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/ ;11/1/"T1I A7"1 fe..;'rNR' / R L /J()/Jd"'~ e / /1'8) CACTUS ALKALOIDS. 50. A COMPREHENSIVE TABULAR SUMMARY· Rachel Mala and Jerry L. McLaughlin Department of Medicinal Chemistry and Pharmacognosy School of Pharmacy and Pharmacal Science Purdue University. West Lafayette, Indiana 47907 U.S.A. ABSTRACT. The puhlished lil<ralUre onthe identification and characleriution ofcactusalk.loids has mushroomed ,;nC% the la" compr<hensi~e rniew thiny ~ears 8,0 (130). This repon n:prr-sents an attempt 10 labulate (Table I) all of Ihe cum:nlly know alka loidb<arinf cactUS species and their contained alkaloids. Species containinE uncharacteriud alkaloids and sp<ci.- ,i\'inf nefati ve alkaloid tests are not included. The alkaloids ar< usually listed by Iheirtrivial names; structures C>in be ohtained by consuhinF the referrnces cited. The survey i.< belined to be complete Ihrou,h 1980. and the authors requtSt' notifIcation of omilled references. Botanical synonymsmay.be misleadinj!.and readers are referred to the included taxonomic rdere"""s (7 . 9.10. 12.1.3. 28. 30. 46.95. 151) . • ucturr presented at the VIII Simposio Internacional de Quimica de ProduclOs Naturales. Institulo Tecnol6,ico y de Estudios Superiores de Monte""}". ~8/4/198J. Much ()f this research has bttn sup­ ported by l!rants from Ihe Cactus and Succulent Society of America. Iable 1. Occurrence of Alkaloids in the Caetaceae as Reported in the Literature Criteria of Botanical Name Common Name Habitat Alkaloid Content Identif iea­ Re1erences . tion Ariocarpus agavOides Magueyitos lula and lama­ ,Hordeuine tlc.Sc.Bc....... 19 (Caslaiieda)E.F. Anderson (little ulipas (Mexico) ag~ves) ! - Methyl-3,4-dime thoxy­ phenet hylamine - tlc.gc.gc-ms ~.~-Dimethyl-4-hydroxy- - 3-methoxyphenelhylamine ~lc,gc,gc .... s Ariocarpu8 fissuratuB Peyote Zacatec.as and Hordenine tlc,mp,mmp, 102 var. lloydl1 (Rose) Chaute Coahuila iT Mars~ (Mexico) ~-Methyltyramlne tlc Ariocarpus f1 SOuTatuB living rock. Zacatecas and Hordenine mp 47,102,112 var .. fissuratu6 (Engel.) chautle, Coahuila Schum. peyote, BU­ (Mexico); ~Methyltyramin~ tlc nami or dry le.x.as . whiske)" ~-Methyl-3.4-dimethoxy- pezufia de phenet hylamine tlc ,mp.mmp venado, peyote cimar ron, star cactus, star rock Arioc.arpus kotsLnou­ Pe..zuna de Northern and !lordenine ~lc,mp._p 109.127 ~(Lem.) Schum. venac!o, pata Central Mexico iT .de veRBdo. chaute.peyott ~-Methy1tyramine tlc,mp,anp, ir Ariocllrpus ~ Chaute, San Luis POLosi Hordenine tlc.mp,mmp, 11.47,107, Scheid. Anha1on iUIII choulle, (Mexico) ir, 130,131. PI' lsmat ic"," Lem. pe yote !!-~I..chyl tyramine tIc Imp,ramp 155 ir ~-Methyl-3. 4-dimethoxy­ tlc,mp,mmp, phenet hylamin~ ir ~-Methyl-4-methoxyphene- tlc,mp,lamp, r.hylamine ir - 96 Table 1. (cont inued) Criteria of , Botanical Name Common 'Name Habitat Alkaloid Cont ent Ident 1f1ca­ References tion Ar10carEus "cha~harD6tru6 Chaute Nuevo Leon Hordenine tlc,gc,8C-mS 22 Boed. (Mexico) ~-Methyltyramine tlc,gc~gc-m5 ~,~-Dimethyl-3,4-di- tlc,gc,gc--ms methoxyphenethylamine ~-Methyl-3,4-dimetboxy- tlc.gc,gC-tDS I phenet hvlamine Ar10carpus trigonus Chaut e Mex1cD ~-Methyl-3,4-dimethoxy- Llc.,mp,mmp, 145 (Web. ) Schum. p hen ethy lam ine uv,1r ,nmr Hordenine tlc,mp,mmp, ir ~-Methyltyramine tIc Azureocereus a~acuchens1s Peru Tyramine tlc,mp,mmp 81 Johns ir Backebergia militaris Guerrero, 3,4-Dimethoxyphenethyla­ tIc ,mp. iT ,ms 97,121,149 (Andot) Bravo ex Sanchez Michoacan mine Mejorada (Mexico) Hel1amine tlc,mp, ir. DiS ,m1k.es 3-Hethoxytyramine tlc,mp,mmp, ir,as \ Lemaireocereioe tlc,mp,mmp, , 1r ,ms ,mikes Carnegiea gigantea Saguaro, Arizona, Cal1­ Carnegine gC,mp 14,16-18,26 (Engel. ) Br. and R. sajuaro, forn1a (USA); 58,59,138, pitahaya SODora (Mexico) Gigantine gC,mp - 140,149 Salsol1dine mp,mmp,ir, nmr ,gc-ms 3-Methoxytyramine gc-ms gc__ 3,4-Dimethoxyphenethyl­ amine Arizonine tlc,mp,mmp, iT ,nmr ,m5 gc-ms Dopamine tIc Cereus aethiops Argent ina, Hordenine t le ,mp ,mmp, ir 13b Hs1ol. Brazil Tyramine tlc,mp,mmp,1r Cand1cine t.lc,mp,mmp Cereus alacriEortanus Braz 11 and Hordenine iT 2 Pfeilf. Paraguay ---Cereus forbe611 O. Cordoba, Cata­ Tyramine ir.nmr,ms 2 marcs, 1\JcuUlan (Argent ina) - I Cereus !!laucus SD. Tyramine gc 2 I I '''"o~ Hordenine gc Table 1. (continued) Criteria of Botanical Name Common Name Hallitat Alkaloid Content Ident1f ica- Ref ere.nces tion ~ Jamacaru DC. Brazil Caffeine (unconfinned) No ~eported 25,45 Tyramine tlc,mp,ir,ms Cereus Eeruv ianul; (L.) Southeastern Tyramine gc 2 , 32,131 Mill. South America Hordenine gc ~ validus Haw. I:. Bolivia ·to 3-Nitrotyramine mp, tic ,uv,1r. 111 Argent ina nmr,lIls Cereus pe ruv ianu5 ~- Southeastern Tyramine tr,ms 2. truosus DC . South America Coryphantha bumamma Morelos. Hordenine tlc,gc-ms 20,23 (Ehren. ) Br . and R. Guerrero (Mexico) ~-M e thyl-3,4-d1methox y- tlc,gc-ms phenethylamine ~-Meth y l-4-methoxyphen- ethylamine t.lc..gc-ms Coryphantha calipensis Calipan ~-Methyl-3,4-dimethoxy- 21,23,156 H. Bravo (Mexico) phenethyla..ine tlc,gc-ms,mp, ir , mmp .. I Normacromerineo tlc,gc:-ms,lnp, ""p, ir 6-D-Methylnormacro- mp,t.lc,ms,gc, merlne (calipamine) nmr . 6-0-Methylmacromerine mp, t1c. gc. IDS, nmr ~,~-Dimethyl - 3,4,-d1me- thoxyphenethylamine tlc',gc-ms . ~ Hordenine tlc,gc..",s ~-Methyltyram1ne tlc,gc-IIlS Cornhantha corn!!era Central Mexico 4-Methoxyphenethylamine tIe,lIe . .- . -' 60 (DC.) Lem. ~Methyl - 3,4-dimethox ~- . ­ phenethylam1ne tIc,gc 4-Methoxy-B-hydroxy­ phenethylamine tlc, gc I Hordenine tIc I I Synephrine tIc tIc B-D-MethyIsynephriRe 1 Table 1. (continued) CriteriB of Botanical Name Common Name . Habitat Alkaloid Content Ident1fica- References tioD Coryphantha eornifers North Mexico; ~-Methyl-4-~ethoxy- 60 (DC . ) ·Br. snd R. var. W. Texas (USA) phenethy18mine tlc,mp ..mnp, eehinus (Engel. ) L- ir Ben50n ~-MethyI-3.4-di~ethoxy- phenethylamine tlc,mp,mmp. ir Mac romer ille gC,ms I 4-Methoxy-B-hydroX)­ phenethy1amine nmr,ms Hordenine tlc.mp,tmnp, ir ~-Methyltyran1ne tlc,1bp,tnmP, ir P-Q-Methylsynephrine tlc,nmr,ms -. Synephrine tlc . I Cor:il~hantha Northern l1exico ~-Methyl-3.4-dimethoxy- duranguensis phenethylamine tlc,ge 60 (Rtinl\e) BT. and R. Hordenine tle,ge ~l1ethyltyramine tlc,~e . Synephrine tlc,ge Corvphantha e1ephana- I l-1ichoacan ~-Methyl-3,4-dimethoxy- I tidens Lem. I (Mexico) phenethylamine tle,!!e 60 I Macromerine tic ­ .I I 4-MethoxY-6-hydroxyphen I ethylamine tlc,se I i Hordenine tlc,ge I ~-l1ethy1tyramine , tIc Synephrine tIc ~-Methyl-4-Methoxy- . I I I phenethylamine tic Coryphantha Vera Cruz N.N-Dimethvl-3.4-dime- 23,125 ETeen...,oodi1 H. Bravo (Mexico) th;xy?henethylamine tle,ge-ms I Hordenine tlc,ge-tns l\ormac romer ioe tlc.gc-ms ~-Meth)'I-3 ,4-dimethoxy- mp,mmp,ir phenethy1amine t.lc.gc-ms B-Q-Methylsynephrine tIc ,gc-... Synephrine tIc o-2-l1et hy Ino",.• e ro- tlc,1r,ms. merine runr Table 1. (continued) Criteria of I Identi fica­ . Botanical N~me Common Name I. Habi~at Al kaloid Content References J I tion Coryphantha macroroeris Dona Ana Southern N. Macro~er1ne ir,nmr.ms,uv 15.~9,77 (Engel.) Lem. Mexico, \Je6tern Texas (USA); Chihuahua (Mexico) Coryphantha macromeris Dona Ana; Northern Mexico; Nonnacromerine tlc,mp,mmp 2,5,8,77-79 var .. rur-vonii l. Benson dumpling S. Texas (USA) cactus N-Me~hyl-3,4-dimethoxy- ir,nmr,tlc, phenet hylamine' mp,l1J'np,it', nmr,tI'Is ~-Me~hylme~Bnephrine dc ~-Methyl-4-methoxy- tlc,m.p,mmp, phenethylamine ir,nmr, l:e-<l>9 Hordenine ~lc ,mp,mcp, ir ,nmr ,ms Macromerine tlc,mp,mmp, ir,nmr ~-MethyltyrBmine t.lc,mp,mmp, ir ,nmr Metanephrine tlc,mp,mmp, ir,nmr N-Formylnormacromerine tlc,mp,mmp, , ir,nmr Tyramine tle,lIlp,mmp, ir,se Synephrine tlc - Corvphantha missour1­ M1ssouri pin­\Jest ern USA Hordenine tlc,!Dp,mmp, 122 ensis (Sloleet) Br. and R. cusion ir,ms ~-Methyltyram1ne tIc ,mp,mmp, 1r,1I15 Tyramine tIc ,ms N-Methyl-3,4-dimethoxy­ tlc,1D5 phenethylam1ne Co'ryphantha oHonis Central Mexico 4-MethoxyphenethylBmine tlc,se 60 (PfeH.) Lem. Hordenine tlc,se ~-Me~hyltyramine tle,se Synephrine tlc,se CoryphanthB pectinata Southern Texas N-Methyl-3,4-dimethoxy­ tle,se 41,60 (Engel.) Br. and R. (USA) ethylamine ~-Methyl-3,4-d1methoxy- tle,ge phenethylam1ne . Mac r o :nf" T ine ~lc,ge 4-Methoxy-e~hydroxy- tIc .ge phenethylamine Hordenine tIc ~-Me:h ~ lt~Tacine tlc Criteria of Botanical Name Common Name Habitat Alkaloid Content Identifica- IReference. tion Synephrine tIc , S-Q-MethylsynephriDe tIc Cor:n~ha n t ha Eose lseriana Nuevo Leon, 4-Methoxyphenethylamine tlc,gc 60 (Dietr.) Br. and R. 2.acatec8S, Coahuila Horden:lne tle,ge (Mexico) I ~-Heth y ltyramine tle,ge Synephrine tle,ge CorYEhantha ~ Central Mexico N-Hethyltyramine tlc,ge-ms 23 (DC.) Br. and R. Hordenine tlc ,gC-1D6 CorYEhantha ramillosa Southern i exas ~-Methyl-4-methoxy- tlc,mp,mmp, 137 Cutal<.. (USA); and phenethylamine ir northcentral Hexico ~-Methyltyramine tlc,mp,mmp ir Synephr:lne tlc,mp,mmp ir S-Q-Hethylsynephrine tlc,mp,mmp, ir Hordenine t.lc,mp.,tDmp, ir CoryEhantha viviEara Manitoba to Hordenine tle,ge-1IlS 14,23 (Nutt. ) Eng. Alberta (Cana­, da); Kansas, Texa.s, Colorado (USA) l.riteria 01 Botanical Name Common Name -Habitat Alkaloid Content Ident1fiea- References tion - CoryEhantha vivipara Arizona (USA) Hordenine tlc.,lDp,mmp, 62 (Nutt. ) Br- and R. var .. ir ari%onitl (Engelm.) W.T. Marahall Doliehothele baum1i iamaulipas Doliehotheline tIc 34 (&oed.) Werd. and F. (Hexieo) Boyb. Dol1ehothele Iongimamma Peyot1l10, Cent.ral Hex_ieo Dolichothel in" tIc 34,80,124,127 (DC.) Br. and R. peyote - --"­ Longima=ine nmr,ms,ir,uv. - mp,mmp Longimammosine nmr,ms,ir,uv, mp,l!lID.p Longimammid ine nmr ,ms., 1r tU~.
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