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Glucosinolate

January 31, 2023

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.[1]

Glucosinolate structure; side group R varies

Plants with glucosinolates

Glucosinolates occur as secondary metabolites of almost all plants of the order Brassicales. Ordered in the Brassicales are for example the economically important family Brassicaceae as well as Capparaceae and Caricaceae. Outside of the Brassicales, the genera Drypetes[2] and Putranjiva in the family Putranjivaceae, are the only other known occurrence of glucosinolates. Glucosinolates occur in various edible plants such as cabbage (white cabbage, Chinese cabbage, broccoli), Brussels sprouts, watercress, horseradish, capers, and radishes where the breakdown products often contribute a significant part of the distinctive taste. The glucosinolates are also found in seeds of these plants.[1]

Chemistry

Glucosinolates constitute a natural class of organic compounds that contain sulfur and nitrogen and are derived from glucose and an amino acid. They are water-soluble anions and belong to the glucosides. Every glucosinolate contains a central carbon atom, which is bound to the sulfur atom of the thioglucose group, and via a nitrogen atom to a sulfate group (making a sulfated aldoxime). In addition, the central carbon is bound to a side group; different glucosinolates have different side groups, and it is variation in the side group that is responsible for the variation in the biological activities of these plant compounds. The essence of glucosinolate chemistry is their ability to convert into an isothiocyanate (a "mustard oil") upon hydrolysis of the thioglucoside bond by the enzyme myrosinase.[3]

The semisystematic naming of glucosinolates consists of the chemical name of the aforementioned side group followed by "(-)glucosinolate". The spelling of a glucosinolate name as one word or two (e.g. allylglucosinolate versus allyl glucosinolate) has the same meaning, and both spellings are in use. But isothiocyanates must be spelled as two words.[3]

The following are some glucosinolates and their isothiocyanate products:[3]

Biochemistry

Natural diversity from a few amino acids

About 132 different glucosinolates are known to occur naturally in plants. They are synthesized from certain amino acids: So-called aliphatic glucosinolates derived from mainly methionine, but also alanine, leucine, isoleucine, or valine. (Most glucosinolates are actually derived from chain-elongated homologues of these amino acids, e.g. glucoraphanin is derived from dihomomethionine, which is methionine chain-elongated twice). Aromatic glucosinolates include indolic glucosinolates, such as glucobrassicin, derived from tryptophan and others from phenylalanine, its chain-elongated homologue homophenylalanine, and sinalbin derived from tyrosine.[3]

Enzymatic activation

Main article: Mustard oil bomb

The plants contain the enzyme myrosinase, which, in the presence of water, cleaves off the glucose group from a glucosinolate.[4] The remaining molecule then quickly converts to an isothiocyanate, a nitrile, or a thiocyanate; these are the active substances that serve as defense for the plant. Glucosinolates are also called mustard oil glycosides. The standard product of the reaction is the isothiocyanate (mustard oil); the other two products mainly occur in the presence of specialised plant proteins that alter the outcome of the reaction.[5]

 
A mustard oil glycoside 1 is converted to an isothiocyanate 3 (mustard oil). Glucose 2 is liberated as well, only the β-form is shown.– R = allyl, benzyl, 2-phenylethyl etc.[citation needed]

In the chemical reaction illustrated above, the red curved arrows in the left side of figure are simplified compared to reality, as the role of the enzyme myrosinase is not shown. However, the mechanism shown is fundamentally in accordance with the enzyme-catalyzed reaction.

In contrast, the reaction illustrated by red curved arrows at the right side of the figure, depicting the rearrangement of atoms resulting in the isothiocyanate, is expected to be non-enzymatic. This type of rearrangement can be named a Lossen rearrangement, or a Lossen-like rearrangement, since this name was first used for the analogous reaction leading to an organic isocyanate (R-N=C=O).

To prevent damage to the plant itself, the myrosinase and glucosinolates are stored in separate compartments of the cell or in different cells in the tissue, and come together only or mainly under conditions of physical injury (see Myrosinase).

Biological effects

Humans and other mammals

Toxicity

The use of glucosinolate-containing crops as primary food source for animals can have negative effects if the concentration of glucosinolate is higher than what is acceptable for the animal in question, because some glucosinolates have been shown to have toxic effects (mainly as goitrogens and anti-thyroid agents) in both humans and animals[failed verification] at high doses.[6] However, tolerance level to glucosinolates varies even within the same genus (e.g. Acomys cahirinus and Acomys russatus).[7]

Taste and eating behavior

The glucosinolate sinigrin, among others, was shown to be responsible for the bitterness of cooked cauliflower and Brussels sprouts.[1][8] Glucosinolates may alter animal eating behavior.[9]

Research

The isothiocyanates formed from glucosinolates are under laboratory research to assess the expression and activation of enzymes that metabolize xenobiotics, such as carcinogens.[10] Observational studies have been conducted to determine if consumption of cruciferous vegetables affects cancer risk in humans, but there is insufficient clinical evidence to indicate that consuming isothiocyanates in cruciferous vegetables is beneficial, according to a 2017 review.[10]

Insects

Glucosinolates and their products have a negative effect on many insects, resulting from a combination of deterrence and toxicity. In an attempt to apply this principle in an agronomic context, some glucosinolate-derived products can serve as antifeedants, i.e., natural pesticides.[11]

In contrast, the diamondback moth, a pest of cruciferous plants, may recognize the presence of glucosinolates, allowing it to identify the proper host plant.[12] Indeed, a characteristic, specialised insect fauna is found on glucosinolate-containing plants, including butterflies, such as large white, small white, and orange tip, but also certain aphids, moths, such as the southern armyworm, sawflies, and flea beetles.[citation needed] For instance, the large white butterfly deposits its eggs on these glucosinolate-containing plants, and the larvae survive even with high levels of glucosinolates and eat plant material containing glucosinolates.[citation needed] The whites and orange tips all possess the so-called nitrile specifier protein, which diverts glucosinolate hydrolysis toward nitriles rather than reactive isothiocyanates.[13] In contrast, the diamondback moth possesses a completely different protein, glucosinolate sulfatase, which desulfates glucosinolates, thereby making them unfit for degradation to toxic products by myrosinase.[14]

Other kinds of insects (specialised sawflies and aphids) sequester glucosinolates.[15] In specialised aphids, but not in sawflies, a distinct animal myrosinase is found in muscle tissue, leading to degradation of sequestered glucosinolates upon aphid tissue destruction.[16] This diverse panel of biochemical solutions to the same plant chemical plays a key role in the evolution of plant-insect relationships.[17]

Induced production

The amount produced varies with the degree of herbivory being suffered. The CO2 x herbivory effect is more complex however, and defies generalization: Increased CO2 produces increased, decreased, and unchanged production levels in studies reviewed by Bidart-Bouzat and Imeh-Nathaniel 2008, and there may in fact be genetic variation within the Brassicales.[18]

See also

References

  1. ^ a b c Ishida M, Hara M, Fukino N, Kakizaki T, Morimitsu Y (May 2014). "Glucosinolate metabolism, functionality and breeding for the improvement of Brassicaceae vegetables". Breeding Science. 64 (1): 48–59. doi:10.1270/jsbbs.64.48. PMC 4031110. PMID 24987290.
  2. ^ Rodman JE, Karol KG, Price RA, Sytsma KJ (1996). "Molecules, Morphology, and Dahlgren's Expanded Order Capparales". Systematic Botany. 21 (3): 289–307. doi:10.2307/2419660. JSTOR 2419660.
  3. ^ a b c d Agerbirk N, Olsen CE (May 2012). "Glucosinolate structures in evolution". Phytochemistry. 77: 16–45. doi:10.1016/j.phytochem.2012.02.005. PMID 22405332.
  4. ^ Bongoni R, Verkerk R, Steenbekkers B, Dekker M, Stieger M (September 2014). "Evaluation of different cooking conditions on broccoli (Brassica oleracea var. italica) to improve the nutritional value and consumer acceptance". Plant Foods for Human Nutrition. 69 (3): 228–234. doi:10.1007/s11130-014-0420-2. PMID 24853375. S2CID 35228794.
  5. ^ Burow M, Bergner A, Gershenzon J, Wittstock U (January 2007). "Glucosinolate hydrolysis in Lepidium sativum--identification of the thiocyanate-forming protein". Plant Molecular Biology. 63 (1): 49–61. doi:10.1007/s11103-006-9071-5. PMID 17139450. S2CID 22955134.
  6. ^ "Plants Poisonous to Livestock: Glucosinolates (Goitrogenic Glycosides)". Cornell University, Department of Animal Science. 10 September 2015. Retrieved 16 August 2018.
  7. ^ Samuni-Blank M, Arad Z, Dearing MD, Gerchman Y, Karasov WH, Izhaki I (2013). "Friend or foe? Disparate plant–animal interactions of two congeneric rodents". Evolutionary Ecology. 27 (6): 1069–1080. doi:10.1007/s10682-013-9655-x. S2CID 280376.
  8. ^ Van Doorn HE, Van der Kruk GC, van Holst GJ, Raaijmakers-Ruijs NC, Postma E, Groeneweg B, Jongen WH (1998). "The glucosinolates sinigrin and progoitrin are important determinants for taste preference and bitterness of Brussels sprouts". Journal of the Science of Food and Agriculture. 78: 30–38. doi:10.1002/(SICI)1097-0010(199809)78:1<30::AID-JSFA79>3.0.CO;2-N.
  9. ^ Samuni-Blank M, Izhaki I, Dearing MD, Gerchman Y, Trabelcy B, Lotan A, Karasov WH, Arad Z (July 2012). "Intraspecific directed deterrence by the mustard oil bomb in a desert plant". Current Biology. 10 (22): 1218–1220. doi:10.1016/j.cub.2012.04.051.
  10. ^ a b "Isothiocyanates". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 1 April 2017. Retrieved 26 June 2022.
  11. ^ Furlan L, Bonetto C, Finotto A, Lazzeri L, Malaguti L, Patalano G, Parker W (2010). "The efficacy of biofumigant meals and plants to control wireworm populations". Industrial Crops and Products. 31 (2): 245–254. doi:10.1016/j.indcrop.2009.10.012.
  12. ^ Badenes-Pérez FR, Reichelt M, Gershenzon J, Heckel DG (January 2011). "Phylloplane location of glucosinolates in Barbarea spp. (Brassicaceae) and misleading assessment of host suitability by a specialist herbivore". The New Phytologist. 189 (2): 549–556. doi:10.1111/j.1469-8137.2010.03486.x. PMID 21029103.
  13. ^ Wittstock U, Agerbirk N, Stauber EJ, Olsen CE, Hippler M, Mitchell-Olds T, et al. (April 2004). "Successful herbivore attack due to metabolic diversion of a plant chemical defense". Proceedings of the National Academy of Sciences of the United States of America. 101 (14): 4859–4864. Bibcode:2004PNAS..101.4859W. doi:10.1073/pnas.0308007101. PMC 387339. PMID 15051878.
  14. ^ Ratzka A, Vogel H, Kliebenstein DJ, Mitchell-Olds T, Kroymann J (August 2002). "Disarming the mustard oil bomb". Proceedings of the National Academy of Sciences of the United States of America. 99 (17): 11223–11228. Bibcode:2002PNAS...9911223R. doi:10.1073/pnas.172112899. PMC 123237. PMID 12161563.
  15. ^ Müller C, Agerbirk N, Olsen CE, Boevé JL, Schaffner U, Brakefield PM (December 2001). "Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae". Journal of Chemical Ecology. 27 (12): 2505–2516. doi:10.1023/A:1013631616141. PMID 11789955. S2CID 24529256.
  16. ^ Bridges M, Jones AM, Bones AM, Hodgson C, Cole R, Bartlet E, et al. (January 2002). "Spatial organization of the glucosinolate-myrosinase system in brassica specialist aphids is similar to that of the host plant". Proceedings. Biological Sciences. 269 (1487): 187–191. doi:10.1098/rspb.2001.1861. PMC 1690872. PMID 11798435.
  17. ^ Wheat CW, Vogel H, Wittstock U, Braby MF, Underwood D, Mitchell-Olds T (December 2007). "The genetic basis of a plant-insect coevolutionary key innovation". Proceedings of the National Academy of Sciences of the United States of America. 104 (51): 20427–20431. Bibcode:2007PNAS..10420427W. doi:10.1073/pnas.0706229104. PMC 2154447. PMID 18077380.
  18. ^ Zavala JA, Nabity PD, DeLucia EH (7 January 2013). "An emerging understanding of mechanisms governing insect herbivory under elevated CO2". Annual Review of Entomology. Annual Reviews. 58 (1): 79–97. doi:10.1146/annurev-ento-120811-153544. PMID 22974069.

External links

  • Glucosinolate metabolism pathways from MetaCyc

January 31, 2023
glucosinolate, natural, components, many, pungent, plants, such, mustard, cabbage, horseradish, pungency, those, plants, mustard, oils, produced, from, glucosinolates, when, plant, material, chewed, otherwise, damaged, these, natural, chemicals, most, likely, . 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 1 Glucosinolate structure side group R varies Contents 1 Plants with glucosinolates 2 Chemistry 3 Biochemistry 3 1 Natural diversity from a few amino acids 3 2 Enzymatic activation 4 Biological effects 4 1 Humans and other mammals 4 1 1 Toxicity 4 1 2 Taste and eating behavior 4 1 3 Research 4 2 Insects 5 Induced production 6 See also 7 References 8 External linksPlants with glucosinolates EditGlucosinolates occur as secondary metabolites of almost all plants of the order Brassicales Ordered in the Brassicales are for example the economically important family Brassicaceae as well as Capparaceae and Caricaceae Outside of the Brassicales the genera Drypetes 2 and Putranjiva in the family Putranjivaceae are the only other known occurrence of glucosinolates Glucosinolates occur in various edible plants such as cabbage white cabbage Chinese cabbage broccoli Brussels sprouts watercress horseradish capers and radishes where the breakdown products often contribute a significant part of the distinctive taste The glucosinolates are also found in seeds of these plants 1 Chemistry EditGlucosinolates constitute a natural class of organic compounds that contain sulfur and nitrogen and are derived from glucose and an amino acid They are water soluble anions and belong to the glucosides Every glucosinolate contains a central carbon atom which is bound to the sulfur atom of the thioglucose group and via a nitrogen atom to a sulfate group making a sulfated aldoxime In addition the central carbon is bound to a side group different glucosinolates have different side groups and it is variation in the side group that is responsible for the variation in the biological activities of these plant compounds The essence of glucosinolate chemistry is their ability to convert into an isothiocyanate a mustard oil upon hydrolysis of the thioglucoside bond by the enzyme myrosinase 3 The semisystematic naming of glucosinolates consists of the chemical name of the aforementioned side group followed by glucosinolate The spelling of a glucosinolate name as one word or two e g allylglucosinolate versus allyl glucosinolate has the same meaning and both spellings are in use But isothiocyanates must be spelled as two words 3 The following are some glucosinolates and their isothiocyanate products 3 Allylglucosinolate sinigrin is the precursor of allyl isothiocyanate Benzylglucosinolate Glucotropaeolin is the precursor of benzyl isothiocyanate Phenethylglucosinolate Gluconasturtiin is the precursor of phenethyl isothiocyanate R 4 methylsulfinyl butylglucosinolate Glucoraphanin is the precursor of R 4 methylsulfinyl butyl isothiocyanate sulforaphane R 2 hydroxybut 3 enylglucosinolate progoitrin is probably the precursor of S 2 hydroxybut 3 enyl isothiocyanate which is expected to be unstable and immediately cyclize to form S 5 vinyloxazolidine 2 thione goitrin Biochemistry EditNatural diversity from a few amino acids Edit About 132 different glucosinolates are known to occur naturally in plants They are synthesized from certain amino acids So called aliphatic glucosinolates derived from mainly methionine but also alanine leucine isoleucine or valine Most glucosinolates are actually derived from chain elongated homologues of these amino acids e g glucoraphanin is derived from dihomomethionine which is methionine chain elongated twice Aromatic glucosinolates include indolic glucosinolates such as glucobrassicin derived from tryptophan and others from phenylalanine its chain elongated homologue homophenylalanine and sinalbin derived from tyrosine 3 Enzymatic activation Edit Main article Mustard oil bomb This section needs additional citations for verification Please help improve this article by adding citations to reliable sources Unsourced material may be challenged and removed Find sources Glucosinolate news newspapers books scholar JSTOR March 2019 Learn how and when to remove this template message The plants contain the enzyme myrosinase which in the presence of water cleaves off the glucose group from a glucosinolate 4 The remaining molecule then quickly converts to an isothiocyanate a nitrile or a thiocyanate these are the active substances that serve as defense for the plant Glucosinolates are also called mustard oil glycosides The standard product of the reaction is the isothiocyanate mustard oil the other two products mainly occur in the presence of specialised plant proteins that alter the outcome of the reaction 5 A mustard oil glycoside 1 is converted to an isothiocyanate 3 mustard oil Glucose 2 is liberated as well only the b form is shown R allyl benzyl 2 phenylethyl etc citation needed In the chemical reaction illustrated above the red curved arrows in the left side of figure are simplified compared to reality as the role of the enzyme myrosinase is not shown However the mechanism shown is fundamentally in accordance with the enzyme catalyzed reaction In contrast the reaction illustrated by red curved arrows at the right side of the figure depicting the rearrangement of atoms resulting in the isothiocyanate is expected to be non enzymatic This type of rearrangement can be named a Lossen rearrangement or a Lossen like rearrangement since this name was first used for the analogous reaction leading to an organic isocyanate R N C O To prevent damage to the plant itself the myrosinase and glucosinolates are stored in separate compartments of the cell or in different cells in the tissue and come together only or mainly under conditions of physical injury see Myrosinase Biological effects EditHumans and other mammals Edit Toxicity Edit The use of glucosinolate containing crops as primary food source for animals can have negative effects if the concentration of glucosinolate is higher than what is acceptable for the animal in question because some glucosinolates have been shown to have toxic effects mainly as goitrogens and anti thyroid agents in both humans and animals failed verification at high doses 6 However tolerance level to glucosinolates varies even within the same genus e g Acomys cahirinus and Acomys russatus 7 Taste and eating behavior Edit The glucosinolate sinigrin among others was shown to be responsible for the bitterness of cooked cauliflower and Brussels sprouts 1 8 Glucosinolates may alter animal eating behavior 9 Research Edit The isothiocyanates formed from glucosinolates are under laboratory research to assess the expression and activation of enzymes that metabolize xenobiotics such as carcinogens 10 Observational studies have been conducted to determine if consumption of cruciferous vegetables affects cancer risk in humans but there is insufficient clinical evidence to indicate that consuming isothiocyanates in cruciferous vegetables is beneficial according to a 2017 review 10 Insects Edit Glucosinolates and their products have a negative effect on many insects resulting from a combination of deterrence and toxicity In an attempt to apply this principle in an agronomic context some glucosinolate derived products can serve as antifeedants i e natural pesticides 11 In contrast the diamondback moth a pest of cruciferous plants may recognize the presence of glucosinolates allowing it to identify the proper host plant 12 Indeed a characteristic specialised insect fauna is found on glucosinolate containing plants including butterflies such as large white small white and orange tip but also certain aphids moths such as the southern armyworm sawflies and flea beetles citation needed For instance the large white butterfly deposits its eggs on these glucosinolate containing plants and the larvae survive even with high levels of glucosinolates and eat plant material containing glucosinolates citation needed The whites and orange tips all possess the so called nitrile specifier protein which diverts glucosinolate hydrolysis toward nitriles rather than reactive isothiocyanates 13 In contrast the diamondback moth possesses a completely different protein glucosinolate sulfatase which desulfates glucosinolates thereby making them unfit for degradation to toxic products by myrosinase 14 Other kinds of insects specialised sawflies and aphids sequester glucosinolates 15 In specialised aphids but not in sawflies a distinct animal myrosinase is found in muscle tissue leading to degradation of sequestered glucosinolates upon aphid tissue destruction 16 This diverse panel of biochemical solutions to the same plant chemical plays a key role in the evolution of plant insect relationships 17 Induced production EditThe amount produced varies with the degree of herbivory being suffered The CO2 x herbivory effect is more complex however and defies generalization Increased CO2 produces increased decreased and unchanged production levels in studies reviewed by Bidart Bouzat and Imeh Nathaniel 2008 and there may in fact be genetic variation within the Brassicales 18 See also EditIsothiocyanate Gluconasturtiin Glucobrassicin Progoitrin Sinigrin SinalbinReferences Edit a b c Ishida M Hara M Fukino N Kakizaki T Morimitsu Y May 2014 Glucosinolate metabolism functionality and breeding for the improvement of Brassicaceae vegetables Breeding Science 64 1 48 59 doi 10 1270 jsbbs 64 48 PMC 4031110 PMID 24987290 Rodman JE Karol KG Price RA Sytsma KJ 1996 Molecules Morphology and Dahlgren s Expanded Order Capparales Systematic Botany 21 3 289 307 doi 10 2307 2419660 JSTOR 2419660 a b c d Agerbirk N Olsen CE May 2012 Glucosinolate structures in evolution Phytochemistry 77 16 45 doi 10 1016 j phytochem 2012 02 005 PMID 22405332 Bongoni R Verkerk R Steenbekkers B Dekker M Stieger M September 2014 Evaluation of different cooking conditions on broccoli Brassica oleracea var italica to improve the nutritional value and consumer acceptance Plant Foods for Human Nutrition 69 3 228 234 doi 10 1007 s11130 014 0420 2 PMID 24853375 S2CID 35228794 Burow M Bergner A Gershenzon J Wittstock U January 2007 Glucosinolate hydrolysis in Lepidium sativum identification of the thiocyanate forming protein Plant Molecular Biology 63 1 49 61 doi 10 1007 s11103 006 9071 5 PMID 17139450 S2CID 22955134 Plants Poisonous to Livestock Glucosinolates Goitrogenic Glycosides Cornell University Department of Animal Science 10 September 2015 Retrieved 16 August 2018 Samuni Blank M Arad Z Dearing MD Gerchman Y Karasov WH Izhaki I 2013 Friend or foe Disparate plant animal interactions of two congeneric rodents Evolutionary Ecology 27 6 1069 1080 doi 10 1007 s10682 013 9655 x S2CID 280376 Van Doorn HE Van der Kruk GC van Holst GJ Raaijmakers Ruijs NC Postma E Groeneweg B Jongen WH 1998 The glucosinolates sinigrin and progoitrin are important determinants for taste preference and bitterness of Brussels sprouts Journal of the Science of Food and Agriculture 78 30 38 doi 10 1002 SICI 1097 0010 199809 78 1 lt 30 AID JSFA79 gt 3 0 CO 2 N Samuni Blank M Izhaki I Dearing MD Gerchman Y Trabelcy B Lotan A Karasov WH Arad Z July 2012 Intraspecific directed deterrence by the mustard oil bomb in a desert plant Current Biology 10 22 1218 1220 doi 10 1016 j cub 2012 04 051 a b Isothiocyanates Micronutrient Information Center Linus Pauling Institute Oregon State University 1 April 2017 Retrieved 26 June 2022 Furlan L Bonetto C Finotto A Lazzeri L Malaguti L Patalano G Parker W 2010 The efficacy of biofumigant meals and plants to control wireworm populations Industrial Crops and Products 31 2 245 254 doi 10 1016 j indcrop 2009 10 012 Badenes Perez FR Reichelt M Gershenzon J Heckel DG January 2011 Phylloplane location of glucosinolates in Barbarea spp Brassicaceae and misleading assessment of host suitability by a specialist herbivore The New Phytologist 189 2 549 556 doi 10 1111 j 1469 8137 2010 03486 x PMID 21029103 Wittstock U Agerbirk N Stauber EJ Olsen CE Hippler M Mitchell Olds T et al April 2004 Successful herbivore attack due to metabolic diversion of a plant chemical defense Proceedings of the National Academy of Sciences of the United States of America 101 14 4859 4864 Bibcode 2004PNAS 101 4859W doi 10 1073 pnas 0308007101 PMC 387339 PMID 15051878 Ratzka A Vogel H Kliebenstein DJ Mitchell Olds T Kroymann J August 2002 Disarming the mustard oil bomb Proceedings of the National Academy of Sciences of the United States of America 99 17 11223 11228 Bibcode 2002PNAS 9911223R doi 10 1073 pnas 172112899 PMC 123237 PMID 12161563 Muller C Agerbirk N Olsen CE Boeve JL Schaffner U Brakefield PM December 2001 Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae Journal of Chemical Ecology 27 12 2505 2516 doi 10 1023 A 1013631616141 PMID 11789955 S2CID 24529256 Bridges M Jones AM Bones AM Hodgson C Cole R Bartlet E et al January 2002 Spatial organization of the glucosinolate myrosinase system in brassica specialist aphids is similar to that of the host plant Proceedings Biological Sciences 269 1487 187 191 doi 10 1098 rspb 2001 1861 PMC 1690872 PMID 11798435 Wheat CW Vogel H Wittstock U Braby MF Underwood D Mitchell Olds T December 2007 The genetic basis of a plant insect coevolutionary key innovation Proceedings of the National Academy of Sciences of the United States of America 104 51 20427 20431 Bibcode 2007PNAS 10420427W doi 10 1073 pnas 0706229104 PMC 2154447 PMID 18077380 Zavala JA Nabity PD DeLucia EH 7 January 2013 An emerging understanding of mechanisms governing insect herbivory under elevated CO2 Annual Review of Entomology Annual Reviews 58 1 79 97 doi 10 1146 annurev ento 120811 153544 PMID 22974069 External links EditGlucosinolate metabolism pathways from MetaCyc Retrieved from https en wikipedia org w index php title Glucosinolate amp oldid 1136415217, wikipedia, wiki, book, books, library,

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