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S.H. Hwang et al. / Food Chemistry 214 (2017) 726–735
inhibitory effects at each stage. Our results show that generally,
AGE-inhibitory activities were 2–10 times stronger for VPs than
APs (VPs > APs > AG or Ps > AA). These results indicate that syn-
thetic compounds created via a chemo-enzymatic method are
effective in either preventing or retarding glycation protein
formation.
d 167.2 (C-9), 150.5 (C-3), 147.6 (C-5), 143.5 (C-7), 142.4 (C-10),
136.6 (C-4), 127.2 (C-1), 114.7 (C-8), 105.6 (C-2, 6), 97.1 (C-20),
55.2 (–OCH3).
Ascorbyl 4-hydroxycinnamate
A white solid powder
MW: 322.27 g/mol
ESI-MS (m/z) 323.27 [M+H]+
MF: C15H14O8
Conflict of interest
IUPAC name: (E)-(2S)-2-(3,4-dihydroxy-5-oxo-2,5-dihydro
furan-2-yl)-2-hydroxyethyl 3-(4-hydroxyphenyl)acrylate
1H NMR [400 MHz, (CD3)2SO]: d 7.62 (d, 1H, J = 16.02 Hz, H-70),
7.23 (d, 1H, J = 7.81 Hz, H-50), 7.14 (d, 1H, J = 7.79 Hz, H-60), 7.04 (s,
1H, H-20), 6.84 (d, 1H, J = 8.03, H-40), 6.52 (d, 1H, J = 16.01 Hz, H-80),
4.78 (d, 1H, J = 1.59 Hz, H-4), 4.18 (t, 2H, J = 5.49 Hz, H-6ab), 4.06
(m, 1H, H-5). 13C NMR [100 MHz, (CD3)2SO]: d 171.2 (C-1), 166.8
(C-90), 158.5 (C-40), 153.1 (C-3), 145.9 (C-70), 136.1 (C-20), 130.8
(C-60), 127.8 (C-10), 120.1 (C-2), 118.5 (C-80), 115.5 (C-50), 115.5
(C-30), 75.9 (C-4), 66.4 (C-6), 65.6 (C-5)
The authors declare that there are no conflicts of interest.
Chemical compounds studies in this article
Vinyl 4-hydroxycinnamate
A white solid powder
MW: 190.20 g/mol
ESI-MS (m/z) 191.20 [M+H]+
MF: C11H10O3
Ascorbyl 4-hydroxy-3-methoxycinnamate
A white solid powder
IUPAC name: (E)-vinyl 3-(4-hydroxyphenyl)acrylate
1H NMR [400 MHz, CDCl3]: d 7.76 (d, 1H, J = 15.95 Hz, H-7),
7.46-7.43 (m, H-10, 2, 6), 6.90-6.89 (m, 2H, H-3, 5), 6.34 (d, 1H,
J = 15.99 Hz, H-8), 5.01 (d, 1H, J = 14.01 Hz, H-20b), 4.67 (d, 1H,
J = 6.35 Hz, H-20a). 13C NMR [100 MHz, CDCl3]: d 163.8 (C-9),
157.2 (C-4), 144.8 (C-7), 142.4 (C-10), 134.09 (C-2), 128.7 (C-6),
128.1 (C-1), 117.2 (C-8), 114.2.5 (C-5), 113.7 (C-3), 97.4 (C-20).
Vinyl 4-hydroxy-3-methoxycinnamate
MW: 352.29 g/mol
ESI-MS (m/z) 353.29 [M+H]+
MF: C16H16O9
IUPAC name: (E)-(2S)-2-(3,4-dihydroxy-5-oxo-2,5-dihydro
furan-2-yl)-2-hydroxyethyl
acrylate
3-(4-hydroxy-3-methoxyphenyl)
1H NMR [400 MHz, (CD3)2SO]: d 7.48 (d, 1H, J = 13.88 Hz, H-70),
7.13 (d, 1H, J = 8.23 Hz, H-60), 7.07 (s, 1H, H-20), 6.79 (d, 1H,
J = 8.20 Hz, H-50), 6.35 (d, 1H, J = 15.97 Hz, H-80), 4.77 (d, 1H,
J = 1.76 Hz, H-4), 4.19 (t, 2H, J = 6.64 Hz, H-6ab), 4.13 (m, 1H,
H-5), 3.82 (s, 3H, –OCH3). 13C NMR [100 MHz, (CD3)2SO]: d 170.7
(C-1), 168.3 (C-90), 152.6 (C-3), 149.4 (C-30), 148.2 (C-40), 144.8
(C-70), 126.1 (C-10), 123.5 (C-60), 118.5 (C-2), 115.9 (C-50), 114.6
(C-20), 111.6 (C-80), 75.6 (C-4), 66.0 (C-6), 64.9 (C-5), 56.0 (–OCH3).
Ascorbyl 3, 4-dimethoxycinnamate
A yellow liquid
MW: 220.22 g/mol
ESI-MS (m/z) 221.22 [M+H]+
MF: C12H12O4
IUPAC name: (E)-vinyl 3-(4-hydroxy-3-methoxyphenyl)
acrylate
1H NMR [400 MHz, CDCl3]: d 7.65 (d, 1H, J = 16.02 Hz, H-7), 7.35
(dd, 1H, J = 14.02 Hz, H-10), 7.03 (d, 1H, J = 8.21 Hz, H-5), 6.98 (s,
1H, H-2), 6.86 (d, 1H, J = 8.16 Hz, H-6), 6.23 (d, 1H, J = 15.95 Hz,
H-8), 4.89 (d, 1H, J = 14.03 Hz, H-20b), 4.67 (d, 1H, J = 6.43 Hz,
H-20a), 3.86 (s, 3H, –OCH3). 13C NMR [100 MHz, CDCl3]: d 163.3
(C-9), 148.3 (C-3), 147.0 (C-4), 142.5 (C-7), 142.4 (C-10), 125.3
(C-1), 124.1 (C-6), 113.9 (C-5), 112.6 (C-2), 110.6 (C-8), 96.8
(C-20), 55.6 (–OCH3).
A white solid powder
MW: 366.32 g/mol
ESI-MS (m/z) 367.32 [M+H]+
MF: C17H18O9
IUPAC name: (E)-(2S)-2-(3,4-dihydroxy-5-oxo-2,5-dihydro
furan-2-yl)-2-hydroxyethyl 3-(3,4 dimethoxyphenyl)acrylate
1H NMR [400 MHz, (CD3)2SO]: d 7.64 (d, 1H, J = 15.99 Hz, H-70),
7.36 (s, 1H, H-20), 6.97 (d, 1H, J = 6.06 Hz, H-50), 6.58 (d, 1H,
J = 15.97 Hz, H-80), 6.58 (d, 1H, J = 15.97 Hz, H-60), 4.77 (d, 1H,
J = 1.57 Hz, H-4), 4.16 (t, 2H, J = 5.56 Hz, H-6ab), 4.13 (m, 1H,
H-5), 3.80 (s, 6H, –OCH3). 13C NMR [100 MHz, (CD3)2SO]: d 171.2
(C-1), 167.1 (C-90), 153.1 (C-3), 151.9 (C-30), 149.8 (C-40), 145.9
(C-70), 127.7 (C-10), 123.9 (C-60), 119.0 (C-2), 116.1 (C-80), 112.4
(C-50), 111.1 (C-20), 75.9 (C-4), 66.5 (C-6), 65.4 (C-5), 56.3 (–OCH3).
Vinyl 3, 4-dimethoxycinnamate
A yellow solid powder
MW: 234.25 g/mol
ESI-MS (m/z) 235.25 [M+H]+
MF: C13H14O4
IUPAC name: (E)-vinyl 3-(3,4-dimethoxyphenyl)acrylate
1H NMR [400 MHz, CDCl3]: d 7.72 (d, 1H, J = 15.80 Hz, H-7), 7.41
(dd, 1H, J = 14.00 Hz, H-10), 7.12 (d, 1H, J = 8.29 Hz, H-5), 7.08 (s,
1H, H-2), 6.95 (d, 1H, J = 8.36 Hz, H-6), 6.31 (d, 1H, J = 16.0 Hz,
H-8), 4.95 (d, 1H, J = 14.04 Hz, H-20b), 4.60 (d, 1H, J = 6.20 Hz,
H-20a), 3.90 (s, 6H, –OCH3). 13C NMR [100 MHz, CDCl3]: d 164.1
(C-9), 150.5 (C-3), 147.6 (C-4), 143.5 (C-7), 142.4 (C-10), 127.2
(C-1), 121.9 (C-6), 114.7 (C-8), 111.5 (C-5), 110.4 (C-2), 96.5
(C-20), 55.2 (–OCH3).
Acknowledgements
This research was supported by Basic Science Research Program
through the National Research Foundation (NRF) of South Korea
funded by the Ministry of Education (2015R1D1A1A01059199)
and Priority Research Centers Program through the National
Research Foundation of Korea (NRF) funded by the Ministry of
Education, Science and Technology (NRF-2009-0094071).
Vinyl 4-hydroxy-3, 5-dimethoxycinnamate
A white solid powder
MW: 250.25 g/mol
ESI-MS (m/z) 251.25 [M+H]+
MF: C13H14O5
IUPAC name: (E)-vinyl 3-(4-hydroxy-3,5-dimethoxyphenyl)
acrylate
References
1H NMR [400 MHz, CDCl3]: d 7.67 (d, 1H, J = 15.88 Hz, H-7), 7.39
(dd, 1H, J = 13.98 Hz, H-10), 6.89 (S, 2H, H-2, 6), 6.37 (d, 1H,
J = 15.17 Hz, H-8), 4.93 (d, 1H, J = 14.04 Hz, H-20b), 4.60 (d, 1H,
J = 6.45 Hz, H-20a), 3.85 (s, 6H, –OCH3). 13C NMR [100 MHz, CDCl3]: