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. 2015 Mar 18;2015:357357. doi: 10.1155/2015/357357

Table 1.

Chemical structure of NOAQs in different plants.

S. number IUPAC names Structure Species
R1 R2 R3 R4 R5 R6 R7 R8
1 Tectoquinone (2-methyl-AQ) H Me H H H H H H Prismatomeris  malayana [40], Rubia cordifolia [41],  Rubia oncotricha [32],and  Rubia tinctorum [42]
2 2-(Hydroxymethyl)-AQ H HOCH2 H H H H H H Rubia yunnanensis [43] and  Rubia tinctorum [44]
3 2-Methoxy-AQ H MeO H H H H H H Rubia tinctorum [42]
4 2-Hydroxy-AQ H OH H H H H H H Rubia tinctorum [42]
5 1-Methoxy-AQ OH H H H H H H H Rubia cordifolia [45, 46]
6 1-Hydroxy-2-methyl AQ OH Me H H H H H H Rubia tinctorum [42], Rubia cordifolia [46], Rubia akane [39],  Rubia lanceolata [39], Rubia oncotricha [39], Rubia sylvatica [39], and Rubia yunnanensis [43]
7 1-Hydroxy-2-(hydroxymethyl)-AQ OH HOCH2 H H H H H H Rubia cordifolia [32]
8 2-(Ethoxycarbonyl)-1-hydroxy-AQ OH EtOOC H H H H H H Rubia akane [39]
9 1-Methoxy-2-methyl-AQ MeO Me H H H H H H Rubia tinctorum
10 Alizarin (1,2-dihydroxy-AQ) OH OH H H H H H H Rubia lanceolata [39],  Rubia akane [39], and  Galium sinaicum [47]
11 Alizarin 2-methyl ether
(1-hydroxy-2-methoxy-AQ)		 OH MeO H H H H H H Rubia tinctorum [42], Rubia oncotricha [39],  Rubia cordifolia [32], and Galium sinaicum [47]
12 Alizarin 1-methyl ether
(2-hydroxy-1-methoxy-AQ)		 MeO OH H H H H H H Rubia tinctorum [42]
13 Alizarin 1,2-dimethyldiether
(1,2-dimethoxy-AQ)		 MeO MeO H H H H H H Rubia tinctorum [42]
14 Rubiadin (1,3-dihydroxy-2-
methyl-AQ)		 OH MeO OH H H H H H Prismatomeris  malayana [40], Rubia tinctorum [42], Rubia cordifolia [32], and  Rubia lanceolata [39], Rubia yunnanensis [43]
15 Lucidin (1,3-dihydroxy-2-
(hydroxymethyl)-AQ)		 OH HOCH2 OH H H H H H Rubia cordifolia [32], Rubia tinctorum [42], and  Rubia iberica [33]
16 Nordamnacanthal (1,3-dihydroxy-2-formyl-AQ) OH CHO OH H H H H H Rubia cordifolia [32] and Rubia iberica [33]
17 Munjistin (1,3-dihydroxy-2-carboxy-AQ) OH HOOC OH H H H H H Rubia tinctorum [42]
18 1,3-Dihydroxy-2-(methoxycarbonyl)-AQ OH MeOOC OH H H H H H Rubia tinctorum [32]
19 2-(Ethoxymethyl)-1,3-dihydroxy-AQ OH EtOCH2 OH H H H H H Rubia cordifolia [32]
20 1,3-Dihydroxy-2-(methoxymethyl)-AQ OH MeOCH2 OH H H H H H Rubia cordifolia [32]
21 Lucidin dimethyl ether MeOH HOCH2 MeO H H H H H Rubia lanceolata [39]
22 Munjistin dimethyl ether (2-carboxy-
1,3-dimethoxy-AQ)		 MeOH HOOC MeO H H H H H Rubia cordifolia [32]
23 2-Benzylxanthopurpurin OH PhCH2 OH H H H H H Rubia tinctorum [32]
24 Anthragallol 3-methyl ether OH OH MeO H H H H H Rubia tinctorum [42]
25 Anthragallol 2,3-dimethyl ether OH MeO MeO H H H H H Rubia tinctorum [32]
26 2-Carboxy-1-hydroxy-3-methoxy-AQ OH HOOC MeO H H H H H Rubia cordifolia [48]
27 3-Hydroxy-1-methoxy-2-(methoxymethyl)-AQ MeO MeOCH2 OH H H H H H Rubia cordifolia [49]
28 Anthragallol (1,2,3-trihydroxy-AQ) OH OH OH H H H H H Rubia tinctorum [32]
29 Purpurin (1,2,4-trihydroxy AQ) OH OH H OH H H H H Rubia tinctorum [32, 42], Rubia cordifolia [32],  Rubia munjista [33], Rubia sikkimensis [33], and Rubia tetragona [32]
30 Quinizarin (1,4-dihydroxy-AQ) OH H H OH H H H H Rubia cordifolia [32] and Rubia tinctorum [32]
31 1,4-Dihydroxy-2-(hydroxymethyl)-AQ OH HOCH2 H OH H H H H Rubia cordifolia [32] and Rubia yunnanensis [32]
32 2-(Ethoxycarbonyl)-1,4-dihydroxy-AQ OH EtOOC H OH H H H H Rubia cordifolia [32]
33 Christophine (2-(ethoxymethyl)-
1,4-dihydroxy-AQ)		 OH EtOCH2 H OH H H H H Rubia tinctorum [32]
34 1,4-Dihydroxy-2-methyl-AQ OH Me H OH H H H H Rubia cordifolia [32] and Rubia lanceolata [32]
35 Xanthopurpurin (1,3-dihydroxy-AQ) OH H OH H H H H H Rubia tinctorum [32],  Rubia cordifolia [32],  Rubia oncotricha [39], and Rubia yunnanensis [43],
36 Xanthopurpurin 3-methyl ether
(1-hydroxy-3-methoxy-AQ)		 OH H MeO H H H H H Rubia tinctorum [32]
37 Xanthopurpurin dimethyl ether (1,3-dimethoxy-AQ) MeO H MeO H H H H H Rubia tinctorum [32]
38 1-Hydroxy-3-(methoxycarbonyl)-AQ OH H MeOOC H H H H H Rubia tinctorum [32], Rubia lanceolata [39], and Rubia oncotricha [39]
39 Pseudopurpurin (3-(carboxy)-1,2,4-trihydroxy-AQ) OH OH HOOC OH H H H H Rubia tinctorum [32],  Rubia cordifolia [32], and Rubia peregrine [32]
40 1,4-Dihydroxy-2-methyl-5-methoxy-AQ OH Me H OH MeO H H H Rubia cordifolia [50]
41 1,4-Dihydroxy-2-methyl-8-methoxy-AQ OH Me H OH H H H MeO Rubia cordifolia [50]
42 1,4-Dihydroxy-6-methyl-AQ OH H H OH H Me H H Rubia cordifolia [51]
43 1,5-Dihydroxy-2-methyl-AQ OH Me H H OH H H H Rubia cordifolia [51]
44 Physcion (1,8-dihydroxy-3-methoxy-6-methyl-AQ) OH H Me H H Me H OH Rubia cordifolia [50] and  Fallopia japonica [52]
45 2-Methyl-1,3,6-trihydroxy-AQ OH Me OH H H OH H H Rubia cordifolia [32],  Rubia sylvatica [32],  Rubia yunnanensis [43], Rubia lanceolata [32], and  Rubia schumanniana [32]
46 1,4-Dihydroxy-7-methyl-AQ OH H H OH H H Me H Rubia cordifolia [50]
47 4,5-Dihydroxy-2-methoxy-7-methyl-AQ H Me H OH OH H MeO H Rubia cordifolia [50]
48 2,7-Dihydroxy-4-methoxy-3-methyl-AQ H OH Me MeO H H OH H Rubia yunnanensis [32]
49 2-Hydroxy-7-methyl-AQ H Me H H H H OH H Rubia tinctorum [32]
50 2-Carboxy-4-hydroxy-AQ H HOOC H OH H H H H Rubia cordifolia [32]
51 3-(β-D-Glucopyranosyloxy)-1,6-dihydroxy-2-methyl-AQ OH Me GluO H H OH H H Rubia cordifolia [32]
52 3-(6-O-Acetyl-β-D-glucopyranosyloxy)-1,6-dihydroxy-2-methyl-AQ OH Me 6-OAc-
GluO		 H H OH H H Rubia cordifolia [32]
53 3-[(2-O-6-Deoxy-α-L-mannopyranosyl-β-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQ OH Me 6-dManO-GluO H H OH H H Rubia cordifolia [32], Rubia schumanniana [32],  Rubia akane [39], and Rubia yunnanensis [43]
54 3-[(3-O-Acetyl-2-O-6-deoxy-β-D-mannopyranosyl-β-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQ OH Me 3-OAc-
6-dManO-GluO		 H H OH H H Rubia cordifolia [32]
55 3-[(6-O-Acetyl-2-O-6-deoxy-β-D-mannopyranosyl-β-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQ OH Me 6-OAc-
6-dManO-GluO		 H H OH H H Rubia cordifolia [32],  Rubia akane [39],  Rubia yunnanensis [43], and Rubia schumanniana [32]
56 3-[(3,6-O-Diacetyl-2-O-6-deoxy-β-D-mannopyranosyl-β-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQ OH Me 3,6-[OAc]2-6-dManO-
GluO		 H H OH H H Rubia cordifolia [32]
57 3-[(4,6-O-Diacetyl-2-O-6-deoxy-β-D-mannopyranosyl-β-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQ OH Me 4,6-[OAc]2-6-dManO-
GluO		 H H OH H H Rubia cordifolia [32]
58 3-[(4-O-Acetyl-2-O-6-deoxy-β-D-mannopyranosyl-β-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQ OH Me 4-OAc-6-
dManO-
GluO		 H H OH H H Rubia cordifolia [32]
59 3-[(6-O-Acetyl-2-O-β-D-xylopyranosyl-β-D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQ OH Me 6-OAc-
XylO-
GluO		 H H OH H H Rubia cordifolia [32]
60 Ruberythric acid (1-hydroxy-2-[(6-O-β-D-xylopyranosyl-β-D-glucopyranosyl)oxy]-AQ) OH XylO-
GluO		 H H H OH H H Rubia cordifolia [32],  Rubia tinctorum [32], and  Rubia iberica [45]
61 Lucidin primeveroside (1-hydroxy-2-(hydroxymethyl)-3-[(6-O-β-D-xylopyranosyl-β-D-glucopyranosyl)oxy]-AQ) OH HOCH2 XylO-
GluO		 H H OH H H Rubia cordifolia [32],  Rubia tinctorum [32],  Rubia iberica [45], and Rubia yunnanensis  [43]
62 1-Acetyl-3-[(4-O-6-deoxy-β-D-mannopyranosyl-β-D-glucopyranosyl)oxy]-6-hydroxy-2-methyl-AQ MeCO Me 6-dManO-GluO H H OH H H Rubia cordifolia [32]
63 2-[(6-O-β-D-Glucopyranosyl-β-D-glucopyranosyl)oxy]methyl-11-hydroxy-AQ H H H H H H H GluO-GluO Rubia cordifolia [32] and  Rubia schumanniana [32]
64 3-[(2-O-6-Deoxy-β-D-mannopyranosyl-β-D-glucopyranosyl)oxy]-1-hydroxy-2-(methoxycarbonyl)-AQ OH MeOOC 6-dManO-GluO H H H H H Rubia cordifolia [32]
65 3-(β-D-Glucopyranosyloxy)-2-(hydroxymethyl)-AQ H HOCH2 GluO H H H H H Rubia tinctorum [32]
66 3-(β-D-Glucopyranosyloxy)-8-hydroxy-2-(hydroxymethyl)-AQ H HOCH2 GluO H H H H OH Rubia tinctorum [32]
67 2-(β-D-Glucopyranosyloxy)-1,3-dihydroxy-AQ OH GluO OH H H H H H Rubia tinctorum [32]
68 3-(β-D-Glucopyranosyloxy)-1-hydroxy-2-(hydroxymethyl)-AQ OH HOCH2 GluO H H H H H Rubia cordifolia [32]
69 Emodin (1,3,8-trihydroxy-6-methyl-AQ) OH H Me H H OH H OH F. japonica [28, 52]
70 Cascarin (emodin 6-O-rhamnoside) OH H Me H H RhaO H OH Rhamnus sp. [28]
71 Rhein (1,8-dihydroxy-3-carboxyl-AQ) OH H HOOC H H H H OH Cassiasp. [28]
72 Catenarin (1,4,6,8-tetrahydroxy-3-methyl-AQ) OH H Me OH H OH H OH Helminthosporium catenarium [28]
73 Aloe-emodin (1,8-dihydroxy 3-hydroxy methyl anthraquinone) OH H CH2OH H H H H OH Aloe vera [53], Cassiasp. [53], Rhamnus frangula,Cascara Sagrada  [53],  Rhamnus purshiana [53], and Rheum rhaponticum [53]
74 Chrysophanol (1,8-dihydroxy-3-methyl-AQ) OH H Me H H MeO H OH Cassia sp. [54]
75 Rhein-8-glucoside OH H HOOC H H H H GluO Cassia sp. [54]
76 Alatinone (1,5,7-trihydroxy-3-methyl-AQ) OH H Me H OH H OH H Cassia sp. [54]
77 Diacerein (diacerhein) OAc H HOOC H H H H OAc Cassia sp. [54]
78 Fistulic acid OH Me HOOC OH H MeO MeO OH Cassia sp. [54]
79 5-Hydroxy emodin OH H Me H OH OH H OH Cassia sp. [54]
80 1,3-hihydroxy-6,8-dimethoxy-AQ OH H OH H H MeO H MeO Cassia sp. [54]
81 1,3,5,8-Tetrahydroxy-2-methyl-AQ OH Me OH H OH MeO H OH Cassia sp. [54]
82 1,2-Dihydro-1,3,8-trihydroxy-2-methyl-AQ OH Me OH H H H H OH Cassia sp. [54]
83 1,8-Dihydroxy-6-methoxy-2-methyl-AQ OH Me H H H MeO H OH Cassia sp. [54]
84 1,8-Dihydroxy-6-methoxy-3-methyl-AQ OH H Me H H MeO H OH Cassia sp. [54]
85 Citreorosein (1,3,8-trihydroxy-6-hydroxymethyl-AQ) OH H CH2OH H H OH H OH Cassia sp. [54]
86 Emodic acid (1,6,8-trihydroxy-AQ-3-carboxylic acid) OH H HOOC H H OH H OH Cassia sp. [54]
87 Obtusifolin (2,8-dihydroxy-1-methoxy-3-methyl-AQ) MeO OH Me H H H H OH Cassia sp. [54]
88 2-Formyl-1,3,8-trihydroxy-AQ OH CHO OH H H H H OH Cassia sp. [54]
89 3-Formyl-1-hydroxy-8-methoxy-AQ OH H CHO H H H H MeO Cassia sp. [54]

Glu: glucosyl; dMan: deoxymannosyl; Rha: rhamnosyl; Xyl: xylosyl; Me: methyl; Et: ethyl; Ph: phenyl; Ac: acetyl.