1932

Abstract

Dietary organosulfur-containing compounds (DOSCs) in fruits, vegetables, and edible mushrooms may hold the key to the health-promotion benefits of these foods. Yet their action mechanisms are not clear, partially due to their high reactivity, which leads to the formation of complex compounds during postharvest processing. Among postharvest processing methods, thermal treatment is the most common way to process these edible plants rich in DOSCs, which undergo complex degradation pathways with the generation of numerous derivatives over a short time. At low temperatures, DOSCs are biotransformed slowly during fermentation to different metabolites (e.g., thiols, sulfides, peptides), whose distinctive biological activity remains largely unexplored. In this review, we discuss the bioavailability of DOSCs in human digestion before illustrating their potential mechanisms for health promotion related to cardiovascular health, cancer chemoprevention, and anti-inflammatory and antimicrobial activities. In particular, it is interesting that different DOSCs react with glutathione or cysteine, leading to the slow release of hydrogen sulfide (HS), which has broad bioactivity in chronic disease prevention. In addition, DOSCs may interact with protein thiol groups of different protein targets of importance related to inflammation and phase II enzyme upregulation, among other action pathways critical for health promotion.

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2022-03-25
2024-04-25
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Literature Cited

  1. Abbaoui B, Lucas CR, Riedl KM, Clinton SK, Mortazavi A. 2018. Cruciferous vegetables, isothiocyanates, and bladder cancer prevention. Mol. Nutr. Food Res. 62:181800079
    [Google Scholar]
  2. Amano H, Kazamori D, Itoh K 2016. Pharmacokinetics of S-allyl-l-cysteine in rats is characterized by high oral absorption and extensive renal reabsorption. J. Nutr. 146:2456–59
    [Google Scholar]
  3. Amano H, Kazamori D, Itoh K, Kodera Y. 2015. Metabolism, excretion, and pharmacokinetics of S-allyl-l-cysteine in rats and dogs. Drug Metab. Dispos. 43:5749–55
    [Google Scholar]
  4. Andreadou I, Schulz R, Papapetropoulos A, Turan B, Ytrehus K et al. 2020. The role of mitochondrial reactive oxygen species, NO and H2S in ischaemia/reperfusion injury and cardioprotection. J. Cell. Mol. Med. 24:126510–22
    [Google Scholar]
  5. Aoyagi M, Imai S, Kamoi T 2021. Novel bisthiolane polysulfides from lachrymatory factor synthase-suppressed onion and their in vitro cyclooxygenase-1 inhibitory activity. Food Chem 344:128636
    [Google Scholar]
  6. Aprea E, Biasioli F, Carlin S, Versini GD, Mark T et al. 2007. Rapid white truffle headspace analysis by proton transfer reaction mass spectrometry and comparison with solid-phase microextraction coupled with gas chromatography/mass spectrometry. Rapid Commun. Mass Spectrom. 21:2564–72
    [Google Scholar]
  7. Areekul S. 1979. Djenkol bean, djenkolic acid and djenkolism. J. Med. Assoc. Thail. 62:10530–31
    [Google Scholar]
  8. Bagul M, Kakumanu S, Wilson TA 2015. Crude garlic extract inhibits cell proliferation and induces cell cycle arrest and apoptosis of cancer cells in vitro. J. Med. Food 18:7731–37
    [Google Scholar]
  9. Bahadoran Z, Mirmiran P, Momenan AA, Azizi F. 2017. Allium vegetable intakes and the incidence of cardiovascular disease, hypertension, chronic kidney disease, and type 2 diabetes in adults: a longitudinal follow-up study. J. Hypertens. 35:91909–16
    [Google Scholar]
  10. Bassil D, Makris DP, Kefalas P. 2005. Oxidation of caffeic acid in the presence of l-cysteine: isolation of 2-S-cysteinylcaffeic acid and evaluation of its antioxidant properties. Food Res. Int. 38:4395–402
    [Google Scholar]
  11. Batiha GES, Beshbishy AM, Wasef LG, Elewa YHA, Al-Sagan AA et al. 2020. Chemical constituents and pharmacological activities of garlic (Allium sativum L.): a review. Nutrients 12:3872–92
    [Google Scholar]
  12. Bauer D, Mazzio E, Soliman KF, Taka E, Oriaku E et al. 2014. Diallyl disulfide inhibits TNFα-induced CCL2 release by MDA-MB-231 cells. Anticancer Res 34:62763–70
    [Google Scholar]
  13. Bellesia F, Pinetti A, Tirillini B, Bianchi A. 2001. Temperature-dependent evolution of volatile organic compounds in Tuber borchii from Italy. Flavour Fragr. J. 16:11–6
    [Google Scholar]
  14. Benavides GA, Squadrito GL, Mills RW, Patel HD, Isbell TS et al. 2007. Hydrogen sulfide mediates the vasoactivity of garlic. PNAS 104:4617977–82
    [Google Scholar]
  15. Block E, Dethier B, Bechand B, Cotelesage JJH, George GN et al. 2018. Ajothiolanes: 3,4-dimethylthiolane natural products from garlic (Allium sativum). J. Agric. Food Chem. 66:3910193–204
    [Google Scholar]
  16. Bo P, Lien JC, Chen YY, Yu FS, Lu HF et al. 2016. Allyl isothiocyanate induces cell toxicity by multiple pathways in human breast cancer cells. Am. J. Chin. Med. 44:2415–37
    [Google Scholar]
  17. Bunawan NC, Rastegar A, White KP, Wang NE. 2014. Djenkolism: case report and literature review. Int. Med. Case Rep J. 7:179–84
    [Google Scholar]
  18. Cairns TL, Evans GL, Larchar AW, McKusick BC. 1952. gem-Dithiols. J. Am. Chem. Soc. 74:163982–89
    [Google Scholar]
  19. Chang HP, Huang SY, Chen YH. 2005. Modulation of cytokine secretion by garlic oil derivatives is associated with suppressed nitric oxide production in stimulated macrophages. J. Agric. Food Chem. 53:72530–34
    [Google Scholar]
  20. Chang PY, Tsai FJ, Bau DT, Hsu YM, Yang JS et al. 2021. Potential effects of allyl isothiocyanate on inhibiting cellular proliferation and inducing apoptotic pathway in human cisplatin-resistant oral cancer cells. J. Formos. Med. Assoc. 120:1515–23
    [Google Scholar]
  21. Chen HE, Lin JF, Tsai TF, Lin YC, Chou KY et al. 2018. Allyl isothiocyanate induces autophagy through the up-regulation of beclin-1 in human prostate cancer cells. Am. J. Chin. Med. 46:71625–43
    [Google Scholar]
  22. Chhikara N, Devi HR, Jaglan S, Sharma P, Gupta P et al. 2018. Bioactive compounds, food applications and health benefits of Parkia speciosa (stinky beans): a review. Agric. Food Sec. 7:146
    [Google Scholar]
  23. Citi V, Martelli A, Testai L, Marino A, Breschi MC et al. 2014. Hydrogen sulfide releasing capacity of natural isothiocyanates: Is it a reliable explanation for the multiple biological effects of Brassicaceae?. Planta Med 80:8–9610–13
    [Google Scholar]
  24. Cramer JM, Teran-Garcia M, Jeffery EH. 2012. Enhancing sulforaphane absorption and excretion in healthy men through the combined consumption of fresh broccoli sprouts and a glucoraphanin-rich powder. Br. J. Nutr. 107:91333–38
    [Google Scholar]
  25. Dann JR, Gates JW. 1957. The reaction of djenkolic acid and aqueous calcium hydroxide: the isolation and identification of racemic thiazolidine-4-carboxylic. J. Am. Chem. Soc. 288: 1854.1650–51
    [Google Scholar]
  26. Eady CC, Kamoi T, Kato M, Porter NG, Davis S et al. 2008. Silencing onion lachrymatory factor synthase causes a significant change in the sulfur secondary metabolite profile. Plant Physiol 147:42096–106
    [Google Scholar]
  27. Favela-González KM, Hernández-Almanza AY, De la Fuente-Salcido NM. 2020. The value of bioactive compounds of cruciferous vegetables (Brassica) as antimicrobials and antioxidants: a review. J. Food Biochem. 44:10e13414
    [Google Scholar]
  28. Fischer NS, Steinhaus M. 2020. Identification of an important odorant precursor in durian: first evidence of ethionine in plants. J. Agric. Food Chem. 68:3810397–402
    [Google Scholar]
  29. Foroutan-Rad M, Tappeh KH, Khademvatan S 2017. Antileishmanial and immunomodulatory activity of Allium sativum (garlic): a review. J. Evid. Based Complement. Altern. Med. 22:1141–55
    [Google Scholar]
  30. Frerot E, Velluz A, Bagnoud A, Delort E. 2008. Analysis of the volatile constituents of cooked petai beans (Parkia speciosa) using high-resolution GC/TOF-MS. Flavour Fragr. J. 23:434–40
    [Google Scholar]
  31. Fujii T, Matsutomo T, Kodera Y. 2018. Changes of S-allylmercaptocysteine and γ-glutamyl-S-allylmercaptocysteine contents and their putative production mechanisms in garlic extract during the aging process. J. Agric. Food Chem. 66:4010506–12
    [Google Scholar]
  32. Gardner CD, Lawson LD, Block E, Chatterjee LM, Kiazand A et al. 2007. Effect of raw garlic versus commercial garlic supplements on plasma lipid concentrations in adults with moderate hypercholesterolemia: a randomized clinical trial. Arch. Int. Med. 167:4346–53
    [Google Scholar]
  33. Gmelin R, Susilo R, Fenwick GR. 1981. Cyclic polysulfides from Parkia speciosa. Phytochemistry 20:112521–23
    [Google Scholar]
  34. Gómez-Plaza E, Cano-López M. 2011. A review on micro-oxygenation of red wines: claims, benefits and the underlying chemistry. Food Chem 125:41131–40
    [Google Scholar]
  35. Greenberg DM, Mastalerz P, Nagabhushanam A. 1964. Mechanism of djenkolic acid decomposition by cystathionase. Biochim. Biophys. Acta 81:1158–64
    [Google Scholar]
  36. Hanahan D, Weinberg RA. 2011. Hallmarks of cancer: the next generation. Cell 144:5646–74
    [Google Scholar]
  37. Hanschen FS, Lamy E, Schreiner M, Rohn S. 2014. Reactivity and stability of glucosinolates and their breakdown products in foods. Angew. Chem. Int. Ed. 53:4311430–50
    [Google Scholar]
  38. Hiraide M, Miyazaki Y, Shibata Y. 2004. The smell and odorous components of dried shiitake mushroom, Lentinula edodes I: relationship between sensory evaluations and amounts of odorous components. J. Wood Sci. 50:4358–64
    [Google Scholar]
  39. Hitchcock JK, Mkwanazi N, Barnett C, Graham LM, Katz AA et al. 2021. The garlic compound Z-ajoene, S-thiolates COX2 and STAT3 and dampens the inflammatory response in RAW264.7 macrophages. Mol. Nutr. Food Res. 65:3e2000854
    [Google Scholar]
  40. Horn T, Bettray W, Slusarenko AJ, Gruhlke MCH. 2018. S-Allylmercaptoglutathione is a substrate for glutathione reductase (E.C. 1.8.1.7) from yeast (Saccharomyces cerevisiae). Antioxidants 7:786
    [Google Scholar]
  41. Hosono T, Fukao T, Ogihara J, Ito Y, Shiba H et al. 2005. Diallyl trisulfide suppresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of β-tubulin. J. Biol. Chem. 280:5041487–93
    [Google Scholar]
  42. How YK, Siow LF. 2020. Effects of convection-, vacuum-and freeze-drying on antioxidant, physicochemical properties, functional properties and storage stability of stink bean (Parkia speciosa) powder. J. Food Sci. Technol. 57:124637–48
    [Google Scholar]
  43. Hsu CN, Tain YL. 2021. Preventing developmental origins of cardiovascular disease: hydrogen sulfide as a potential target?. Antioxidants 10:2247
    [Google Scholar]
  44. Huang Z, Zhou Q, Wu WL, Wan J, Jiang AM 2019. Thermal kinetics of enzyme inactivation, color changes, and allicin degradation of garlic under blanching treatments. J. Food Process Eng. 42:3e12991
    [Google Scholar]
  45. Ioannou YM, Burka LT, Matthews HB. 1984. Allyl isothiocyanate: comparative disposition in rats and mice. Toxicol. Appl. Pharmacol. 75:2173–81
    [Google Scholar]
  46. Izzah Ahmad N, Abdul Rahman S, Leong YH, Azizul NH 2019. A review on the phytochemicals of Parkia speciosa, stinky beans as potential phytomedicine. J. Food Sci. Nutr. Res. 2:3151–73
    [Google Scholar]
  47. Jang M, Hong E, Kim GH 2010. Evaluation of antibacterial activity of 3-butenyl, 4-pentenyl, 2-phenylethyl, and benzyl isothiocyanate in Brassica vegetables. J. Food Sci. 75:7412–16
    [Google Scholar]
  48. Jiang X, Zhu X, Huang W, Xu H, Zhao Z et al. 2017. Garlic-derived organosulfur compound exerts antitumor efficacy via activation of MAPK pathway and modulation of cytokines in SGC-7901 tumor-bearing mice. Int. Immunopharmacol. 48:135–45
    [Google Scholar]
  49. Jing P, Zhao SJ, Ruan SY, Xie ZH, Dong Y et al. 2012. Anthocyanin and glucosinolate occurrences in the roots of Chinese red radish (Raphanus sativus L.), and their stability to heat and pH. Food Chem 133:41569–76
    [Google Scholar]
  50. Kamitani H, Esaki N, Tanaka H, Soda K. 1991. Degradation of l-djenkolate catalyzed by S-alkylcysteine α,β-lyase from Pseudomonas putida. J. Biochem. 109:4645–49
    [Google Scholar]
  51. Kapusta-Duch J, Kusznierewicz B, Leszczyńska T, Borczak B 2016. Effect of cooking on the contents of glucosinolates and their degradation products in selected Brassica vegetables. J. Funct. Foods 23:412–22
    [Google Scholar]
  52. Kaschula CH, Tuveri R, Ngarande E, Dzobo K, Barnett C. et al. 2019. The garlic compound ajoene covalently binds vimentin, disrupts the vimentin network and exerts anti-metastatic activity in cancer cells. BMC Cancer 19:248
    [Google Scholar]
  53. Kim S, Lee S, Shin D, Yoo M 2016a. Change in organosulfur compounds in onion (Allium cepa L.) during heat treatment. Food Sci. Biotechnol. 25:1115–19
    [Google Scholar]
  54. Kim S, Park SL, Lee S, Lee SY, Ko S et al. 2016b. UPLC/ESI-MS/MS analysis of compositional changes for organosulfur compounds in garlic (Allium sativum L.) during fermentation. Food Chem 211:555–59
    [Google Scholar]
  55. Kodera Y, Ichikawa M, Yoshida J, Kashimoto N, Uda N et al. 2002. Pharmacokinetic study of allixin, a phytoalexin produced by garlic. Chem. Pharm. Bull. 50:3354–63
    [Google Scholar]
  56. Kreitman GY, Danilewicz JC, Jeffery DW, Elias RJ. 2016a. Reaction mechanisms of metals with hydrogen sulfide and thiols in model wine. Part 1: copper-catalyzed oxidation. J. Agric. Food Chem. 64:204095–104
    [Google Scholar]
  57. Kreitman GY, Danilewicz JC, Jeffery DW, Elias RJ. 2016b. Reaction mechanisms of metals with hydrogen sulfide and thiols in model wine. Part 2: iron- and copper-catalyzed oxidation. J. Agric. Food Chem. 64:204105–13
    [Google Scholar]
  58. Kyung KH. 2012. Antimicrobial properties of allium species. Curr. Opin. Biotechnol. 23:2142–47
    [Google Scholar]
  59. Lawson LD, Gardner CD. 2005. Composition, stability, and bioavailability of garlic products used in a clinical trial. J. Agric. Food Chem. 53:166254–61
    [Google Scholar]
  60. Lawson LD, Hunsaker SM. 2018. Allicin bioavailability and bioequivalence from garlic supplements and garlic foods. Nutrients 10:7812–60
    [Google Scholar]
  61. Lawson LD, Wang ZJ. 2005. Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability. J. Agric. Food Chem. 53:61974–83
    [Google Scholar]
  62. Lee CF, Chiang NN, Lu YH, Huang YS, Yang JS. et al. 2018. Benzyl isothiocyanate (BITC) triggers mitochondria-mediated apoptotic machinery in human cisplatin-resistant oral cancer CAR cells. Biomedicine 8:313–22
    [Google Scholar]
  63. Lee PR, Saputra A, Yu B, Curran P, Liu SQ. 2012. Biotransformation of durian pulp by mono- and mixed-cultures of Saccharomyces cerevisiae and Williopsis saturnus. LWT Food Sci. Technol. 46:184–90
    [Google Scholar]
  64. Lee PR, Toh M, Yu B, Curran P, Liu SQ 2013. Manipulation of volatile compound transformation in durian wine by nitrogen supplementation. Int. J. Food Sci. Technol. 48:3650–62
    [Google Scholar]
  65. Lee S, Chang NI, Yoo M, Choi JH, Shin D. 2015. Development and validation of S-allyl-l-cysteine in rat plasma using a mixed-mode reversed-phase and cation-exchange LC-ESI-MS/MS method: application to pharmacokinetic studies. J. Chromatogr. Sci. 53:154–59
    [Google Scholar]
  66. Lee YM, Cho HJ, Ponnuraj SP, Kim J, Kim JS et al. 2011. Phenethyl isothiocyanate inhibits 12–tetradecanoylphorbol-13-acetate-induced inflammatory responses in mouse skin. J. Med. Food 14:4377–85
    [Google Scholar]
  67. Li D, Shu Y, Li P, Zhang W, Ni H et al. 2013. Synthesis and structure-activity relationships of aliphatic isothiocyanate analogs as antibiotic agents. Med. Chem. Res. 22:73119–25
    [Google Scholar]
  68. Li H, Xu F, Gao G, Gao X, Wu B et al. 2020. Hydrogen sulfide and its donors: novel antitumor and antimetastatic therapies for triple-negative breast cancer. Redox Biol 34:101564
    [Google Scholar]
  69. Li N, Chen K, Dong H, Yang J, Yoshizawa M et al. 2021. Alliin inhibits adipocyte differentiation by downregulating Akt expression: implications for metabolic disease. Exp. Ther. Med. 21:6563
    [Google Scholar]
  70. Liang D, Bian J, Deng LW, Huang D. 2017. Cyclic polysulphide 1,2,4-trithiolane from stinky bean (Parkia speciosa seeds) is a slow releasing hydrogen sulfide (H2S) donor. J. Funct. Foods 35:197–204
    [Google Scholar]
  71. Liang D, Wang C, Tocmo R, Wu H, Deng LW et al. 2015a. Hydrogen sulfide (H2S) releasing capacity of essential oils isolated from organosulphur rich fruits and vegetables. J. Funct. Foods 14:634–40
    [Google Scholar]
  72. Liang D, Wu H, Wong MW, Huang D. 2015b. Diallyl trisulfide is a fast H2S donor, but diallyl disulfide is a slow one: the reaction pathways and intermediates of glutathione with polysulfides. Org. Lett. 17:174196–99
    [Google Scholar]
  73. Lin Y, Yang X, Lu Y, Liang D, Huang D. 2019. Isothiocyanates as H2S donors triggered by cysteine: reaction mechanism and structure and activity relationship. Org. Lett. 21:155977–80
    [Google Scholar]
  74. Lu Y, Chua JY, Huang D, Lee PR, Liu SQ. 2017a. Chemical consequences of three commercial strains of Oenococcus oeni co-inoculated with Torulaspora delbrueckii in durian wine fermentation. Food Chem 215:209–18
    [Google Scholar]
  75. Lu Y, Fong ASYL, Chua JY, Huang D, Lee PR et al. 2018a. The possible reduction mechanism of volatile sulfur compounds during durian wine fermentation verified in modified buffers. Molecules 23:61456
    [Google Scholar]
  76. Lu Y, Huang D, Lee PR, Liu SQ. 2015. Effects of cofermentation and sequential inoculation of Saccharomyces bayanus and Torulaspora delbruckii on durian wine composition. Int. J. Food Sci. Technol. 50:122653–63
    [Google Scholar]
  77. Lu Y, Huang D, Lee PR, Liu SQ. 2016. Assessment of volatile and non-volatile compounds in durian wines fermented with four commercial non-Saccharomyces yeasts. J. Sci. Food Agric. 96:51511–21
    [Google Scholar]
  78. Lu Y, Putra SD, Liu SQ. 2018b. A novel non-dairy beverage from durian pulp fermented with selected probiotics and yeast. Int. J. Food Microbiol. 265:1–8
    [Google Scholar]
  79. Lu Y, Voon MKW, Chua JY, Huang D, Lee PR et al. 2017b. The effects of co- and sequential inoculation of Torulaspora delbrueckii and Pichia kluyveri on chemical compositions of durian wine. Appl. Microbiol. Biotechnol. 101:217853–63
    [Google Scholar]
  80. Lu Y, Voon MKW, Huang D, Lee PR, Liu SQ. 2017c. Combined effects of fermentation temperature and pH on kinetic changes of chemical constituents of durian wine fermented with Saccharomyces cerevisiae. Appl. Microbiol. Biotechnol. 101:73005–14
    [Google Scholar]
  81. Lu Y, Vos RDM, Zhang Y, Zhang M, Liu Y et al. 2021. The degradation kinetics and mechanism of moringin in aqueous solution and the cytotoxicity of degraded products. Food Chem. 364:130424
    [Google Scholar]
  82. Lu Y, Wang X, Pu H, Lin Y, Li D et al. 2020. Moringin and its structural analogues as slow H2S donors: their mechanisms and bioactivity. J. Agric. Food Chem. 68:277235–45
    [Google Scholar]
  83. Manchali S, Chidambara Murthy KN, Patil BS 2012. Crucial facts about health benefits of popular cruciferous vegetables. J. Funct. Foods 4:194–106
    [Google Scholar]
  84. Mansingh D, Dalpati N, Sali V, Rachel Vasanthi A. 2018. Alliin the precursor of allicin in garlic extract mitigates proliferation of gastric adenocarcinoma cells by modulating apoptosis. Pharmacogn. Mag. 14:5584–91
    [Google Scholar]
  85. Maslin D. 2008. Effects of garlic on cholesterol: not down but not out either. Arch. Int. Med. 168:1111–13
    [Google Scholar]
  86. Mohd Ali M, Hashim N, Aziz SA, Lasekan O 2020. Exploring the chemical composition, emerging applications, potential uses, and health benefits of durian: a review. Food Control 113:107189
    [Google Scholar]
  87. Morales-González JA, Madrigal-Bujaidar E, Sánchez-Gutiérrez M, Izquierdo-Vega JA, Carmen Valadez-Vega MD et al. 2019. Garlic (Allium sativum L.): a brief review of its antigenotoxic effects. Foods 8:8343
    [Google Scholar]
  88. Müller A, Eller J, Albrecht F, Prochnow P, Kuhlmann K et al. 2016. Allicin induces thiol stress in bacteria through S-allylmercapto modification of protein cysteines. J. Biol. Chem. 291:2211477–90
    [Google Scholar]
  89. Munday R, Zhang Y, Fahey JW, Jobson HE, Munday CM et al. 2006. Evaluation of isothiocyanates as potent inducers of carcinogen-detoxifying enzymes in the urinary bladder: critical nature of in vivo bioassay. Nutr. Cancer 54:2223–31
    [Google Scholar]
  90. Mustafa AM, Angeloni S, Nzekoue FK, Abouelenein D, Sagratini G et al. 2020. An overview on truffle aroma and main volatile compounds. Molecules 25:245948
    [Google Scholar]
  91. Navarro SL, Schwarz Y, Song X, Wang CY, Chen C et al. 2014. Cruciferous vegetables have variable effects on biomarkers of systemic inflammation in a randomized controlled trial in healthy young adults. J. Nutr. 144:111850–57
    [Google Scholar]
  92. Nicastro HL, Ross SA, Milner JA. 2015. Garlic and onions: their cancer prevention properties. Cancer Prev. Res. 8:3181–89
    [Google Scholar]
  93. Nikolantonaki M, Chichuc I, Teissedre PL, Darriet P. 2010. Reactivity of volatile thiols with polyphenols in a wine-model medium: impact of oxygen, iron, and sulfur dioxide. Anal. Chim. Acta 660:1–2102–9
    [Google Scholar]
  94. Ogita A, Fujita K, Toshio T. 2009. Enhancement of the fungicidal activity of amphotericin B by allicin: effects on intracellular ergosterol trafficking. Afr. J. Range Forage Sci. 75:222–26
    [Google Scholar]
  95. Olaimat AN, Holley RA. 2016. Inhibition of Listeria monocytogenes on cooked cured chicken breasts by acidified coating containing allyl isothiocyanate or deodorized Oriental mustard extract. Food Microbiol 57:90–95
    [Google Scholar]
  96. Oliviero T, Lamers S, Capuano E, Dekker M, Verkerk R. 2018a. Bioavailability of isothiocyanates from broccoli sprouts in protein, lipid, and fiber gels. Mol. Nutr. Food Res. 62:181700837
    [Google Scholar]
  97. Oliviero T, Verkerk R, Dekker M. 2018b. Isothiocyanates from Brassica vegetables: effects of processing, cooking, mastication, and digestion. Mol. Nutr. Food Res. 62:181701069
    [Google Scholar]
  98. Padla EP, Solis LT, Levida RM, Shen CC, Ragasa CY. 2012. Antimicrobial isothiocyanates from the seeds of Moringa oleifera Lam. Z. Naturforsch. C 67:557–64
    [Google Scholar]
  99. Pan JH, Abernathy B, Kim YJ, Lee JH, Kim JH et al. 2018. Cruciferous vegetables and colorectal cancer prevention through microRNA regulation: a review. Crit. Rev. Food Sci. Nutr. 58:122026–38
    [Google Scholar]
  100. Park T, Oh JH, Lee JH, Park SC, Jang YP et al. 2017. Oral administration of (S)-allyl-l-cysteine and aged garlic extract to rats: determination of metabolites and their pharmacokinetics. Planta Med 83:171351–60
    [Google Scholar]
  101. Pawlik A, Wała M, Hać A, Felczykowska A, Herman-Antosiewicz A. 2017. Sulforaphene, an isothiocyanate present in radish plants, inhibits proliferation of human breast cancer cells. Phytomedicine 29:1–10
    [Google Scholar]
  102. Pennazza G, Fanali C, Santonico M, Dugo L, Cucchiarini L et al. 2013. Electronic nose and GC-MS analysis of volatile compounds in Tuber magnatum Pico: evaluation of different storage conditions. Food Chem 136:2668–74
    [Google Scholar]
  103. Pérez-Serradilla JA, de Castro MDL. 2008. Role of lees in wine production: a review. Food Chem 111:2447–56
    [Google Scholar]
  104. Petropoulos S, Di Gioia F, Ntatsi G. 2017. Vegetable organosulfur compounds and their health promoting effects. Curr. Pharm. Des. 23:192850–75
    [Google Scholar]
  105. Putnik P, Gabrić D, Roohinejad S, Barba FJ, Granato D et al. 2019. An overview of organosulfur compounds from Allium spp.: from processing and preservation to evaluation of their bioavailability, antimicrobial, and anti-inflammatory properties. Food Chem 276:680–91
    [Google Scholar]
  106. Qi LL, Zhang M, Mujumdar AS, Meng XY, Chen HZ. 2014. Comparison of drying characteristics and quality of shiitake mushrooms (Lentinus edodes) using different drying methods. Dry. Technol. 32:151751–61
    [Google Scholar]
  107. Qin L, Gao JX, Xue J, Chen D, Lin SY et al. 2020. Changes in aroma profile of shiitake mushroom (Lentinus edodes) during different stages of hot air drying. Foods 9:4444
    [Google Scholar]
  108. Ramírez EC, Whitaker JR. 1999. Biochemical characterization of cystine lyase from broccoli (Brassica oleracea Var. italica). J. Agric. Food Chem. 47:62218–25
    [Google Scholar]
  109. Roy R, Hahm ER, White AG, Anderson CJ, Singh SV 2019. AKT-dependent sugar addiction by benzyl isothiocyanate in breast cancer cells. Mol. Carcinog. 58:6996–1007
    [Google Scholar]
  110. Ryu JH, Kang D. 2017. Physicochemical properties, biological activity, health benefits, and general limitations of aged black garlic: a review. Molecules 22:6919
    [Google Scholar]
  111. Saad B, Mona O. 2013. Antimicrobial activity of garlic juice (Allium sativum), honey, and garlic-honey mixture on some sensitive and multi-resistant microorganisms. Life Sci J. 10:42429–35
    [Google Scholar]
  112. Sánchez-Sánchez MA, Zepeda-Morales ASM, Carrera-Quintanar L, Viveros-Paredes JM, Franco-Arroyo NN et al. 2020. Alliin, an allium sativum nutraceutical, reduces metaflammation markers in DIO mice. Nutrients 12:3624–39
    [Google Scholar]
  113. Sansom CE, Jones VS, Joyce NI, Smallfield BM, Perry NB et al. 2015. Flavor, glucosinolates, and isothiocyanates of nau (Cooks scurvy grass, Lepidium oleraceum) and other rare New Zealand lepidium species. J. Agric. Food Chem. 63:61833–38
    [Google Scholar]
  114. Sarvan I, Kramer E, Bouwmeester H, Dekker M, Verkerk R. 2017. Sulforaphane formation and bioaccessibility are more affected by steaming time than meal composition during in vitro digestion of broccoli. Food Chem 214:580–86
    [Google Scholar]
  115. Schmidberger PC, Schieberle P. 2020. Changes in the key aroma compounds of raw shiitake mushrooms (Lentinula edodes) induced by pan-frying as well as by rehydration of dry mushrooms. J. Agric. Food Chem. 68:154493–506
    [Google Scholar]
  116. Sehrawat A, Croix CS, Baty CJ, Watkins S, Tailor D et al. 2016. Inhibition of mitochondrial fusion is an early and critical event in breast cancer cell apoptosis by dietary chemopreventative benzyl isothiocyanate. Mitochondrion 30:67–77
    [Google Scholar]
  117. Shang A, Cao SY, Xu XY, Gan RY, Tang GY et al. 2019. Bioactive compounds and biological functions of garlic (Allium sativum L.). Foods 8:7246
    [Google Scholar]
  118. Shi L, Lin Q, Li X, Nie Y, Sun S et al. 2017. Alliin, a garlic organosulfur compound, ameliorates gut inflammation through MAPK-NF-κB/AP-1/STAT-1 inactivation and PPAR-γ activation. Mol. Nutr. Food Res. 61:91601013
    [Google Scholar]
  119. Singh D, Arora R, Bhatia A, Singh H, Singh B et al. 2020. Molecular targets in cancer prevention by 4-(methylthio)butyl isothiocyanate: a comprehensive review. Life Sci 241:117061
    [Google Scholar]
  120. Smith MT, Guyton KZ, Gibbons CF, Fritz JM, Portier CJ et al. 2016. Key characteristics of carcinogens as a basis for organizing data on mechanisms of carcinogenesis. Environ. Health Perspect. 124:6713–21
    [Google Scholar]
  121. Sørensen JC, Frandsen HB, Jensen SK, Kristensen NB, Sørensen S et al. 2016. Bioavailability and in vivo metabolism of intact glucosinolates. J. Funct. Foods 24:450–60
    [Google Scholar]
  122. Sotelo T, Lema M, Soengas P, Cartea ME, Velasco P. 2015. In vitro activity of glucosinolates and their degradation products against Brassica-pathogenic bacteria and fungi. Appl. Environ. Microbiol. 81:1432–40
    [Google Scholar]
  123. Splivallo R, Ottonello S, Mello A, Karlovsky P. 2011. Truffle volatiles: from chemical ecology to aroma biosynthesis. New Phytol 189:3688–99
    [Google Scholar]
  124. Štefanová I, Zápal J, Moos M, Kuzma M, Kubec R. 2019. Isoalliin-derived thiolanes formed in homogenized onion. J. Agric. Food Chem. 67:359895–906
    [Google Scholar]
  125. Suvachittanont W, Kurashima Y, Esumi H, Tsuda M. 1996. Formation of thiazolidine-4-carboxylic acid (thioproline), an effective nitrite-trapping agent in human body, in Parkia speciosa seeds and other edible leguminous seeds in Thailand. Food Chem 55:4359–63
    [Google Scholar]
  126. Teh BT, Lim K, Yong CH, Ng CCY, Rao SR et al. 2017. The draft genome of tropical fruit durian (Durio zibethinus). Nat. Genet. 49:111633–41
    [Google Scholar]
  127. Teshika JD, Zakariyyah AM, Zaynab T, Zengin G, Rengasamy KR et al. 2019. Traditional and modern uses of onion bulb (Allium cepa L.): a systematic review. Crit. Rev. Food Sci. Nutr. 59:39–70
    [Google Scholar]
  128. Tocmo R, Lai AN, Wu Y, Liang D, Fogliano V et al. 2017a. Organosulfide profile and hydrogen sulfide-releasing activity of garlic fermented by Lactobacillus plantarum. J. Funct. Foods 30:254–59
    [Google Scholar]
  129. Tocmo R, Liang D, Lin Y, Huang D 2015. Chemical and biochemical mechanisms underlying the cardioprotective roles of dietary organopolysulfides. Front. Nutr. 2:1
    [Google Scholar]
  130. Tocmo R, Liang D, Wang C, Poh J, Huang D 2016. Organosulfide profile and hydrogen sulfide-releasing capacity of stinky bean (Parkia speciosa) oil: effects of pH and extraction methods. Food Chem 190:1123–29
    [Google Scholar]
  131. Tocmo R, Wu Y, Liang D, Fogliano V, Huang D 2017b. Boiling enriches the linear polysulfides and the hydrogen sulfide-releasing activity of garlic. Food Chem 221:1867–73
    [Google Scholar]
  132. Townsend BE, Chen YJ, Jeffery EH, Johnson RW 2014. Dietary broccoli mildly improves neuroinflammation in aged mice but does not reduce lipopolysaccharide-induced sickness behavior. Nutr. Res. 34:11990–99
    [Google Scholar]
  133. Townsend BE, Johnson RW 2016. Sulforaphane induces Nrf2 target genes and attenuates inflammatory gene expression in microglia from brain of young adult and aged mice. Exp. Gerontol. 73:42–48
    [Google Scholar]
  134. Tracz BL, Bordin K, Bocate KCP, Hara RV, Luz C et al. 2018. Devices containing allyl isothiocyanate against the growth of spoilage and mycotoxigenic fungi in mozzarella cheese. J. Food Process. Pres. 42:11e13779
    [Google Scholar]
  135. Van Veen AG, Hyman AJ. 1933. On the toxic component of the djenkol bean. Geneesk. Tijdschr. Nederl. Indie 73:991
    [Google Scholar]
  136. Vermeulen M, Klöpping-Ketelaars IWAA, Van Den Berg R, Vaes WHJ 2008. Bioavailability and kinetics of sulforaphane in humans after consumption of cooked versus raw broccoli. J. Agric. Food Chem. 56:2210505–9
    [Google Scholar]
  137. Voon YY, Abdul Hamid NS, Rusul G, Osman A, Quek SY 2007. Characterisation of Malaysian durian (Durio zibethinus Murr.) cultivars: relationship of physicochemical and flavour properties with sensory properties. Food Chem 103:41217–27
    [Google Scholar]
  138. Wang H, Wang L, Cao L, Zhang Q, Song Q et al. 2018. Inhibition of autophagy potentiates the anti-metastasis effect of phenethyl isothiocyanate through JAK2/STAT3 pathway in lung cancer cells. Mol. Carcinog. 57:4522–35
    [Google Scholar]
  139. Wang X, Liu Y, Liu X, Lin Y, Zheng X et al. 2018. Hydrogen sulfide (H2S) releasing capacity of isothiocyanates from Moringa oleifera Lam. Molecules 23:112890–902
    [Google Scholar]
  140. Waterman C, Cheng DM, Rojas-Silva P, Poulev A, Dreifus J et al. 2014. Stable, water extractable isothiocyanates from Moringa oleifera leaves attenuate inflammation in vitro. Phytochemistry 103:114–22
    [Google Scholar]
  141. Wei Z, Shan Y, Tao L, Liu Y, Zhu Z et al. 2017. Diallyl trisulfides, a natural histone deacetylase inhibitor, attenuate HIF-1α synthesis, and decreases breast cancer metastasis. Mol. Carcinog. 56:102317–31
    [Google Scholar]
  142. Wu CM, Wang Z. 2000. Volatile compounds in fresh and processed shiitake mushrooms (Lentinus edodes Sing.). Food Sci. Technol. Res. 6:3166–70
    [Google Scholar]
  143. Xiao J, Xing F, Liu Y, Lv Y, Wang X. et al. 2018. Garlic-derived compound S-allylmercaptocysteine inhibits hepatocarcinogenesis through targeting LRP6/Wnt pathway. Acta Pharm. Sin. B 8:4575–86
    [Google Scholar]
  144. Xu YS, Feng JG, Zhang D, Zhang B, Luo M et al. 2014. S-Allylcysteine, a garlic derivative, suppresses proliferation and induces apoptosis in human ovarian cancer cells in vitro. Acta Pharmacol. Sin. 35:2267–74
    [Google Scholar]
  145. Yeh YT, Hsu YN, Huang SY, Lin JS, Chen ZF et al. 2016. Benzyl isothiocyanate promotes apoptosis of oral cancer cells via an acute redox stress-mediated DNA damage response. Food Chem. Toxic. 97:336–45
    [Google Scholar]
  146. Yuan S, Shen X, Kevil CG. 2017. Beyond a gasotransmitter: hydrogen sulfide and polysulfide in cardiovascular health and immune response. Antioxid. Redox Signal. 27:10634653
    [Google Scholar]
  147. Zhang C, Shu L, Kim H, Khor TO, Wu R et al. 2016. Phenethyl isothiocyanate (PEITC) suppresses prostate cancer cell invasion epigenetically through regulating microRNA-194. Mol. Nutr. Food Res. 60:61427–36
    [Google Scholar]
  148. Zhang G, Parkin KL. 2013. A tissue homogenate method to prepare gram-scale allium thiosulfinates and their disulfide conjugates with cysteine and glutathione. J. Agric. Food Chem. 61:123030–38
    [Google Scholar]
  149. Zhang QC, Pan ZH, Liu BN, Meng ZW, Wu X et al. 2017. Benzyl isothiocyanate induces protective autophagy in human lung cancer cells through an endoplasmic reticulum stress-mediated mechanism. Acta Pharm. Sin. 38:4539–50
    [Google Scholar]
  150. Zhang Y. 2010. Allyl isothiocyanate as a cancer chemopreventive phytochemical. Mol. Nutr. Food Res. 54:1127–35
    [Google Scholar]
  151. Zhang Y, Li HY, Zhang ZH, Bian HL, Lin G. 2014. Garlic-derived compound S-allylmercaptocysteine inhibits cell growth and induces apoptosis via the JNK and p38 pathways in human colorectal carcinoma cells. Oncol. Lett. 8:62591–96
    [Google Scholar]
  152. Zhang Z, Bergan R, Shannon J, Slatore CG, Bobe G et al. 2018. The role of cruciferous vegetables and isothiocyanates for lung cancer prevention: current status, challenges, and future research directions. Mol. Nut. Food Res. 62:18e1700936
    [Google Scholar]
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