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Alkylresorcinol

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Alkylresorcinols (ARs), also known as resorcinolic lipids, are amphiphilic phenolic lipids characterised by a non-polar odd-numbered alkyl side chain with up to 27 carbon atoms attached to a polar resorcinol (1,3-dihydroxybenzene) ring.[1][2][3]

Chemistry diagram of general structure of those found in cereals
Common structure of those in cereals
Bilobol (5-[(Z)-pentadec-8-enylo]resorcinol)

Natural sources of alkylresorcinols

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Alkylresorcinols are relatively rare in nature and are reported to be found in fungi, bacteria, and some lower and higher plants. DB-2073 is an antibiotic isolated from the broth culture of Pseudomonas sp.[4] They are also the main constituents of the outer shell of the cyst of Azotobacter.[5]

Among the plant sources, the shell oil of cashew nut (Anacardium occidentale L.) has the highest amount of ARs, which consists of 20% phenolic lipids.[2] Moreover, ARs were found in the peels and pulp of peas (Pisum sativum L.),[6] pulp and leaves of ginkgo (Ginkgo biloba L.),[7] pulp and peels of mango (Mangifera indica L.),[8] and in some cereals. In the case of cereals, the hyaline layer, inner pericarp, and testa showed the highest amounts of AR.[3][9]

 
DB-2073 (2-n-hexyl-5-n-propylresorcinol)

Occurrence in cereals

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The alkylresorcinols alkyl chain, present in cereals, ranges from 15 to 25 carbon atoms.[3][10] ARs have been reported to be present in high amounts in rye, wheat, and triticale, and in low concentrations in barley, maize, oat, and millet,[11][12] while no information is at present available for Khorasan wheat. They are most abundant in the bran fractions (2600-4100 μg/g; 0.1-0.3% of dry weight),[13] whereas they are in trace amounts in strachy endosperm and germ.[9] They can also be found in rice, though not in the edible parts of the rice plant.[14]

Their presence in the endosperm (the part of cereal grain that is used to make white flour), means that alkylresorcinols can be used as 'biomarkers' for people who eat foods containing wholegrain wheat and rye, rather than cereal products based on white flour.[15] Moreover, they were thought to have anti-nutritive properties (e.g. decreasing growth of pigs and chickens fed rye), but this theory has been discredited, and a number of animal studies have demonstrated that they have no obvious negative effect on animals or humans.[15]

Biomarkers of a whole grain diet

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Increasing evidence from human intervention trials suggests that they are the most promising biomarker of whole grain wheat and rye intake.[16][17] Alkylresorcinol metabolites, 3,5-dihydroxybenzoic acid (DHBA) and 3,5-dihydroxyphenylpropionoic acid (DHPPA) were first identified in urine[18] and can be quantified in urine[19] and plasma,[20] and may be an alternative, equivalent biomarker of whole grain wheat intake.[21]

The average intake of alkylresorcinols in the UK is around 11 mg/person/day, and in Sweden is around 20 mg/person/day.[22] This varies widely depending on whether people normally consume wholegrain/wholemeal/brown bread, which is high in alkylresorcinols (300-1000 μg/g), or white wheat bread, which has very low concentrations of alkylresorcinols (<50 μg/g).

Biomarkers of cereal presence in archaeological pottery

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Recently, alkylresorcinols have been widely recognised as a biomarker for the presence of cereals in archaeological pottery. They were previously found in a well-preserved Bronze Age wooden container from Switzerland,[23] and coarse ware vessels from a Roman cavalry barrack at Vindolanda.[24] A study[24] demonstrated that the survival of ARs is highly dependent on the cooking procedures and burial conditions. However, if recoverable, analysis of these phenolic lipids in archaeological contexts is valuable as it can help explain the uptake and spread of cereal processing of past communities in particular regions.[23][25]

Possible biological activities

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In vitro studies have shown that alkylresorcinols may prevent cells turning cancerous, but that they do not have any effect on cells that are already cancerous.[15] Alkylresorcinols also increase gamma-tocopherol levels in rats when fed in high amounts (0.2% of total diet and above).[18]

The alkylresorcinols in Grevillea banksii and Grevillea 'Robyn Gordon' are responsible for contact dermatitis.[26]

Trivial names of some resorcinolic lipids

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Derivatives

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Sorgoleone is a hydrophobic root exudate of Sorghum bicolor.[27]

References

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  1. ^ Baerson, S. R.; Schröder, J.; Cook, D.; Rimando, A. M.; Pan, Z.; Dayan, F. E.; Noonan, B. P.; Duke, S. O. (2010). "Alkylresorcinol biosynthesis in plants: New insights from an ancient enzyme family?". Plant Signaling & Behavior. 5 (10): 1286–1289. doi:10.4161/psb.5.10.13062. PMC 3115369. PMID 20861691.
  2. ^ a b c Kozubek, Arkadiusz; Tyman, John H. P. (1999-01-13). "Resorcinolic Lipids, the Natural Non-isoprenoid Phenolic Amphiphiles and Their Biological Activity". Chemical Reviews. 99 (1): 1–26. doi:10.1021/cr970464o. ISSN 0009-2665. PMID 11848979.
  3. ^ a b c Ross, Alastair B.; Shepherd, Martin J.; Schüpphaus, Meike; Sinclair, Vicky; Alfaro, Begoña; Kamal-Eldin, Afaf; Åman, Per (2003-07-01). "Alkylresorcinols in Cereals and Cereal Products". Journal of Agricultural and Food Chemistry. 51 (14): 4111–4118. doi:10.1021/jf0340456. ISSN 0021-8561. PMID 12822955.
  4. ^ Kanda, N.; Ishizaki, N.; Inoue, N.; Oshima, M.; Handa, A. (1975). "DB-2073, a new alkylresorcinol antibiotic. I. Taxonomy, isolation and characterization". The Journal of Antibiotics. 28 (12): 935–942. doi:10.7164/antibiotics.28.935. PMID 1206006.
  5. ^ Funa, N.; Ozawa, H.; Hirata, A.; Horinouchi, S. (2006). "Phenolic lipid synthesis by type III polyketide synthases is essential for cyst formation in Azotobacter vinelandii". Proceedings of the National Academy of Sciences. 103 (16): 6356–6361. Bibcode:2006PNAS..103.6356F. doi:10.1073/pnas.0511227103. PMC 1458882. PMID 16597676.
  6. ^ Zarnowski, Robert; Kozubek, Arkadiusz (1999-02-01). "Alkylresorcinol Homologs in Pisum sativum L. Varieties". Zeitschrift für Naturforschung C. 54 (1–2): 44–48. doi:10.1515/znc-1999-1-208. ISSN 1865-7125.
  7. ^ Żarnowska, Ewa D.; Żarnowski, Robert; Kozubek, Arkadiusz (2000-12-01). "Alkylresorcinols in Fruit Pulp and Leaves of Ginkgo biloba L." Zeitschrift für Naturforschung C. 55 (11–12): 881–885. doi:10.1515/znc-2000-11-1206. ISSN 1865-7125. PMID 11204190.
  8. ^ Knödler, Matthias; Reisenhauer, Katharina; Schieber, Andreas; Carle, Reinhold (2009-05-13). "Quantitative Determination of Allergenic 5-Alk(en)ylresorcinols in Mango (Mangifera indica L.) Peel, Pulp, and Fruit Products by High-Performance Liquid Chromatography". Journal of Agricultural and Food Chemistry. 57 (9): 3639–3644. doi:10.1021/jf803934p. ISSN 0021-8561. PMID 19338352.
  9. ^ a b Landberg, Rikard; Kamal-Eldin, Afaf; Salmenkallio-Marttila, Marjatta; Rouau, Xavier; Åman, Per (September 2008). "Localization of alkylresorcinols in wheat, rye and barley kernels". Journal of Cereal Science. 48 (2): 401–406. doi:10.1016/j.jcs.2007.09.013.
  10. ^ Ziegler, Jochen U.; Steingass, Christof B.; Longin, Carl Friedrich H.; Würschum, Tobias; Carle, Reinhold; Schweiggert, Ralf Martin (September 2015). "Alkylresorcinol composition allows the differentiation of Triticum spp. having different degrees of ploidy". Journal of Cereal Science. 65: 244–251. doi:10.1016/j.jcs.2015.07.013. ISSN 0733-5210.
  11. ^ Chen, Yan; Ross, Alastair B.; Åman, Per; Kamal-Eldin, Afaf (2004-12-01). "Alkylresorcinols as Markers of Whole Grain Wheat and Rye in Cereal Products". Journal of Agricultural and Food Chemistry. 52 (26): 8242–8246. doi:10.1021/jf049726v. ISSN 0021-8561. PMID 15612824.
  12. ^ Andersson, Annica A. M.; Lampi, Anna-Maija; Nyström, Laura; Piironen, Vieno; Li, Li; Ward, Jane L.; Gebruers, Kurt; Courtin, Christophe M.; Delcour, Jan A.; Boros, Danuta; Fraś, Anna; Dynkowska, Wioletta; Rakszegi, Mariann; Bedő, Zoltan; Shewry, Peter R. (2008-11-12). "Phytochemical and Dietary Fiber Components in Barley Varieties in the HEALTHGRAIN Diversity Screen". Journal of Agricultural and Food Chemistry. 56 (21): 9767–9776. doi:10.1021/jf802037f. ISSN 0021-8561. PMID 18921979.
  13. ^ Suzuki, Y. (1999). "Structures of 5-alkylresorcinol-related analogues in rye". Phytochemistry. 52 (2): 281–289. doi:10.1016/S0031-9422(99)00196-X.
  14. ^ Suzuki, Y.; Kurano, M.; Esumi, Y.; Yamaguchi, I.; Doi, Y. (2003). "Biosynthesis of 5-alkylresorcinol in rice: Incorporation of a putative fatty acid unit in the 5-alkylresorcinol carbon chain". Bioorganic Chemistry. 31 (6): 437–452. doi:10.1016/j.bioorg.2003.08.003. PMID 14613765.
  15. ^ a b c Ross, A. B.; Kamal-Eldin, A.; Aman, P. (2004). "Dietary alkylresorcinols: Absorption, bioactivities, and possible use as biomarkers of whole-grain wheat- and rye-rich foods". Nutrition Reviews. 62 (3): 81–95. doi:10.1301/nr.2004.mar.81-95. PMID 15098855.
  16. ^ Landberg, R.; Kamal-Eldin, A.; Andersson, A.; Vessby, B.; Aman, P. (2008). "Alkylresorcinols as biomarkers of whole-grain wheat and rye intake: Plasma concentration and intake estimated from dietary records". The American Journal of Clinical Nutrition. 87 (4): 832–838. doi:10.1093/ajcn/87.4.832. PMID 18400704.
  17. ^ Landberg, R.; Kamal-Eldin, A.; Andersson, S. -O.; Johansson, J. -E.; Zhang, J. -X.; Hallmans, G.; Aman, P. (2009). "Reproducibility of Plasma Alkylresorcinols during a 6-Week Rye Intervention Study in Men with Prostate Cancer". Journal of Nutrition. 139 (5): 975–980. doi:10.3945/jn.108.099952. PMID 19321581.
  18. ^ a b Ross, A. B.; Åman, P.; Kamal-Eldin, A. (2004). "Identification of cereal alkylresorcinol metabolites in human urine—potential biomarkers of wholegrain wheat and rye intake". Journal of Chromatography B. 809 (1): 125–130. doi:10.1016/j.jchromb.2004.06.015. PMID 15282102.
  19. ^ Koskela, A.; Linko-Parvinen, A. -M.; Hiisivuori, P.; Samaletdin, A.; Kamal-Eldin, A.; Tikkanen, M. J.; Adlercreutz, H. (2007). "Quantification of Alkylresorcinol Metabolites in Urine by HPLC with Coulometric Electrode Array Detection". Clinical Chemistry. 53 (7): 1380–1383. doi:10.1373/clinchem.2006.084764. PMID 17495018.
  20. ^ Koskela, A.; Samaletdin, A.; Aubertin-Leheudre, M. N.; Adlercreutz, H. (2008). "Quantification of Alkylresorcinol Metabolites in Plasma by High-Performance Liquid Chromatography with Coulometric Electrode Array Detection". Journal of Agricultural and Food Chemistry. 56 (17): 7678–7681. CiteSeerX 10.1.1.533.1473. doi:10.1021/jf801252s. PMID 18690683.
  21. ^ Aubertin-Leheudre, M.; Koskela, A.; Marjamaa, A.; Adlercreutz, H. (2008). "Plasma Alkylresorcinols and Urinary Alkylresorcinol Metabolites as Biomarkers of Cereal Fiber Intake in Finnish Women". Cancer Epidemiology, Biomarkers & Prevention. 17 (9): 2244–2248. doi:10.1158/1055-9965.EPI-08-0215. PMID 18768490.
  22. ^ Ross, A. B.; Becker, W.; Chen, Y.; Kamal-Eldin, A.; Aman, P. (2005). "Intake of alkylresorcinols from wheat and rye in the United Kingdom and Sweden". The British Journal of Nutrition. 94 (4): 496–499. doi:10.1079/bjn20051511. PMID 16197572.
  23. ^ a b Colonese, Andre Carlo; Hendy, Jessica; Lucquin, Alexandre; Speller, Camilla F.; Collins, Matthew J.; Carrer, Francesco; Gubler, Regula; Kühn, Marlu; Fischer, Roman; Craig, Oliver E. (2017-07-26). "New criteria for the molecular identification of cereal grains associated with archaeological artefacts". Scientific Reports. 7 (1): 6633. doi:10.1038/s41598-017-06390-x. ISSN 2045-2322. PMC 5529501. PMID 28747692.
  24. ^ a b Hammann, Simon; Cramp, Lucy J.E. (May 2018). "Towards the detection of dietary cereal processing through absorbed lipid biomarkers in archaeological pottery". Journal of Archaeological Science. 93: 74–81. doi:10.1016/j.jas.2018.02.017. hdl:1983/b7951ec2-3400-474c-ab5e-e0a173bf6ca0. ISSN 0305-4403.
  25. ^ Roffet-Salque, Mélanie; Dunne, Julie; Altoft, David T.; Casanova, Emmanuelle; Cramp, Lucy J.E.; Smyth, Jessica; Whelton, Helen L.; Evershed, Richard P. (December 2017). "From the inside out: Upscaling organic residue analyses of archaeological ceramics". Journal of Archaeological Science: Reports. 16: 627–640. doi:10.1016/j.jasrep.2016.04.005. hdl:1983/a7881ecd-60f1-4f39-b90c-7c5d8bc17946. ISSN 2352-409X.
  26. ^ Menz, J.; Rossi, E. R.; Taylor, W. C.; Wall, L. (1986). "Contact dermatitis from Grevillea 'Robyn Gordon'". Contact Dermatitis. 15 (3): 126–131. doi:10.1111/j.1600-0536.1986.tb01311.x. PMID 2946534. S2CID 2846186.
  27. ^ Dayan, F. E.; Rimando, A. M.; Pan, Z.; Baerson, S. R.; Gimsing, A. L.; Duke, S. O. (2010). "Sorgoleone". Phytochemistry. 71 (10): 1032–1039. doi:10.1016/j.phytochem.2010.03.011. PMID 20385394.
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