{"title":"Response surface methodology for optimization of enzymatic acylation of (R)-(‒)-linalool application to essential oils","authors":"Chaibrassou Naouel, Zeror Saoussen, Merabet-Khelassi Mounia, Kilani-Morakchi Samira, Sifi Karima","doi":"10.1002/ffj.3735","DOIUrl":"https://doi.org/10.1002/ffj.3735","url":null,"abstract":"<p>The essential oils of Lavender (<i>Lavandula angustifolia</i>) and Tropical Basil (<i>Ocimum basilicum</i>) are characteristically high in both linalool and linalyl acetate esters, key constituents determining essential oil (EO) quality and activity. The enrichment of these products in linalyl acetate has a great interest in the industry. Herein, we report the production of linalyl acetate using the free lipase <i>PPL</i> as a catalyst in a solvent-free medium. Parametric studies referring response surface methodology (RSM) were applied to optimize the conversion. The optimal experimental condition for (<i>R</i>)-linalool acylation (temperature at 60°C, catalyst amount at 150 mg, volume of acetic anhydride at 1 mL, and reaction time at 5 days) was obtained from an experimental design analysis. Under these conditions, the enzymatic acylation was carried out for both pure linalool<i>, Lavandula angustifolia</i> and <i>O. basilicum</i> essential oils as substrates. 24.94% conversion of pure linalool to linalyl acetate was obtained; however, essential oils gave lower conversions (conv = 13%).</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 3","pages":"183-192"},"PeriodicalIF":2.6,"publicationDate":"2023-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5793215","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xinhao Dong, Hua Zheng, Dan Li, Qunzhi Hu, Peiyong Guo, Tiancheng Liu, Yun Gu, Yafei Tan
{"title":"A practical synthesis of 8-methyldecanal","authors":"Xinhao Dong, Hua Zheng, Dan Li, Qunzhi Hu, Peiyong Guo, Tiancheng Liu, Yun Gu, Yafei Tan","doi":"10.1002/ffj.3737","DOIUrl":"https://doi.org/10.1002/ffj.3737","url":null,"abstract":"<p>8-methyldecanal is a characteristic ingredient of Australian finger lime (<i>Citrus australasica</i>), and has found important applications in flavour and fragrance industry. A novel and practical preparation method of 8-methyldecanal is presented. Starting from cheap and readily available 6-chloro-1-hexanol, 8-methyldecanal was prepared in five steps with an overall yield of 50.7%.</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 3","pages":"163-167"},"PeriodicalIF":2.6,"publicationDate":"2023-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"6004577","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Cristina Barallat Pérez, Teresa Oliviero, Vincenzo Fogliano, Hans-Gerd Janssen, Sara I. F. S. Martins
{"title":"Flavour them up! Exploring the challenges of flavoured plant-based foods","authors":"Cristina Barallat Pérez, Teresa Oliviero, Vincenzo Fogliano, Hans-Gerd Janssen, Sara I. F. S. Martins","doi":"10.1002/ffj.3734","DOIUrl":"https://doi.org/10.1002/ffj.3734","url":null,"abstract":"<p>Food flavourings are often added to enhance overall flavour experience during food consumption and their use in plant-based food analogues is crucial. The flavour sensory perception is strongly mediated by flavour–food matrix interactions. Aroma molecules establish chemical and physical bonds with lipids and carbohydrates, but proteins play a pivotal role having a strong flavour binding minimizing aroma release and quenching flavour perception. Consequently, final food quality is reduced and so is consumer acceptance. Depending on the chemical structure of the flavour and the type of protein involved, the strength of the flavour–protein binding can vary. It is of great importance to understand if this interaction remains under dynamic conditions such as the oral processing during food consumption. This review aims to gain insights into the influence of the chemical structure and physicochemical features of both proteins and flavours on the binding mechanism. Moreover, the potentiality of coupling in vivo instrumental analysis with sensory methods to study flavour release in real time is explored. Elucidating the drivers of flavour interaction with, and release from, the food matrix is essential to develop flavour solutions for the new generation of plant-based food products.</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 3","pages":"125-134"},"PeriodicalIF":2.6,"publicationDate":"2023-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ffj.3734","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5686586","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Isolation and identification of progenitors, glycoconjugates of β-damascenone precursors, in sweet potato (Ipomoea batatas)","authors":"Tai Kaneshima, Satoshi Nojima, Shoko Mori, Takao Myoda, Koichi Nakahara, Yoshihide Matsuo","doi":"10.1002/ffj.3736","DOIUrl":"https://doi.org/10.1002/ffj.3736","url":null,"abstract":"<p>β-Damascenone, which has a characteristic sweet and fruity aroma, is a key flavour of various food and drinks, including sweet potato shochu, a Japanese traditional spirit. The compound in the spirits is known to be hydrolytically generated and liberated from progenitors in sweet potato during the manufacturing processes. However, thus far, the progenitors have not been well investigated. In this study, we isolated and identified 11 glycosidic progenitor compounds 1–11 using various chromatographic and spectroscopic techniques combined with a hydrolysis assay. These progenitors consist of two types of aglycones [3,5,9-trihydroxymegastigma-6,7-diene (<b>A1</b>) and 3,9-dihydroxymegastigma-4,6,7-triene (<b>A2</b>)] and four types of glycones [β-<span>d</span>-glucopyranoside (<b>G1</b>), (2-<i>O</i>-β-apiofuranosyl)-β-<span>d</span>-glucopyranoside (<b>G2</b>), (6-<i>O</i>-β-xylopyranosyl)-β-<span>d</span>-glucopyranoside (<b>G3</b>) and (2-<i>O</i>-β-<span>d</span>-apiofuranosyl,6-<i>O</i>-β-<span>d</span>-xylopyranosyl)-β-<span>d</span>-glucopyranoside (<b>G4</b>)]. Aglycones <b>A1</b> and <b>A2</b> are known as direct precursors of β-damascenone, and compounds <b>1</b>–<b>3</b>, which have <b>A1</b> as an aglycone, have been previously reported from other plant materials. On the other hand, compounds <b>4</b>–<b>11</b> are newly characterized as glycosidic progenitors of β-damascenone.</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 3","pages":"152-162"},"PeriodicalIF":2.6,"publicationDate":"2023-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5876229","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kaixiong Peng, Qunyong Tang, Yuhan Zheng, Fang Ji, Xiaoming Chen
{"title":"Analysis of volatile components in different broken rice by HS-SPME/GC-TOFMS","authors":"Kaixiong Peng, Qunyong Tang, Yuhan Zheng, Fang Ji, Xiaoming Chen","doi":"10.1002/ffj.3733","DOIUrl":"https://doi.org/10.1002/ffj.3733","url":null,"abstract":"<p>In this study, headspace solid-phase microextraction (HS-SPME) combined with gas chromatography-time-of-flight mass spectrometry (GC-TOFMS) was used to detect and analyse the volatile components of five samples with different degrees of fragmentation, combined with cluster analysis, orthogonal partial least squares discrimination analysis (OPLS-DA) and relative odour activity value (ROAV) analysis. The results showed that 70 volatile components were detected and identified in samples with different degrees of fragmentation. 40 were co-containing components. Cluster analysis revealed a high degree of similarity between samples B (20 mesh sieve top) and C (40 mesh sieve top), which were grouped into one category. The order of variation in the relative content of volatile components was A (unbroken) > E (120 mesh sieve top) > D (80 mesh sieve top) > B. C; the OPLS-DA analysis revealed significant differences in the volatile composition of rice samples with different degrees of fragmentation, This variation between samples is mainly due to the relative content of volatile components of 36 projections of variable importance (VIP > 1), such as ethyl butyrate, ethyl phenylacetate, and dimethyl trisulfide. A total of 12 volatile components with ROAV > 1, including ethyl hexanoate, 2-acetyl-1-pyrroline, and <i>E</i>-2-nonenal, were found to be the key volatile components in five samples based on their ROAV, the different degrees of crushing had a greater impact on the overall aroma of the rice, and the results can be used as a reference for further rice processors.</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 3","pages":"204-216"},"PeriodicalIF":2.6,"publicationDate":"2023-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5927370","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kellyann Clarke, Roy Porter, Petrea Facey, Camille Thoms-Rodriguez
{"title":"Chemical composition and biological activities of Jamaican Cannabis sativa essential oils as the plant matures","authors":"Kellyann Clarke, Roy Porter, Petrea Facey, Camille Thoms-Rodriguez","doi":"10.1002/ffj.3732","DOIUrl":"https://doi.org/10.1002/ffj.3732","url":null,"abstract":"<p><i>Cannabis sativa</i> is a flowering plant belonging to the Cannabinaceae family. There have been numerous ongoing studies globally on <i>C. sativa</i> which include investigating the yield and quality of essential oils. However, this study is the first to assess the chemical composition and biological activities of Jamaican <i>C. sativa</i> essential oils (EOs) extracted via hydrodistillation as the plants mature from week 8 through to week 12. EOs from fresh landrace female plants were analysed by gas chromatography–mass spectrometry (GC–MS) and GC coupled to a flame ionization detector (GC-FID). <i>Cannabis sativa</i> essential oils were screened for their in vitro antimicrobial activity using the disc diffusion method and further with tube dilution method. The antioxidant properties were investigated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. In total, 36 constituents were identified in the <i>C. sativa</i> EOs by comparison of the Kováts retention indices (RI), the mass spectra data with those in the Natural Institute of Standards and Technology (NIST) library and by co-elution with authentic samples where available. The major constituents were β-caryophyllene (25.34%) and α-humulene (α-caryophyllene) (10.94%) both at the highest levels in week nine and were the most abundant constituents present at all stages of maturity. All extracted <i>C. sativa</i> essential oils did not exhibit antioxidant properties. However, the <i>C. sativa</i> essential oils exhibit significant to moderate antimicrobial property against the test gram-positive microorganisms, <i>Enterococcus faecalis</i>, <i>Streptococcus Group A</i> and <i>Streptococcus Group B</i> with MIC values ranging from 16 to 125 μg/mL.</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 3","pages":"144-151"},"PeriodicalIF":2.6,"publicationDate":"2023-02-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"5728306","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Julio César Barros-Castillo, Montserrat Calderón-Santoyo, Luis Fernando Cuevas-Glory, Carolina Calderón-Chiu, Juan Arturo Ragazzo-Sánchez
{"title":"Contribution of glycosidically bound compounds to aroma potential of jackfruit (Artocarpus heterophyllus lam)","authors":"Julio César Barros-Castillo, Montserrat Calderón-Santoyo, Luis Fernando Cuevas-Glory, Carolina Calderón-Chiu, Juan Arturo Ragazzo-Sánchez","doi":"10.1002/ffj.3730","DOIUrl":"https://doi.org/10.1002/ffj.3730","url":null,"abstract":"<p>Volatile compounds are present in fruits in two forms, free and glycosidically bound. The latest has been studied in several fruits and are considered important aroma precursors because their release by acid or enzymatic hydrolysis has been reported higher than the free fraction. Recently, volatiles released by acid hydrolysis in jackfruit were reported, however, enzymatic hydrolysis of glycosidically bound fraction has not been studied yet. Thus, in this study, the free and glycosidically bound volatile compounds from jackfruit were isolated by absorption onto a column of Amberlite XAD-2. Enzymatic hydrolysis with <i>β</i>-glucosidase was carried out to release the glycosidically bound compounds and identified by GC–MS. Fifty-four volatiles encompassed both fractions with 14 compounds in common. 2,4-dimethylbenzaldehyde, 4-methylpentan-2-ol, 2,6-dimethylheptan-4-one, neral, butan-1-ol, and hexadecanoic acid were prominent in the free fraction. Meanwhile, 3-hydroxy-<i>β</i>-ionol, 2-phenylethanol, benzyl alcohol, lavandulol, 3-oxo-<i>α</i>-ionol, and hexadecanoic acid were predominant in the bound form. Odor activity values (OAV) and relative odor contribution (ROC) of free and glycosidically bound compounds were calculated. Thus, ethyl 3-methylbutanoate, methyl 2-methylbutanoate, methyl butanoate, 3-methyl-3-buten-1-ol, octan-1-ol, 3-methylbutanal, hexanal, 2-nonanone, 2-phenylethanol, and limonene showed OAV >1 after hydrolysis, contributing to the overall aroma. Results revealed that the bound fraction of jackfruit volatiles is eight times fold that their free counterpart. Information about the first research of glycosidically bound compounds in jackfruit released by enzymatic hydrolysis is provided. The results reinforce the importance of aroma precursors to suggest the raw material according to the applied pretreatment and thus take advantage of the aromatic potential that they can develop.</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 3","pages":"193-203"},"PeriodicalIF":2.6,"publicationDate":"2023-02-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"6204403","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Rui Han, Zixuan Wang, Xiangxun Zhuansun, Yuan Gao, Yao Li, Qi Liu
{"title":"Preparation of tea tree oil nanoemulsion: Characterisation, antibacterial mechanism and evaluation of apoptosis","authors":"Rui Han, Zixuan Wang, Xiangxun Zhuansun, Yuan Gao, Yao Li, Qi Liu","doi":"10.1002/ffj.3731","DOIUrl":"https://doi.org/10.1002/ffj.3731","url":null,"abstract":"<p>Tea tree oil (TTO) is a natural plant essential oil that has strong bactericidal properties and low toxicity. However, owing to its irritability, volatility, instability under light/oxygen and hydrophobicity, the application of TTO in pharmaceutical production technology and the food industry is limited. To overcome these problems, TTO nanoemulsions (TTONs) were prepared using a high-speed shearing method. The mean droplets size of TTON was measured. TTON droplets were observed using confocal laser scanning microscopy and analysed using a Turbiscan scanning spectrum. The most suitable nanoemulsion formula was obtained as follows: TTO content, 10% (w/w); Tw-40 content, 8% (w/w); deionised water content, 82% (w/w); shearing time, 5 minutes. The antibacterial effect of TTON was studied, and it was found that its antibacterial activity against <i>Escherichia coli</i> was more potent than that against <i>Staphylococcus aureus</i>. The antibacterial mechanism of TTON was also investigated by observing bacterial morphology using scanning electron microscopy and testing the levels of bacterial reactive oxygen species. The effect of TTON on L-02 cells was evaluated. The results showed that the cell survival rates of L-02 cells treated with TTON at 0.05-0.25 μg/μL were all >90%. At each concentration, the total apoptosis rate of L-02 cells was <10%. These results indicated the high biocompatibility and biological safety of TTON. Therefore, the preparation of TTO into a nanoemulsion can improve its bioavailability, which has positive implications for further applications of TTO.</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 3","pages":"135-143"},"PeriodicalIF":2.6,"publicationDate":"2023-02-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"6150911","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Mechanism of palmitoleic acid oxidation into volatile compounds during heating","authors":"Pengxun Gao, Yuxiang Bao, Shuo Wang, Liming Lei, Binchen Wang, Lin Xiao, Kunya Cheng, Yian Wang, Sufang Zhang, Liang Dong","doi":"10.1002/ffj.3728","DOIUrl":"https://doi.org/10.1002/ffj.3728","url":null,"abstract":"<p>To better understand the mechanism of palmitoleic acid oxidation into volatile compounds during heating, volatile profiling was investigated by combining thermal-desorption cryo-trapping with gas chromatography–mass spectrometry. A total of 49 volatile compounds were detected and identified during this process, including aldehydes (18), ketones (14), alcohols (9), furans (3) and acids and ester (5). The forming temperature of each volatile was determined. Most of the volatiles with short carbon chains were generated at low temperatures, while those with long carbon chains were generated at high temperatures. Results of principal component analysis show that nearly all of the identified volatiles were considered as the characteristic ones of the high temperature points. Meanwhile, the oxidative products of the C7–C11 saturated and unsaturated aldehydes were also detected and identified during heating to intensively investigate the oxidative mechanism of palmitoleic acid during heating. Results demonstrated that only the C10 saturated and unsaturated aldehydes could continue to be oxidized during heating. Therefore, the oxidation reactions above the secondary level of lipids mainly occurred in the C10 saturated and unsaturated aldehydes.</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 2","pages":"95-107"},"PeriodicalIF":2.6,"publicationDate":"2023-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"6225052","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"A sensory characterization of some N-heterocycles in model spirit matrix: Influence of ethanol and several chemical features on aroma perception","authors":"Agathe Goullet, Farnaz Hanaei, Nadine Vallet, Marie-Fran?oise Nonier, Nathalie Vivas, Nicolas Vivas, Magali Picard","doi":"10.1002/ffj.3729","DOIUrl":"https://doi.org/10.1002/ffj.3729","url":null,"abstract":"<p>The qualitative spirit ageing bouquet, developed during maturation in oak casks through a complex transformation process, can result in a broad palette of nuances where roasted and nutty aromas are often identified. Nitrogen heterocycles (pyrazines, thiazoles, pyrroles), produced during the heating step of the barrel-manufacturing, contribute to the perception of these nuances. However, their specific sensory characteristics within the spirit matrix have been poorly studied until now. The current study consisted in an overall olfactory characterization of nine targeted N-heterocycles molecules previously identified in oak wood and detected in spirits. In a first step, the olfactory perception thresholds (detection and recognition) were measured in a spirit model medium (23% hydroalcoholic solution, pH 4), revealing that the presence of ethanol at such level minimally affected the olfactory perception of the studied compounds. A first sensory description of the set of N-heterocycles also highlighted a large spectrum of aromatic nuances, mostly related to the semantic field of wood (nut, roasted, smoky, spicy). In a second step, a profile of the key aromatic attributes of the studied molecules was compiled, on the basis of their corresponding intensity scores given by a trained expert panel. Principal Component Analysis followed by Hierarchical Cluster Analysis categorized the pool of N-heterocycles according to their sensory similarities. The presence of ethanol in spirit model matrix did not affect detection and recognition thresholds of studied N-heterocycles. Wood-derived nuances accounted among the most representative aromas characterized the studied N-heterocycles. Functionals groups carried out by the chemical ring modified the aromatic perception of N-heterocycles.</p>","PeriodicalId":170,"journal":{"name":"Flavour and Fragrance Journal","volume":"38 2","pages":"108-120"},"PeriodicalIF":2.6,"publicationDate":"2023-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ffj.3729","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"6225057","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}