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. 2021 Feb 8;11:608199. doi: 10.3389/fphar.2020.608199

TABLE 3.

The isolated and synthesized compounds derived from DRF.

No Name Parts of plant Source References(s)
Phenylalanine dipeptide compounds
Lead compound
1 N-[(N-benzoyl-L-phenylalanyl)-O-acetyl]-L-phenylalanol (MTS) Whole plant Ethanol extracts Liang et al. (2002a); Liu et al. (2003)
Derivatives containing ether structure
2 Bentysrepinine Based on MTS Liang et al. (2002b)
3 N-[N-(4-propargyloxy benzoyl)-O-2-dimethylaminoethyl) -l-tyrosyl]-L-phenylalanol Based on MTS Yuan (2015)
4 N-[(N-benzoyl-L-phenylalanyl)-O-2-(dimethylaminoethyl) -l-tyrosyl]-O-propargyl-L-phenylalanol Based on MTS Yuan (2015)
5 N-[(2S)-1-{[(2S)-1-Hydroxy-3-phenylpropan-2-yl]amino}-3-(4-methoxyphenyl)-1-oxopropan-2-yl]benzamide Based on MTS Qiu et al. (2016)
6 N-[(2S)-3-(4-Ethoxyphenyl)-1-{[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino}-1-oxopropan-2-yl]benzamide Based on MTS Qiu et al. (2016)
7 N-[(2S)-1-{[(2S)-1-Hydroxy-3-phenylpropan-2-yl]amino}-1-oxo-3-(4-propoxyphenyl)propan-2-yl]benzamide Based on MTS Qiu et al. (2016)
8 N-{(2S)-1-{[(2S)-1-Hydroxy-3-phenylpropan-2-yl]amino}-1-oxo-3-[4-(propan-2-yloxy)phenyl]propan-2-yl}benzamide Based on MTS Qiu et al. (2016)
9 N-[(2S)-3-(4-Butoxyphenyl)-1-{[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino}-1-oxopropan-2-yl]benzamide Based on MTS Qiu et al. (2016)
10 N-{(2S)-1-{[(2S)-1-Hydroxy-3-phenylpropan-2-yl]amino}-3-[4-(2-methylpropoxy)phenyl]-1-oxopropan-2-yl} benzamide Based on MTS Qiu et al. (2016)
11 N-{(2S)-1-{[(2S)-1-Hydroxy-3-phenylpropan-2-yl]amino}-1-oxo-3-[4-(pentyloxy)phenyl]propan-2-yl}benzamide Based on MTS Qiu et al. (2016)
12 N-[(2S)-3-[4-(Hexyloxy)phenyl]-1-{[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino}-1-oxopropan-2-yl]benzamide Based on MTS Qiu et al. (2016)
13 N-[(2S)-3-[4-(Cyanomethoxy)phenyl]-1-{[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino}-1-oxopropan-2-yl]benzamide Based on MTS Qiu et al. (2016)
14 N-{(2S)-1-{[(2S)-1-Hydroxy-3-phenylpropan-2-yl]amino}-1-oxo-3-[4-(prop-2-en-1-yloxy)phenyl]propan-2-yl} benzamide Based on MTS Qiu et al. (2016)
15 (2S)-2-{[(2S)-2-Benzamido-3-(4-methoxyphenyl)propanoyl]amino}-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
16 (2S)-2-{[(2S)-2-Benzamido-3-(4-ethoxyphenyl)propanoyl] amino}-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
17 (2S)-2-{[(2S)-2-Benzamido-3-(4-propoxyphenyl)propanoyl]amino}-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
18 (2S)-2-({(2S)-2-Benzamido-3-[4-(propan-2-yloxy)phenyl] propanoyl}amino)-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
19 (2S)-2-{[(2S)-2-Benzamido-3-(4-butoxyphenyl)propanoyl] amino}-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
20 (2S)-2-({(2S)-2-Benzamido-3-[4-(2-methylpropoxy)phenyl]propanoyl}amino)-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
21 (2S)-2-({(2S)-2-Benzamido-3-[4-(pentyloxy)phenyl] propanoyl}amino)-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
22 (2S)-2-({(2S)-2-Benzamido-3-[4-(hexyloxy)phenyl] propanoyl}amino)-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
23 (2S)-2-({(2S)-2-Benzamido-3-[4-(cyanomethoxy)phenyl] propanoyl}amino)-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
24 (2S)-2-({(2S)-2-Benzamido-3-[4-(prop-2-en-1-yloxy) phenyl]propanoyl}amino)-3-phenylpropyl acetate Based on MTS Qiu et al. (2016)
Fluorine or chlorine-substituted derivatives
25 N-[N-(2-chlorobenzoyl)-l-tyrosyl]-L-phenylalanine methyl ester Based on MTS Kuang et al. (2019a)
26 N-[N-(4-fluorobenzoyl)-l-tyrosyl]-L-phenylalanine methyl ester Based on MTS Kuang et al. (2019a)
27 N-[N-(2-chlorobenzoyl)-l-tyrosyl]-L-phenylalanol Based on MTS Kuang et al. (2019a)
28 N-[N-(4-fluorobenzoyl)-l-tyrosyl]-L-phenylalanol Based on MTS Kuang et al. (2019a)
29 N-[N-(4-chlorobenzoyl)-l-tyrosyl]-L-phenylalanol Based on MTS Kuang et al. (2019a)
30 N-[N-(4-chlorobenzoyl)-O-methyl-l-tyrosyl]-L-phenylalanol Based on MTS Kuang et al. (2019a)
31 N-[N-(4-chlorobenzoyl)-O-ethyl-l-tyrosyl]-L-phenylalanol Based on MTS Kuang et al. (2019a)
32 N-[N-(4-chlorobenzoyl)-O-propyl-l-tyrosyl]-L-phenylalanol Based on MTS Kuang et al. (2019a)
33 N-[N-(4-chlorobenzoyl)-O-isopropyl-l-tyrosyl]-L-phenylalanol Based on MTS Kuang et al. (2019a)
34 N-[N-(4-chlorobenzoyl)-O-dimethylaminoethyl-l-tyrosyl]-L-phenylalanol Based on MTS Kuang et al. (2019a)
Derivatives containing veratric acid
35 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl]-L-tyrosine methyl ester Based on MTS Kuang et al. (2019b)
36 N-[N-(3, 4-dimethoxy-benzoyl)-l-tyrosyl]-L-phenylalanine methyl ester Based on MTS Kuang et al. (2019b)
37 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl]-L-phenylalanine methyl ester Based on MTS Kuang et al. (2019b)
38 N-[N-(3, 4-dimethoxy-benzoyl)-O-acetyl-l-tyrosyl] -L-phenylalanine methyl ester Based on MTS Kuang et al. (2019b)
39 N-[N-(3, 4-dimethoxy-benzoyl)-O-(2-diethyllaminoethyl)-l-tyrosyl]-L-phenylalanine methyl ester Based on MTS Kuang et al. (2019b)
40 N-[N-(3, 4-dimethoxy-benzoyl)-O-ethyl-l-tyrosyl]-L-phenylalanine methyl ester Based on MTS Kuang et al. (2019b)
41 N-[N-(3, 4-dimethoxy-benzoyl)-O-propyl-l-tyrosyl]-L-phenylalanine methyl ester Based on MTS Kuang et al. (2019b)
42 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl-O-ethyl]-L-tyrosine methyl ester Based on MTS Kuang et al. (2019b)
43 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl-O-propyl] -L-tyrosine methyl ester Based on MTS Kuang et al. (2019b)
44 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl-O-isopropyl] -L-tyrosine methyl ester Based on MTS Kuang et al. (2019b)
45 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl-O-n-butyl] -L-tyrosine methyl ester Based on MTS Kuang et al. (2019b)
46 N-[N-(3,4-dimethoxy-benzoyl)-L-phenylalanyl-O-n-octyl]-L-tyrosine methyl ester Based on MTS Kuang et al. (2019b)
47 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl]-L -phenylalanol Based on MTS Kuang et al. (2019b)
48 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl]-L-tyrosinol Based on MTS Kuang et al. (2019b)
49 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl]-O-acetyl-L-phenylalanol Based on MTS Kuang et al. (2019b)
50 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl]-O-propionyl-L-phenylalanol Based on MTS Kuang et al. (2019b)
51 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl]-4-ethoxy-L-phenylalanol Based on MTS Kuang et al. (2019b)
52 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl]-4-ethoxycarbonylmethyl-L-tyrosinol Based on MTS Kuang et al. (2019b)
53 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl] -O-acetyl-(O-acetyl)-L-tyrosinol Based on MTS Kuang et al. (2019b)
54 N-[N-(3, 4-dimethoxy-benzoyl)-L-phenylalanyl]-4-propionyloxy-O-propionyl -L-phenylalanol Based on MTS Kuang et al. (2019b)
Ester derivatives
55 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(4-fluorobenzoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
56 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(4-chlorobenzoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
57 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(4-methylbenzoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
58 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(2-methoxybenzoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
59 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(3-trifluoromethoxybenzoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
60 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(3-bromobenzoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
61 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(2-methylbenzoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
62 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(2-furoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
63 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(2-thenoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
64 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(4-picolinoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
65 N-[N-benzoyl-O-(2-dimethylaminoethyl)-l-tyrosyl] -O-(3-picolinoyl)-L-phenylalanol Based on MTS Liang et al. (2013)
Derivatives with aromatic heterocycles
66 N-[N-(2-furoyl)-L-phenylalanyl]-L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
67 N-[N-nicotinoyl-L-phenylalanyl]-L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
68 N-[N-nicotinoyl-L-phenylalanyl]-L-phenylalanine methyl ester Based on MTS Qiu et al. (2015)
69 N-[N-nicotinoyl-L-phenylalanyl]-L-tyrosine Based on MTS Qiu et al. (2015)
70 N-[N-nicotinoyl-L-phenylalanyl]-O-acetyl-tyrosine methyl ester Based on MTS Qiu et al. (2015)
71 N-[N-(2-furoyl)-O-(2-dimethylaminoethyl)-l- tyrosyl]-L-phenylalanol Based on MTS Qiu et al. (2015)
72 N-[N-(2-furoyl)-O-(2-diethyllaminoethyl)-l-tyrosyl]-L-phenylalanol Based on MTS Qiu et al. (2015)
73 N-[N-nicotinoyl-O-(2-dimethylaminoethyl)-l-tyrosyl]-L-phenylalanol Based on MTS Qiu et al. (2015)
74 N-[N-nicotinoyl-O-(2-diethyllaminoethyl)-l-tyrosyl]-L-phenylalanol Based on MTS Qiu et al. (2015)
75 N-[N-(2-furoyl)-O-acetoxy-l-tyrosyl]-L-phenylalanol Based on MTS Qiu et al. (2015)
76 N-(N-nicotinoyl-O-acetoxy-l-tyrosyl)-L-phenylalanol Based on MTS Qiu et al. (2015)
Derivatives with nitrogen-containing heterocycles
77 N-[N-benzoyl)-L-(5-bromonicotinoy)-O-acetoxy -acetoxy]-L-phenylalanine methyl ester Based on MTS Qiu et al. (2015)
78 N-[N-benzoyl)-L-(5-bromonicotinoy)-O-acetoxy -acetoxy]-L-phenylalaninol Based on MTS Qiu et al. (2015)
79 N-[N-benzoyl)-L-(5-bromonicotinoy)-O-acetoxy -acetoxy]-L-phenylalanine Based on MTS Qiu et al. (2015)
80 N-[N-benzoyl)-L-(5-bromonicotinoy)-O-acetoxy -acetoxy]-L-methyl chloride Based on MTS Qiu et al. (2015)
81 N-[N-benzoyl)-L-(5-bromonicotinoy)-O-acetoxy -acetoxy]-L-methyl acetate Based on MTS Qiu et al. (2015)
82 N-[N-benzoyl)-L-(5-bromonicotinoy)-O-acetoxy -acetoxy]-L-methyl propanoate Based on MTS Qiu et al. (2015)
Derivatives containing trifluoromethyl
83 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-L-phenylalanol Based on MTS Cui et al., 2019
84 N-[N-(3-trifluoromethylbenzoyl)-l-tyrosyl]-L-phenylalanol Based on MTS Qiu et al. (2015)
85 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
86 N-[N-(3-trifluoromethylbenzoyl)-l-tyrosyl]-L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
87 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-L-phenylalanine methyl ester Based on MTS Qiu et al. (2015)
88 N-[N-(3-trifluoromethylbenzoyl)-l-tyrosyl]-L-phenylalanine methyl ester Based on MTS Qiu et al. (2015)
89 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O-acetyl-L-phenylalanol Based on MTS Qiu et al. (2015)
90 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O-propionyl-L-phenylalanol Based on MTS Qiu et al. (2015)
91 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O-acetyl-L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
92 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O-propionyl-L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
93 N-[N-(3-trifluoromethylbenzoyl)-O-(2-dimethylaminoethyl)-l-tyrosyl]-L-phenylalanol Based on MTS Qiu et al. (2015)
94 N-[N-(3-trifluoromethylbenzoyl)-O-(2-diethylaminoethyl)-l-tyrosyl]-L-phenylalanol Based on MTS Qiu et al. (2015)
95 N-[N-(3-trifluoromethylbenzoyl)-O-carboxymethyl-l-tyrosyl]-L-phenylalanol Based on MTS Qiu et al. (2015)
96 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O- ethoxycarbonylmethyl-L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
97 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O-methyl -L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
98 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O-ethyl -L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
99 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O-propyl -L-tyrosine methyl ester Based on MTS Qiu et al. (2015)
100 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-L-phenylalanine Based on MTS Qiu et al. (2015)
101 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O-methyl -L-tyrosine Based on MTS Qiu et al. (2015)
102 N-[N-(3-trifluoromethylbenzoyl)-L-phenylalanyl]-O-ethyl -L-tyrosine Based on MTS Qiu et al. (2015)
Derivatives containing sulfonamide structure
103 N-[N-(p-toluenesulfonyl)-L-phenylalanyl]-L-tyrosine methyl ester Based on MTS Xu et al. (2014)
104 N-[N-(p-toluenesulfonyl)-L-phenylalanyl]-L-phenylalanine methyl ester Based on MTS Xu et al. (2014)
105 N-(N-phenylsulfonyl-L-phenylalanyl)-L-phenylalanine methyl ester Based on MTS Xu et al. (2014)
106 N-(N-phenylsulfonyl-L-phenylalanyl)-L-phenylalanol Based on MTS Xu et al. (2014)
107 N-(N-benzenesulfonyl-L-phenylalanyl)-L-tyrosine methyl ester Based on MTS Xu et al. (2014)
108 N-[N-(p-toluenesulfonyl)-L-phenylalanyl]-L-phenylalanine Based on MTS Xu et al. (2014)
109 N-[N-octyl-(p-toluenesulfonyl)-L-phenylalanyl)]-O-(n-octyl) -tyrosine methyl ester Based on MTS Xu et al. (2014)
Resin glycosides
110 (11S)-dihydroxyhexadecanoic acid 11-O-(3-O-(2R,3R)-3 -hydroxy-2-methybutyryl)-α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranose-(1→2)-[(2-O-(2R,3R)-3-hydroxy-2-methybutyryl)-α-l-rhamnopyranosyl-(1→6)]-O-β-d -glucopyranose (dichondrin A) Whole plant Acetone–H2O (4:1, v/v) extracts Song et al. (2015)
111 (3S,11S)-dihydroxyhexadecanoic acid 11-O-(3-O-(2R,3R)-3 -hydroxy-2-methybutyryl)-α-l-rhamnopyranosyl-(1→4)-O-β-d-glucopyranose-(1→2)-[(2-O-(2R,3R)-3-hydroxy -2-methybutyryl)-α-l-rhamnopyranosyl-(1→6)]-O-β-d -glucopyranose (dichondrin B) Whole plant Acetone–H2O (4:1, v/v) extracts Song et al. (2015)
112 α-l-rhamnopyranosyl-(1→3)-[1-O-(11S)-11-hydroxyhexadecanoyl]-[4-O-(2R,3R)-3-hydroxy-2-methybutyryl]-α-l-rhamnopyranosyl-(1→2)-O-d -glucopyranose (dichondrin C) Whole plant Acetone–H2O (4:1, v/v) extract Song et al. (2015)
113 Resin glycoside cus-1 Whole plant Acetone–H2O (4:1, v/v) extract Song et al. (2015)
114 Resin glycoside cus-2 Whole plant Acetone–H2O (4:1, v/v) extract Song et al. (2015)
115 Resin glycoside cuse 3 Whole plant Acetone–H2O (4:1, v/v) extract Song et al. (2015)
Terpenoids
116 Tormentic acid Whole plant n-BuOH extract Liu et al. (2002); Liu et al. (2003)
117 Ursolic acid Whole plant n-BuOH extract Liu et al. (2002); Liu et al. (2003)
118 (2E, 6E)-8,10,11-trihydroxyl-7,11-dimethyl-3-hydroxymethyl-2,6-dodecadienoic acid Whole plant H2O/acetone extract (2:8, v/v) Wang and Xuan (2015)
119 (2E,6E)-8,10,11-trihydroxyl-7,11-dimethyl-3-hydroxymethyl-2,6-dodecadienoic acid 13-O-β-d-glucopyranoside Whole plant H2O/acetone extract Wang and Xuan (2015)
120 6,6-Dimethyl-2-methlenebicyclo [3.1.1]hept-3-O-(6-O-apiofuranosyl)-β-D-gluco-pyranoside Whole plant H2O/acetone extract Wang and Xuan (2015)
Coumarins
121 Skimmin Whole plant n-BuOH extract Liu et al. (2002)
122 Scopoletin Whole plant n-BuOH extract Liu et al. (2002)
123 Umbelliferone Whole plant n-BuOH extract Liu et al. (2002)
124 Uracils Whole plant n-BuOH extract Liu et al. (2003)
125 Uracil Steroids β-sitosterol Whole plant n-BuOH extract Liu et al. (2003)