Glycosides and Tannins | Vanilla | Organic Compounds

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  GLYCOSIDES AND TANNINS - Yield one or more sugars among the products of hydrolysis - Β-D-glucose -> most frequently occurring sugar  - Glucose = glucoside = glucoside - GLUCO!D - acetals- hydro#yl of the sugar is condensed $ith a hydro#yl group of the non sugar component- second hydro#yl% condensed $ithin the sugar molecule itself to form an o#ide ring - Glycosides may &e considered sugar ethers - 'glycone% nonsugar component - Glycone% sugar component- alpha and &eta glycosides are possi&le - depends on the stereoconfiguration of the glycosidic lin(age - mulsin and most other natural en)ymes hydroly)e only the &eta *arieties - !mportant roles% - regulatory- protecti*e- sanitary function - D-glucose -> most common sugar  - 'll natural glycosides are hydroly)ed into a sugar and another organic compound +&y &oiling$ith mineral acids, - mulsion +of almond (ernels, and myrosin +&lac( mustard seeds, each hydroly)e a considera&le num&er of glycosides - Glycosides that are deri*ati*es of rhamnose require a special en)yme -> rhamnase BIOSYNTHESIS OF GLYCOSIDES -  parts%- general reactions couple a sugar residue to an aglycone - .rincipal path$ay of glycoside formation- transfer of a uridylyl group from uridine triphosphate to a sugar /-phosphate0- en)ymes% uridylyl transferases/0u&sequent reaction +mediated &y glycosyl transferases,01ransfer of the sugar from uridine diphosphate to a suita&le acceptor +aglycone, -> glycoside - Classification of the glycoside-containing drugs follo$s this scheme% /0 Cardioacti*e group0 'nthraquinone group20 aponin group30 Cyanophore group40 !sothiocyanate group50 6la*onol group70 'lcohol group 80 'ldehyde group90 Lactone group/:0 .henol group//0 tannins ANTHRAQUINONE GLYCOSIDES - Chrysaro&in +too irritating, - ;ydrolysis -> algycones +di-<tri- or tetra- hydro#yanthraquinones- e#ample% - frangulin - hydroly)es -> emodin and rhamnose - 'nthraquinone and related glycosides are stimulant cathartics- &y increasing the tone of the smooth muscle in the $all of the large intestine - Glycosides of anthranols and anthrones elicit a more drastic action- can cause discomforting griping action - BIOSYNTHESIS OF ANTHRAQUINONE GLYCOSIDES - 6eedings of la&eled acetate to .enicillium islandicum +produces se*eral anthraquinone deri*ati*es, - 1ransglycosylation reaction  creates a glycoside +occurs at a late stage,C'C'' 'G'D' - '(a hamnus purshiana -  Rhamnus    pushianus  +rhamnaceae, - hould &e aged for at least one yr  - Glycosides are con*erted to monomeric o#idi)ed glycosides +$hich e#hi&it a milder cathartic acti*ity - 1$o types of anthracene compounds%- normal O- glycosides +/:?-:?,- aloinli(e C  glycosides +8:?-9:?, - 1$o of the c- glycosides%- &ar&aloin- deo#y&ar&aloin +chrysaloin, - 6our additional compounds%- cascarosides '<@<C< and D - Cascarosides ' and @  &ased on optical isomers of &ar&aloin - Cascarosides C and D  optical isomers of chrysaloin - @ar&aloin and chrysaloin are &oth O- and C- glycosides - Yields not less than 7? of total hydrocyanthracene deri*ati*es - ;ydrolysis -> rhamnose and glucose +/%/, - U % cathartic- .!AC!.'L U % correction of ha&itual constipation + not only acts as la#ati*e &ut restores natural tone to the colon, - @itter taste and the acti*ity are reduced &y treating it $ith al(aline earthsB magnesium o#ide - UU'L DO % - cascara sagrada fluid e#tract +&itter cascara, / mL- aromatic cascara sagrada +s$eet cascara, 4l- cascara sagrada e#tract 2:: mg 6'AGUL' B @UC1;OA @' - Dried &ar( -  Rhamnus frangula - Composition and acti*ity correspond to those of cascara sagrada - Cathartic - Other spp contain anthraquinons glycosides - o*icol = frangula E(araya'LO - 'loe or aloes - Dried late# +Fuice, of the lea*es -  Aloe barbadensis - Commerce% curacao aloe -  A. ferox, A. Africana, A. spicata - commerce% cape aloe - Yields not less than 4:? of $ater solu&le e#tracti*e - Curacao aloe- often called @ar&ados aloe - Occurs in the mar(et% opaque reddish &lac( to  &ro$nish &lac( to dar( &ro$n in color  - .rinciple constituent% &ar&aloin - 'cti*e constituents of aloe may *ary - Curacao aloe is superior to cape aloe- cause it contains t$o and one half times as much aloe emodin- also contains an apprecia&le amount of free and com&ined chrysophanic acid not present in the other types - U % pharmaceutic aid< cathartic +acts chiefly on the large intestine,'LO H ' G L - 6resh mucilaginous gel - Contained in the parenchymatous tissue in the center of the lea*es of 'loe &ar&adensis - 1reatment of &urns< a&rasions and other s(in irritations - ecommended in treating third degree #ray  &urns and more recently has &een ad*ocated for its moisturi)ing and emollient effects;U@'@ - heum< rhu&ar& or chinese rhu&ar& - Dried rhi)ome and root -  Rheum officinale ; R. palmatum; Rheum spp.  +e#cept  R. rhaponticum   common garden rhu&ar&, - 6am% .olygonaceae!AD!'A ;U@'@B ;!'L'Y'A ;U@'@ - Dried rhi)ome and root -  R. emodi, R. spp 0 - .rinciple contistuents% rhein anthrones - Cathartic AA' - senna lea*es - dried leaflet - Cassia acutifolia -commerce% 'le#andria senna - C. angustifolia - commerce% tinne*elly senna - 6am leguminosae - 'L I'AD!'  AA'- cutting off the tops< drying them< stems and  pods are separated &y sie*es< sediments are thentossed +lea*es are at the top< stal( sin( to the  &ottom, - 1!AA H LLY  AA'- gathered &y hand and dried - Graded according to%- si)e of the leaf - color of the leaflets - @lue green lea*es  &est - Yello$ish lea*es  poorest - .rincipal acti*e constituents% dimeric glycosides- composed of aloe emodin andBor rhein - ennosides ' and @  greatest concentration- algycones% rhein dianthrone +sennidin ' and @, - ennosides C and D  minor constituents- dimeric algycones composed of / molecule of rhein and / molecule of aloe-emodin0 - U % cathartic - UU'L DO % gC;Y'O@!A - i#ture of neutral principles - O&tained from goa po$der  - 6rom the lysogenous ca*ities in the $ood -  Andira araroba - 6am% leguminosae  - ;ot &en)ene is used to e#tract chrysaro&in +4:-7:?, - Contains appro#0- 2:?-3:? chrysophenolanthroneB chrysophenolanthranol- :? emodinanthrone- monomethyl ether - 2:? of dehydro-emodinanthrone-monomethylether  - U % (eratolytic agent< treatment of psoriasis< trichophytosis and chronic ec)ema - Hery irritating to mucous mem&ranes - hould not &e used on the face or scalp - 'A1;'L!A +synthetic anthracenetriol, has replaced the use of chrysaro&inD'A1;OA - Danthron and chrysa)in - /<8-dihydro#yanthraquinone - !nsolu&le in $ater - olu&le in alcohol< ether< &en)ene< and other sol*ents - Difficult to isolate in a pure state - U % cathartic intermediate in the manufacture of anthralin and of ali)arin and indanthrene dyestuffs - UU'L DO % 74-/4: mg SAPONIN GLYCOSIDES - 6orm colloidal solutions in $ater -foams upon sha(ing - !rritating to the mucous mem&rane - Destroy red &lood corpuscles &y hemolysis - 1o#ic +esp to cold &looded animals, - .resent in fish poisons +many, - ;ydrolysis -> sapogenin +algycone, - Can form readily crystalli)a&le compounds upon acetylation- can &e used to purify sapogenins - apato#ins  poisonous saponins - #ample% - Chlorogalum pomeridianum +California soap  plant, -> +yields amolonin,- source of saponin that is used for the industry - Determination of the initial desira&ility of any gi*en steroid compound as a cortisone precursor is &ased on%- hydro#yl groups +in the 2- and //- positions, or - the a&ility to &e con*erted readily to this structure - ost outstanding plant steroids%- diosgenin and &otogenin +genus dioscorea,- ;ecogenin<< manogenin and gitogenin +aga*e spp0,- sarsasapogenin and smilagenin +genus smila#,- sitosterol +from crude *egeta&le oils, - tophanthus in the apocynaceae $as formerly thought to &e the most promising of the dicotyledons BIOSYNTHESIS OF SAPONIN GLYCOSIDES -  types +&ased on chemical structure,- neutral saponins % deri*ati*es of steroids $ith spiro(etal side chains- acid saponins  possess triterpenoid structures - ain path$ay leading to &oth types of sapogenins is similar and in*ol*es the head to tail coupling of acetate unitsGLYCY;!J' - '(a licorice root - Dried rhi)ome and roots - Glycyrrhiza glabra - commerce% panish licorice - G. glabra  +*ar0 glandulifera,- commerce% ussian licorice - Contains glycyrrhi)in +glycyrrhi)ic acid,- 4:# as s$eet as sugar  - Upon hydrolysis- loses its s$eet taste- con*erted to the aglycone glycyrrhetic acid  plus  molecules of glucuronic acid - Glycyrrhetic acid  pentacyclic tritrepene deri*ati*e of the K-amyrin type0 - Other constituents%- fla*onoid glycosides + liquiritin< isoliquiritin< liquiritoside< isoliquiritoside< rhamnoliquiritin< and rhamnoisoliquiritin,- coumarin deri*ates + herniarin and um&elliferone,- asparagine - < 2-dihydrostigmasterol- glucose- mannitol- :? starch - U % demulcent< e#pectorant  fla*oring agent +mas( the &itter taste of aloe< ammonium chloride< quinine and others, facilitate a&sorption of poorly a&sor&ed drugs +due the surfactant property such as anthraquinone glycosides, - hen it is added to - &eer = increases the foaminess- root&eer< stout< and porter = imparts a &itter taste - Glycyrrhetic acid uses%- anti inflammatory - treatment of peptic ulcer and of addisonMs disease +chronic adrenocortical insufficiency,- ingredient on Lydia 0 pin(ham ta&lets and *egeta&le compound liquid for menstrual  pro&lems - !ncreases fluid and sodium retention and  promotes potassium depletion - .U GLYCY;!J' I1'C1 O .U L!CO!C OO1 I1'C1- ingredient in aromatic cascara sagrada fluide#tract - GLYCY;!J' 6LU!D I1'C1- pharmaceutic aidD!OCO ' - Yam - e#ican yams% rich sources of the principles used as cortisone precursors - @otogenin and diosgenin -from  Dioscorea spiculiflora  +culti*ated species,- root -  Aote% the steroid nucleus of &otogenin $as altered &y transferring an o#ygen atom from the /- to the //- position of the polycyclic molecule &efore it could &e utili)ed as an intermediate in the production of cortisone - Diosgenin -o&tained upon hydrolysis of dioscin-maFor precursor of glucocorticosteroids -  I!C'A Y'-  D. floribunda - &est source of steroids CYANOPHORE GLYCOSIDES - Commonly found in rosaceous plants - ometimes designated as cyanogenic glycosides - ost $idely distri&uted of these is amygladin +another hydrolytic product is &en)aldehyde, - Common cyanophore glycosides are deri*ati*es of madelinitrile - eeds - 'mygdalin and prunasin yield D- mandelonitrile - am&unigrin +from am&ucus nigra, li&erates L   mandelonitrile - 'mygdalin is hydroly)ed -> glucose E glucose- true glucoside rather than a maltoside - ;ydrolysis ta(es place in 2 steps 1. olecule is hydroly)ed to li&erate / moleculeof glucose and / molecule of mandelonitrile glucoside0 econd molecule of glucose is li&erated $ith the formation of mandelonitrile20 andelonitrile then &rea(s do$n $ith the formation of &en)aldehyde and hydrocyanic acid - mulsin +from almond (ernels, consists of  en)ymes%- amygdalase +causes the first step,- prunase +causes the second step, - Nit is said that the emulsion consists of 3 en)ymes - U % fla*oring agents< anticancer claimsP +not recogni)ed, < possi&ility for control of sic(le cellanemia !LD C; Y - '(a0 .runus *irginiana< $ild &lac( cherry tree - Dried stem &ar(  -  Prunus serotina - 6am0 osaceae - Contains a cyanogenic glycoside< prunasin +D- mandelonitrile glucoside,- formed &y the partial hydrolysis of amygdalin - Other constituents%- hydrolytic en)yme< prunase< p  coumaric acid< trimethyl gallic acid< starch< and traces of a*olatile oil - esin yields- :02  :02? in inner &ar( - :0:2? in trun( &ar(  - #posure is such that the chloroplastids are a&undant in the cells of the &ar( = D-mandelonitrile glucoside is higher  - #posure is such that the cells donMt ta(e an acti*e part in photosynthesis  glucoside is lo$er  - U % fla*ored *ehicle +esp in cough remedies, sedati*e e#pectorant ISOTHIOCYANATE GLYCOSIDES - a(a glucosinolates- represent a group of &ound poisons li(e the cyanogenic glycosides - 'glycones = isothiocyanates - 6rom cruciferous plants - ay &e aromatic or aliphatic - .rincipal among these glycosides are- sinigrin +from &lac( mustard, - hydroly)e to allyl isothiocyanate- sinal&in +from $hite mustard, - hydroly)e to acrinyl isothiocyanate- gluconapin +from rape seed, - #amples% horse radish< turnips< mustard<  &roccoli< ca&&age -  atom is conFugated $ith glucose as the  glycoside  - ;ydroly)ed -> mustard oils - en)yme% myrosin - U % feeding deterrent +insects,  anticarcinogenic propertyU1'D@L'C U1'D - inapis nigraB &ro$n mustard - Dried ripe seed -  rassica nigra, . !uncea - 6am0 Cruciferae - U % condiment local irritant< emetic< ru&efacient< *esicant - Contains% - fi#ed oil +2:?-24?, - .rincipal constituent% sinigrin +potassium myronate,- usually accompanied &y the en)yme myrosin - 'llyl isothiocyanate is *olatile- commonly called *olatile mustard oil;!1 U1'DB !A'.! 'L@' - dried< ripe seeds -  rassica alba, oo#er filis - 6am0 Cruciferae - Commercially important as &lac( mustard - Contains% - myrosin +en)yme,- sinal&in +glucoside - ;ydrolysis -> acrinyl isothiocyanate- less *olatile than allyl isothiocyanate- contains : to 4? of fi#ed oilG'L!C - U % antihyperlipidemic enhances &lood fi&rinolytic and inhi&its platelets aggregation - 'llium sati*um +liliaceae, - 'llin +inacti*e, E ;O; -> allicin -> aFoene E J aFoene- J aFoene  more &ioacti*e- @oth has antithrom&ic property +&ut J is more acti*e, - 'llicin  anti&ac< responsi&le for odor and fla*or  FLAVONOL GLYCOSIDES - 6la*onoids = fla*onol glycosides and their aglycones - @est (no$n fla*onoid constituents%- rutin< quercitrin< and the citrus &iofla*onoids +hesperidin< hesperetin< diosmin and naringen, - U1!A 'AD ; . !D!A- a(a *it0 . B permea&ility factors- U % treatment of *arious conditions characteri)ed &y capillary &leeding and increased capillary fragility - C!1U @!O6L'HOAO!D - U % treating s! t#!s #$ t%e &#!!#n &#'()  A H  U !1; ;O1 '1   - 1hey are included in some preparations as dietary supplements - Yello$ pigments in higher plants ALCOHOL GLYCOSIDES 'L!C!A - ali# spp0 < populous spp0 - ost $illo$ and poplar &ar(s yield salicin - .rincipal sources% $alix purpurea, $. fragilis - .opulin +&en)oyl salicin, is associated $ith the salicin in the &ar(s of salicaceae - ;ydroly)ed -> D-glucose and saligenin +salicyl alcohol,- &y emulsion - U % antir%e*!ati&  closely resem&les that of salicylic acid - DO % /g ALDEHYDE GLYCOSIDES - Hanilla is a drug that has an aldehydic aglycone as its chief constituent - Hanillin  aglycone de*eloped- methylprotocatechuic aldehydeH'A!LL' +de*elops during the curing process, - Hanilla &ean - 6ull gro$n< unripe fruit - %anilla planifolia - commerce% me#icanB &our&on *anilla - %. tehitensis - commerce% 1ahiti *anilla - 6am0 Orchidaceae - Green *anilla contains t$o glycosides%- GLUCOH'A!LL!A +a*enein,- GLUCOH'A!LL!C 'LCO;OL - Gluco*anillin- hydroly)ed +during the curing process, -> glucose E *anillin - Gluco*anillic alcohol- hydroly)ed -> glucose E *anillic alcohol- o#idi)ed -> *anillic aldehyde +*anillin, - U % principal fla*oring constituent +fla*oring agent, pharmaceutic aid source of *anillin - Contains a&out /:? of sugar< /:? of fi#ed oil and calcium o#alate CO++ERCIAL VARIETIES,  I!C'AB H ' CUJ H'A!LL' - @est grade - .ods are usually 2:-24 cm@OU@OA H'A!LL' - esem&les the e#ican *ariety - 1$o thirds as long - @lac(er in color  - Co*ered $ith a su&limate of needle shaped *anillin crystals - .ossesses a coumarinli(e odor 1';!1! H'A!LL' - eddish &ro$n in color  - 's long as the e#ican *ariety - harply attenuated - 1$isted in the lo$er portion - Unpleasant odor  - Less suita&le for fla*oringH'A!LL' .L!1 'AD CU1 - ore mature fruits in $hich dehiscence has ta(en placeH'A!LL!A - 3-hydro#y-2-metho#y&en)aldehydeB methylprotocatechuic aldehyde - ay &e natural or semi syntheticor from other sources%- coniferin +glycoside preset in the cam&ium sapof pine trees,- eugenol +phenol present in clo*e oil,- lignin +&y product of the pulp industry, - ost of the *anillin in commerce is made from lignin - lightly solu&le in $ater and glycerin - 6reely solu&le in alcohol< chloroform and ether  - U % fla*oring agent -  Aote%- lignin is found in the rings- responsi&le for the color of the tree 1;YL H'A!LL!A - ynthetic analog of *anillin - 6la*oring agent LACTONE GLYCOSIDES - Glycosides containing coumarin are rare -  Aone of the hydro#ycoumarin glycosides is of  particular medicinal importance - (imming +Qapanese star anise, - 'esculin +horse chestnut tree, - Daphnin +ash &ar(, - copolin +&elladona, - Coumarin - 1on(a &eans -  Dipteryx odorata -  D. oppositifolia - %iburnum prunifolium  +&lac(ha$,- antispasmodic acti*ity - %. opulus  +true cramp &ar(,- fam0 Caprifoliaceae- attri&uted to scopolefin +5-metho#y-7-hydro#y-coumarin, - Others ha*e antispasmodic acti*ity - Once $as used as uterine sedati*es - Lactone containing natural products%- cantharidin- metho#salen- santonin - from  Artemisia cina, A. maritima, Artemisia  spp.  - fam0 Compositae - formerly used as an anthelmintic - discontinued &ecause of potential to#icityCOU'!A - Lactone of o-hydro#ycinnamic acid - olu&le in alcohol - Can &e synthesi)ed readily - Occurrence in ton(a &eans +/?-2?,- from s$eet *ernal grass +  Anthoxanthum odoratum& -> fam0 Gramineae - s$eet col*er +  'elilotus albus , -  '. officinalis  +fam0 Leguminosae,- s$eet scented &ed stra$ + Galium triflorum , -> fam0 u&iaceae- red clo*er + (rifolium pretense , -> fam0 Leguminosae - 6ormerly fla*oring agents - @anned - U % 'ntispasmodic< fla*oring agent< anticoagulant +dicumarolB &ishydro#ycoumarin,<uterine sedati*es< dermatologic purposes +cantharidin R metho#salen,< anthelmintic +santonin, @!;YDOIYCOU'!AB D!CU'OL - elated to coumarin -  'elilotus officinalis  +leguminosae, -  Ao$ prepared synthetically - U % anticoagulant +include $arfarin salts, - UU'L DO % ::-2:: mg initially then 4 -:: mg once a dayC'A1;'!D   - '(a0 panish flies< ussian flies< &listering flies - Dried $hole insect - Cantharis *esicatoria +meloidae, - Dried not higher than 3: degrees - ChloroformB car&on tetrachloride- added occasionally to preser*e the drug from attac( &y other insects - Chief constituents- cantharidin +:05? - /:?, - *esicating principle - lactoneB anhydride or cantharidic acid- /? of a fat is associated $ith the cantharidin - U % irritant< *esicant< ru&efacient - #creted &y the (idney - !rritates the urinary tract- can result in priapism
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