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Alkaloidal Relationships in the Genus Arctomecon (Papaveraceae) and Herbivory in A. Humilis

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Alkaloidal Relationships in the Genus Arctomecon (Papaveraceae) and Herbivory in A. Humilis Great Basin Naturalist Volume 51 Number 4 Article 11 12-27-1991 Alkaloidal relationships in the genus Arctomecon (Papaveraceae) and herbivory in A. humilis Douglas A. Raynie Brigham Young University Deanna R. Nelson Brigham Young University Kimball T. Harper Brigham Young University Follow this and additional works at: https://scholarsarchive.byu.edu/gbn Recommended Citation Raynie, Douglas A.; Nelson, Deanna R.; and Harper, Kimball T. (1991) "Alkaloidal relationships in the genus Arctomecon (Papaveraceae) and herbivory in A. humilis," Great Basin Naturalist: Vol. 51 : No. 4 , Article 11. Available at: https://scholarsarchive.byu.edu/gbn/vol51/iss4/11 This Article is brought to you for free and open access by the Western North American Naturalist Publications at BYU ScholarsArchive. It has been accepted for inclusion in Great Basin Naturalist by an authorized editor of BYU ScholarsArchive. For more information, please contact [email protected], [email protected]. Great Basin Naturalist 51(4), 1991, pp. 397-403 ALKALOIDAL RELATIONSHIPS IN THE GENUS ARCTOMECON (PAPAVERACEAE) AND HERBIVORY IN A. HUMILIS Douglas E. Raynie!, Deanna R. Nelson", and Kimball T. Harper" ABSTRACT.-The previously reported alkaloids (including protopines, benzophenanthridines, tetrahydrobenzyliso­ qUinolines, and protoberberines) ofthe genus Arctomecon (Papaveraceae) are discussed in relation to theirdistribution in theplantkingdom, in the Papaveraceae, and among the three species ofArctomecon. Thebiological activity ofthese alkaloids is discussed, and possible implications for herbivore and planHnsect interactions inA. humilisare presented. Key words: Arctomecon, Papaveraceae, alkaloicls, herbivory. The Papaveraceae genus Arctomecon con­ tains only three species, all rate endemics in the western United States. The geographic distribution of the bear or desert poppies, Arctomecon spp., is shown in Figure 1. The uTAH great bear poppy (A. merriamii Coville) is the most common ofthese species, extending NEVADA from the Las Vegas area of southern Nevada to the Death Valley region of southeastern California. A. californica Torr. & Fremont, the yellow bear poppy, was once common in the vicinity ofLas Vegas and the Lake Mead region of southern Nevada and northwestern Arizona, but numbers have rapidly declined due to habitat loss. The dwarfbearclawpoppy (A. humilis Coville) is disjunct from the other species, growing exclusively in Washington County, Utah. A. humilis has been declared CAL.lFORNIA an endangered species by the U. S. Fish and Wildlife Service under the Endangered Spe­ A. californlca • ARIZONA cies Act of 1973 as amended, while both A.hiJmil1s • A. merriamii and A. californica are presently A.merriamil A under consideration for such protection. Habitat requirements and ecological relations of A. humilis and A. californica have been studied by Meyer (1986, 1989) and Nelson (1989). Both are obligate gypsophiles. Unlike Fig. 1. Distribution ofArctomecon (Papaveraceae). the other two species, A. merriamii is not restricted to gypsum-rich so:ils but often oc~ curs on shallow soils derived from limestone. were determined. The structures of the We have reported elsewhere (Raynie et al. alkaioids known for these species are shown 1990) the alkaloid chemicals found in this in Figure 2. the alkaloids identified include genus. Sixteen different isoquinoline alka~ the protopines allocryjJtopine, protopiJ1e, loids from fOur cla,sses were found, and the cryptopine, and 12-methoxyaUocryptopine; structural details (for 14 of those alkalOids) the benzophenanthridines chelerythrine, lDepartment of Chemistry, Brigham Yonng University, Provo, Utah 84602. Present address: Procter & Camble Company, Corporate Research Division, Miami Valley Laboratories, Box 398707, Cincinnati, Ohio 45239-8707. 2Department ofBotany and Range Science, Brigham Young University, Provo, Utah 84602. 397 398 GREAT BASIN NATURALIST [Volume 51 TETRAHYDROBENZYUSOQUINOUNES ORa Rs OR.! AIIocryptopine: R1-R2 =~. Ra == R.! '= c~ As:: H RetiCiJline: Rl == ~ == OC~ R2 == Ra '" OH Protoplne: R1-Ri and Ra,R.! =CH2 Rs == H Pseudolaudanine: Rl = OH R2 == Ra '" F!.l == OCHa Cryptopine: R1 = R~ = CHa Ra-R.! == CH2 As;= H Armepavine: R1 .. ~ = OOHa Ra = H R.! '" OH 12-MethoxyaIIocryptopine: R1-R2 == C~ Ra '" F4 .. C/-Is As=OCHa RRQtQBE:REH:BIN§S eENZQRHcNANtHRIDINIES C~O ORa QR2 OCHa Chelerytlirine: Rl == R2 = CHa R$-F!.l '" CH2 As '" H Telrahydropalrtla.tlne Sanguinarine: R1-R2 and Ra-F!.l '" CH2 As== H N,Methy~etra.hydropaltnatine $angLJitubine: Rl-R2 = CH2 Ra '" ~ == CHa Rs == OCHa Fig. 2 continued. values of these alkaloids to the species that produce them are also discussed. DIStRIBUTIONAND PHYSIOLOGICAL ACTIVITY OF ARCTOMECON ALKALOIDS OR2 The presence ofalkaloids (i. e., the ability to i)ihYcltochelerythrine synthesize or accumulate alkalOids) occurs ill Dihydrosahguinarirte many lineages within the plant kingdom, es­ pecially among the dicotyledons. A briefsum­ Fig. 2. Structures of alkaloids found in Arctomecon mary ofthe distribution ill the plant kingdom (Papaveraceae). ofthe alkaloid types reported in Arctomecon and their!mownphysiological activity follows. sanguinarine, sanguirubine, dihydrochelery, Cordell (1981) reviewed the phylogenetic thrine, and dihydrosanguinarine; the tetra, distribution and pharmacologJcal activity of hydiobenzylisoquinolines armepavine, pseu, alkaloids, In addition to the Papaveracea.e, dolaudanine, and reticuline; and the proto­ the protopines are found in four plant fami­ berberines tetrahydropalmatine a.nd N­ lies (Berberidaceae, Fumariaceae, Ranuncu­ rnethyltetra.hydropalmatine. One of these, laceae, 'and Rutaceae) and are represented 12-methoxyallocryptopine, was reported for by about 20 compounds. The physiological the first tirne in our earlier study (Raynie et al. effects of the protopines on. mammals in~ 1990). In this contribution, the alkaloids of elude active dilation of coronary vessels Arctomecon are compared with the alkaloids and local anesthetic effects (Preininger 1975). ofother genera ofPapaveraceae. The possible The benzophenanthridines are limited to the 1991] ALKALOIDS IN ARCTOMECON 399 OH OH OH .OH Norlauganosoline 1 Reticuline DihydroXYRhenyl~ acetl'ilaehyde Fig. 3. Initial steps in biosynthetic scheme ofPapaveraceae alkaloids from phenylalanine (after Preininger 1986). Papaveraceae, Fumariaceae, and Rutaceae. Papaveraceae is the presence of alkaloids Chelerythrine and sanguinarine, representa­ derived from tetrahydroisoquipolines (prei~ tive benzophenanthridines found in Arctome~ ninger 1986). Preininger (1986) has reviewed, can, are reported to have cytotoxic, antifun~ by genus, the alkaloids of the Papaveraceae gal, antiprotozoal, antibacterial, and potential and demonstrated how the biodiversity of anticancer activity (Cordell 1981). The tetra~ the poppy family is reflected in its chemical hydrobenzylisoquinolines, especially reticu~ diversity. The isoquinoline alkaloids can be line, are best lmown as b:iosynthetic inter­ biosynthesized from the am:ino acid phenyl­ mediates for many other alkaloids. The alanine by the condensation ofdopamine with protoberberines are among the most widely 3,4~dih)'droxyphenylacetaldehyde followed distributed of the isoquinoline alkaloids, by the Mannich condensation, )':ielding nOr~ occurring in n:ine plant families, includ:ing laudanosoline. From norlaudanosoline, inter," Annonaceae, Berberidaceae, Fumariaceae, mediates such as reticuline and orientaline Lauraceae, Menispermaceae, Papaveraceae, are formed in the biosynthesis ofa variety of and Rutaceae. Over 40 Protoberberines are isoquinoline types (Preininger 1986). This lmown. They display at least three types biosynthetic scheme is shown in Figure 3. of biological activity; antimicrobial, stimula­ According to Preininger's review (1986), tion ofuterine contractions, and antileukemic protoberberines, benzophenanthridines, and and antineoplastic. protopines are the mostwidespread alkaloids in the Papaveraceae, present in almost all RELATIONSHIP OF ARCTOMECONALKALOIDS genera. Quaternary tetrahydroprotoberbep IN THE PAPAVERACEAE ines serve as intermediates inthebiosynthetic processes that produce the foregoing alka­ The Fumariaceae and Papaveraceae are loids. Consequentlythese alkaloids were con­ closely related families in the order Papa­ sidered as a chemotaxonomically significant verales. According to Cronquist (1981), the characteristic of the Papaveraceae. As dis­ poppy family, Papaveraceae, contains 25 cussed earlier, alkaloids from each of these genera and about 200 species. This family is classes, as well as tetrahydrobenZ)'lisoquino~ unusual in that all ofits species are reported line alkaloids, occur in Arctomecon. Table 1 to contain alkaloids (Pelletier 1970). A major shows the distri.bution of the alkaloids found feature of both the Fumariaceae and the in Arctomecon among other Papaveraceae 400 GREATBASIN NATURALIST [Volume 51 TABLE 1. Distribution of alkaloids known to occur in widely distributed alkaloids in the Papaver­ Arctomecon among other genera of the Papaveraceae. aceae. As indicated in Table 1, Meconella The numbers at the head ofeach column represent Arc­ tomecon alkaloids, each ofwhich is identified in the foot­ and Roemeria are the only genera that do not note. contain at least one of the five benzophenan­ thridines reported in Arctomecon. Dendro­ Alkaloid mecon and Meconopsis are the only genera in Aa B CD which sanguinarine is reported in the absence Genus 123 45 6 7 8 9 10 II 12 13 of chelerythrine; however, the
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