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Glucotropaeolin

Glucotropaeolin or benzyl glucosinolate is a glucosinolate found in cruciferous vegetables, particularly garden cress.[1] Upon enzymatic activity, it is transformed into benzyl isothiocyanate, which contributes to the characteristic flavor of these brassicas.

Glucotropaeolin
Names
IUPAC name
1-S-[(1Z)-2-Phenyl-N-(sulfooxy)ethanimidoyl]-1-thio-beta-D-glucopyranose
Other names
Benzyl glucosinolate
Identifiers
  • 499-26-3
3D model (JSmol)
  • Interactive image
61369
ChEBI
  • CHEBI:17127
ChemSpider
  • 5020503 Y
KEGG
  • C02153
  • 6537197
  • DTXSID10964467
  • InChI=1S/C14H19NO9S2/c16-7-9-11(17)12(18)13(19)14(23-9)25-10(15-24-26(20,21)22)6-8-4-2-1-3-5-8/h1-5,9,11-14,16-19H,6-7H2,(H,20,21,22)/b15-10-/t9-,11-,12+,13-,14+/m1/s1 Y
    Key: QQGLQYQXUKHWPX-RFEZBLSLSA-N Y
  • c1ccc(cc1)C/C(=N/OS(=O)(=O)O)/S[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
C14H19NO9S2
Molar mass 409.42 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Occurrence edit

The compound was first reported in 1899, after its isolation from Tropaeolum majus, a nasturtium species.[2]: Section 2  Glucotropaeolin is now known to occur widely in other brassica families including Caricaceae, Phytolaccaceae, Resedaceae, Salvadoraceae and Tovariaceae.[3]

Structure edit

 
E isomer

The chemical structure of glucotropaeolin was confirmed by total synthesis in 1957. This showed that it is a glucose derivative with β-D-glucopyranose configuration. At that time it was unclear whether the C=N bond was in the Z form, with sulfur and oxygen substituents on the same side of the double bond, or the alternative E form in which they are on opposite sides. The suggestion was made that the Z form was more likely, based on the known decomposition to benzyl isothiocyanate by a mechanism analogous to the Lossen rearrangement.[4] However, when an identical product was obtained by an alternative route in 1963, it was pointed out that the E form would be expected to rearrange in a similar way.[5] The matter was settled by X-ray crystallography and other spectroscopic studies and it is now known that all natural glucosinolates are of Z form.[2]

Synthesis edit

Biosynthesis edit

Glucotropaeolin is biosynthesised from the amino acid phenylalanine in a multi-step pathway.[2]

Laboratory synthesis edit

The first laboratory syntheses served to confirm the compound's structure.[4][5] Later work allowed many glucosinolates including this benzyl derivative to be made. These processes are more efficient than isolating pure materials from the plants in which they are naturally found.[2]: Section 3 

Function edit

The natural role of glucosinolates are as plant defense compounds. The enzyme myrosinase removes the glucose group in glucotropaeolin to give an intermediate which spontaneously rearranges to benzyl isothiocyanate. This is a reactive material which is toxic to many insect predators and its production is triggered when the plant is damaged.[6] This effect has been called the mustard oil bomb.[7] At concentrations typically found in foods, the glucosinolates are not toxic to humans and can be useful flavor components.[8]

References edit

  1. ^ "Isothiocyanates". Linus Pauling Institute, Oregon State University.
  2. ^ a b c d Blažević, Ivica; Montaut, Sabine; Burčul, Franko; Olsen, Carl Erik; Burow, Meike; Rollin, Patrick; Agerbirk, Niels (2020). "Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants". Phytochemistry. 169: 112100. doi:10.1016/j.phytochem.2019.112100. PMID 31771793. S2CID 208318505.
  3. ^ 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. PMID 11198818.
  4. ^ a b Ettlinger, Martin G.; Lundeen, Allan J. (1957). "First Synthesis of a Mustard Oil Glucoside; the Enzymatic Lossen Rearrangement". Journal of the American Chemical Society. 79 (7): 1764–1765. doi:10.1021/ja01564a066.
  5. ^ a b Benn, M. H. (1963). "A New Mustard Oil Glucoside Synthesis: The Synthesis of Glucotropaeolin". Canadian Journal of Chemistry. 41 (11): 2836–2838. doi:10.1139/v63-415.
  6. ^ Morant, Anne Vinther; Jørgensen, Kirsten; Jørgensen, Charlotte; Paquette, Suzanne Michelle; Sánchez-Pérez, Raquel; Møller, Birger Lindberg; Bak, Søren (2008). "β-Glucosidases as detonators of plant chemical defense". Phytochemistry. 69 (9): 1795–1813. doi:10.1016/j.phytochem.2008.03.006. PMID 18472115.
  7. ^ Matile, Ph. (1980). ""Die Senfolbombe": Zur Kompartimentierung des Myrosinasesystems". Biochemie und Physiologie der Pflanzen. 175 (8–9): 722–731. doi:10.1016/S0015-3796(80)80059-X.
  8. ^ Fenwick, G. Roger; Heaney, Robert K.; Mullin, W. John; Vanetten, Cecil H. (1983). "Glucosinolates and their breakdown products in food and food plants". C R C Critical Reviews in Food Science and Nutrition. 18 (2): 123–201. doi:10.1080/10408398209527361. PMID 6337782.

glucotropaeolin, benzyl, glucosinolate, glucosinolate, found, cruciferous, vegetables, particularly, garden, cress, upon, enzymatic, activity, transformed, into, benzyl, isothiocyanate, which, contributes, characteristic, flavor, these, brassicas, namesiupac, . Glucotropaeolin or benzyl glucosinolate is a glucosinolate found in cruciferous vegetables particularly garden cress 1 Upon enzymatic activity it is transformed into benzyl isothiocyanate which contributes to the characteristic flavor of these brassicas Glucotropaeolin NamesIUPAC name 1 S 1Z 2 Phenyl N sulfooxy ethanimidoyl 1 thio beta D glucopyranoseOther names Benzyl glucosinolateIdentifiersCAS Number 499 26 33D model JSmol Interactive imageBeilstein Reference 61369ChEBI CHEBI 17127ChemSpider 5020503 YKEGG C02153PubChem CID 6537197CompTox Dashboard EPA DTXSID10964467InChI InChI 1S C14H19NO9S2 c16 7 9 11 17 12 18 13 19 14 23 9 25 10 15 24 26 20 21 22 6 8 4 2 1 3 5 8 h1 5 9 11 14 16 19H 6 7H2 H 20 21 22 b15 10 t9 11 12 13 14 m1 s1 YKey QQGLQYQXUKHWPX RFEZBLSLSA N YSMILES c1ccc cc1 C C N OS O O O S C H 2 C H C H C H C H O2 CO O O OPropertiesChemical formula C 14H 19N O 9S 2Molar mass 409 42 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Occurrence 2 Structure 3 Synthesis 3 1 Biosynthesis 3 2 Laboratory synthesis 4 Function 5 ReferencesOccurrence editThe compound was first reported in 1899 after its isolation from Tropaeolum majus a nasturtium species 2 Section 2 Glucotropaeolin is now known to occur widely in other brassica families including Caricaceae Phytolaccaceae Resedaceae Salvadoraceae and Tovariaceae 3 Structure edit nbsp E isomerThe chemical structure of glucotropaeolin was confirmed by total synthesis in 1957 This showed that it is a glucose derivative with b D glucopyranose configuration At that time it was unclear whether the C N bond was in the Z form with sulfur and oxygen substituents on the same side of the double bond or the alternative E form in which they are on opposite sides The suggestion was made that the Z form was more likely based on the known decomposition to benzyl isothiocyanate by a mechanism analogous to the Lossen rearrangement 4 However when an identical product was obtained by an alternative route in 1963 it was pointed out that the E form would be expected to rearrange in a similar way 5 The matter was settled by X ray crystallography and other spectroscopic studies and it is now known that all natural glucosinolates are of Z form 2 Synthesis editBiosynthesis edit Glucotropaeolin is biosynthesised from the amino acid phenylalanine in a multi step pathway 2 Laboratory synthesis edit The first laboratory syntheses served to confirm the compound s structure 4 5 Later work allowed many glucosinolates including this benzyl derivative to be made These processes are more efficient than isolating pure materials from the plants in which they are naturally found 2 Section 3 Function editMain article Glucosinolate The natural role of glucosinolates are as plant defense compounds The enzyme myrosinase removes the glucose group in glucotropaeolin to give an intermediate which spontaneously rearranges to benzyl isothiocyanate This is a reactive material which is toxic to many insect predators and its production is triggered when the plant is damaged 6 This effect has been called the mustard oil bomb 7 At concentrations typically found in foods the glucosinolates are not toxic to humans and can be useful flavor components 8 References edit Isothiocyanates Linus Pauling Institute Oregon State University a b c d Blazevic Ivica Montaut Sabine Burcul Franko Olsen Carl Erik Burow Meike Rollin Patrick Agerbirk Niels 2020 Glucosinolate structural diversity identification chemical synthesis and metabolism in plants Phytochemistry 169 112100 doi 10 1016 j phytochem 2019 112100 PMID 31771793 S2CID 208318505 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 PMID 11198818 a b Ettlinger Martin G Lundeen Allan J 1957 First Synthesis of a Mustard Oil Glucoside the Enzymatic Lossen Rearrangement Journal of the American Chemical Society 79 7 1764 1765 doi 10 1021 ja01564a066 a b Benn M H 1963 A New Mustard Oil Glucoside Synthesis The Synthesis of Glucotropaeolin Canadian Journal of Chemistry 41 11 2836 2838 doi 10 1139 v63 415 Morant Anne Vinther Jorgensen Kirsten Jorgensen Charlotte Paquette Suzanne Michelle Sanchez Perez Raquel Moller Birger Lindberg Bak Soren 2008 b Glucosidases as detonators of plant chemical defense Phytochemistry 69 9 1795 1813 doi 10 1016 j phytochem 2008 03 006 PMID 18472115 Matile Ph 1980 Die Senfolbombe Zur Kompartimentierung des Myrosinasesystems Biochemie und Physiologie der Pflanzen 175 8 9 722 731 doi 10 1016 S0015 3796 80 80059 X Fenwick G Roger Heaney Robert K Mullin W John Vanetten Cecil H 1983 Glucosinolates and their breakdown products in food and food plants C R C Critical Reviews in Food Science and Nutrition 18 2 123 201 doi 10 1080 10408398209527361 PMID 6337782 Retrieved from https en wikipedia org w index php title Glucotropaeolin amp oldid 1189375396, wikipedia, wiki, book, books, library,

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