Aroma characterization based on aromatic series analysis in table. grapes
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1 Aroma characterization based on aromatic series analysis in table grapes Yusen Wu, Shuyan Duan, Liping Zhao, Zhen Gao, Meng Luo, Shiren Song, Wenping Xu, Caixi Zhang, Chao Ma*, Shiping Wang* Department of Plant Science, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai, China. * Corresponding author: Department of Plant Science, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai, China. Tel& Fax: address: fruit@sjtu.edu.cn, chaoma215@sjtu.edu.cn
2 Supplementary information Figures Jumeigui Fujiminori Italian Seto Giants Shine Muscat Red Alexandria Rizamat Zuijinxiang Heibaladuo Yoho Oriental Star Kyoho Suiho Black Swan Jingya Black Beet Gold Finger High Bailey Damina Centennial Seedless
3 Figure S1. Aromatic fingerprints of table grapes. Green line with triangle indicated the fingerprints of pulp juice; yellow line with dot indicated the fingerprints of skin; wine red line with square indicated the fingerprints of whole berries. Scale range of nine cultivars (Jumeigui, Shine Muscat, Red Alexandria, Yoho, Jingya, Black Beet, High Bailey, Tamina, Centennial Seedless) was -4; the others was -2. Kyoho Cannon hall muscat Shenyang muscat Jujing Early niabel Kuroshio Pione Jumeigui Kuixiangyi Xiyanghong Zuijinxiang Olympia Centenial Furuidaoniya Black olympia Yoho Golden muscat Ikawa 682 Takatsuma Suiho Michikeiyi Jingya Pione Fujiminori Pione Black Beet Cross breeding Seeding selection Figure S2. Part pedigree chart of Kyoho grapevine series (Kyoho or its offspring). The eight cultivars (A, B, H, J, L, M, O, P) in this study were underlined. Cross indicated cross breeding; circle indicated seeding selection.
4 a b Figure S3. Synthesis mechanisms of monoterpenes in grapes obtained from the previous report 25. (a) indicated synthetic pathway of cyclic monoterpenes; (b) indicated synthetic pathway of acyclic monoterpenes. The mainly compounds in this study are underlined, including cyclics (α-pinene, β-pinene, phellandrene, limonene, γ-terpinene, α-terpineol, terpinolene) and acyclics (linalool, β-myrcene, geraniol).
5 Figure S4. Metabolic pathway of C 6 compounds in grapes obtained from the previous report 11,2. Route A, B, C indicated the different metabolic pathways, respectively.
6 A B C D E F G H I J K L M N O P Q R S T relative row min row max Figure S5. The relationship between aromatic series values (whole berries) and aroma preference intensity scores (scale: 1-5) obtained from sensory evaluation analysis. Data were means (n=3). Ten aromatic series were shown across the top and the colour scale was shown at the bottom. The higher values for each aromatic series were presented in red; otherwise, green was used; white represents the value less than 1. Capital letters (right) referred to the table grape cultivars listed in Figure 1, and their aroma preference scores (left) were shown.
7 Total peak area Total peak area Total peak area Total peak area a 8.E+8 56 b 1.E E+8 4.E E+8 6.E+8 4.E E+8 2.E+8 c.e+ DVB/CAR/PDMS PA PDMS SPME fibres 1.2E+9 1.E E E+8 d.e+ 1.E+9 8.E+8 6.E Extraction time (min) E+8 4.E+8 2.E+8 2.E+8.E+.E+ 4 C 5 C 6 C Extraction temperature ( C) Sample amount (ml) Figure S6. The optimization of headspace solid phase microextraction (HS-SPME) method. Performance characteristics obtained for tested solid phase microextraction (SPME) fibres (a) during 4 min at 4 C, extraction time (b) using divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS) fibre at 4 C, extraction temperature (c) using DVB/CAR/PDMS fibre during 3 min and volume/headspace volume ratio (d) using DVB/CAR/PDMS fibre during 3 min at 5 C on total aroma peak area in this work. Number indicated the number of kinds of identified compounds. The best results were obtained using 6 ml of sample (pulp juice or skin extraction solutions) in a 2 ml glass vial with addition of 1.5 g of sodium chloride (NaCl) (1/β =.5), and after equilibrating, a DVB/CAR/PDMS (5/3 μm) fibre was selected for extraction at 5 C for 3 min under agitation. Note: in Figure S6 (a), DVB/CAR/PDMS, PA, PDMS indicated divinylbenzene/carboxen/polydimethylsiloxane (5/3 μm), polyacrylate (85 μm), polydimethylsiloxane (1 μm) fiber, respectively.
8 Tables Monoterpenes Cultivars A B C D E F G H I J K L M N O P Q R S T Cyclics α-pinene Phellandrene Terpineol D-Limonene γ-terpinene α-terpineol Terpinolene P-Cymene SubTOTAL % 14.17% 72.2% 12.44% 6.87% 5.2% 9.85% 7.74% 19.2% 5.1% 35.95% 1.82% 34.76% 84.38% 1.% 45.12% 2.9% 1.% 28.64% 14.4% 2.48% Acyclics Roseoxide II (cis) Roseoxide I (trans) Nerol oxide Linalool Hotrienol Neral β-myrcene Geranial Citronellol Nerol Geraniol Geranic acid SubTOTAL % 85.83% 27.8% 87.56% 93.13% 94.98% 9.15% 92.26% 8.8% 94.99% 64.5% 98.18% 65.24% 15.63%.% 54.88% 79.1%.% 71.36% 85.6% 79.52% TOTAL terpenes % a 1.% 97.31% 99.41% 89.81% 99.34% 99.68% 82.33% 88.2% 82.43% 91.58% 99.1% 92.19% 89.1% 38.36% 86.44% 97.24% 99.1% 99.72% 99.77% 99.44% Table S1. Concentrations (μg/kg) of monoterpenes determined in pulp juice of table grapes. Data are shown as the means (n=3). % a indicated that the percentage of monoterpenes contents account for the total terpenes contents. - indicated that the compound was not detected. Capital letters refer to the table grape cultivars listed in Figure 1.
9 Monoterpenes Cultivars A B C D E F G H I J K L M N O P Q R S T Cyclics α-pinene β-pinene Phellandrene D-Limonene γ-terpinene P-Cymene Terpinolene Terpineol α-terpineol Myrtenol SubTOTAL % 2.71% 9.32% 1.6% 53.19% 2.16% 2.1% 37.23% 63.84% 31.95% 16.% 1.72% 23.4% 29.9% 97.34% 8.62% 21.3% 81.33% 1.1% 1.73% 1.25% Acyclics RoseoxideII (cis) RoseoxideI (trans) Nerol oxide Linalool Hotrienol Neral β-myrcene Geranial Citronellol Nerol Geraniol E-Nerolidol Geranic acid SubTOTAL % 97.29% 9.68% 98.94% 46.81% 97.84% 97.99% 62.77% 36.16% 68.5% 84.% 98.28% 76.6% 7.91% 2.66% 91.38% 78.97% 18.67% 98.99% 98.27% 98.75% TOTAL terpenes % a 99.93% 97.28% 99.94% 98.79% 99.85% 99.95% 94.66% 98.6% 98.79% 95.22% 99.89% 93.22% 94.92% 96.87% 93.38% 98.65% 91.55% 99.96% 99.97% 99.94% Table S2. Concentrations (μg/kg) of monoterpenes determined in skin of table grapes. Data are shown as the means (n=3). % a indicated that percentage of monoterpenes contents account for the total terpenes contents. - indicated that the compound was not detected. Capital letters refer to the table grape cultivars listed in Figure 1.
10 Compounds Cultivars A B C D E F G H I J K L M N O P Q R S T acids derivatives Hexanal (Z)-3-Hexenal (E)-2-Hexenal Hexanol (E)-3-Hexenol (Z)-3-Hexenol (E)-2-Hexenol Octen-3-ol Heptanol Octanol Nonanol Ethyl acetate Ethyl Propionate Propyl acetate Ethyl butyrate Butyl acetate Ethyl pentanoate Ethyl hexanoate Hexyl acetate (Z)-3-Hexenyl acetate Ethyl heptanoate Hexanoic acid Hexenoic acid Octanoic acid SubTOTAL Pentanal Octanal Nonanal SubTOTAL % % 9.25% 98.18% 66.7% 98.16% 75.58% 58.35% 98.69% 99.32% 97.86% 97.52% 88.31% 99.6% 99.35% 99.36% 99.6% 99.41% 95.51% 87.22% 49.12% 89.79% Isoprenoid derivatives α-pinene Phellandrene β-myrcene D-Limonene γ-terpinene P-Cymene Terpinolene Rose oxide II (cis) Rose oxide I (trans) Nerol oxide Linalool Terpineol Hotrienol
11 Neral α-terpineol Geranial Citronellol Nerol Geraniol Cedrol Geranic acid β-damascenone Geranyl acetone β-ionone SubTOTAL % 9.68% 1.64% 32.65%.81% 22.95% 41.1%.81%.55% 1.58%.41% 1.92%.26%.44%.2%.22%.41% 4.% 12.67% 5.57% 9.94% Amino acids derivatives 2-Ethyl hexanol Phenylethyl alcohol Ethyl isobutyrate Ethyl 3-methylbutanoate Ethyl 3-hydroxybutyrate Methyl salicylate Methylbutanal Methylbutanal Benzaldehyde Phenylacetaldehyde SubTOTAL %.7%.19%.65% 1.3% 1.47%.55%.5%.13%.56% 2.7%.77%.14%.2%.44%.18%.18%.5%.11%.3%.27% Table S3. Concentrations (μg/kg) of volatile compounds from different synthesis pathwaysd determined in pulp juice of table grapes. Data are shown as the means (n=3). - indicated that the compound was not detected. Capital letters refer to the table grape cultivars listed in Figure 1.
12 Compounds Cultivars A B C D E F G H I J K L M N O P Q R S T acids derivatives Hexanal (Z)-3-Hexenal (E)-2-Hexenal Hexanol (E)-3-Hexenol (Z)-3-Hexenol (E)-2-Hexenol Heptanol Octen-3-ol Heptanol Octanol Nonanol Ethyl acetate Ethyl Propionate Propyl acetate Ethyl butyrate Butyl acetate Ethyl hexanoate Hexyl acetate Ethyl heptanoate Ethyl octanoate Hexanoic acid Hexenoic acid Octanoic acid Pentanal Octanal Nonanal (E)-2-Octenal SubTOTAL % 25.74% 91.99% 11.95% 89.28% 31.4% 9.67% 94.45% 92.48% 86.52% 96.9% 39.6% 96.24% 89.75% 87.1% 94.62% 9.41% 96.16% 13.19% 8.92% 13.21% Isoprenoid derivatives α-pinene β-pinene Phellandrene β-myrcene D-Limonene γ-terpinene P-Cymene Terpinolene Rose oxide II (cis) Rose oxide I (trans) Nerol oxide Linalool Terpineol
13 Hotrienol Neral α-terpineol Geranial Citronellol Myrtenol Nerol Geraniol E-Nerolidol Cedrol Geranic acid β-damascenone Geranyl acetone β-ionone SubTOTAL % 74.4% 5.3% 87.58% 9.34% 67.2% 9.15% 2.86% 5.44% 1.72% 1.67% 6.2% 1.88% 4.32% 11.95% 1.47% 8.1% 2.75% 86.77% 9.97% 86.33% Amino acids derivatives 2-Ethyl hexanol Benzyl alcohol Phenylethyl alcohol Ethyl isobutyrate Ethyl 3-methylbutanoate Methyl salicylate Methylbutanal Benzaldehyde Phenylacetaldehyde SubTOTAL %.22% 2.99%.47% 1.38% 1.94%.19% 2.68% 2.9% 2.75% 2.24%.37% 1.88% 5.93% 1.4% 3.92% 1.57% 1.9%.3%.11%.47% Table S4. Concentrations (μg/kg) of volatile compounds from different synthesis pathwaysd determined in skin of table grapes. Data are shown as the means (n=3). - indicated that the compound was not detected. Capital letters refer to the table grape cultivars listed in Figure 1.
14 Compounds Pulp juice Skin Calibration graphs r 2 Calibration graphs r 2 (A) C 6 alcohols Hexanal y = x y = x (Z)-3-Hexenal y = 1.835x y = x (E)-2-Hexenal y = x y = x Hexanol y = 9.289x y = x (Z)-3-Hexenol y = 11.24x y = 17.82x (E)-2-Hexenol y = x y = x (B) Alcohols 1-Octen-3-ol y = 1.325x y = 1.618x Heptanol y = x y = 1.341x Octanol y =.9754x y = 1.166x Benzyl alcohol y = 1.395x y =.9843x Phenylethyl alcohol y =.6585x y =.7681x (C) Esters Ethyl acetate y = x y = x Ethyl isobutyrate y = x y = 7.292x Ethyl butyrate y = x y = x Butyl acetate y =.7849x y =.6986x Ethyl pentanoate y = x y = x Ethyl hexanoate y =.9127x y =.9278x Hexyl acetate y =.9114x y =.8568x Methyl salicylate y = x y = x (D) Acids Hexanoic acid y = x y = 25.74x Hexenoic acid y = x y = x Octanoic acid y = 9.389x y = x (E)Aldehydes 3-Methylbutanal y = x y = x Octanal y = 1.466x y = x Pentanal y = 1.875x y = 2.521x Nonanal y = x y = 3.318x Benzaldehyde y = x y = x (F) Terpenes Phellandrene y = x y = x β-myrcene y = x y = 1.133x D-Limonene y = 1.673x y = x P-Cymene y =.8372x y =.594x Terpinolene y = x y =.9242x Rose oxide II (cis) y =.8258x y =.7654x Rose oxide I (trans) y =.8469x y =.7236x Linalool y = 1.45x y =.986x Terpineol y = 1.788x y = x Neral y = x y = x α-terpineol y = x y = 2.973x Geranial y = 5.511x y = 9.5x Citronellol y = x y = 2.652x Nerol y = x y = 1.867x Geraniol y = x y = x Geranic acid y = 48.15x y = x (G) C 13-Norisoprenoids β-damascenone y =.8996x y =.7654x Geranyl acetone y =.6941x y =.5892x β-ionone y =.4747x y =.541x Table S5. Quantitative standards and calibration graphs for quantification of volatile compounds in pulp juice and skin of table grape. y, concentration ratio of a compound to the 2-octanol (internal standard); x, peak area ratio of a compound to the 2-octanol. r, regression coefficient.
15 Compounds Pulp juice Skin Concentration Added Recovery Reproducibility Concentration Added Recovery Reproducibility in (μg/kg) (μg/l) (%) r.s.d. (%) (n=4) in (μg/kg) (μg/l) (%) r.s.d. (%) (n=4) (A) C 6 alcohols Hexanal 33.6 ± ± ± ± ± ± ± ± (Z)-3-Hexenal ± ± ± ± ± ± (E)-2-Hexenal 8.85 ± ± ± ± ± ± ± ± Hexanol ± ± ± ± ± ± ± ± (E)-3-Hexenol ± ± ± ± ± ± ± (E)-2-Hexenol 5.11 ± ± ± ± ± ± ± ± (B) Alcohols 1-Octen-3-ol ± ± ± ± ± ± Heptanol ± ± ± ± ± ± ± Octanol.78 ± ± ± ± ± ± ± ± Benzyl alcohol ± ± ± ± ± ± Phenylethyl alcohol ± ± ± ± ± ± (C) Esters Ethyl acetate ± ± ± ± ± ± ± ± Ethyl isobutyrate ± ± ± ± ± ± Ethyl butyrate.53 ± ± ± ± ± ± ± ± Butyl acetate ± ± ± ± ± ± Ethyl pentanoate ± ± ± ± ± ± Ethyl hexanoate 1.98 ± ± ± ± ± ± ± ± Hexyl acetate 1.8 ± ± ± ± ± ± ± ± Methyl salicylate 2.54 ± ± ± ± ± ± ± (D) Acids Hexanoic acid ± ± Hexenoic acid ± ± ± ± ± ± Octanoic acid ± ± ± ± (E)Aldehydes 3-Methylbutanal ± ± ± ± ± ± Octanal.32 ± ± ± ± ± ± ± ±
16 Compounds Pulp juice Skin Concentration Added Recovery Reproducibility Concentration Added Recovery Reproducibility in (μg/kg) (μg/l) (%) r.s.d. (%) (n=4) in (μg/kg) (μg/l) (%) r.s.d. (%) (n=4) Pentanal ± ± ± ± ± ± Nonanal 6.24 ± ± ± ± ± ± ± ± Benzaldehyde 2.36 ± ± ± ± ± ± ± ± (F) Terpenes Phellandrene.11 ± ± ± ± ± ± ± ± β-myrcene.98 ± ± ± ± ± ± ± ± D-Limonene 4.24 ± ± ± ± ± ± ± ± P-Cymene ± ± ± ± ± ± ± Terpinolene.54 ± ± ± ± ± ± ± ± Rose oxide ± ± ± ± ± ± Linalool ± ± ± ± ± ± ± ± Terpineol 1.4 ± ± ± ± ± ± ± ± Neral ± ± ± ± ± ± α-terpineol 3.59 ± ± ± ± ± ± ± ± Geranial.11 ± ± ± ± ± ± ± ± Citronellol 1.1 ± ± ± ± ± ± ± ± Nerol ± ± ± ± ± ± Geraniol 4.59 ± ± ± ± ± ± ± ± Geranic acid.79 ± ± ± ± ± ± ± ± C 13-Norisoprenoids β-damascenone ± ± ± ± ± ± Geranyl acetone.7 ± ± ± ± ± ± ± ± β-ionone.4 ± ± ± ± ± ± ± ± Table S6. Recovery (%) and reproducibility (relative standard deviation, r.s.d.) (%) of the target skin and pulp juice volatile compounds in table grape.
a-terpinolene Ethyl butanoate 3-Carene Ethyl acetate Ethyl 2-butenoate
a-terpinolene Ethyl butanoate 3-Carene Ethyl acetate Ethyl 2-butenoate a-terpinene a-thujene Dimethyl sulfide Limonene b-phellandrene Myrcene p-cymen-8-ol b-caryophyllene cis-3-hexene-1-ol hexadecyl acetate
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