4 research outputs found
Nonanthocyanin Secondary Metabolites of Black Raspberry (<i>Rubus occidentalis</i> L.) Fruits: Identification by HPLC-DAD, NMR, HPLC-ESI-MS, and ESI-MS/MS Analyses
Nonanthocyanin
secondary metabolites potentially contributing to
the antiproliferative bioactivity of black raspberry (Rubus occidentalis L.) fruits were extracted in ethyl
acetate and isolated by semipreparative and analytical HPLC and analyzed
by NMR, HPLC-ESI-MS, and ESI-MS/MS techniques. Here we present complete
and partial structures of a variety of the chemical entities such
as quercetin 3-glucoside, quercetin 3-rutinoside, myricetin glucoside,
dihydrokaempferol glucoside, benzoic acid β-d-glucopyranosyl
ester, 3,4-dihydroxybenzoic acid, epicatechin, caffeic acid, <i>p-</i>coumaric acid, <i>p-</i>coumaryl glucoside, <i>p-</i>coumaryl sugar ester, ellagic acid, methyl ellagic acid
acetylpentose, methyl ellagic acid valerylpentose, <i>trans</i>-piceid, phloretin glucoside (phloridzin), dihydrosinapic acid, salicylic
acid β-d-glucopyranosyl ester, a salicylic acid derivative
without attached sugar, <i>p-</i>alkylphenyl glucoside,
and a citric acid derivative. To our knowledge, 15 of these compounds
were not previously reported in black raspberry fruits
NMR-Based Metabolomic Investigation of Bioactivity of Chemical Constituents in Black Raspberry (Rubus occidentalis L.) Fruit Extracts
Black
raspberry (Rubus occidentalis L.) (BR)
fruit extracts with differing compound profiles have shown
variable antiproliferative activities against HT-29 colon cancer cell
lines. This study used partial least-squares (PLS) regression analysis
to develop a high-resolution <sup>1</sup>H NMR-based multivariate
statistical model for discerning the biological activity of BR constituents.
This model identified specific bioactive compounds and ascertained
their relative contribution against cancer cell proliferation. Cyanidin
3-rutinoside and cyanidin 3-xylosylrutinoside were the predominant
contributors to the extract bioactivity, but salicylic acid derivatives
(e.g., salicylic acid glucosyl ester), quercetin 3-glucoside, quercetin
3-rutinoside, <i>p</i>-coumaric acid, epicatechin, methyl
ellagic acid derivatives (e.g., methyl ellagic acetyl pentose), and
citric acid derivatives also contributed significantly to the antiproliferative
activity of the berry extracts. This approach enabled the identification
of new bioactive components in BR fruits and demonstrates the utility
of the method for assessing chemopreventive compounds in foods and
food products