Structure Elucidation of New Kavalactone Dimers From Alpinia zerumbet Pericarps Using NMR Calculations

ABSTRACT Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm, known as shell ginger, is an aromatic plant widely distributed in tropical and subtropical regions. In Guizhou Province of China, its mature fruits have been used by the Miao people for the treatment of cardiovascular diseases. Although the b...

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Published in:Magnetic resonance in chemistry Vol. 63; no. 3; pp. 180 - 185
Main Authors: Nishidono, Yuto, Tanaka, Ken
Format: Journal Article
Language:English
Published: England Wiley Subscription Services, Inc 01.03.2025
Subjects:
13C NMR
1H NMR
Alpinia - chemistry
Alpinia zerumbet
Chemical equilibrium
cyclobutane
Density Functional Theory
DFT
Dimerization
Dimers
Fruit - chemistry
Fruits
Lactones - chemistry
Lactones - isolation & purification
Magnetic Resonance Spectroscopy
Molecular Structure
NMR
NMR chemical shift calculations
Nuclear magnetic resonance
Seeds
α‐pyrone
DFT
α‐pyrone
cyclobutane
Alpinia zerumbet
1H NMR
13C NMR
NMR chemical shift calculations
ISSN:0749-1581, 1097-458X, 1097-458X
Online Access:Get full text
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Summary:ABSTRACT Alpinia zerumbet (Pers.) B.L.Burtt & R.M.Sm, known as shell ginger, is an aromatic plant widely distributed in tropical and subtropical regions. In Guizhou Province of China, its mature fruits have been used by the Miao people for the treatment of cardiovascular diseases. Although the bioactivities of mature fruits of A. zerumbet are derived from phytochemicals in the seeds and pericarps of the plant, there remains a dearth of reports on the isolation of phytochemicals from the pericarp of A. zerumbet. In the present study, the pericarps of mature fruits of A. zerumbet were extracted, and two new kavalactone dimers, alpingsin E (1) and aniba dimer D (2), were isolated. Their structures were determined on the basis of extensive spectroscopic analysis and NMR calculations. Especially, density functional theory–based NMR chemical shift calculations were employed to elucidate and confirm the relative configuration of 1 and 2. The structures of alpingsin E (1) and aniba dimer D (2) were determined on the basis of extensive spectroscopic and DFT‐based NMR chemical shift calculations.
Bibliography:This research was funded by the AJI research advancement promotion program (2024‐III‐2) (Ritsumeikan University, Asia‐Japan Research Institute, Ibaraki, Osaka, Japan).
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ISSN:0749-1581
1097-458X
1097-458X
DOI:10.1002/mrc.5501