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ANALYSIS of ALKALOIOS in LEAVES of CULTIVATED Feryth­ Lloxylum and CHARACTERIZATION of ALKALINE SURSTANCES USED DURING COCA Chewfng*

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ANALYSIS of ALKALOIOS in LEAVES of CULTIVATED Feryth­ Lloxylum and CHARACTERIZATION of ALKALINE SURSTANCES USED DURING COCA Chewfng* ,J ,mmal o{ Ftl111 opharmacolog y, 3 ( 198 1) Jl 3 · 335 : JI~ O El sevier .Scquo ia S .A ., Lau sannc - Printed in lhe Neihcrlands ANALYSIS OF ALKALOIOS IN LEAVES OF CULTIVATED fERYTH­ llOXYLUM AND CHARACTERIZATION OF ALKALINE SURSTANCES USED DURING COCA CHEWfNG* LAURENT RIVIER fnst ítu te o{ Plant Bio logy and Ph ysiolo¡.;y o f thl' University, 6 Place d e la Riponne, J 005 I...ausanne (S witze rland) ond D epart ment ol T oxico/o¡.!y, Karo fin :;;;k a lnslitule t. / M 0 1 Stochholm (Sweclen) ..;ummary Severa! salven t.s were tested far the ex traction of the alkaloids in ··:rythroxylum coca. The resulting crude extracts were analyzcd by gas ·hromalography- mass spectrometry. Ethanol ex traction was found to be the ·nly quantitativc method presenting no artifacts. lt was established thal ncain P and cis- and trans-cinnamoylcocaine wcrc the endogenous alkaloids 1 E. enea leaves. From the severa] breakdown compounds arising during n1g-term extraction wi th H2S04 or CHC1 3 , ccgonine mc thyl ester was the nly alkaloid fully identificd ; ccgonidine methyl ester was tentativcly •ent.ified on the basis of its mass spectrum frah'Tllentation pattem. Quant.ification by mass fragmcntography of the three cndogenous nnpounds was performed using a stable-isotope dilution technique on dividua! !caves of single branches of E. coca, E. novugranatense and E. ·vogranatense var. truxillense. The relative amounts of thesc alkaloids anged with leaf age as WPll as betwcen species and varieties. The variation alkaloid levels between individual leaves was too grcat to allow the use uf ·' ratio between cocaine and the einnamoylcocainC' levels as a taxonomic ·rk er. The initial pH value uf 17 differcnt alkaline substances traditionally ·d during coca leaf chewing was mcasured after dissolution in H2 0; values gcd bctween 10.1and12.8. Buffer capacity was determined by titration h l!Cl. Three types of curve shapes were obtained which could correspond 'faOII, Na2 C03 and NaHC03 titration curves. One sample of alkaline ·erial had no buffer capacity at ali. Thc recovery and breakdown of thc ·tine contained in E. coca lcaf powder was monitorcd for onc hour at ''lis pHs at 37 "C. The levels of cocaine and bcnzoylecgonine did not ·1gc by more than 17% at any of the pHs test:c•d (6.0, 9.0 and 11.5). Jt concludC' d that the alkaline su bstances are mainly responsible for the * Based on a paper presented at the Symposium on Erythrox y lnn - New Histo rical ~c i e ntifi c Aspecb;, sponsored by the Bolanical Museum o f Ha rvard University and de la Cultura del Ecuador, Quito, Equador, Deccmber 3 · 5, 1979. 314 transformation of the alkalo ids to free bases and not for a major hydrolysis of co c ain ~_. \ - - - - - --- - - - - - - - - --- ·--- - ---- -·- - - ·--- -- Introduction Two closely related species o( thc genus F:ry throxy lum, namely E. coca Lam. and E. nouogranatense (M orris) Hieran., have long been cultivated in South America. For thousands of years Indians have used it as a mild stimu­ lant and medicine. The principal active constituent of the leaves of cultivated Erythroxy/um species is cocaine which is traditionally absorbed during chewing. Wh en the coca leaf is masticated, an alkaline suhstance is ge nerally added to the quid. Without su ch a su hstance the chewer does not experience fully the desired effects. lt has been suggested that when cocaine is ingested, as in the case of coca chewing, a complex metabolic p rocess takes place (Montesinos, 1965). Although it has been demonstrated that cocaine is present in the ph1sma of coca leaf chewers (Holmstedt et al., 1979), consider­ able controversy still exists concern ing the fate o f the alkaloids durin i; chewing. Variability in the alkaloid content of Erythroxylum species has long been recognized (Morris, 1889; de J ong, 1906). Many chemical analyses haw been carried out on cultivated coca lcaves of uncertain origin using methods that were at best only scmi-quantitative. Consequently thcre is a real lack of reliable data on the alkaloids of Erythroxylum species. The principal o bjectives sout(ht in this study werc : (1) to identify by gas chroma tography- mass spec trometry (GC--MS ) the principal coca alkaloid· present in well-preserved Erythroxylum leaf materials collect0d in Pcru and cultivated in North America; (2) to compare the efficacy of extraetion o f these alkaloids by different organic solvents and to determine tlw alkaloid levels in leaves by using a stable-isotope dílution technique ; and (3) to detcr mine the buffer capacity of alkaline substanccs commonly uscd during coca leaf chewing in Peru and Colombia, and to in vestigate thr stability o f the alkaloids in leaf material during incubation in aqucous buff<'rs under simu­ lated conditions of mastication. Materials and methods Chemícals Cocaine hydrochloride was obt.ained from the Karolinska Apo tekct, Stockholm, Sweden. Cocaine deuterated on the mcthyl-cster moicty (cocaine-d3 ) had been synthesized previously (Holmste<lt el al. , 1977). Trai: cinnamoylcocaine was prepared foll o win g the procedure dcscri bed by Moo ( 1973) starting with ecgonine hydrochloride. Ali other chemicals were of t "pro analysis" grade from MPrck (Darmstadt, F.R.G.). l'la11 l ma terials Descriptions of thP vouclwr lwrharia specinw ns used in t his study arP given in T able l. Alk alinc s11 bstances In gPneral, coca !paf ch(•Wf' rs add alkaline su bstances to thf' !caves - some times lime, some times vegctable aslws pn'pared in tllC' shape o f halls or rolls. Dcscriptions o f thc vo ucher specimens used in this study are given in TablE> 2. The cal is prPpared by buming calcium-containing rock fragm ents o r shells and grinding the remains in to fim' po wdPr. To form l/ipta, thc ashes of thc stalks of quinua (Ch eno podium quinua \Villd.) and cañih11a (Ch. pallidi· cau/c Aellen) cwo indigenous crops of th!' Peruvian Andes, ar!' mixed with water to form a paste which is formed in to small ¡,'Tey halls and dried in tlw sun. A small pi<'ce is brokf'n off and takf' n with each m outhful uf coca lf'avf's. O thf'r plant materials - su ch as plan ta in roo ts or cacao pods -- may also lw USf'd for thr samc purpose. In the Amazon, leaves of Cecropia spp. are burn('d and mixed with coca leaf powder (Schultes, 1957 ; llolmst.ed t e t al. , 1979 : l'lowman, 1981). l·:.draction mclhods Accura!A' measun •nwnt u f tlw total alkaloid con !A•n t in plan! maU:·rial should hL• obtained u s in ~ an extractio n proci>dun: that is as complPte as pussihl!'. Sine•• tlw cliff(•rent ulkaloids that havP so far ht'!'ll found in coca l1•av(•s vary in tlwir chemical natun' (bas0s, esters, acids and/o r PthPrs), th(•ir iw lation fro m biological rnaU:·rial is difficult. At the prcse 11 t time no singl(' nw thod o f ('Xlradion for ali lhe coca alkalo ids is availahl<'. Ouring this >ludy , six Px lractio n m('thods were t<'SlNI a11d com pan·d , using a singl<' col· ... ctio n o f ctriPd f;_ coca it'aVPS (vouchrr S[H•cimr n "lo. 7351) ¡;round to a ·1owd.,r: mr thods A . D wpn• qualit.ative and mcthocls E and F wPn· quanti­ ativt> . .\ 1c tlwd A ( ..aci d ex tract "") Fo ur grams u f tlw l<>a f powd(•r wcrl' rxtrac t;:>d with 200 mi uf 1 N 12 S04 al room t!'mp<>rature for 20 h. ,\fter filtration un a G4 glass fil ter, lhP <1 lutiu 11 was brought to pll 9 hy th(• addit io n of solid Na2 C0 3 . Thc alkaloids •·n• ('Xtract.ed hy partitioning tlw aqueo us phase thn'e times wi th 100 mi u f .- hloroform- <liethyl ether ( 1 :4, v/v) mix ture. The urganic layers werc d riPd 1 v t.h P at ditio n of anhydrous '.'la 2 S0 4 and ta ken to dryrn•ss undcr rcduc('d n•ssurc at 40 ºC. ThP residt1(' was t ak~ n up in a mínimum volume of chlo ro­ inn o r sil ylated with Sylo n STZ (Supelco , Crans, S wi tzrrland) pyridinr .'. :3, v/v) ami injecu•d dir!'ctly in to tllC' (;C :\IS system. Mctho d H ("vo latile alkalo id ex tracl ") Four grams o f the leaf powder wPre m ix('d with 100 mi o f H 2 0 , 1 50 ml anhyd ro us glycerin and 20 g of NaOll (Fikenschrr, 1959); 100 mi of thP lution w1•rp (•vaporat.i'd un<lrr mild vacuum i11 a rolary !'vaporatur. ThP TABLE 1 Voucher specimens of cultivated coca for chemical analysis and biological experiments Plowman No.* Description 7351 Erythroxylum coca Lam. Air-dried leaves obtained from Empresa Nacional de la Coca, Lima, Peru, May 10, 1978, and mai~tained at - 20 º C in the dark until analyzed. 7611 E. coca Grown from see<ls of Plowman 4711, Peru, Ayacucho Rio Apurímac ; collected August 1 , 1979, cultivated in greenhouse. Branch A: leaf No. 1 = first unrolled leaf, linear. No. 2 = new growth, newly expanded leaf. No. 3 = old growth leaf. Nos. 4 and 5 = idem. No. 6 = old, yellowing leaf. Branch B: leaf No. 1 = first unrolled leaf, linear. Nos. 2 · 5 = as in branch A. 6275 E. nouogranatense (Morris) Hieran. Leaves Nos. 1 - 10 (continua! production), collected August 1, 1979, cultivated in greenhouse.
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