Title. Author(s)Kato, Eisuke; Uenishi, Yuta; Inagaki, Yosuke; Kuroka. CitationBioscience biotechnology and biochemistry, 80(11): 2. Issue Date
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1 Title Isolation of rugosin A, B and related compounds as d Author(s)Kato, Eisuke; Uenishi, Yuta; Inagaki, Yosuke; Kuroka CitationBioscience biotechnology and biochemistry, 80(11): 2 Issue Date Doc URL Rights This is an Accepted Manuscript of an article publish biochemistry on 01 Aug 2016, available online: http: Type article (author version) Additional There Information are other files related to this item in HUSCAP File Information tbbb_a_ _sm1895.pdf (Supplementary Material) Instructions for use Hokkaido University Collection of Scholarly and Aca
2 Supplementary material Isolation of rugosin A, B and related compounds as dipeptidyl peptidase-iv inhibitors from rose bud extract powder Eisuke Kato 1 *, Yuta Uenishi 1, Yosuke Inagaki 2, Mihoko Kurokawa 2, Jun Kawabata 1 * 1 Laboratory of Food Biochemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita-ku, Sapporo, Hokkaido , Japan 2 Q'sai Co., Ltd., Kusagae, Fukuoka, Fukuoka , Japan * Corresponding Author; Tel/Fax: ; address eikato@chem.agr.hokudai.ac.jp (E. Kato) junk@chem.agr.hokudai.ac.jp (J. Kawabata) 1H NMR spectrum data of the isolated compounds in CD3OD... 2 Tellimagrandin I (1, mixture of α, β-anomer)... 2 Rugosin B (2)... 3 Heterophyllin A (3)... 4 Rugosin B ethyl ester (4)... 5 Eugeniin (5)... 7 Rugosin A (6)... 8 Rugosin A decarboxylated (7)... 9 NMR spectrums of rugosin A decarboxylated (7) in DMSO-d UPLC-MS quantitation of rugosin A, B in rose buds extract powder S1
3 1 H NMR spectrum data of the isolated compounds in CD 3 OD Tellimagrandin I (1, mixture of α, β-anomer) 1H NMR (500 MHz, CD3OD, rt) α-anomer: 3.82 (1H, d, J = 12.8 Hz), 4.63 (1H, dd, J = 6.9, 9.9 Hz), 5.09 (1H, dd, J = 3.7, 9.9 Hz), 5.12 (1H, dd, J = 9.9, 10.0 Hz), 5.31 (1H, dd, J = 6.9, 12.8 Hz), 5.48 (1H, d, J = 3.7 Hz), 5.83 (1H, dd, J = 9.9, 10.0 Hz), 6.49 (1H, s), 6.60 (1H, s), 6.92 (2H, s), 7.01 (2H, s) ppm; β-anomer: 3.89 (1H, d, J = 12.9 Hz), 4.20 (1H, dd, J = 6.3, 9.5 Hz), 4.95 (1H, d, J = 7.9 Hz), 5.14 (1H, t, J = 10.2 Hz), 5.19 (1H, t, J = 8.9 Hz), 5.34 (1H, dd, J = 6.3, 13.2 Hz), 5.58 (1H, t, J = 9.6 Hz), 6.44 (1H, s), 6.60 (1H, s), 6.88 (2H, s), 6.99 (2H, s) ppm S2
4 Rugosin B (2) 1H NMR (500 MHz, CD3OD, rt) α-anomer: 3.75 (1H, d, J = 13.2 Hz), 4.59 (1H, dd, J = 6.6, 10.1 Hz), (2H, m), (1H, m), 5.45 (1H, d, J = 3.8 Hz), 5.80 (1H, t, J = 9.9 Hz), 6.21 (1H, s), 6.50 (1H, s), 6.93 (2H, s), 7.02 (2H, s), 7.09 (1H, s) ppm; β-anomer: 3.83 (1H, d, J = 13.2 Hz), 4.16 (1H, dd, J = 6.6, 10.1 Hz), 4.93 (1H, d, J = 8.2 Hz), (1H, m), (2H, m), 5.56 (1H, t, J = 9.8 Hz), 6.20 (1H, s), 6.46 (1H, s), 6.89 (2H, s), 7.00 (2H, s), 7.09 (1H, s) ppm S3
5 Heterophyllin A (3) 1H-NMR (270 MHz, CD3OD, rt): 3.82 (1H, d, J = 13.3 Hz), 4.15 (1H, dd, J = 4.1, 9.9 Hz), 4.52 (1H, dd, J = 6.2, 10.2 Hz), 5.13 (1H, dd, J = 10.0, 10.2 Hz), 5.28 (1H, dd, J = 6.2, 13.3 Hz), 5.66 (1H, dd, J = 9.9, 10.0 Hz), 6.40 (1H, d, J = 4.1 Hz), 6.48 (1H, s), 6.59 (1H, s), 7.03 (2H, s), 7.21 (2H, s) S4
6 Rugosin B ethyl ester (4) S5
7 S6
8 Eugeniin (5) 1H-NMR (270 MHz, CD3OD, rt): 3.93 (1H, d, J = 13.4 Hz), 4.43 (1H, dd, J = 6.6, 10.0 Hz), 5.23 (1H, dd, J = 9.5, 10.0 Hz), 5.38 (1H, dd, J = 6.6, 13.4 Hz), 5.55 (1H, dd, J = 8.2, 9.2 Hz), 5.76 (1H, dd, J = 9.2, 9.5 Hz), 6.11 (1H, d, J = 8.2 Hz), 6.49 (1H, s), 6.62 (1H, s), 6.92 (2H, s), 6.95 (2H, s), 7.06 (2H, s) S7
9 Rugosin A (6) 1H-NMR (500 MHz, CD3OD, rt): 3.85 (1H, d, J = 13.3 Hz), 4.38 (1H, dd, J = 6.4, 9.9 Hz), 5.18 (1H, dd, J = 9.5, 9.9 Hz), 5.29 (1H, dd, J = 6.4, 13.3 Hz), 5.54 (1H, dd, J = 8.4, 9.4 Hz), 5.74 (1H, dd, J = 9.4, 9.5 Hz), 6.09 (1H, d, J = 8.4 Hz), 6.23 (1H, s), 6.49 (1H, s), 6.93 (2H, s), 6.95 (2H, s), 7.05 (2H, s), 7.07 (1H, s) S8
10 Rugosin A decarboxylated (7) 1H-NMR (500 MHz, CD3OD, rt): 3.86 (1H, d, J = 13.4 Hz), 4.40 (1H, dd, J = 6.3, 10.0 Hz), 5.20 (1H, dd, J = 9.8, 10.0 Hz), 5.31 (1H, dd, J = 6.3, 13.4 Hz), 5.54 (1H, dd, J = 8.6, 9.3 Hz), 5.74 (1H, dd, J = 9.3, 9.8 Hz), 6.09 (1H, d, J = 8.6 Hz), 6.36 (1H, d, J = 9.2 Hz), 6.43 (1H, s), 6.44 (1H, d, J = 9.2 Hz), 6.50 (1H, s), 6.93 (2H, s), 6.95 (2H, s), 7.04 (2H, s) S9
11 NMR spectrums of rugosin A decarboxylated (7) in DMSO-d 6 1H, 13 C spectrum in DMSO-d6 S10
12 1H- 1 H COSY spectrum in DMSO-d6 S11
13 HMQC spectrum in DMSO-d6 S12
14 HMBC spectrum in DMSO-d6 S13
15 ROESY spectrum in DMSO-d6 S14
16 UPLC-MS quantitation of rugosin A, B in rose buds extract powder Condition Column: Inertsustain C18 ( mm, GL Science Co.) Mobile phase: gradient elution, 5% aq. MeCN with 0.1% TFA to 95% MeCN with 0.1% TFA (20 min) Flow rate: 0.2 ml/min Temperature: room temperature Detection: negative mode ([M-H]-) Samples: 4 L injection (Rose buds extract powder dissolved in water:1 mg/ml) Supplementary Figure 1. UPLC-MS analysis of rugosin A in the rose buts extract powder. Top: Rugosin A (isolated sample); Middle: Selected ion chromatogram of rose buts extract powder; Bottom: Total ion chromatogram of rose buts extract powder. S15
17 Supplementary Figure 2. UPLC-MS analysis of rugosin B in the rose buts extract powder. Top: Rugosin B (isolated sample); Middle: Selected ion chromatogram of rose buts extract powder; Bottom: Total ion chromatogram of rose buts extract powder. S16
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