Synthesis and Biological Activity of Tyrosol Ester Derivatives†

doi:10.7503/cjcu20170391

Abstract

Abstract:

A series of tyrosol derivatives was synthesized via the modification of alcohol hydroxyl groups of tyrosol, twenty-five target compounds were obtained and characterized by NMR and HR-MS. The experimental results show that most compounds exhibit some 1,1-diphenyl-2-picrylhydrazyl(DPPH) scavenging activities, compounds 3k and 3y have good DPPH scavenging activities, especially compound 3y shows the highest DPPH scavenging activities which is stronger than 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid(Trolox). The results show that most compounds exhibit some 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium(ABTS) scavenging activities, compounds 3k, 3x and 3y have good ABTS scavenging activities, especially compound 3y shows the highest ABTS scavenging activities which is stronger than Trolox. Ferric reducing antioxidant power(FRAP) experimental results show that most compounds exhibited some reduction activities to ferric ion-2,4,6-tri(2-pyridyl)-s-triazine(Fe³⁺-TPTZ) complex, compounds 3k, 3w and 3y have good reduction activities to Fe³⁺-TPTZ complex, especially compound 3y shows the highest reduction activities to Fe³⁺-TPTZ complex which is stronger than Trolox.

Key words: Tyrosol derivative, 1,1-Diphenyl-2-picrylhydrazyl, 2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium, Ferric reducing antioxidant power

CLC Number:

O623.42

TrendMD:

ZANG Hao, SHEN Peng, WANG Enpeng, XU Qian, ZHANG Luyun, XIA Guangqing, ZHU Junyi, ZHANG Hui, YANG Xiaohong. Synthesis and Biological Activity of Tyrosol Ester Derivatives^†[J]. Chem. J. Chinese Universities, 2018, 39(1): 64.

Figures/Tables 6

References 21

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Compd.	Appearance	Yield(%)	m. p./℃	HR-MS, m/z
3a	White solid	92	73—76	265.0419[M+Na]⁺
3b	White solid	97	142—144	279.0583[M+Na]⁺
3c	White solid	81	169—172	341.0771[M+Na]⁺
3d	White solid	75	91—92	299.0131[M+Na]⁺
3e	White solid	65	211—214	281.0295[M+Na]⁺
3f	Light yellow oil	81	None	279.0618[M+Na]⁺
3g	Yellow oil	81	None	293.0825[M+Na]⁺
3h	White solid	97	87—89	323.0231[M-H]^-
3i	White solid	90	129—131	291.0674[M+Na]⁺
3j	Light yellow solid	88	79—80	381.0887[M+Na]⁺
3k	White solid	67	91—94	337.0645[M+Na]⁺
3l	Light yellow oil	83	None	245.0736[M+Na]⁺
3m	White solid	89	214—216	307.0528[M+Na]⁺
3n	White solid	63	52—53	205.1298[M-H]^-
3o	White solid	73	65—68	204.0708[M-H]^-
3p	White solid	90	104—106	255.0300[M+Na]⁺
3q	White solid	88	133—135	311.1797[M-H]^-
3r	White solid	70	78—81	271.1012[M+Na]⁺
3s	White solid	88	135—136	333.0375[M+Na]⁺
3t	White solid	76	147—148	244.0685[M+H]⁺
3u	White solid	78	82—84	322.0586[M+Na]⁺
3v	Light yellow oil	80	None	349.1431[M+Na]⁺
3w	Colorless oil	75	None	287.1015[M-H]^-
3x	White solid	41	117—119	341.0610[M+Na]⁺
3y	White solid	82	48—49	311.0482[M+Na]⁺

Compd.	Appearance	Yield(%)	m. p./℃	HR-MS, m/z
3a	White solid	92	73—76	265.0419[M+Na]⁺
3b	White solid	97	142—144	279.0583[M+Na]⁺
3c	White solid	81	169—172	341.0771[M+Na]⁺
3d	White solid	75	91—92	299.0131[M+Na]⁺
3e	White solid	65	211—214	281.0295[M+Na]⁺
3f	Light yellow oil	81	None	279.0618[M+Na]⁺
3g	Yellow oil	81	None	293.0825[M+Na]⁺
3h	White solid	97	87—89	323.0231[M-H]^-
3i	White solid	90	129—131	291.0674[M+Na]⁺
3j	Light yellow solid	88	79—80	381.0887[M+Na]⁺
3k	White solid	67	91—94	337.0645[M+Na]⁺
3l	Light yellow oil	83	None	245.0736[M+Na]⁺
3m	White solid	89	214—216	307.0528[M+Na]⁺
3n	White solid	63	52—53	205.1298[M-H]^-
3o	White solid	73	65—68	204.0708[M-H]^-
3p	White solid	90	104—106	255.0300[M+Na]⁺
3q	White solid	88	133—135	311.1797[M-H]^-
3r	White solid	70	78—81	271.1012[M+Na]⁺
3s	White solid	88	135—136	333.0375[M+Na]⁺
3t	White solid	76	147—148	244.0685[M+H]⁺
3u	White solid	78	82—84	322.0586[M+Na]⁺
3v	Light yellow oil	80	None	349.1431[M+Na]⁺
3w	Colorless oil	75	None	287.1015[M-H]^-
3x	White solid	41	117—119	341.0610[M+Na]⁺
3y	White solid	82	48—49	311.0482[M+Na]⁺

Compd.	¹H NMR(600 MHz), δ	¹³C NMR(150 MHz), δ
3a^a	9.21(s, 1H, —OH), 7.92(d, J=8.4 Hz, 2H), 7.65(s, 1H), 7.52(t, 2H), 7.10(d, J=8.4 Hz, 2H), 6.69(d, J=8.4 Hz, 2H), 4.40(t, 2H), 2.91(s, 2H)	165.6, 155.8, 133.2, 129.8, 129.8, 129.8, 129.0, 129.0, 128.7, 128.7, 127.9, 115.1, 115.1, 65.6, 33.6
3b^b	7.90(d, J=8.4 Hz, 2H), 7.22(d, J=8.4 Hz, 2H), 7.12(d, J=8.4 Hz, 2H), 6.79(d, J=8.4 Hz, 2H), 5.45(s, 1H, —OH), 4.47(t, J=6.6 Hz, 2H), 2.99(t, J=6.6 Hz, 2H)	166.9, 154.4, 143.7, 130.1, 130.1, 129.8, 129.6, 129.6, 129.1, 129.1, 127.4, 115.4, 115.4, 65.7, 34.3, 21.6
3c^b	8.07(s, 2H), 7.65(d, J=8.4 Hz, 2H), 7.62(d, 2H), 7.46(d, J=8.4 Hz, 2H), 7.39(s, 1H), 7.24(s, 1H, —OH), 7.16(d, J=8.4 Hz, 2H), 6.80(d, J=8.4 Hz, 2H), 4.50(d, 2H), 3.02(s, 2H)	166.5, 154.3, 145.7, 140.0, 130.1, 130.1, 130.1, 130.1, 130.0, 129.0, 128.9, 128.9, 128.1, 127.3, 127.3, 127.1, 127.1, 115.4, 115.4, 65.7, 34.4
3d^b	7.93(d, J=8.4 Hz, 2H), 7.39(d, J=8.4 Hz, 2H), 7.11(d, J=8.4 Hz, 2H), 6.79(d, J=8.4 Hz, 2H), 5.54(s, 1H, —OH), 4.48(t, 2H), 2.99(s, 2H)	166.0, 154.5, 139.4, 130.9, 130.9, 130.0, 130.0, 129.6, 128.7, 128.7, 128.6, 115.4, 115.4, 66.0, 34.3
3e^a	10.30(s, 1H, —OH), 9.21(s, 1H, —OH), 7.78(d, J=8.4 Hz, 2H), 7.08(d, J=8.4 Hz, 2H), 6.84(d, J=8.4 Hz, 2H), 6.69(d, J=8.4 Hz, 2H), 4.33(s, 2H), 2.87(s, 2H)	165.5, 161.9, 155.8, 131.3, 131.3, 129.8, 129.8, 128.1, 120.4, 115.3, 115.3, 115.1, 115.1, 65.0, 33.7
3f^b	7.20—7.28(m, 5H), 6.94(d, J=8.4 Hz, 2H), 6.69(d, J=8.4 Hz, 2H), 6.20(s, 1H, —OH), 4.25(t, J=6.6 Hz, 2H), 3.59(s, 2H), 2.80(t, J=6.6 Hz, 2H)	172.3, 154.5, 133.6, 129.8, 129.8, 129.2, 129.2, 129.1, 128.5, 128.5, 127.0, 115.3, 115.3, 65.8, 41.3, 33.9
3g^b	7.25(t, 2H), 7.18(d, 1H), 7.13(d, 2H), 6.99(d, J=8.4 Hz, 2H), 6.75(d, J=8.4 Hz, 2H), 6.40(s, 1H, —OH), 4.23(s, 2H), 2.90(s, 2H), 2.80(s, 2H), 2.61(d, 2H)	173.6, 154.5, 140.2, 129.9, 129.9, 129.2, 128.4, 128.4, 128.1, 128.1, 126.2, 115.3, 115.3, 65.4, 35.8, 34.0, 30.8
3h^b	7.35(d, 1H), 7.11(d, 2H), 6.94(d, J=8.4 Hz, 2H), 6.69(d, J=8.4 Hz, 2H), 6.15(s, 1H, —OH), 4.28(t, J=6.6 Hz, 2H), 3.77(s, 2H), 2.82(t, J=6.6 Hz, 2H)	170.6, 154.4, 134.4, 133.2, 132.8, 129.8, 129.8, 129.6, 129.4, 129.1, 127.2, 115.3, 115.3, 66.1, 40.0, 33.9
3i^a	9.22(s, 1H, —OH), 7.70(d, 2H), 7.63(d, J=16.2 Hz, 1H), 7.42(s, 3H), 7.07(d, J=7.2 Hz, 2H), 6.70(d, J=7.2 Hz, 2H), 6.61(d, J=16.2 Hz, 1H), 4.28(s, 2H), 2.84(s, 2H)	166.1, 155.9, 144.5, 134.0, 130.4, 129.7, 129.7, 128.9, 128.9, 128.3, 128.3, 127.8, 118.0, 115.2, 115.2, 64.9, 33.6
3j^b	7.59(d, J=16.2 Hz, 1H), 7.10(d, J=8.4 Hz, 2H), 6.81(d, J=8.4 Hz, 2H), 6.74(s, 2H), 6.34(d, J=16.2 Hz, 1H), 6.31(s, 1H, —OH), 4.39(t, 2H), 3.88(s, 3H, —OCH₃), 3.87(s, 6H, —OCH₃), 2.94(s, 2H)	167.2, 154.7, 153.3, 153.3, 145.0, 140.0, 129.9, 129.9, 129.8, 129.3, 117.1, 115.4, 115.4, 105.3, 105.3, 65.4, 60.9, 56.1, 56.1, 34.2
3k^b	7.59(d, J=16.2 Hz, 1H), 7.08(d, J=8.4 Hz, 2H), 7.01(s, 1H), 6.97(s, 1H), 6.89(d, 1H), 6.81(d, J=8.4 Hz, 2H), 6.45(s, 1H, —OH), 6.26(d, J=16.2 Hz, 1H), 6.17(s, 1H, —OH), 4.37(t, J=6.6 Hz, 2H), 3.86(s, 3H, —OCH₃), 2.92(s, 2H)	167.8, 154.6, 148.0, 146.8, 145.3, 129.9, 129.9, 129.4, 126.8, 123.1, 115.4, 115.4, 115.0, 114.7, 109.5, 65.4, 55.8, 34.2
3l^b	7.05(d, J=8.4 Hz, 2H), 6.78(d, J=8.4 Hz, 2H), 6.43(s, 1H, —OH), 4.23(t, 2H), 2.85(s, 2H), 1.16(s, 9H, —CH₃)	179.3, 154.6, 130.0, 130.0, 129.4, 115.3, 115.3, 65.4, 38.7, 34.1, 27.1, 27.1, 27.1
3m^a	10.00(s, 1H, —OH), 9.21(s, H, —OH), 7.52—7.55(q, 3H), 7.06(d, J=8.4 Hz, 2H), 6.79(d, J=8.4 Hz, 2H), 6.69(d, 2H), 6.36(d, 1H), 4.25(t, 2H), 2.82(s, 2H)	166.5, 159.8, 155.8, 144.7, 130.3, 130.3, 129.7, 129.7, 127.9, 125.0, 115.7, 115.7, 115.1, 115.1, 114.1, 64.7, 33.7
3n^b	7.05(d, J=8.4 Hz, 2H), 6.97(t, J=7.2 Hz, 2H), 6.78(d, J=8.4 Hz, 2H), 6.59(s, 1H, —OH), 5.84(dd, J=15.6, 1.8 Hz, 1H), 4.30(s, 2H), 2.87(s, 2H), 1.85(dd, J=7.2, 1.8 Hz, 3H)	167.2, 154.6, 145.4, 129.9, 129.9, 129.3, 122.4, 115.4, 115.4, 65.2, 34.2, 17.9
3o^b	7.04(d, J=8.4 Hz, 2H), 6.78(d, J=8.4 Hz, 2H), 6.41(s, 1H, —OH), 4.33(t, J=6.6 Hz, 2H), 3.42(s, 2H), 2.87(t, J=6.6 Hz, 2H, —CH₂)	163.0, 154.7, 129.9, 129.9, 128.5, 125.4, 125.4, 113.1, 67.4, 33.7, 24.5
3p^b	7.55(s, 1H, —OH), 7.16(d, 1H), 7.09(d, J=8.4 Hz, 2H), 6.81(d, J=8.4 Hz, 2H), 6.48(t, 1H), 6.40(s, 1H), 4.45(t, J=6.6 Hz, 2H), 2.96(t, 2H)	159.0, 154.6, 146.5, 144.4, 123.0, 123.0, 129.1, 118.2, 115.4, 115.4, 111.8, 65.8, 34.2
3q^a	9.21(s, 1H, —OH), 7.54(d, J=15.6 Hz, 1H), 7.40(s, 1H), 7.18(d, J=7.8 Hz, 1H), 7.06(d, J=7.8 Hz, 2H), 6.94(d, J=7.8 Hz, 2H), 6.69(d, J=7.8 Hz, 2H), 6.47(d, J=15.6 Hz, 1H), 6.07(s, 2H), 4.26(t, 2H), 2.83(t, 2H)	166.4, 155.8, 149.3, 148.0, 144.4, 129.7, 129.7, 128.4, 127.8, 125.0, 115.9, 115.1, 108.4, 106.7, 101.6, 64.8, 33.6
3r^b	7.05(d, J=8.4 Hz, 2H), 6.78(d, J=8.4 Hz, 2H), 6.18(s, 1H, —OH), 4.23(d, 2H), 2.85(s, 2H), 2.28(s, 1H, —CH), 1.86(d, J=12.6 Hz, 2H), 1.72(d, J=12.6 Hz, 2H), 1.63(s, 1H), 1.40(d, 2H), 1.24(t, 3H)	176.8, 154.5, 129.9, 129.9, 129.5, 115.3, 115.3, 65.1, 43.2, 34.2, 28.9, 28.9, 25.6, 25.3, 25.3
3s^a	9.22(s, 1H, —OH), 8.68(s, 1H), 7.90(s, 1H), 7.42(s, 2H), 7.11(d, J=7.8 Hz, 2H), 6.70(d, J=7.8 Hz, 2H), 4.37(t, 2H), 2.90(t, 2H)	162.4, 155.9, 154.5, 148.7, 134.5, 130.2, 129.9, 129.9, 127.6, 124.8, 117.7, 117.5, 116.1, 115.2, 115.2, 115.2, 66.0, 33.5
3t^a	9.21(s, 1H, —OH), 9.04(t, 1H), 8.80—8.81(q, 1H), 8.23—8.25(m, 1H), 7.55—7.57(m, 1H), 7.10(d, 2H), 6.69—6.70(q, 2H), 4.44(t, J=6.6 Hz, 2H), 2.92(t, J=6.6 Hz, 2H)	164.6, 155.9, 153.6, 149.9, 136.7, 129.8, 129.8, 127.8, 125.7, 123.9, 115.2, 115.2, 65.9, 33.5
3u^a	9.20(s, 1H, —OH), 8.93(s, 1H, —NH), 7.87(d, J=7.2 Hz, 2H), 7.55(d, 1H), 7.50(d, J=7.2 Hz, 2H), 7.03(d, J=7.8 Hz, 2H), 6.65(d, J=7.8 Hz, 2H), 4.20(s, 2H), 3.99(d, 2H), 2.77(s, 2H)	169.8, 166.6, 155.8, 133.6, 131.5, 129.8, 129.8, 129.6, 128.4, 128.4, 127.2, 127.2, 115.1, 115.1, 65.3, 41.3, 33.5
3v^b	7.07(d, J=8.4 Hz, 2H), 6.77(d, J=8.4 Hz, 2H), 5.23(s, 1H, —OH), 4.24—4.27(m, 2H), 3.52(t, 1H), 3.17(t, 1H), 3.11(t, 1H), 2.86(s, 2H), 2.45(d, 1H), 2.29(d, 2H), 1.89(t, 1H), 1.63(q, 4H), 1.42(s, 1H), 1.38(s, 1H)	173.7, 154.4, 130.0, 130.0, 129.7, 115.4, 115.4, 65.1, 56.4, 40.2, 38.4, 34.5, 34.2, 34.1, 28.7, 24.6
3w^b	7.59(dd, J=8.4, 1.8 Hz, 1H), 7.47(d, J=1.8 Hz, 1H), 7.08(d, J=8.4 Hz, 2H), 6.90(d, J=8.4 Hz, 1H), 6.81(d, J=8.4 Hz, 2H), 6.58(s, 2H, —OH), 4.44(s, 2H), 3.79(s, 3H), 2.95(s, 2H)	167.0, 154.6, 150.1, 146.2, 130.0, 130.0, 129.5, 124.1, 121.9, 115.4, 115.4, 114.2, 111.8, 65.8, 55.8, 34.2
3x^b	7.28(s, 2H), 6.78(d, J=8.4 Hz, 2H), 7.14(d, J=8.4 Hz, 2H), 6.79(d, J=8.4 Hz, 2H), 5.93(s, 1H, —OH), 5.19(s, 1H, —OH), 4.46(s, 2H), 3.92(s, 6H, —OCH₃), 3.00(s, 2H)	166.4, 154.4, 146.6, 146.6, 139.2, 130.1, 130.1, 130.0, 121.2, 115.4, 115.4, 106.6, 106.6, 65.7, 56.4, 56.4, 34.4
3y^a	9.21(s, 1H, —OH), 8.85(s, 1H, —OH), 8.80(s, 1H, —OH), 6.98(d, 2H), 6.67—6.70(m, 4H), 6.47—6.49(q, 1H), 4.14(t, J=6.6 Hz, 2H), 3.43(s, 2H), 2.74(s, 2H)	171.5, 155.9, 145.2, 144.3, 129.9, 129.9, 128.0, 125.1, 120.2, 116.8, 115.5, 115.2, 115.2, 65.2, 40.0, 33.7

Compd.	¹H NMR(600 MHz), δ	¹³C NMR(150 MHz), δ
3a^a	9.21(s, 1H, —OH), 7.92(d, J=8.4 Hz, 2H), 7.65(s, 1H), 7.52(t, 2H), 7.10(d, J=8.4 Hz, 2H), 6.69(d, J=8.4 Hz, 2H), 4.40(t, 2H), 2.91(s, 2H)	165.6, 155.8, 133.2, 129.8, 129.8, 129.8, 129.0, 129.0, 128.7, 128.7, 127.9, 115.1, 115.1, 65.6, 33.6
3b^b	7.90(d, J=8.4 Hz, 2H), 7.22(d, J=8.4 Hz, 2H), 7.12(d, J=8.4 Hz, 2H), 6.79(d, J=8.4 Hz, 2H), 5.45(s, 1H, —OH), 4.47(t, J=6.6 Hz, 2H), 2.99(t, J=6.6 Hz, 2H)	166.9, 154.4, 143.7, 130.1, 130.1, 129.8, 129.6, 129.6, 129.1, 129.1, 127.4, 115.4, 115.4, 65.7, 34.3, 21.6
3c^b	8.07(s, 2H), 7.65(d, J=8.4 Hz, 2H), 7.62(d, 2H), 7.46(d, J=8.4 Hz, 2H), 7.39(s, 1H), 7.24(s, 1H, —OH), 7.16(d, J=8.4 Hz, 2H), 6.80(d, J=8.4 Hz, 2H), 4.50(d, 2H), 3.02(s, 2H)	166.5, 154.3, 145.7, 140.0, 130.1, 130.1, 130.1, 130.1, 130.0, 129.0, 128.9, 128.9, 128.1, 127.3, 127.3, 127.1, 127.1, 115.4, 115.4, 65.7, 34.4
3d^b	7.93(d, J=8.4 Hz, 2H), 7.39(d, J=8.4 Hz, 2H), 7.11(d, J=8.4 Hz, 2H), 6.79(d, J=8.4 Hz, 2H), 5.54(s, 1H, —OH), 4.48(t, 2H), 2.99(s, 2H)	166.0, 154.5, 139.4, 130.9, 130.9, 130.0, 130.0, 129.6, 128.7, 128.7, 128.6, 115.4, 115.4, 66.0, 34.3
3e^a	10.30(s, 1H, —OH), 9.21(s, 1H, —OH), 7.78(d, J=8.4 Hz, 2H), 7.08(d, J=8.4 Hz, 2H), 6.84(d, J=8.4 Hz, 2H), 6.69(d, J=8.4 Hz, 2H), 4.33(s, 2H), 2.87(s, 2H)	165.5, 161.9, 155.8, 131.3, 131.3, 129.8, 129.8, 128.1, 120.4, 115.3, 115.3, 115.1, 115.1, 65.0, 33.7
3f^b	7.20—7.28(m, 5H), 6.94(d, J=8.4 Hz, 2H), 6.69(d, J=8.4 Hz, 2H), 6.20(s, 1H, —OH), 4.25(t, J=6.6 Hz, 2H), 3.59(s, 2H), 2.80(t, J=6.6 Hz, 2H)	172.3, 154.5, 133.6, 129.8, 129.8, 129.2, 129.2, 129.1, 128.5, 128.5, 127.0, 115.3, 115.3, 65.8, 41.3, 33.9
3g^b	7.25(t, 2H), 7.18(d, 1H), 7.13(d, 2H), 6.99(d, J=8.4 Hz, 2H), 6.75(d, J=8.4 Hz, 2H), 6.40(s, 1H, —OH), 4.23(s, 2H), 2.90(s, 2H), 2.80(s, 2H), 2.61(d, 2H)	173.6, 154.5, 140.2, 129.9, 129.9, 129.2, 128.4, 128.4, 128.1, 128.1, 126.2, 115.3, 115.3, 65.4, 35.8, 34.0, 30.8
3h^b	7.35(d, 1H), 7.11(d, 2H), 6.94(d, J=8.4 Hz, 2H), 6.69(d, J=8.4 Hz, 2H), 6.15(s, 1H, —OH), 4.28(t, J=6.6 Hz, 2H), 3.77(s, 2H), 2.82(t, J=6.6 Hz, 2H)	170.6, 154.4, 134.4, 133.2, 132.8, 129.8, 129.8, 129.6, 129.4, 129.1, 127.2, 115.3, 115.3, 66.1, 40.0, 33.9
3i^a	9.22(s, 1H, —OH), 7.70(d, 2H), 7.63(d, J=16.2 Hz, 1H), 7.42(s, 3H), 7.07(d, J=7.2 Hz, 2H), 6.70(d, J=7.2 Hz, 2H), 6.61(d, J=16.2 Hz, 1H), 4.28(s, 2H), 2.84(s, 2H)	166.1, 155.9, 144.5, 134.0, 130.4, 129.7, 129.7, 128.9, 128.9, 128.3, 128.3, 127.8, 118.0, 115.2, 115.2, 64.9, 33.6
3j^b	7.59(d, J=16.2 Hz, 1H), 7.10(d, J=8.4 Hz, 2H), 6.81(d, J=8.4 Hz, 2H), 6.74(s, 2H), 6.34(d, J=16.2 Hz, 1H), 6.31(s, 1H, —OH), 4.39(t, 2H), 3.88(s, 3H, —OCH₃), 3.87(s, 6H, —OCH₃), 2.94(s, 2H)	167.2, 154.7, 153.3, 153.3, 145.0, 140.0, 129.9, 129.9, 129.8, 129.3, 117.1, 115.4, 115.4, 105.3, 105.3, 65.4, 60.9, 56.1, 56.1, 34.2
3k^b	7.59(d, J=16.2 Hz, 1H), 7.08(d, J=8.4 Hz, 2H), 7.01(s, 1H), 6.97(s, 1H), 6.89(d, 1H), 6.81(d, J=8.4 Hz, 2H), 6.45(s, 1H, —OH), 6.26(d, J=16.2 Hz, 1H), 6.17(s, 1H, —OH), 4.37(t, J=6.6 Hz, 2H), 3.86(s, 3H, —OCH₃), 2.92(s, 2H)	167.8, 154.6, 148.0, 146.8, 145.3, 129.9, 129.9, 129.4, 126.8, 123.1, 115.4, 115.4, 115.0, 114.7, 109.5, 65.4, 55.8, 34.2
3l^b	7.05(d, J=8.4 Hz, 2H), 6.78(d, J=8.4 Hz, 2H), 6.43(s, 1H, —OH), 4.23(t, 2H), 2.85(s, 2H), 1.16(s, 9H, —CH₃)	179.3, 154.6, 130.0, 130.0, 129.4, 115.3, 115.3, 65.4, 38.7, 34.1, 27.1, 27.1, 27.1
3m^a	10.00(s, 1H, —OH), 9.21(s, H, —OH), 7.52—7.55(q, 3H), 7.06(d, J=8.4 Hz, 2H), 6.79(d, J=8.4 Hz, 2H), 6.69(d, 2H), 6.36(d, 1H), 4.25(t, 2H), 2.82(s, 2H)	166.5, 159.8, 155.8, 144.7, 130.3, 130.3, 129.7, 129.7, 127.9, 125.0, 115.7, 115.7, 115.1, 115.1, 114.1, 64.7, 33.7
3n^b	7.05(d, J=8.4 Hz, 2H), 6.97(t, J=7.2 Hz, 2H), 6.78(d, J=8.4 Hz, 2H), 6.59(s, 1H, —OH), 5.84(dd, J=15.6, 1.8 Hz, 1H), 4.30(s, 2H), 2.87(s, 2H), 1.85(dd, J=7.2, 1.8 Hz, 3H)	167.2, 154.6, 145.4, 129.9, 129.9, 129.3, 122.4, 115.4, 115.4, 65.2, 34.2, 17.9
3o^b	7.04(d, J=8.4 Hz, 2H), 6.78(d, J=8.4 Hz, 2H), 6.41(s, 1H, —OH), 4.33(t, J=6.6 Hz, 2H), 3.42(s, 2H), 2.87(t, J=6.6 Hz, 2H, —CH₂)	163.0, 154.7, 129.9, 129.9, 128.5, 125.4, 125.4, 113.1, 67.4, 33.7, 24.5
3p^b	7.55(s, 1H, —OH), 7.16(d, 1H), 7.09(d, J=8.4 Hz, 2H), 6.81(d, J=8.4 Hz, 2H), 6.48(t, 1H), 6.40(s, 1H), 4.45(t, J=6.6 Hz, 2H), 2.96(t, 2H)	159.0, 154.6, 146.5, 144.4, 123.0, 123.0, 129.1, 118.2, 115.4, 115.4, 111.8, 65.8, 34.2
3q^a	9.21(s, 1H, —OH), 7.54(d, J=15.6 Hz, 1H), 7.40(s, 1H), 7.18(d, J=7.8 Hz, 1H), 7.06(d, J=7.8 Hz, 2H), 6.94(d, J=7.8 Hz, 2H), 6.69(d, J=7.8 Hz, 2H), 6.47(d, J=15.6 Hz, 1H), 6.07(s, 2H), 4.26(t, 2H), 2.83(t, 2H)	166.4, 155.8, 149.3, 148.0, 144.4, 129.7, 129.7, 128.4, 127.8, 125.0, 115.9, 115.1, 108.4, 106.7, 101.6, 64.8, 33.6
3r^b	7.05(d, J=8.4 Hz, 2H), 6.78(d, J=8.4 Hz, 2H), 6.18(s, 1H, —OH), 4.23(d, 2H), 2.85(s, 2H), 2.28(s, 1H, —CH), 1.86(d, J=12.6 Hz, 2H), 1.72(d, J=12.6 Hz, 2H), 1.63(s, 1H), 1.40(d, 2H), 1.24(t, 3H)	176.8, 154.5, 129.9, 129.9, 129.5, 115.3, 115.3, 65.1, 43.2, 34.2, 28.9, 28.9, 25.6, 25.3, 25.3
3s^a	9.22(s, 1H, —OH), 8.68(s, 1H), 7.90(s, 1H), 7.42(s, 2H), 7.11(d, J=7.8 Hz, 2H), 6.70(d, J=7.8 Hz, 2H), 4.37(t, 2H), 2.90(t, 2H)	162.4, 155.9, 154.5, 148.7, 134.5, 130.2, 129.9, 129.9, 127.6, 124.8, 117.7, 117.5, 116.1, 115.2, 115.2, 115.2, 66.0, 33.5
3t^a	9.21(s, 1H, —OH), 9.04(t, 1H), 8.80—8.81(q, 1H), 8.23—8.25(m, 1H), 7.55—7.57(m, 1H), 7.10(d, 2H), 6.69—6.70(q, 2H), 4.44(t, J=6.6 Hz, 2H), 2.92(t, J=6.6 Hz, 2H)	164.6, 155.9, 153.6, 149.9, 136.7, 129.8, 129.8, 127.8, 125.7, 123.9, 115.2, 115.2, 65.9, 33.5
3u^a	9.20(s, 1H, —OH), 8.93(s, 1H, —NH), 7.87(d, J=7.2 Hz, 2H), 7.55(d, 1H), 7.50(d, J=7.2 Hz, 2H), 7.03(d, J=7.8 Hz, 2H), 6.65(d, J=7.8 Hz, 2H), 4.20(s, 2H), 3.99(d, 2H), 2.77(s, 2H)	169.8, 166.6, 155.8, 133.6, 131.5, 129.8, 129.8, 129.6, 128.4, 128.4, 127.2, 127.2, 115.1, 115.1, 65.3, 41.3, 33.5
3v^b	7.07(d, J=8.4 Hz, 2H), 6.77(d, J=8.4 Hz, 2H), 5.23(s, 1H, —OH), 4.24—4.27(m, 2H), 3.52(t, 1H), 3.17(t, 1H), 3.11(t, 1H), 2.86(s, 2H), 2.45(d, 1H), 2.29(d, 2H), 1.89(t, 1H), 1.63(q, 4H), 1.42(s, 1H), 1.38(s, 1H)	173.7, 154.4, 130.0, 130.0, 129.7, 115.4, 115.4, 65.1, 56.4, 40.2, 38.4, 34.5, 34.2, 34.1, 28.7, 24.6
3w^b	7.59(dd, J=8.4, 1.8 Hz, 1H), 7.47(d, J=1.8 Hz, 1H), 7.08(d, J=8.4 Hz, 2H), 6.90(d, J=8.4 Hz, 1H), 6.81(d, J=8.4 Hz, 2H), 6.58(s, 2H, —OH), 4.44(s, 2H), 3.79(s, 3H), 2.95(s, 2H)	167.0, 154.6, 150.1, 146.2, 130.0, 130.0, 129.5, 124.1, 121.9, 115.4, 115.4, 114.2, 111.8, 65.8, 55.8, 34.2
3x^b	7.28(s, 2H), 6.78(d, J=8.4 Hz, 2H), 7.14(d, J=8.4 Hz, 2H), 6.79(d, J=8.4 Hz, 2H), 5.93(s, 1H, —OH), 5.19(s, 1H, —OH), 4.46(s, 2H), 3.92(s, 6H, —OCH₃), 3.00(s, 2H)	166.4, 154.4, 146.6, 146.6, 139.2, 130.1, 130.1, 130.0, 121.2, 115.4, 115.4, 106.6, 106.6, 65.7, 56.4, 56.4, 34.4
3y^a	9.21(s, 1H, —OH), 8.85(s, 1H, —OH), 8.80(s, 1H, —OH), 6.98(d, 2H), 6.67—6.70(m, 4H), 6.47—6.49(q, 1H), 4.14(t, J=6.6 Hz, 2H), 3.43(s, 2H), 2.74(s, 2H)	171.5, 155.9, 145.2, 144.3, 129.9, 129.9, 128.0, 125.1, 120.2, 116.8, 115.5, 115.2, 115.2, 65.2, 40.0, 33.7

Compd.	Scavenging ratio(%)	Compd.	Scavenging ratio(%)
3a	9.7±1.4	3n	3.1±2.2
3b	21.4±1.2	3o	16.7±1.5
3c	7.1±0.6	3p	2.1±0.5
3d	11.9±0.3	3q	13.0±1.0
3e	0.2±0.3	3r	2.5±2.4
3f	12.1±0.6	3s	13.0±1.2
3g	12.0±0.9	3t	13.0±0.6
3h	12.5±0.4	3u	14.3±0.4
3i	13.6±0.9	3v	7.0±2.5
3j	13.4±0.0	3w	4.2±1.2
3k	70.4±0.5	3x	16.2±1.3
3l	5.1±1.1	3y	86.3±4.5
3m	15.2±0.4	Trolox	75.8±0.9