Erysimum cheiranthoides

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Erysimum cheiranthoides
Gewone steenraket bloemen.jpg
Status TNC G5.svg
Secure  (NatureServe) [1]
Scientific classification OOjs UI icon edit-ltr.svg
Kingdom: Plantae
Clade: Tracheophytes
Clade: Angiosperms
Clade: Eudicots
Clade: Rosids
Order: Brassicales
Family: Brassicaceae
Genus: Erysimum
Species:
E. cheiranthoides
Binomial name
Erysimum cheiranthoides
L.
Synonyms

Cheirinia cheiranthoides

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.

Contents

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]

Taxonomy

It was formerly described by the Swedish botanist Carl Linnaeus in his seminal publication 'Species Plantarum' in 1753, on page 661. [10] [11]

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 mustard' arose from the seeds of the plant being made into treacle, to treat intestinal worms in children. [6]

Distribution

Erysimum cheiranthoides Gewone steenraket plant.jpg
Erysimum cheiranthoides

Erysimum cheiranthoides is native to temperate areas of Europe and Asia. [5]

Range

It is found in Asia within China (in the provinces of Heilongjiang, Jilin, Nei Monggol and Xinjiang), Japan, Korea, Mongolia and Siberia. In Eastern Europe, it is found in Belarus, Estonia, Latvia, Lithuania, Moldova and Ukraine. In middle Europe, it is found within Austria, Belgium, the Czech Republic, Germany, Hungary, the Netherlands, Poland, Slovakia and Switzerland. In Northern Europe, in Denmark, Finland, Norway, Sweden and the United Kingdom. In Southeastern Europe, within Bosnia and Herzegovina, Bulgaria, Croatia, France, Romania, Serbia and Slovenia. [2] [3] [4] [5]

It is also widely naturalised outside of its native range, [9] [12] from New Zealand, other parts of Europe, [5] to North America [13] (including parts of Canada), and Argentina (in Tierra del Fuego). [5]

Habitat

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] In 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]

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). [36] 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

Erysimum cheiranthoides variety Elbtalaue in a growth chamber Erysimum cheiranthoides variety Elbtalaue.jpg
Erysimum cheiranthoides variety Elbtalaue in a growth chamber

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. [37] [38] 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. [38] [39] The genome of E. cheiranthoides variety Elbtalaue has been sequenced. [40] [41] 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. [38] Mutated isolates of E. cheiranthoides with altered cardiac glycoside content have been identified. [42]

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. [43] [44] [45] [46] [47] [48] 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. [49] 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]

Related Research Articles

<span class="mw-page-title-main">Cardiac glycoside</span> Class of organic compounds

Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.

<i>Erysimum</i> Genus of flowering plants

Erysimum, or wallflower, is a genus of flowering plants in the cabbage family, Brassicaceae. It includes more than 150 species, both popular garden plants and many wild forms. The genus Cheiranthus is sometimes included here in whole or in part. Erysimum has since the early 21st century been ascribed to a monogeneric cruciferous tribe, Erysimeae, characterised by sessile, stellate (star-shaped) and/or malpighiaceous (two-sided) trichomes, yellow to orange flowers and multiseeded siliques.

<i>Asclepias</i> Genus of flowering plants

Asclepias is a genus of herbaceous, perennial, flowering plants known as milkweeds, named for their latex, a milky substance containing cardiac glycosides termed cardenolides, exuded where cells are damaged. Most species are toxic to humans and many other species, primarily due to the presence of cardenolides. However, as with many such plants, some species feed upon them or from them. The most notable of them is the monarch butterfly, which uses and requires certain milkweeds as host plants for their larvae.

Saponins, also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed but found particularly in soapwort, a flowering plant, the soapbark tree and soybeans. They are used in soaps, medicines, fire extinguishers, speciously as dietary supplements, for synthesis of steroids, and in carbonated beverages. Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin and quillaia, a bark extract used in beverages.

<i>Pieris rapae</i> Species of butterfly

Pieris rapae is a small- to medium-sized butterfly species of the whites-and-yellows family Pieridae. It is known in Europe as the small white, in North America as the cabbage white or cabbage butterfly, on several continents as the small cabbage white, and in New Zealand as the white butterfly. The butterfly is recognizable by its white color with small black dots on its wings, and it can be distinguished from P. brassicae by its larger size and the black band at the tip of its forewings.

<i>Iberis</i> Genus of flowering plants

Iberis, commonly called candytuft, is a genus of flowering plants belonging to the family Brassicaceae. It comprises annuals, evergreen perennials and subshrubs native to the Old World. The name "candytuft" is not related to candy, but derives from Candia, the former name of Iraklion on the Island of Crete.

<span class="mw-page-title-main">Glucosinolate</span> Class of chemical compounds

Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damaged. These natural chemicals most likely contribute to plant defence against pests and diseases, and impart a characteristic bitter flavor property to cruciferous vegetables.

<span class="mw-page-title-main">Sinigrin</span> Chemical compound

Sinigrin or allyl glucosinolate is a glucosinolate that belongs to the family of glucosides found in some plants of the family Brassicaceae such as Brussels sprouts, broccoli, and the seeds of black mustard. Whenever sinigrin-containing plant tissue is crushed or otherwise damaged, the enzyme myrosinase degrades sinigrin to a mustard oil, which is responsible for the pungent taste of mustard and horseradish. Seeds of white mustard, Sinapis alba, give a less pungent mustard because this species contains a different glucosinolate, sinalbin.

<i>Barbarea vulgaris</i> Species of flowering plant

Barbarea vulgaris, also called wintercress, or alternatively winter rocket, rocketcress, yellow rocketcress, yellow rocket, wound rocket, herb barbara, creases, or creasy greens, is a biennial herb of the genus Barbarea, belonging to the family Brassicaceae.

<span class="mw-page-title-main">Glucobrassicin</span> Chemical compound

Glucobrassicin is a type of glucosinolate that can be found in almost all cruciferous plants, such as cabbages, broccoli, mustards, and woad. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, this specific isothiocyanate is expected to be highly unstable, and has indeed never been detected. The observed hydrolysis products when isolated glucobrassicin is degraded by myrosinase are indole-3-carbinol and thiocyanate ion, which are envisioned to result from a rapid reaction of the unstable isothiocyanate with water. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue or in intact plants.

<i>Asclepias curassavica</i> Species of flowering plant

Asclepias curassavica, commonly known as tropical milkweed, is a flowering plant species of the milkweed genus, Asclepias. It is native to the American tropics and has a pantropical distribution as an introduced species. Other common names include bloodflower or blood flower, cotton bush, hierba de la cucaracha, Mexican butterfly weed, redhead, scarlet milkweed, and wild ipecacuanha.

<i>Delia</i> (fly) Genus of flies

Delia flies are members of the Anthomyiidae family within the superfamily Muscoidae. The identification of different species of Delia can be very difficult for non-specialists as the diagnostic characteristics used for immature and/or female specimens may be inconsistent between species. Past taxonomic keys were not as comprehensive in their identification of Delia specimens; they were either too reliant on genetic characteristics, focused solely on a specific life stage, or were focused only on certain species. However current taxonomic keys aim to be more thorough by not only including morphological diagnostics for males, females, and immature specimens of various species, but also their genetic make-up or molecular barcode.

<span class="mw-page-title-main">Cardenolide</span> Chemical compound

A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycosides are often toxic; specifically, they are heart-arresting. Cardenolides are toxic to animals through inhibition of the enzyme Na+/K+‐ATPase, which is responsible for maintaining the sodium and potassium ion gradients across the cell membranes.

<span class="mw-page-title-main">Gluconasturtiin</span> Chemical compound

Gluconasturtiin or phenethyl glucosinolate is one of the most widely distributed glucosinolates in the cruciferous vegetables, mainly in the roots, and is probably one of the plant compounds responsible for the natural pest-inhibiting properties of growing crucifers, such as cabbage, mustard or rape, in rotation with other crops. This effect of gluconasturtiin is due to its degradation by the plant enzyme myrosinase into phenethyl isothiocyanate, which is toxic to many organisms.

<i>Reseda luteola</i> Species of flowering plant

Reseda luteola is a flowering plant species in the family Resedaceae. Common names include dyer's rocket, dyer's weed, weld, woold, and yellow weed. A native of Europe and Western Asia, the plant can be found in North America as an introduced species and common weed. While other resedas were used for the purpose, this species was the most widely used source of the natural dye known as weld. The plant is rich in luteolin, a flavonoid which produces a bright yellow dye. The yellow could be mixed with the blue from woad to produce greens such as Lincoln green.

<span class="mw-page-title-main">Glucotropaeolin</span> Chemical compound

Glucotropaeolin or benzyl glucosinolate is a glucosinolate found in cruciferous vegetables, particularly garden cress. Upon enzymatic activity, it is transformed into benzyl isothiocyanate, which contributes to the characteristic flavor of these brassicas.

<span class="mw-page-title-main">Calotropin</span> Chemical compound

Calotropin is a toxic cardenolide found in plants in the family Asclepiadoideae. In extreme cases, calotropin poisoning can cause respiratory and cardiac failure. Accidental poisoning is common in livestock who have ingested milkweed. Calotropin is commonly stored as a defense mechanism by insects that eat milkweeds as their main food source.

<i>Erysimum collinum</i> Species of plant

Erysimum collinum is a plant species in the family Brassicaceae. It is a member of the genus Erysimum, which includes between 150 and 350 species in the Northern Hemisphere.

<span class="mw-page-title-main">Georg Jander</span> American plant biologist

Georg Jander is an American plant biologist at the Boyce Thompson Institute in Ithaca, New York. He has an adjunct appointment in the Plant Biology Section of the School of Integrative Plant Sciences at Cornell University. Jander is known for his molecular research identifying genes for biochemical compounds of ecological and agricultural importance, particularly those plant traits involved in resistance to insect pests.

<i>Erysimum crepidifolium</i> Species of plant

Erysimum crepidifolium, the pale wallflower, is a plant species in the crucifer family, Brassicaceae. It is a member of the genus Erysimum, which includes between 150 and 350 species in the Northern Hemisphere.

References

  1. ↑ NatureServe (2023). "Erysimum cheiranthoides". Arlington, Virginia. Retrieved 6 December 2023.
  2. 1 2 Flora Europaea: Erysimum cheiranthoides
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  4. 1 2 3 Flora of China: Erysimum cheiranthoides
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  6. 1 2 3 4 5 6 7 Reader's Digest Field Guide to the Wild Flowers of Britain. Reader's Digest. 1981. p. 47. ISBN   9780276002175.
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  18. ↑ Hugentobler, U.; Renwick, J. A. A. (1995). "Effects of plant nutrition on the balance of insect relevant cardenolides and glucosinolates in Erysimum cheiranthoides". Oecologia. 102 (1): 95–101. Bibcode:1995Oecol.102...95H. doi:10.1007/bf00333315. ISSN   0029-8549. PMID   28306812. S2CID   12564977.
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  21. ↑ Lei, Zhen-Huan; Jin, Zhe-Xion; Ma, Ying-Li; Tai, Bao-Shan; Kong, Qi; Yahara, Shoji; Nohara, Toshihiro (1998). "Cardiac glycosides from erysimum cheiranthoides". Phytochemistry. 49 (6): 1801–1803. doi:10.1016/S0031-9422(98)00264-7. ISSN   0031-9422. PMID   11711105.
  22. ↑ Lei, Zhen-Huan; Yahara, Shoji; Nohara, Toshihiro; Tai, Bao-Shan; Xiong, Jin-Zhe; Ma, Ying-Li (2000). "Cardiac Glycosides form Erysimum cheiranthoides". Chemical and Pharmaceutical Bulletin. 48 (2): 290–292. doi: 10.1248/cpb.48.290 . ISSN   0009-2363. PMID   10705523.
  23. ↑ Lei, Zhen-Huan; Kuniyasu, Akihiko; Tai, Bao-Shin; Nakayama, Hitoshi; Nohara, Toshihiro (2001). "Na+,K+-ATPase Inhibiting Activity of Cardiac Glycosides from Erysimum cheiranthoides". Planta Medica. 67 (4): 369–370. doi:10.1055/s-2001-14309. ISSN   0032-0943. PMID   11458460. S2CID   260279206.
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  25. ↑ Alani, Martin L.; Younkin, Gordon C.; Mirzaei, Mahdieh; Kumar, Pavan; Jander, Georg (October 2, 2021). "Acropetal and basipetal cardenolide transport in Erysimum cheiranthoides (wormseed wallflower)". Phytochemistry. 192: 112965. doi:10.1016/j.phytochem.2021.112965. PMC   8655687 . PMID   34610557.
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  35. ↑ 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. ISSN   0307-6962. S2CID   86576260.
  36. ↑ 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. ISSN   0098-0331. PMID   17453324. S2CID   25675444.
  37. ↑ 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. PMID   21767854.
  38. 1 2 3 Züst, Tobias; Mirzaei, Mahdieh; Jander, Georg (2018). "Erysimum cheiranthoides, an ecological research system with potential as a genetic and genomic model for studying cardiac glycoside biosynthesis". Phytochemistry Reviews. 17 (6): 1239. doi:10.1007/s11101-018-9562-4. S2CID   53857970.
  39. ↑ 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. PMID   23078229.
  40. ↑ "Erysimum Genome Site". www.erysimum.org. September 17, 2019.
  41. ↑ Züst, Tobias; Strickler, Susan R; Powell, Adrian F; Mabry, Makenzie E; An, Hong; Mirzaei, Mahdieh; York, Thomas; Holland, Cynthia K; Kumar, Pavan; Erb, Matthias; Petschenka, Georg; Gómez, José-María; Perfectti, Francsco; Müller, Caroline; Pires, J Chris; Mueller, Lukas; Jander, Georg (2020-04-07). "Independent evolution of ancestral and novel defenses in a genus of toxic plants (Erysimum, Brassicaceae)". eLife. 9: e51712. doi: 10.7554/eLife.51712 . ISSN   2050-084X. PMC   7180059 . PMID   32252891.
  42. ↑ Mirzaei, Mahdieh; Züst, Tobias; Younkin, Gordon C.; Hastings, Amy P.; Alani, Martin L.; Agrawal, Anurag A.; Jander, Georg (2020). "Less Is More: a Mutation in the Chemical Defense Pathway of Erysimum cheiranthoides (Brassicaceae) Reduces Total Cardenolide Abundance but Increases Resistance to Insect Herbivores". Journal of Chemical Ecology. 46 (11–12): 1131–1143. doi:10.1007/s10886-020-01225-y. ISSN   0098-0331. PMID   33180277. S2CID   218539206.
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