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Cactaceae Alkaloids. I. Closely Related to Cactus Are Presented in fig

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Cactaceae Alkaloids. I. Closely Related to Cactus Are Presented in fig :*K,. ,^M*t.^Af^^i%£^ ^i*&fa&M&&£i june 1969] A( The structures of the Cactaceae Alkaloids. I. closely related to cactus are presented in fig. 2. ^ ] Stig Agurell alkaloids in several spec obtained suggested that 1 (Department of Pharmacognosy, Faculty of Pharmacy, Box 6804, 118 86 Stockholm) About 120 species of cac in our laboratory and the The family Cactaceae comprises some 3000 species of cacti, frequently growing (i). The presence or in the arid regions of North, Central and South America and the West Indies (4, 5).; Cereus, Echinops Open hybridization in cacti has induced large morphological variability which | (it). The identity of t often has caused the same species to acquire different names. This in turn has, Our major object in th created further taxonomical complications. The number of synonyms for a| the ones of biosynthetic i single species is often exasperating, e.g., Lophocereus schottii (Eng.) Br. & R., onej able chemotaxonomic crit of the large "organ pipe" cacti, has eight synonyms (22). The well known peyotei such a taxonomically com cactus, Lophophora williamsii (Lem. ex SD.) Coult (T.) is also recorded under atj least three other names (27). The classification suggested by Backeberg (4, 5) willj' be followed in this paper. hcXT In spite of the remarkable interest in peyote, whose hallucinogenic effects^ were described as early as in 1560 by the missionary Bernardino de Sahagunf (cf., 27), the family Cactaceae has not been extensively investigated phyto-j chemically. One of the most accurate and critical reviews of the cactus alkaloids seems \M be the survey by Reti in 1950 (27), listing only nine species containing alkaloidf of known structure. Since then only a few new structurally clarified alkaloi&|| JX and species containing previously known cactus alkaloids have been recordedLi « N-METHYl-t-Mi Some more important later contributions are summarized below. ?| PHENETHYLAMI Djerassi and co-workers have isolated pilocereine (12), first believed to be a "dimer" but then shown to be a "trimeric" alkaloid (11) from Lophocereus schottii (Eng.) Br. & R.,1 Lophocereus gatesii M. E. Jon. and Marginatocereus margiiiatusi C H 3 0 ^ y (DC.) Backbg.' A "monomeric" alkaloid lophocerine has also been isolated fronSI L. schottii (13). Anhalonidine is known from Pachycereus weberi (Coult.) Backbgjr C H 3 0 ^ / 3,4-DIMETHOXYP (14) and mescaline from Trichocereus pachanoi (26). Recently Hodgkins et alM ETHYLAMINE (7 (16) isolated macromerine from Lepidocoryphantha macromeris (Eng.) Backbg. (T.i and the same alkaloid is also present in Lepidocoryphantha runyonii (Br. & RJf Backbg. (6) (synonyms: Coryphantha macromeris (Engl.) Lem. Br. & R. anl C C. runyonii Br. & R.). The structure proposed by Hodgkins et al.y (16) foj i C H j C y ^ y gigantine isolated from Carnegia gigantea (Eng.) Br. & R. (T.) was apparently not correct (10, 15). Dopamine, however, is known to occur in this species (32^1 Three new phenylethylamines, 3-methoxytyramine, 3,5-dimethoxy-4-hydroxy^ MACROMERINE phenylethylamine and 3,4-dimethoxyphenylethylamine, were identified by us (11 together with mescaline in Trichocereus pachanoi Br. & R. and Trichocereus werdem mannianus Backbg. In peyote, 3,4-dimethoxy-5-hydroxyphenylethylamine ancJ 3,4-dimethoxyphenylethylamine are known to occur (2, 24). Kapadia and C0| workers have recently isolated from peyote some quarternary alkaloids, vi^ CH30-M CH30 peyonine, anhalotine, lophotine and peyotine (19, 20), all closely related to me|^ |2> caline and the tetrahydroisoquinolines. These workers have further isolated th§ Wit' MESCALINE 113 alkaloid peyophorine from peyote (17) and, after the preparation of this nianuj fflG- 1. Structures of known ca script, published (18) on the occurrence of no less than fourteen amides froc from cacti in subsequei Quarternary or neutra peyote, all closely related to the known alkaloids and using a similar technique f is also known as 3-metl s u g g e s t e d h e r e . j Other surveys have been published, e.g., chapters on cactus alkaloids in Boi|| monograph (9) and in The Alkaloids (28) and an index of species containm'' |f For our purpose it was 1 alkaloids by Willaman (36). See also Reti's review for other references. ^ |nown compounds were r< "Impounds were easily obs Pilocereine was also isolated from L. australis which now is considered as a variej| J*!* specificity of mass spe L. schottii.(22). , . ||,pointed out by Thomas 2 0 6 - Wee. ^ • •.. -*'m Ui^M^llZM^&i^^i&ii ^^rfsyi^^^^feii^^^^^s^™ Pf^Vtl June 1969] agurell: cactaceae alkaloids i 207 I t " ' s * * i^The structures of the known cactus alkaloids are shown in fig. 1. Compounds Iclosely related to cactus alkaloids and which may be expected to occur in cacti "31 fare presented in fig. 2. In connection with our biogenetic studies, a screening for falkaloids in several species of Trichocereus was carried out (1). The results fbbtained suggested that the occurrence of alkaloids in Cactaceae was wide spread. >m£, iiS S0 Stockholm) f About 120 species of cacti have been tested for basic, non-quarternary alkaloids r cacti, frequently growing j |in our laboratory and the following data is presented in this paper: (i). The presence or absence of alkaloids in some cacti mainly belonging to and the West Indies (4, 5). 1 Cereus, Echinopsis, Helianthocereus and Trichocereus. ological variability which M (ii). The identity of the alkaloids present in the species. names. This in turn has! Our major object in this investigation was to identify new alkaloids particularly nber of synonyms for a|| |the ones of biosynthetic interest. Furthermore, this screening may present valu- wttii (Eng.) Br. & R., onel lable chemotaxonomic criteria that may be of significance in the classification of The well known peyote^j I such a taxonomically complex group. ) is also recorded under at ^ ed by Backeberg (4, 5) will j| lose hallucinogenic effects ;| CH3 CH3 v Bernardino de Sahagun TYRAMINE II) N-METHYUYRAMINE <2» HOROENINE 13) ively investigated phyto--' 3 cactus alkaloids seems to |j pecies containing alkaloids;! LCturally clarified alkaloids^ A> xn., c::oa N-METHYl-4-METHOXY- (DOPAMINE (5) 3-METHOXY-4-HYOROXY- ioids have been recorded, f PHENETMYLAMINE (4) ^ed below. l PHENETHYIAMINE (S) (12), first believed to be a | 1) from Lophocereus schottii % Marginatocereus marginatus^ CH30N!°y^y\ CH30Y**>V/\ CH3°Y^V^ has also been isolated from| CH,.CO., „,0CQ. cj3Qv eus weberi (Coult.) Backbg.f 3.4-OIMETHOXYPHEN- N-METHYI-3.4-OIMETHOXY- N,N - 01 METH YL - 3. 4-01 - ' Recently Hodgkins et al.M ETHYLAMINE (7) PHENETMYLAMINE (8) METHOXYPHENETHYl- AMINE 191 romeris (Eng.) Backbg. (T.)l kantha runyonii (Br. & R-)l OH -Ingl.) Hodgkins Lem. etBr. al} & (16) R. and!for*. & R. (T.) was apparently!1 i:qX, ::cn.. c:xn.,CH,0 o occur in this species (32) Js MACROMERINE 110) 3.4-OIMETHOXY-S- 3.S-OIMETHOXY-4-HYO- HYOROXYPHENETHYL- ROXYPHENETHYLAMINE (12) 3,5-dimethoxy-4-hydroxy- ^ AMINE (11) e, were identified by us (1) ^ R. and Trichocereus werder-i droxyphenylethylamine andl CHjO NH2 (2, 24). Kapadia and co- j CH30 CH. quarternary alkaloids, viz.:. CH30 CH30 3 CHjO CH3 CHj WESCAU NE (131 ., all closely, related to mes-; N-MEIHYLMESCAIINE (14? rs have further isolated the TRtCHOCERElNE (15) i preparation of this manu- |?IG. 1. Structures of known cactus alkaloids. Compounds 4 and 9 to be reported as isolated than fourteen amides from :| from cacti in subsequent papers in this series. Norcarnegine also known as salsolidine. Quarternary or neutral alkaloids e.g. N-acetylmescaline not included. Compound 6 using a similar technique as 1 is also known as 3-methoxytyramine and compound 16 as salsolidine. on cactus alkaloids in Bolt's | For our purpose it was necessary to use a simple technique by which previously index of species containing :| gcnown compounds were readily recognized and identified and new interesting or other references. compounds were easily observed and characterized. Due to the great sensitivity m is considered as a variety of | jiind specificity of mass spectrometry combined with gas chromatography (GLC), PS pointed out by Thomas and Biemann (34), it was adopted as the method of Ichoice. 208 Lloydia [vol. 32, no. 2 June 1969] During the preparation of this manuscript, Brown et al., (10) reported on the loid hydrochlorides (e.g., ] occurrence of alkaloids in twelve of sixteen investigated cactus species. Their in chloroform. The chlor< ing with 5 ml chloroform, - qualitative test was based on an alkaloid precipitating reagent and the number of was extracted with 2X50 r alkaloids, which were not further identified, was estimated by gas chromatography. finally, after adjusting to This investigation has been carried out with commercially greenhouse grown chloroform extract dried c cacti, which often differ morphologically from the plants growing under the condi simple amines are quite v( tions of the natural habitat. Furthermore it is not known whether these plants complete dryness. also differ in their ability to produce alkaloids. However, the green-house pro duced, cacti so far tested (Trichocereus pachanoi, T. terschekii, T. lamprochlorus, T. candicans, Lophophora williamsii, Carnegia gigantea, Lophocereus schottii and Lepidocoryphantha runyonii) agreed well in their alkaloid content with the data in the literature pertaining to wild species. CH30v HjCysY"^ CHjO^x^^ CH30^/^ i#> CHH,0^VNH CH3okJ1VN-CHJ CHj0WH NORCARNEGINE 1161 CARNEGINE 117) p - O - M E cHs°no CHjO, RINE ( ch,oSX'n"ch' C H , O i V ^ N H CH.,,oVvnh CHjO ANHALIDINE 1191 ANMAUNINE 120) HALONIDINE 121) C H 3 0 ^ H O " ^ N-METHYL CH,C\ 3 - M E T H 0 ) AMINE 13 CH.O CO-- "W» "TO** PELLOTINE 122) 10PH0PH0RINE 124) C H 3 0 ^ C H , O ^ T C H 3 0 ^ XjVN-c'H5 ch|oWH — J C H 3 ° CIS- (39) I DIMETHYL- O-ME1HVIANHA10- 6.7-DIMETI- PEYOPHORINE 125) NIDINE 126) IOPMOCERINE 127) ROISOQUINi Fig.
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