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Structural investigations of flavonol glycosides from sea buckthorn (Hippophaë rhamnoides) pomace by NMR spectroscopy and HPLC-ESI-MS(n).
J Agric Food Chem. 2004 Jun 30; 52(13):4039-46.JA

Abstract

Four flavonol glycosides were isolated from an extract of sea buckthorn pomace (Hippophaë rhamnoides) by Sephadex LH-20 gel chromatography and semipreparative HPLC. Their structures were elucidated by hydrolysis studies, ESI-MS(n), UV, and (1)H and (13)C NMR spectroscopy. The occurrence of the major flavonol glycoside kaempferol 3-O-beta-sophoroside-7-O-alpha-rhamnoside in sea buckthorn is described here for the first time. A further 21 flavonol glycosides of Sephadex LH-20 fractions of sea buckthorn pomace were characterized by HPLC-DAD-ESI-MS. The characteristic MS-MS and MS(3) fragmentation pattern of flavonol glycosides previously identified in sea buckthorn juice and of flavonol glycosides identified by NMR spectroscopy gave valuable indications for their identification. The results demonstrate that loss of the sugar moiety from C-7 of the aglycon is more favored than fission of the glycosidic linkage at the C-3 position. Thus, most of the compounds identified were 7-rhamnosides of isorhamnetin, kaempferol, and quercetin, which exhibit different substitution patterns at the C-3 position, mainly glucosides, rutinosides, and sophorosides. In addition, numerous flavonol glycosides were detected lacking a sugar moiety at C-7. Finally, eight flavonol derivatives were identified that are acylated by hydroxybenzoic or hydoxycinnamic acids.

Authors+Show Affiliations

Institut für Lebensmitteltechnologie und Lebensmittelchemie, Technische Universität Berlin, Gustav-Meyer-Allee 25, D-13355 Berlin, Germany.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15212446

Citation

Rösch, Daniel, et al. "Structural Investigations of Flavonol Glycosides From Sea Buckthorn (Hippophaë Rhamnoides) Pomace By NMR Spectroscopy and HPLC-ESI-MS(n)." Journal of Agricultural and Food Chemistry, vol. 52, no. 13, 2004, pp. 4039-46.
Rösch D, Krumbein A, Mügge C, et al. Structural investigations of flavonol glycosides from sea buckthorn (Hippophaë rhamnoides) pomace by NMR spectroscopy and HPLC-ESI-MS(n). J Agric Food Chem. 2004;52(13):4039-46.
Rösch, D., Krumbein, A., Mügge, C., & Kroh, L. W. (2004). Structural investigations of flavonol glycosides from sea buckthorn (Hippophaë rhamnoides) pomace by NMR spectroscopy and HPLC-ESI-MS(n). Journal of Agricultural and Food Chemistry, 52(13), 4039-46.
Rösch D, et al. Structural Investigations of Flavonol Glycosides From Sea Buckthorn (Hippophaë Rhamnoides) Pomace By NMR Spectroscopy and HPLC-ESI-MS(n). J Agric Food Chem. 2004 Jun 30;52(13):4039-46. PubMed PMID: 15212446.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structural investigations of flavonol glycosides from sea buckthorn (Hippophaë rhamnoides) pomace by NMR spectroscopy and HPLC-ESI-MS(n). AU - Rösch,Daniel, AU - Krumbein,Angelika, AU - Mügge,Clemens, AU - Kroh,Lothar W, PY - 2004/6/24/pubmed PY - 2004/8/4/medline PY - 2004/6/24/entrez SP - 4039 EP - 46 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 52 IS - 13 N2 - Four flavonol glycosides were isolated from an extract of sea buckthorn pomace (Hippophaë rhamnoides) by Sephadex LH-20 gel chromatography and semipreparative HPLC. Their structures were elucidated by hydrolysis studies, ESI-MS(n), UV, and (1)H and (13)C NMR spectroscopy. The occurrence of the major flavonol glycoside kaempferol 3-O-beta-sophoroside-7-O-alpha-rhamnoside in sea buckthorn is described here for the first time. A further 21 flavonol glycosides of Sephadex LH-20 fractions of sea buckthorn pomace were characterized by HPLC-DAD-ESI-MS. The characteristic MS-MS and MS(3) fragmentation pattern of flavonol glycosides previously identified in sea buckthorn juice and of flavonol glycosides identified by NMR spectroscopy gave valuable indications for their identification. The results demonstrate that loss of the sugar moiety from C-7 of the aglycon is more favored than fission of the glycosidic linkage at the C-3 position. Thus, most of the compounds identified were 7-rhamnosides of isorhamnetin, kaempferol, and quercetin, which exhibit different substitution patterns at the C-3 position, mainly glucosides, rutinosides, and sophorosides. In addition, numerous flavonol glycosides were detected lacking a sugar moiety at C-7. Finally, eight flavonol derivatives were identified that are acylated by hydroxybenzoic or hydoxycinnamic acids. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/15212446/Structural_investigations_of_flavonol_glycosides_from_sea_buckthorn__Hippophaë_rhamnoides__pomace_by_NMR_spectroscopy_and_HPLC_ESI_MS_n__ L2 - https://doi.org/10.1021/jf0306791 DB - PRIME DP - Unbound Medicine ER -