Erysimum cheiranthoides, the treacle-mustard,wormseed wallflower, or wormseed mustard is a species of Erysimum native to most of central and northern Europe and northern and central Asia.[2][3][4][5] Like other Erysimum species, E. cheiranthoides accumulates two major classes of defensive chemicals: glucosinolates and cardiac glycosides.
Description
It is a herbaceous, annual plant similar in appearance to many other mustards, growing an erect stem 15–100 cm (5.9–39.4 in),[6] (rarely 150 cm) tall.[7] The leaves are lanceolate to elliptic, 2–11 cm long and 0.5–1 cm broad, with an entire to coarsely toothed margin. It blooms in summer, between June and August.[6][8] The flowers are bright yellow, 5–12 mm diameter, and produced in an erect inflorescence. Later, it produces a slender cylindrical capsule, 1–3 cm (rarely 5 cm) long, containing several small, pale brown [6] or dark brown seeds.[3][4][9]
It is commonly known as treacle-mustard,[6] or wormseed wallflower.[8][7] The treacle mustard name came from the Greek word 'theriaki' meaning antidote to poisonous bites as the plant was thought to have healing properties. The name 'wormseed wallflower' arose from the seeds of the plant being made into treacle, to treat intestinal worms in children.[6]
Distribution
Erysimum cheiranthoides is native to temperate areas of Europe and Asia.[5]
It grows in disturbed areas, fields,[8] and dry stream beds.[7] It is normally found at altitudes of 0–3,000 m (0–9,843 ft) above sea level.[7]
Chemical ecology
Like other members of the genus Erysimum, E. cheiranthoides produces two major classes of chemical defenses against herbivory: glucosinolates, which are characteristic of the plant family Brassicaceae,[14] and cardiac glycosides (cardenolides), a class of chemicals produced by at least twelve different plant families.[15][16] Glucosinolates found in E. cheiranthoides include glucoiberin, glucoerucin, glucocheirolin, and glucoiberverin.[17][18] Cardenolides reported in E. cheiranthoides seeds include strophanthidin, digitoxigenin, cannogenol, erychroside, erysimoside, erycordin, cheiranthoside, glucoerysimoside, and glucodigifucoside.[19][20][21][22][23][24] Grafting experiments and genetic crosses indicate that cardenolides are produced in the leaves of E. cheiranthoides and are transported to other parts of the plant.[25]
Some crucifer-specialist insect herbivores do not feed and/or oviposit readily on E. cheiranthoides.Anthocharis cardamines (orange tip butterfly), which oviposits on almost all crucifer species, avoids E. cheiranthoides.[26] Similarly, the crucifer-feeding specialist Pieries rapae (white cabbage butterfly) is deterred from feeding and oviposition on E. cheiranthoides.[27][28][29][30][31] However, another pierid species, Pieris napi oleracea (green veined white butterfly), not only is less sensitive to exogenously added cardenolides than P. rapae in oviposition assays, but also oviposits more readily on E. cheiranthoides leaves.[32][33]
In the case of P. rapae, oviposition experiments with extracts of E. cheiranthoides sprayed onto Brassica oleracea (cabbage) identified both attractants and deterrents.[28][29] Whereas 3-methylsulfinylpropyl glucosinolate and 3-methylsufonylpropyl glucosinolate stimulated oviposition,[30][33] erysimoside and erychroside in E. cheiranthoides extracts were deterrent.[31][34] By contrast, another cardiac glycoside, erycordin, was inactive in this oviposition assay. Pieris rapae tarsal sensilla respond to both glucosinolates and cardenolides, indicating that these compounds are detected on the leaf surface prior to oviposition.[35] Consistent with the deterrent effects on oviposition, cardenolides from E. cheiranthoides leaf extracts also served as feeding deterrents for P. rapae caterpillars.[31][30] However, P. rapae adults readily lay eggs and caterpillars feed on mutant E. cheiranthoides plants that lack cardenolides.[36]
Predatory paper wasps (Polistes dominulus) required more time to consume Pieris napi (green-veined white) caterpillars that had fed on E. cheiranthoides than those that had fed on Brassica oleracea (cabbage).[37] This was ascribed to the time that it took the wasps to selectively remove the caterpillar guts, which contained plant material.
Use as a model organism
Because Erysimum is in the family Brassicaceae, it has been proposed that many of the genetic resources that already exist for Arabidopsis thaliana (an extensively studied model organism) can be used with Erysimum to aide in genetic analysis, making this genus particularly attractive for studying the cardenolide biosynthetic pathway.[38][39]E. cheiranthoides itself is diploid and has a relatively small genome (~200 Mbp across 8 chromosomes), can be grown from seed to seed production as fast as 10 weeks, and performs well in a laboratory setting.[39][40] The genome of E. cheiranthoides variety Elbtalaue has been sequenced.[41][42] As E. cheiranthoides has many genetic similarities to A. thaliana, it is likely that techniques for genetically modifying A. thaliana and related research methods will also work for E. cheiranthoides.[39] Mutated isolates of E. cheiranthoides with altered cardiac glycoside content have been identified.[43]
Medicinal uses
Cardiac glycosides, which are abundant in E. cheiranthoides, have been used for treating heart disease and other ailments in traditional and modern medicine.[44][45][46][47][48][49] However, E. cheiranthoides is not a commonly used source of these compounds. Nevertheless, E. cheiranthoides has been used as an herbal remedy in traditional Chinese medicine.[50] European herbalists in the 16th century, used the plant as a remedy for insect and animal bites.[6] The common name wormseed wallflower comes from the use of E. cheiranthoides in treating intestinal worms.[6]
^Fahey, Jed W.; Zalcmann, Amy T.; Talalay, Paul (2001). "The chemical diversity and distribution of glucosinolates and isothiocyanates among plants". Phytochemistry. 56 (1): 5–51. doi:10.1016/S0031-9422(00)00316-2. ISSN0031-9422. PMID11198818.
^Cole, Rosemary A. (1976). "Isothiocyanates, nitriles and thiocyanates as products of autolysis of glucosinolates in Cruciferae". Phytochemistry. 15 (5): 759–762. doi:10.1016/S0031-9422(00)94437-6. ISSN0031-9422.
^Makarevich, I. F.; Kolesnikov, D. G. (1965). "Cardenolides of the seeds ofErysimum cheiranthoides L.". Chemistry of Natural Compounds. 1 (5): 286–287. doi:10.1007/BF00563707. ISSN1573-8388. S2CID4813099.
^ abRenwick, J. A. A.; Radke, Celia D. (1987). "Chemical stimulants and deterrents regulating acceptance or rejection of crucifers by cabbage butterflies". Journal of Chemical Ecology. 13 (7): 1771–1776. doi:10.1007/bf00980217. ISSN0098-0331. PMID24302344. S2CID24473740.
^ abRenwick, J. A. A.; Radke, Celia D. (1985). "Constituents of host- and non-host plants deterring oviposition by the cabbage butterfly, Pieris rapae". Entomologia Experimentalis et Applicata. 39 (1): 21–26. doi:10.1111/j.1570-7458.1985.tb03538.x. ISSN0013-8703. S2CID86713452.
^ abcDimock, M. B.; Renwick, J. A. A.; Radke, C. D.; Sachdev-gupta, K. (1991). "Chemical constituents of an unacceptable crucifer,Erysimum cheiranthoides, deter feeding byPieris rapae". Journal of Chemical Ecology. 17 (3): 525–533. doi:10.1007/bf00982123. ISSN0098-0331. PMID24258803. S2CID32639023.
^ abcSachdev-Gupta, K.; Radke, Cd.; Renwick, J. A. A.; Dimock, M. B. (1993). "Cardenolides fromErysimum cheiranthoides: Feeding deterrents toPieris rapae larvae". Journal of Chemical Ecology. 19 (7): 1355–1369. doi:10.1007/bf00984881. ISSN0098-0331. PMID24249167. S2CID258932.
^Huang, Xinpei; Renwick, J. A. A.; Sachdev-Gupta, K. (1993). "A chemical basis for differential acceptance ofErysimum cheiranthoides by twoPieris species". Journal of Chemical Ecology. 19 (2): 195–210. doi:10.1007/bf00993689. ISSN0098-0331. PMID24248868. S2CID29886753.
^ abHuang, Xinpei; Renwick, J. A. A. (1993). "Differential selection of host plants by two Pieris species: the role of oviposition stimulants and deterrents". Entomologia Experimentalis et Applicata. 68 (1): 59–69. doi:10.1111/j.1570-7458.1993.tb01689.x. ISSN0013-8703. S2CID84979013.
^Renwick, J. A. A.; Radke, C. D.; Sachdev-Gupta, K. (1989). "Chemical constituents ofErysimum cheiranthoides deterring oviposition by the cabbage butterfly,Pieris rapae". Journal of Chemical Ecology. 15 (8): 2161–2169. doi:10.1007/bf01014106. ISSN0098-0331. PMID24272377. S2CID20866270.
^STÄDLER, ERICH; RENWICK, J. A. A.; RADKE, CELIA D.; SACHDEV-GUPTA, KUSUM (1995). "Tarsal contact chemoreceptor response to glucosinolates and cardenolides mediating oviposition in Pieris rape". Physiological Entomology. 20 (2): 175–187. doi:10.1111/j.1365-3032.1995.tb00814.x. ISSN0307-6962. S2CID86576260.
^Rayor, Linda S.; Mooney, Larissa J.; Renwick, J. Alan (2007). "Predatory Behavior of Polistes dominulus Wasps in Response to Cardenolides and Glucosinolates in Pieris napi Caterpillars". Journal of Chemical Ecology. 33 (6): 1177–1185. doi:10.1007/s10886-007-9283-4. ISSN0098-0331. PMID17453324. S2CID25675444.
^Munkert, Jennifer; Bauer, Peter; Burda, Edyta; Müller-Uri, Frieder; Kreis, Wolfgang (2011). "Progesterone 5β-reductase of Erysimum crepidifolium: cDNA cloning, expression in Escherichia coli, and reduction of enones with the recombinant protein". Phytochemistry. 72 (14–15): 1710–1717. doi:10.1016/j.phytochem.2011.06.007. PMID21767854.
^Bainard, Jillian D.; Bainard, Luke D.; Henry, Thomas A.; Fazekas, Aron J.; Newmaster, Steven G. (2012). "A multivariate analysis of variation in genome size and endoreduplication in angiosperms reveals strong phylogenetic signal and association with phenotypic traits". New Phytologist. 196 (4): 1240–50. doi:10.1111/j.1469-8137.2012.04370.x. PMID23078229.
^Withering, William (2014), "AN ACCOUNT OF THE INTRODUCTION of FOXGLOVE INTO MODERN PRACTICE", An Account of the Foxglove, and Some of Its Medical Uses, Cambridge University Press, pp. 1–10, doi:10.1017/cbo9781107706132.004, ISBN9781107706132
^Gurel, Ekrem; Karvar, Serhan; Yucesan, Buhara; Eker, Ismail; Sameeullah, Muhammad (2018). "An Overview of Cardenolides in Digitalis - More Than a Cardiotonic Compound". Current Pharmaceutical Design. 23 (34): 5104–5114. doi:10.2174/1381612823666170825125426. ISSN1381-6128. PMID28847302.
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