基于UHPLC法的巨豆三烯酮前体物同分异构体的定量分析及其在不同产地烟叶中的分布情况

李石头; 毕一鸣; 帖金鑫; 杨晨; 李庆祥; 李永生; 杨鹏飞; 毛多斌

doi:10.12187/2023.05.011

October 2023

Article Contents

LI Shitou, BI Yiming, TIE Jinxin, et al. Quantitative analysis of isomers of megastigmatrienone precursors based on UHPLC method and their distribution in tobacco leaves from various geographic origins[J]. Journal of Light Industry, 2023, 38(5): 83-87. doi: 10.12187/2023.05.011

Citation: LI Shitou, BI Yiming, TIE Jinxin, et al. Quantitative analysis of isomers of megastigmatrienone precursors based on UHPLC method and their distribution in tobacco leaves from various geographic origins[J]. Journal of Light Industry, 2023, 38(5): 83-87. doi: 10.12187/2023.05.011 shu

Quantitative analysis of isomers of megastigmatrienone precursors based on UHPLC method and their distribution in tobacco leaves from various geographic origins

1. Technology Center, China Tobacco Zhejing Industrial Co., Ltd., Hangzhou 310000, China;
2. College of Tobacco Science and Engineering, Zhengzhou University of Light Industry, Zhengzhou 450001, China

Received Date: 2023-03-31
Accepted Date: 2023-05-30

Abstract

Investigating the quantitative analysis of two stereoisomeric compounds, specifically (6R, 9R)-3-oxo-α-ionol-β-D-glucopyranoside (rrOIPG) and (6R, 9S)-3-oxo-α-ionol-β-D-pyranoside (rsOIPG), megastigmatrienone precursors of the prominent aroma components in tobacco leaves, represented the core focus of this study. A meticulously-devised methodology combining ultrasound-assisted extraction with ultra-high-performance liquid chromatography (UHPLC) was deployed to ascertain the precise quantification of rrOIPG and rsOIPG. This robust analytical approach was judiciously employed to elucidate the geographical distribution patterns of these stereoisomers within tobacco leaves sourced from seven diverse global regions. The results revealed the compelling linear response characteristics of rrOIPG and rsOIPG, scanninged concentration ranges of 25.85 to 258.50 μg/mL (R²=0.999 1) and 6.28 to 62.75 μg/mL (R²=0.999 0), respectively. Exceptionally low detection limits of 2.5 μg/mL for rrOIPG and 2.9 μg/mL for rsOIPG underscore the method's inherent precision. The analysis exhibited superb stability and reproducibility, epitomized by recovery rates of 83.94% for rrOIPG and 105.90% for rsOIPG, and RSDs were 1.22% and 1.93%, respectively. According to the content distribution of rrOIPG and rsOIPG, the tobacco leaves from domestic and foreign origins could be well distinguished, and the content of rsOIPG configuration in foreign origins was significantly higher than that in domestic origins. In terms of the distribution of the two configurations, the content of rrOIPG configuration was higher than that of rsOIPG configuration. The developed technique exhibits high feasibility and streamlined pretreatment processes, making it well-suitable for the quantitative analysis of rrOIPG and rsOIPG in tobacco leaves.
- 3-oxo-α-ionol-β-D-glucopyranoside,
- isomers,
- ultrahigh-performance liquid chromatography method,
- quantitative analysis
References
1. [1]
  杨靖,毛多斌,陈芝飞,等. GC-MS/O技术测定卷烟烟气中巨豆三烯酮的香气活力值[J].中国烟草学报,2016,22(6):11-17.
2. [2]
  BANOŽIĆ M,JOKIĆS,A AČG KAR D,et al.Carbohydrates:Key players in tobacco aroma formation and quality determination[J].Molecules,2020,25(7):1734.
3. [3]
  SLAGHENAUFI D,PERELLO M C,MARCHAND S,et al.Quantification of megastigmatrienone,a potential contributor to tobacco aroma in spirits[J]. Food Chemistry,2016,203:41-48.
4. [4]
  蒋举兴,孔维松,吴俊,等.香精中巨豆三烯酮E/Z异构体的相对量比和在4种常用气相色谱柱上的出峰顺序[J].云南大学学报(自然科学版),2018,40(5):984-994.
5. [5]
  KODAMA H,FUJIMORI T,KATO K.Glucosides of ionone-related compounds in several nicotiana species[J].Phytochemistry,1984,23(3):583-585.
6. [6]
  刘冰.高温对烟草巨豆三烯酮前体物代谢及其基因甲基化的影响[D].北京:中国农业科学院,2020.
7. [7]
  LIANG Z J,FANG Z X,PAI A,et al.Glycosidically bound aroma precursors in fruits:A comprehensive review[J].Critical Reviews in Food Science and Nutrition,2022,62(1):215-243.
8. [8]
  李辰.类胡萝卜素合成关键酶基因的调控及在植物中的抗逆效应[D].天津:天津大学,2020.
9. [9]
  TUFARIELLO M,FRAGASSO M,PICO J,et al.Influence of non-saccharomyces on wine chemistry:A focus on aroma-related compounds[J].Molecules,2021,26:644.
10. [10]
  ZENG S T,SUN S H,LIU S,et al.Synthesis of α-ionyl-β-d-glucoside and its property of flavor release[J].Journal of Thermal Analysis and Calorimetry,2014,115:1049-1056.
11. [11]
  SU C,QI B W,WANG J,et al.Megastigmane glycosides from Urena lobata[J].Fitoterapia,2018,127:123-128.
12. [12]
  LIANG Z J,FANG Z X,PAI A,et al.Glycosidically bound aroma precursors in fruits:A comprehensive review[J].Critical Reviews in Food Science and Nutrition,2022,62(1):215-243.
13. [13]
  毛多斌,申思,牟定荣,等.超声萃取-高效液相色谱法测定烟草中β-D-吡喃葡萄糖-3-氧代-α-紫罗兰醇苷[J].分析试验室,2012,31(6):30-34.
14. [14]
  BAUMES R L,AUBERT C C,BAYONOVE C L.Absolute configuration of free and bound 3-hydroxy-beta-damascone and of 3-oxo-alpha-ionol beta-D-glucopyranoside in tobacco[J].Journal of Essential Oil Research,1994,6(6):601-606.
15. [15]
  CAI K,ZHAO H N,XIANG Z M,et al.Enzymatic hydrolysis followed by gas chromatography-mass spectroscopy for determination of glycosides in tobacco and method optimization by response surface methodology[J].Analytical Methods,2014,6(17):7006-7014.
16. [16]
  李锋,朴永革,李宝志,等.延边烟叶糖苷类香味成分分析研究[J].农业与技术,2018,38(17):20-22.
17. [17]
  COLEMAN III W M,DUBE M F,GERARDI A R,et al.Enhancement of volatile aglycone recovery facilitated by acid hydrolysis of glucosides from nicotiana flower species[J].Journal of Agricultural and Food Chemistry,2012,60(46):11483-11490.
18. [18]
  陈敏,董惠忠,沈世豪,等.中心切割反相/反相二维液相色谱-串联质谱法测定烟叶潜香类糖苷[J].质谱学报,2021,42(6):1175-1182.
19. [19]
  JIA C X,ZHU Y H,ZHANG J J,et al.Identification of glycoside compounds from tobacco by high performance liquid chromatography/electrospray ionization linear ion-trap tandem mass spectrometry coupled with electrospray ionization orbitrap mass spectrometry[J].Journal of the Brazilian Chemical Society,2017,28:629-640.
20. [20]
  吴琼,汪阳忠,安彤,等.利用特征中性丢失和非靶向液相色谱-质谱联用技术鉴定烟草中的糖苷成分[J].分析测试学报,2023,42(1):68-74.
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沈阳化工大学材料科学与工程学院沈阳 110142

Quantitative analysis of isomers of megastigmatrienone precursors based on UHPLC method and their distribution in tobacco leaves from various geographic origins

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