The Cyclic Diarylheptanoid Asadanin as the Main Contributor to the Bitter Off-Taste in Hazelnuts (<i>Corylus avellana</i> L.)

Singldinger, Barbara; Dunkel, Andreas; Hofmann, Thomas

doi:10.1021/acs.jafc.7b00026

Cited by 30 publications

(49 citation statements)

References 30 publications

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“…Organoleptic characteristics are attributed to the presence of diarylheptanoids. Singldinger et al (2017) identified asadanin, a cyclic diarylhepatanoids responsible for the bitter off-taste in Corylus avellana.…”

Section: Introductionmentioning

confidence: 99%

Diarylheptanoids as nutraceutical: A review

Ganapathy

Preethi

Moses

et al. 2019

Biocatalysis and Agricultural Biotechnology

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Phenolic compounds are naturally occurring compounds present ubiquitously in plants. They have potential health benefits and substantiate evidence for their nutraceutical applications. Diarylheptanoids are part of the broad class of plant phenolics with structurally divergent compounds. They have been used in traditional medicines and homemade remedies to treat various ailments, as organoleptic additives in foods, and also for aesthetic purposes. With their potential therapeutic and organoleptic characteristics, diarylhepatanoids can be rightly termed as nutraceuticals. This review summarizes the wide range of pharmacological activities of diarylhepatanoids and nutraceutical formulations, with relevance to human health.

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Section: Introductionmentioning

confidence: 99%

Diarylheptanoids as nutraceutical: A review

Ganapathy

Preethi

Moses

et al. 2019

Biocatalysis and Agricultural Biotechnology

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show abstract

“…The extracted diarylheptanoids can be fractionated using open column chromatography (CC), vacuum liquid chromatography (VLC) [34,60,61], middle pressure liquid chromatography (MPLC) [62,63], flash chromatography [64,65], preparative thin-layer chromatography (TLC) [66], or preparative high-performance liquid chromatography (HPLC) ( Table 2) [67]. Cyclic MPLC has also been employed [47].…”

Section: Isolationmentioning

confidence: 99%

“…The mass analyzers used in the characterization of diarylheptanoids are time-of-flight (TOF) MS, which enables accurate mass analysis [50,53,63,136], triple-quadrupole (QQQ) MS [75,146,174] that provides additional structural information by the observation of the fragmentation pattern of the target analytes, while quadrupole-time-of-flight (Q-TOF) technique offers exact mass measurement of both precursor and fragment ions [49,175,176]. High-resolution ion trap MS analyzer was also applied in the characterization of diarylheptanoid fragmentation in Z. officinale [135].…”

Section: Ionization Interfaces Mass Analyzersmentioning

confidence: 99%

“…Asadanin, a bitter tasting cyclic diarylheptanoid has recently been isolated from hazelnut kernels. Sensory analysis of hazelnut samples, followed by LC-MS/MS quantitation of asadanin showed evidence for the box bug (Gonocerus acuteangulatus) infection as the major inductor of asadanin production in hazelnut kernels and, in consequence, as the reason for bitter off-taste development [63]. LC-ESI-MS/MS was applied for the quantification of yakuchinone A together with hexahydrocurcumin in A. officinarum leaves and rhizomes.…”

Section: Quantitative Ms Characterization Of Diarylheptanoidsmentioning

confidence: 99%

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Characterization of diarylheptanoids: An emerging class of bioactive natural products

Alberti

Riethmüller

Béni

2018

Journal of Pharmaceutical and Biomedical Analysis

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Diarylheptanoids are a class of secondary plant metabolites with a wide variety of bioactivity. Research on their phytochemistry and phytoanalysis is rapidly growing and the number of identified structures bearing the aryl-C-aryl skeleton is at present approaching 500. Historically, the yellow pigment curcumin has been characterized as the first diarylheptanoid and the extensive research on naturally occurring analogues is still ongoing. In this review, studies dealing with the characterization of linear and cyclic derivatives are discussed from the phytoanalytical point of view. Isolation, fractionation and purification strategies from natural sources along with their chromatographic behavior and structural characteristics are discussed. The role of various techniques used for the extraction (such as Soxhlet extraction, sonication, maceration/percolation, microwave-assisted extraction, supercritical carbon dioxide extraction); isolation (liquid-liquid extraction, column chromatographic techniques, preparative thin-layer and high-performance liquid chromatography, centrifugal partition chromatography, counter-current chromatography); separation (thin-layer chromatography, high-performance liquid chromatography, gas chromatography, capillary electrophoresis) and structural characterization (UV/Vis spectroscopy, infrared spectroscopy, X-ray crystallography, mass spectrometry, nuclear magnetic resonance spectroscopy and circular dichroism spectroscopy) are critically reviewed.

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“…Additional biphenyl heptanoids, such as deoxoasadanin ( 1b ), epiasadanol ( 1c ), isoasadanol ( 2 ), and di- and trideoxyasadanin-8-ene ( 3 ) were isolated from Ostrya japonica [48]. Recently, Singldinger et al isolated asadanin ( 1a ) from hazelnuts ( Corylus avellana L.) as the main contributor to the bitter off-taste and reported complete analysis and assignment of all the proton and carbon resonances of the molecule [49].…”

Section: Isolation Structural Features and Biological Propertiesmentioning

confidence: 99%

Recent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Jahng

Park

2018

Molecules

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Diarylheptanoids are a family of plant secondary metabolites with a 7 carbon skeleton possessing two phenyl rings at the 1- and 7-positions. They can be subdivided into acyclic and cyclic diarylheptanoids where the latter are further divided into meta,meta-bridged biphenyls ([7.0]metacyclophanes) and meta,para-bridged diphenyl ether heptanoids (oxa[7.1]metapara-cyclophanes). Since the isolation of curcumin from the rhizomes of turmeric (Curcuma longa) in 1815 which was named curcumin, a variety of diarylheptanoids have been isolated from a number of plant families such as Aceraceae, Actinidiaceae, Betulaceae, Burseraceae, Casuarinaceae, Juglandaceae, Leguminosae, Myricaceae, and Zingiberaceae. Earlier studies on these diarylheptanoids have been summarized on several occasions, of which the main themes only focus on isolation, structure elucidation, and the biological properties of linear types. Only a few have covered cyclic diarylheptanoids and their chemical synthesis has been covered lastly by Zhu et al. in 2000. The present paper has, therefore, covered recent progress in cyclic diarylheptanoids focusing on the isolation, structural and biological features, and chemical synthesis.

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The Cyclic Diarylheptanoid Asadanin as the Main Contributor to the Bitter Off-Taste in Hazelnuts (Corylus avellana L.)

Cited by 30 publications

References 30 publications

Diarylheptanoids as nutraceutical: A review

Diarylheptanoids as nutraceutical: A review

Characterization of diarylheptanoids: An emerging class of bioactive natural products

Recent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

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