Treats vaginal yeast infections 39- The following oil is used for treatment of memory loss: A- Zingiber officinale (ginger) B- Eucalyptus smithii (gully gum) C- Lavandula angustifolia (lavender) D- Mentha piperita (peppermint) E- Cymbopogon martinii (palmarosa) 40- The following essential oil is NOT suitable for use in aromatherap; A- Eucalyptus B- Basil C- Grapeseed D- Pine E- Camphor 41- Selection of the suitable method for preparation of essential oils is depends on: A- The type of plant organ B- The amount of the oil C- Physical properties D- Solubility in common organic solvents E- Therapeutic & medicinal uses 42- This apparatus could be used for: A- Oils formed of thermolabile constituents B- Quality control of volatile oils C- Preparation of oils lighter than water D- Distillation of volatile oils E- Preparation of oils heavier than water 43-In Scarification and expression method: ‘A- The rasping is extracted using organic solvent B- Mostly used in the extraction of delicate flowers C- Based on puncturing and squeezing of the plant material D- Suitable for preparation of thermostable oil E- Applied in case of oils present in small amounts 44- Enzymatic hydrolysis method is used for preparation of: ‘A- Essential oils occur in glycosidal combination B- Amygdalin in bitter almond C- Sinigrin in black mustard D- Oils present in very small amounts E- Oils not easily obtained by distillation or expressionPage 8 of 12, Pharmacognosy Department-College of Pharmacy 45- Storage of essential oils should be carried out under the following condition: ‘A- Amber-colored plastic bottles B- Dry places C- Glass bottles D- Well-closed containers E- Moisture-tide dark plastic containers 46- Compound (1): {A- Alicyclic monoterpene hydrocarbon B- Yields citral on auto-oxidation C- Optically active D- Used for treatment of breast cancer ® E- Has antinociceptive effect on oncologic pain 47- Compounds (2) and (3): ZO OH ‘A- Obtained after reduction of limonene ze B- Could be obtained due to bad storage C- Have gastoprotective effect @) 8 D- White solids with camphor like odor ox 2 E- Inhibit the growth of melanoma cells 48- Compound (4): ‘A- Colored hydrocarbons B- Phototoxic C- Neuroprotective D- Forms nitrosochloride derivatives J E- Antinociceptive 49- Compound (5): te A- Has antinociceptive activity B- Occurs in oil of ginger cL C- Has anticatabolic effect ‘D- Occurs in oil of sandal wood 6) E- Sesquiterpene hydrocarbon @) 50- Compound (6) is used a: ‘A- Decongestant in case of rhinitis B- Penetration enhancer C- Strong antimicrobial HOH D- Promising anti-asthmatic | o E- Hypotensive and vasorelaxant 51- The following is true for compound (7): OH ‘A- Forms crystalline derivative B- Occurs in oil of geranium ] C- Yield hydrocarbons with formic acid | D- Hypotensive and vasorelaxant E+ Optically inactive compound 52- Compound (8): ‘A- Synthesized by oxidation of thymo! B- Safely used in tobacco industry C- Synthesized from various pine oils ct @ D- Has lilac-like odor E- Reduces the anticoagulant effect of warfarinPage 9 of 12 Pharmacognosy Department: ‘ollege of Pharmacy 53- The following is true for compound (9): ‘A- Used in fear- and anxiety-related disorders B- Oceurs in pine oil C- Converts to camphene by dehydration au Dé Its isomer exhibited anti-swine flu activity ‘OH E- Could be isolated by cooling 54- Borneol could be separated from isoborneol by: ‘A- Formation of ester with formic acid B- Heating with zinc chloride C- Reaction with hydroxyl amine D- Reaction with stearic anhydride E- Dehydration '55- Select from the following one method NOT used for isolation of terpene alcohols: A- Fractional distillation B- Formation of crystalline derivatives C- Additive compounds with CaCl; D- Counter current extraction E- Dehydration Mateh each sentence (Q 56-58) with only one suitable structure in List 1: 56-.. occurs in spearmint oil (Mentha spicata). 57- [-form of ...oceurs in oils of pennyroyal (Mentha pulegium). 58- ....... has urinary antiseptic activity. It gives intense green color with FeCl. List 1 | , Oo OH , oS 0 oO ‘O° ey, ~~ A Be c D- E 59- N-acyl compounds derived from 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one has antituberculosis activity. A- True B- False 60- Compound (10) ‘A- Can combine with sodium bisulfite B- Pure form — negative Vanillin/HCI test C- Is not safe as penetration enhancer for transdermal drug delivery D- Is prepared from isoborneol (a0) E- Natural is optically inactivePage 10 of 12 Pharmacognosy Department-College of Pharmacy 61+ sau Feacts With neutral Na;SO3 and form hydrosulfonie derivatives, from which if can't be recovered. A-(11) B- (12) c-(13) D-(14) E- (16) 02- hhas 200 times sweet as sucrose. A-(11) B- (12) C- (13) D- (14) E- (15) 63- NaHSO; — complex soluble in water. (This method can be used for separation from its isomer). A- (11) B- (12) C- (13) D- (14) E- (16) 64- as a significant preventative and therapeutic effect on vaginal candidiasis. A-(11) B- (12) c- (13) D- (14) E- (16) HO=NOH ye a 7 A any (12) (13) (4) (13) 0) Match each sentence (Q 65-67) with only one suitable structure in List 2: 65-...0ue. + FeCl > Thymol. 66- A drop of ....+a drop of 3% NaOH saturated with NaBr —> needle and pear-like forms arranged in rosette-like bunches. 67- Photoanethole List 2 OCH; ou OCH; OCH; OCH; ~ ‘0 CH)—CH=CH) CooH CH==CH A Be c - E- cls 68- Compound (17): ‘Ac Is used as gastrointestinal disinfectant in fermentative gastritis B- Stable under the influence of light, air or heat C- Suppressed cell survival and induced apoptosis in human prostate cancer cells D- Cis isomer occurs in aniseed oil 84-93% HE=CHCH; E- Is known as anise camphor ay)Page 11 of 12 Pharmacognosy Department-College of Pharmacy 69- Safrole: A- + conc HjSO,-— intense violet color B- Is widely used as a fragrance and flavoring agent C- Is raw material for vital ingredient of pyrethroid insecticides D- Occurs in oils of sassafras and cinnamon bark E- Acts as a dual antagonist of arachidonic acid and platlet aggregation factor 70- Parsley camphor is 3,6-dimethoxy safrole. A- True B- False 71-1 drop of eineol + 1 drop of 5% hydroquinone solution —> A- Needle B- Leaf-shape C- Rhomboid D- Rectangular 72- Quantitative determination of Eucalyptol can be carried out by: A+ Hoffmann’s reaction B- Tiemann’s reaction C-Cocking & Hymas reaction __C- Reimer Tiemann’s reaction D- Phosphoric acid 73> swsn are powerful broad-spectrum anti-infections, antibacterial, antivi antifungal, antiparasite, immune system stimulant, and general tonic. A- Aromatic aldehydes B- Aldehydes C- Phenols D- Esters E- Ketones 74- Determination of citral in lemon oil can be done by: A- HI method B- Hydroxyl amine C- Phenylhydrazine D- Semicarbazone E- Sodium bisulfite 75-The following equation is used in the synthesis of: OG OCH; HC Pyridine +CH:CH:CHO ——en> Pe HPO, (CHCICH;CH3 A- Safrole B-Apiole C-Eugenol D-Anethole E- Thymol 76- Compound (18): A- Is obtained by steam distillation B- Occurs in citronella and lemon grass oils oH C- Is effective antimicrobial \ D- Acts asa fungicide ] E- Has pleasant fruity odor of rose (18) Ho 77- Compound (19) is: ‘A- Prepared from guaiacol to give one pure form B- By oxidation of lignin + low yield ‘och C- Readily soluble in ether, and hot water bis 9) D- Acidic to litmus. It gives green color with FeCl; solution E- Prepared from eugenol by acetylation then oxidation followed by acid hydrolysisPage 12 of 12 Pharmacognosy Department-College of Pharmacy as an anti-inflammatory potential and has a strong antioxidative effect on ative stress and inflammation in rats. B- (23) C- (24) D- (26) E- (27) hhas a blue-violet fluorescence and occurs in ylang ylang oil. B- (23) C-(24) D- (25) augment protection against influenza virus infection in mice vi of pulmonary inflammatory responses. A- (20) B- (21) C- (23) D- (24) E-(27) 81- could represent a future alternative to monotherapeutic anti-leishmanial agents. A- (20) and (23) B- (22) and (23) C- (23) and (24) D- (23) and (27) E- (24) and (27) 82- War gas when treated in alcoholic solution with excess ammonia —. A- (20) B- (21) C- (23) D- (25) E- (27) 83-, is prepared from Gaultheria procumbens by enzyme hydrolysis followed by distillation. A- (21) B- (23) C- (24) D- (26) E- (27) 84- Determination of cinnamic aldehyde in cassis oil can be done by: A- HI method B- Hydroxyl amine C- Phenylhydrazine D- Semicarbazone E- Sodium bisulfite 85- . has strong antifungal activity on Aspergillus flavus spores from the levels of membrane, organelle and intracellular macromolecule. A- Cineol B- Citral ‘C- Camphor D- Ascaridole E- Phellandral coocHy uc Hy i Ni O Sen, F a Nw, 1) (22) (20) (23) oa COOCH; OH sed KO Ss (4) (26) en Good Luck