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Molecular Catalysis · 2025 · IF 4.9

Multi-enzyme cascade reaction for stereoconvergent synthesis of (R)-decalactones

Shuo Wang,Binhao Wang,Guochao Xu,Ye Ni

Chiral lactones are valuable aroma compounds which have wide applications in food and fragrance industries. However, the synthesis of chiral lactones often faces challenges such as low yield, poor stereoselectivity, high production costs and harsh reaction conditions. To overcome these issues, a novel multi-enzyme cascade reaction was designed to achieve dynamic resolution of decalactones through stereoconvergent preparation of hydroxydecanoic acids. Utilizing lactonase Rpa 3624 for hydrolysis, Hb KR for stereoselective oxidation, and Sm CR V4 for stereoselective reduction, 50 mM racemic γ -decalactone was stereoselectively converted into ( R )- γ -decalactone with 96.5 % ee and 89.2 % yield in 1 h. By replacing Sm CR V4 with Sm CR M5 , 50 mM racemic δ -decalactone was also efficiently converted into ( R )- δ -decalactone with excellent stereoselectivity of 95.5 % and 84.9 % yield. The one-pot process could be operated under mild conditions, enhanced atom economy and reduced production costs, and provides a sustainable approach for the synthesis of chiral decalactones. This work demonstrates the potential of multi-enzyme systems in synthesis of chiral lactones for industrial application.

CAS / MDL: 705-86-2
研究领域: 生物化学 · 工业生物技术 · 香料化学
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FOOD CHEMISTRY · 2024 · IF 8.5

Mechanism of key volatiles in osmanthus scented green tea on the improvement of its aroma and taste quality

Guojian Deng,Lunfang Huang,Wenya Wang,Tianzi Yu,Jingming Ning,Yujie Wang

The intensity of green tea's floral and sweet flavors was enhanced after being scented by osmanthus (OSGT). However, the mechanism of flavor enhancement by key volatiles remains unknown. Here, the role of key volatiles in OSGT on aroma and taste was explored by sensory experiment-guided flavor analysis. Binary mixed models of ( E )- β -ionone, dihydro- β -ionone, and α -ionone showed additive interactions on floral aroma enhancement, the interactions were increased with increasing concentrations. At the concentration in OSGT, binary mixed models of ( E )- β -ionone, geraniol , linalool , and γ -decalactone showed additive interactions on sweet aroma enhancement. ( E )- β -ionone, geraniol , linalool , and γ -decalactone all significantly increased the perceived intensity of sweetness of sucrose solutions. Additionally, molecular docking revealed the perception mechanism of olfactory and taste receptors to the above characterized volatiles, with hydrogen bonding and hydrophobic interactions being the main interactions. This study highlights the importance of characteristic volatiles in enhancing the flavor of OSGT.

CAS / MDL: 127-41-3 17283-81-7
研究领域: 食品科学 · 香气化学 · 感官科学
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PROCESS BIOCHEMISTRY · 2023 · IF 4.4

Combinatorial metabolic engineering and tolerance evolution of Yarrowia lipolytica for improved γ-decalactone synthesis

Meng Zhang,QingYan Li,Feiyu Fan,Fuping Lu,XueLi Zhang

This study highlights an effective strategy based on the synergistic complementarity of metabolic engineering and adaptive evolution.First, the chassis strain YL013 was obtained by deleting five acyl-CoA oxidase genes to reduce the degradation of γ-decalactone(GDL). Then, adaptive laboratory evolution with increasing concentrations of γ-decalactone was employed to obtain the strain YL013–250 with increased γ-decalactone tolerance of up to 250 mg/L. Moreover, this strain produced 664.5 mg/L γ-decalactone, representing a 142 % improvement over the parental strain YL013. Furthermore, four candidate fatty acyl-CoA synthetase genes, FAA1 , FAA2 FAA3 and FAT1, were modulated using the strong, constitutive TEFin promoter to investigate their roles in GDL production. The results showed that overexpression of FAA1 , FAA2 and FAA3 can effectively improve the ability of Yarrowia lipolytica to synthesize GDL using ricinoleic acid as substrate, among which overexpression of FAA1 had the most significant effect on GDL yield. Finally, gene of alcohol acyltransferase ( AAT1 ) from Prunus persica was introduced into Y. lipolytica , leading to a GDL titer of 2.2 g/L, which was a 1.32-fold increase compared with the parental strain without AAT1 . Taken together, this study provides a combinatorial strategy to improve GDL production through rational regulation of pathway genes and non-rational adaptive laboratory evolution.

CAS / MDL: 141-22-0
研究领域: 代谢工程 · 微生物生物技术 · 生物过程工程 · 生物化学
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Food Quality and Safety · 2024 · IF 3

Volatiles profiles and factors affecting absorption of key odorants in Osmanthus black tea

Dai Binwei,Chen Weixuan,Huang Weihong,Liu Junsheng,Li Bo,He Puming,Grierson Donald,Tu Youying,Wu Yuanyuan

Osmanthus black tea (OBT) is produced by reprocessing black tea while it absorbs the fragrance of Osmanthus fragrans (O. fragrans) and this scenting process is crucial for forming the unique aroma of OBT. In this study, more than eighty volatile compounds of OBT were analyzed by gas chromatography-mass spectrometry (GC-MS) and six compounds, α-ionone, β-ionone, γ-decalactone, dihydro-β-ionone, dihydro-β-ionol, and 6-pentyl-2-pyrone, were identified as the key volatiles of OBT by weighted gene co-expression network analysis (WGCNA) and orthogonal partial least squares discriminant analysis (OPLS-DA). Variations in the amounts of these compounds occurred with different scenting process conditions such as scenting time (ST) and the ratio of flower to tea (RFT) were discussed. In addition, base teas with a high proportion of pekoes produced higher quality OBT by absorbing more key volatile compounds from O. fragrans. Comparing OBTs made from the fast-scenting process (FS) and the traditional scenting process (TS), showed that a higher aroma quality was obtained through repeated scenting rounds of TS. This study provides valuable insights into the volatile compounds and base tea requirements for an effective scenting process and a theoretical basis for improving scenting technology.

研究领域: 食品科学 · 农学 · 化学 · 植物科学
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Food Chemistry-X · 2024 · IF 6.5

Sensory-directed flavor analysis reveals the improvement in aroma quality of summer green tea by osmanthus scenting

Yujie Wang,Guojian Deng,Lunfang Huang,Jingming Ning

Flower scenting is an effective way to enhance the aroma of green tea (GT), including those osmanthus scented green tea (OSGT). However, the mechanism of aroma enhancement by scenting is still unclear. Here, the volatiles of GT, OSGT, and osmanthus were detected by GC–MS. The total volatile content of OSGT was significantly increased compared to GT, with the flowery and coconut aromas enhanced. Furthermore, 17 of 139 volatiles were responsible for the enhancement by GC–olfactometry and their absolute odor activity values (OAVs). Aroma recombination, omission and addition experiments showed that dihydro- β -ionone, (E) - β -ionone, (E, E) -2,4-heptadienal, geraniol, linalool, α -ionone, and γ -decalactone were the key aroma volatiles with flowery or coconut aromas. Additionally, the dynamics of the key volatiles (OAVs >1) from different scenting durations were analyzed, proving that the optimal duration was 6–12 h. This study provides new insight into the mechanism of aroma formation during OSGT production.

研究领域: 食品科学 · 农业化学 · 分析化学
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Foods · 2024 ·Vol. 13 ·期 17 ·2653 · IF 4.7

Comparison of Volatile Compounds in Jingshan Green Tea Scented with Different Flowers Using GC-IMS and GC-MS Analyses

Zhiwei Hou,Ziyue Chen,Le Li,Hongping Chen,Huiyuan Zhang,Sitong Liu,Ran Zhang,Qiyue Song,Yuxuan Chen,Zhucheng Su,Liying Xu

Scented green tea (Camellia sinensis) is a type of reprocessed green tea produced by scenting with flowers. To investigate the differences in the volatiles of scented green tea processed with four different flowers (Jasminum sambac,Osmanthus fragrans,Michelia alba, andRosa rugosa), gas chromatography–ion mobility spectrometry (GC–IMS) and gas chromatography–mass spectrometry (GC–MS) were employed to detect and identify the volatile compounds in the four types of scented teas. GC–IMS and GC–MS identified 108 and 101 volatile compounds, respectively. The key characteristic volatile compounds, namely indole, linalool,β-myrcene, benzyl acetate, and ethyl benzoate (jasmine tea); cedrol, (E)-β-ionone,γ-decalactone, and dihydro-β-ionol (osmanthus tea); geraniol, phenylethyl alcohol, jasmone, methyl jasmonate, hexadecanoic acid, 4-ethyl-benzaldehyde, 2-methylbutyl hexanoate, and indole (michelia tea); and 3,5-dimethoxytoluene, (E)-β-ionone, and 2-methylbutyl hexanoate (rose tea), were identified through chemometric analysis combined with relative odor activity values (ROAVs) and sensory evaluation. This study provides new insights into the formation of aroma molecular fingerprints during green tea scenting with flowers, providing theoretical guidance for infusing distinct aroma characteristics into green tea during scented tea processing.

研究领域: 食品科学 · 分析化学 · 农学 · 植物科学
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