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Phytochemical study of Juglans regia L. leaves.
Phytochemistry. 2017 Dec; 144:58-70.P

Abstract

A methanolic extract of Juglans regia L. leaves was fractioned by various chromatographic techniques yielding a total of 40 metabolites belonging to megastigmane, tetralone, phenylpropanoid, neolignane and juglone glycosides. Ten unknown megastigmane glucoside derivatives (juglanionosides A-K, 1-10) and six unknown tetralone glucoside derivatives (juglanosides J-O, 11-16) together with 24 known compounds - among them 16 described for the first time in Juglans - were isolated. As characteristic structural feature, the previously undescribed compounds showed acylation of the sugar units with sinapic, ferulic, coumaric, benzoic or salicylic acid. Their chemical structures were elucidated on the basis of 1D and 2D NMR techniques, HRESIMS as well as CD spectroscopy. Absolute stereochemistry was revealed by mild alkaline hydrolysis and comparison of CD and polarimetric data to literature values.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Schwindl S
Institute of Pharmaceutical Biology, Universitätsstr. 31, Regensburg, D-93053, Germany.
Kraus B
Institute of Pharmaceutical Biology, Universitätsstr. 31, Regensburg, D-93053, Germany.
Heilmann J
Institute of Pharmaceutical Biology, Universitätsstr. 31, Regensburg, D-93053, Germany. Electronic address: joerg.heilmann@chemie.uni-regensburg.de.

MeSH

JuglansMolecular ConformationNorisoprenoidsPhytochemicalsPlant LeavesTetralones

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28888783

Citation

Schwindl, Sebastian, et al. "Phytochemical Study of Juglans Regia L. Leaves." Phytochemistry, vol. 144, 2017, pp. 58-70.
Schwindl S, Kraus B, Heilmann J. Phytochemical study of Juglans regia L. leaves. Phytochemistry. 2017;144:58-70.
Schwindl, S., Kraus, B., & Heilmann, J. (2017). Phytochemical study of Juglans regia L. leaves. Phytochemistry, 144, 58-70. https://doi.org/10.1016/j.phytochem.2017.08.012
Schwindl S, Kraus B, Heilmann J. Phytochemical Study of Juglans Regia L. Leaves. Phytochemistry. 2017;144:58-70. PubMed PMID: 28888783.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Phytochemical study of Juglans regia L. leaves. AU - Schwindl,Sebastian, AU - Kraus,Birgit, AU - Heilmann,Jörg, Y1 - 2017/09/08/ PY - 2017/04/11/received PY - 2017/08/16/revised PY - 2017/08/20/accepted PY - 2017/9/11/pubmed PY - 2017/12/22/medline PY - 2017/9/11/entrez KW - Actinidioionoside KW - Juglandaceae KW - Juglanionoside KW - Juglanoside KW - Juglans regia KW - Kiwiionoside KW - Megastigmane KW - Neolignan KW - Phenylpropanoid KW - Tetralone SP - 58 EP - 70 JF - Phytochemistry JO - Phytochemistry VL - 144 N2 - A methanolic extract of Juglans regia L. leaves was fractioned by various chromatographic techniques yielding a total of 40 metabolites belonging to megastigmane, tetralone, phenylpropanoid, neolignane and juglone glycosides. Ten unknown megastigmane glucoside derivatives (juglanionosides A-K, 1-10) and six unknown tetralone glucoside derivatives (juglanosides J-O, 11-16) together with 24 known compounds - among them 16 described for the first time in Juglans - were isolated. As characteristic structural feature, the previously undescribed compounds showed acylation of the sugar units with sinapic, ferulic, coumaric, benzoic or salicylic acid. Their chemical structures were elucidated on the basis of 1D and 2D NMR techniques, HRESIMS as well as CD spectroscopy. Absolute stereochemistry was revealed by mild alkaline hydrolysis and comparison of CD and polarimetric data to literature values. SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/28888783/Phytochemical_study_of_Juglans_regia_L__leaves_ DB - PRIME DP - Unbound Medicine ER -