Novel colon-available triterpenoids identified in raspberry fruits exhibit anti-genotoxic activities in vitro.

G McDougall, JW Allwood, G Pereira-Caro, Emma Brown, S Verall, D Stewart, C Latimer, Geoffrey McMullan, R Lawther, G O'Connor, I Rowland, A Crozier, C.I.R Gill

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    SCOPE: Ileostomy studies provide a unique insight into digestion of food, allowing identification of physiologically relevant dietary phytochemicals and their metabolites important to gut health. We previously reported the consistent increase of components in ileal fluids of ileostomates after consumption of raspberries with use of non-targeted LC-MSn techniques and data deconvolution software highlighting two major unknown components (m/z 355 and 679).METHODS AND RESULTS: In-depth LC-MSn analyses suggested that the ileal m/z 355 components were p-coumaroyl glucarates. These compounds have not been identified previously and were confirmed in raspberry extracts after partial purification. The major ileal component with m/z 679 was a glycoside with an aglycone of m/z 517 and was present as two peaks in extracts of whole puree, unseeded puree and isolated seeds. These components were purified using Sephadex LH20 and C18 SPE units and identified as major, novel raspberry triterpenoid glycosides. This triterpenoid-enriched fraction (100 nM) protected against H2 O2 -induced DNA damage in both colon cancer and normal cell lines and altered expression of cytoprotective genes.CONCLUSION: The presence of these novel raspberry triterpenoid components in ileal fluids indicates that they would be colon-available in vivo, so confirmation of their anti-cancer bioactivities is of key physiological relevance.
    LanguageEnglish
    Pages1600327
    JournalMolecular Nutrition and Food Research
    Volume61
    Issue number2
    Early online date10 Sep 2016
    DOIs
    Publication statusE-pub ahead of print - 10 Sep 2016

    Fingerprint

    raspberries
    triterpenoids
    colon
    Fruit
    Colon
    fruits
    Glycosides
    glycosides
    Ileostomy
    extracts
    Phytochemicals
    colorectal neoplasms
    DNA damage
    Colonic Neoplasms
    phytopharmaceuticals
    DNA Damage
    Digestion
    Seeds
    Software
    digestive system

    Keywords

    • Raspberries
    • metabolic profiling
    • triterpenoids
    • colon cancer
    • ileal fluid

    Cite this

    McDougall, G ; Allwood, JW ; Pereira-Caro, G ; Brown, Emma ; Verall, S ; Stewart, D ; Latimer, C ; McMullan, Geoffrey ; Lawther, R ; O'Connor, G ; Rowland, I ; Crozier, A ; Gill, C.I.R. / Novel colon-available triterpenoids identified in raspberry fruits exhibit anti-genotoxic activities in vitro. In: Molecular Nutrition and Food Research. 2016 ; Vol. 61, No. 2. pp. 1600327.
    @article{00123625ace5413cb67dfbf8dc0c29f6,
    title = "Novel colon-available triterpenoids identified in raspberry fruits exhibit anti-genotoxic activities in vitro.",
    abstract = "SCOPE: Ileostomy studies provide a unique insight into digestion of food, allowing identification of physiologically relevant dietary phytochemicals and their metabolites important to gut health. We previously reported the consistent increase of components in ileal fluids of ileostomates after consumption of raspberries with use of non-targeted LC-MSn techniques and data deconvolution software highlighting two major unknown components (m/z 355 and 679).METHODS AND RESULTS: In-depth LC-MSn analyses suggested that the ileal m/z 355 components were p-coumaroyl glucarates. These compounds have not been identified previously and were confirmed in raspberry extracts after partial purification. The major ileal component with m/z 679 was a glycoside with an aglycone of m/z 517 and was present as two peaks in extracts of whole puree, unseeded puree and isolated seeds. These components were purified using Sephadex LH20 and C18 SPE units and identified as major, novel raspberry triterpenoid glycosides. This triterpenoid-enriched fraction (100 nM) protected against H2 O2 -induced DNA damage in both colon cancer and normal cell lines and altered expression of cytoprotective genes.CONCLUSION: The presence of these novel raspberry triterpenoid components in ileal fluids indicates that they would be colon-available in vivo, so confirmation of their anti-cancer bioactivities is of key physiological relevance.",
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    author = "G McDougall and JW Allwood and G Pereira-Caro and Emma Brown and S Verall and D Stewart and C Latimer and Geoffrey McMullan and R Lawther and G O'Connor and I Rowland and A Crozier and C.I.R Gill",
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    McDougall, G, Allwood, JW, Pereira-Caro, G, Brown, E, Verall, S, Stewart, D, Latimer, C, McMullan, G, Lawther, R, O'Connor, G, Rowland, I, Crozier, A & Gill, CIR 2016, 'Novel colon-available triterpenoids identified in raspberry fruits exhibit anti-genotoxic activities in vitro.', Molecular Nutrition and Food Research, vol. 61, no. 2, pp. 1600327. https://doi.org/10.1002/mnfr.201600327

    Novel colon-available triterpenoids identified in raspberry fruits exhibit anti-genotoxic activities in vitro. / McDougall, G; Allwood, JW; Pereira-Caro, G; Brown, Emma; Verall, S; Stewart, D; Latimer, C; McMullan, Geoffrey; Lawther, R; O'Connor, G; Rowland, I; Crozier, A; Gill, C.I.R.

    In: Molecular Nutrition and Food Research, Vol. 61, No. 2, 10.09.2016, p. 1600327.

    Research output: Contribution to journalArticle

    TY - JOUR

    T1 - Novel colon-available triterpenoids identified in raspberry fruits exhibit anti-genotoxic activities in vitro.

    AU - McDougall, G

    AU - Allwood, JW

    AU - Pereira-Caro, G

    AU - Brown, Emma

    AU - Verall, S

    AU - Stewart, D

    AU - Latimer, C

    AU - McMullan, Geoffrey

    AU - Lawther, R

    AU - O'Connor, G

    AU - Rowland, I

    AU - Crozier, A

    AU - Gill, C.I.R

    N1 - Compliant in UIR; evidence uploaded to 'Other files'

    PY - 2016/9/10

    Y1 - 2016/9/10

    N2 - SCOPE: Ileostomy studies provide a unique insight into digestion of food, allowing identification of physiologically relevant dietary phytochemicals and their metabolites important to gut health. We previously reported the consistent increase of components in ileal fluids of ileostomates after consumption of raspberries with use of non-targeted LC-MSn techniques and data deconvolution software highlighting two major unknown components (m/z 355 and 679).METHODS AND RESULTS: In-depth LC-MSn analyses suggested that the ileal m/z 355 components were p-coumaroyl glucarates. These compounds have not been identified previously and were confirmed in raspberry extracts after partial purification. The major ileal component with m/z 679 was a glycoside with an aglycone of m/z 517 and was present as two peaks in extracts of whole puree, unseeded puree and isolated seeds. These components were purified using Sephadex LH20 and C18 SPE units and identified as major, novel raspberry triterpenoid glycosides. This triterpenoid-enriched fraction (100 nM) protected against H2 O2 -induced DNA damage in both colon cancer and normal cell lines and altered expression of cytoprotective genes.CONCLUSION: The presence of these novel raspberry triterpenoid components in ileal fluids indicates that they would be colon-available in vivo, so confirmation of their anti-cancer bioactivities is of key physiological relevance.

    AB - SCOPE: Ileostomy studies provide a unique insight into digestion of food, allowing identification of physiologically relevant dietary phytochemicals and their metabolites important to gut health. We previously reported the consistent increase of components in ileal fluids of ileostomates after consumption of raspberries with use of non-targeted LC-MSn techniques and data deconvolution software highlighting two major unknown components (m/z 355 and 679).METHODS AND RESULTS: In-depth LC-MSn analyses suggested that the ileal m/z 355 components were p-coumaroyl glucarates. These compounds have not been identified previously and were confirmed in raspberry extracts after partial purification. The major ileal component with m/z 679 was a glycoside with an aglycone of m/z 517 and was present as two peaks in extracts of whole puree, unseeded puree and isolated seeds. These components were purified using Sephadex LH20 and C18 SPE units and identified as major, novel raspberry triterpenoid glycosides. This triterpenoid-enriched fraction (100 nM) protected against H2 O2 -induced DNA damage in both colon cancer and normal cell lines and altered expression of cytoprotective genes.CONCLUSION: The presence of these novel raspberry triterpenoid components in ileal fluids indicates that they would be colon-available in vivo, so confirmation of their anti-cancer bioactivities is of key physiological relevance.

    KW - Raspberries

    KW - metabolic profiling

    KW - triterpenoids

    KW - colon cancer

    KW - ileal fluid

    U2 - 10.1002/mnfr.201600327

    DO - 10.1002/mnfr.201600327

    M3 - Article

    VL - 61

    SP - 1600327

    JO - Molecular Nutrition and Food Research

    T2 - Molecular Nutrition and Food Research

    JF - Molecular Nutrition and Food Research

    SN - 1613-4125

    IS - 2

    ER -