Evidence-Based Complementary and Alternative Medicine / 2015 / Article / Tab 1

Review Article

Naturally Occurring Anthraquinones: Chemistry and Therapeutic Potential in Autoimmune Diabetes

Table 1

Chemical structure of NOAQs in different plants.

S. numberIUPAC namesStructureSpecies
R1R2 R3R4R5R6R7R8

1Tectoquinone (2-methyl-AQ)H Me HHHHHHPrismatomeris  malayana [40], Rubia cordifolia [41],  Rubia oncotricha [32],and  Rubia tinctorum [42]
22-(Hydroxymethyl)-AQH HOCH2HHHHHHRubia yunnanensis [43] and  Rubia tinctorum [44]
32-Methoxy-AQH MeO HHHHHHRubia tinctorum [42]
42-Hydroxy-AQH OH HHHHHHRubia tinctorum [42]
51-Methoxy-AQOH H HHHHHHRubia cordifolia [45, 46]
61-Hydroxy-2-methyl AQOH Me HHHHHHRubia tinctorum [42], Rubia cordifolia [46], Rubia akane [39],  Rubia lanceolata [39], Rubia oncotricha [39], Rubia sylvatica [39], and Rubia yunnanensis [43]
71-Hydroxy-2-(hydroxymethyl)-AQOH HOCH2HHHHHHRubia cordifolia [32]
82-(Ethoxycarbonyl)-1-hydroxy-AQOH EtOOC HHHHHHRubia akane [39]
91-Methoxy-2-methyl-AQMeO Me HHHHHHRubia tinctorum
10Alizarin (1,2-dihydroxy-AQ)OH OH HHHHHHRubia lanceolata [39],  Rubia akane [39], and  Galium sinaicum [47]
11Alizarin 2-methyl ether
(1-hydroxy-2-methoxy-AQ)
OHMeOHHHHHHRubia tinctorum [42], Rubia oncotricha [39],  Rubia cordifolia [32], and Galium sinaicum [47]
12Alizarin 1-methyl ether
(2-hydroxy-1-methoxy-AQ)
MeOOHHHHHHHRubia tinctorum [42]
13Alizarin 1,2-dimethyldiether
(1,2-dimethoxy-AQ)
MeOMeOHHHHHHRubia tinctorum [42]
14Rubiadin (1,3-dihydroxy-2-
methyl-AQ)
OHMeOOHHHHHHPrismatomeris  malayana [40], Rubia tinctorum [42], Rubia cordifolia [32], and  Rubia lanceolata [39], Rubia yunnanensis [43]
15Lucidin (1,3-dihydroxy-2-
(hydroxymethyl)-AQ)
OHHOCH2OHHHHHHRubia cordifolia [32], Rubia tinctorum [42], and  Rubia iberica [33]
16Nordamnacanthal (1,3-dihydroxy-2-formyl-AQ)OHCHOOHHHHHHRubia cordifolia [32] and Rubia iberica [33]
17Munjistin (1,3-dihydroxy-2-carboxy-AQ)OHHOOCOHHHHHHRubia tinctorum [42]
181,3-Dihydroxy-2-(methoxycarbonyl)-AQOHMeOOCOHHHHHHRubia tinctorum [32]
192-(Ethoxymethyl)-1,3-dihydroxy-AQOHEtOCH2OHHHHHHRubia cordifolia [32]
201,3-Dihydroxy-2-(methoxymethyl)-AQOHMeOCH2OHHHHHHRubia cordifolia [32]
21Lucidin dimethyl etherMeOHHOCH2MeOHHHHHRubia lanceolata [39]
22Munjistin dimethyl ether (2-carboxy-
1,3-dimethoxy-AQ)
MeOHHOOCMeOHHHHHRubia cordifolia [32]
232-BenzylxanthopurpurinOHPhCH2OHHHHHHRubia tinctorum [32]
24Anthragallol 3-methyl etherOHOHMeOHHHHHRubia tinctorum [42]
25Anthragallol 2,3-dimethyl etherOHMeOMeOHHHHHRubia tinctorum [32]
262-Carboxy-1-hydroxy-3-methoxy-AQOHHOOCMeOHHHHHRubia cordifolia [48]
273-Hydroxy-1-methoxy-2-(methoxymethyl)-AQMeOMeOCH2OHHHHHHRubia cordifolia [49]
28Anthragallol (1,2,3-trihydroxy-AQ)OHOHOHHHHHHRubia tinctorum [32]
29Purpurin (1,2,4-trihydroxy AQ)OHOHHOHHHHHRubia tinctorum [32, 42], Rubia cordifolia [32],  Rubia munjista [33], Rubia sikkimensis [33], and Rubia tetragona [32]
30Quinizarin (1,4-dihydroxy-AQ)OHHHOHHHHHRubia cordifolia [32] and Rubia tinctorum [32]
311,4-Dihydroxy-2-(hydroxymethyl)-AQOHHOCH2HOHHHHHRubia cordifolia [32] and Rubia yunnanensis [32]
322-(Ethoxycarbonyl)-1,4-dihydroxy-AQOHEtOOCHOHHHHHRubia cordifolia [32]
33Christophine (2-(ethoxymethyl)-
1,4-dihydroxy-AQ)
OHEtOCH2HOHHHHHRubia tinctorum [32]
341,4-Dihydroxy-2-methyl-AQOHMeHOHHHHHRubia cordifolia [32] and Rubia lanceolata [32]
35Xanthopurpurin (1,3-dihydroxy-AQ)OHHOHHHHHHRubia tinctorum [32],  Rubia cordifolia [32],  Rubia oncotricha [39], and Rubia yunnanensis [43],
36Xanthopurpurin 3-methyl ether
(1-hydroxy-3-methoxy-AQ)
OHHMeOHHHHHRubia tinctorum [32]
37Xanthopurpurin dimethyl ether (1,3-dimethoxy-AQ)MeOHMeOHHHHHRubia tinctorum [32]
381-Hydroxy-3-(methoxycarbonyl)-AQOHHMeOOCHHHHHRubia tinctorum [32], Rubia lanceolata [39], and Rubia oncotricha [39]
39Pseudopurpurin (3-(carboxy)-1,2,4-trihydroxy-AQ)OHOHHOOCOHHHHHRubia tinctorum [32],  Rubia cordifolia [32], and Rubia peregrine [32]
401,4-Dihydroxy-2-methyl-5-methoxy-AQOHMeHOHMeOHHHRubia cordifolia [50]
411,4-Dihydroxy-2-methyl-8-methoxy-AQOHMeHOHHHHMeORubia cordifolia [50]
421,4-Dihydroxy-6-methyl-AQOHHHOHHMeHHRubia cordifolia [51]
431,5-Dihydroxy-2-methyl-AQOHMeHHOHHHHRubia cordifolia [51]
44Physcion (1,8-dihydroxy-3-methoxy-6-methyl-AQ)OHHMeHHMeHOHRubia cordifolia [50] and  Fallopia japonica [52]
452-Methyl-1,3,6-trihydroxy-AQOHMeOHHHOHHHRubia cordifolia [32],  Rubia sylvatica [32],  Rubia yunnanensis [43], Rubia lanceolata [32], and  Rubia schumanniana [32]
461,4-Dihydroxy-7-methyl-AQOHHHOHHHMeHRubia cordifolia [50]
474,5-Dihydroxy-2-methoxy-7-methyl-AQHMeHOHOHHMeOHRubia cordifolia [50]
482,7-Dihydroxy-4-methoxy-3-methyl-AQHOHMeMeOHHOHHRubia yunnanensis [32]
492-Hydroxy-7-methyl-AQHMeHHHHOHHRubia tinctorum [32]
502-Carboxy-4-hydroxy-AQHHOOCHOHHHHHRubia cordifolia [32]
51 3-(-D-Glucopyranosyloxy)-1,6-dihydroxy-2-methyl-AQOHMeGluOHHOHHHRubia cordifolia [32]
523-(6-O-Acetyl--D-glucopyranosyloxy)-1,6-dihydroxy-2-methyl-AQOHMe6-OAc-
GluO
HHOHHHRubia cordifolia [32]
533-[(2-O-6-Deoxy--L-mannopyranosyl--D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQOHMe6-dManO-GluOHHOHHHRubia cordifolia [32], Rubia schumanniana [32],  Rubia akane [39],and Rubia yunnanensis [43]
543-[(3-O-Acetyl-2-O-6-deoxy--D-mannopyranosyl--D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQOHMe3-OAc-
6-dManO-GluO
HHOHHHRubia cordifolia [32]
553-[(6-O-Acetyl-2-O-6-deoxy--D-mannopyranosyl--D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQOHMe6-OAc-
6-dManO-GluO
HHOHHHRubia cordifolia [32],  Rubia akane [39],  Rubia yunnanensis [43], and Rubia schumanniana [32]
563-[(3,6-O-Diacetyl-2-O-6-deoxy--D-mannopyranosyl--D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQOHMe3,6-[OAc]2-6-dManO-
GluO
HHOHHHRubia cordifolia [32]
573-[(4,6-O-Diacetyl-2-O-6-deoxy--D-mannopyranosyl--D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQOHMe4,6-[OAc]2-6-dManO-
GluO
HHOHHHRubia cordifolia [32]
583-[(4-O-Acetyl-2-O-6-deoxy--D-mannopyranosyl--D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQOHMe4-OAc-6-
dManO-
GluO
HHOHHHRubia cordifolia [32]
593-[(6-O-Acetyl-2-O--D-xylopyranosyl--D-glucopyranosyl)oxy]-1,6-dihydroxy-2-methyl-AQOHMe6-OAc-
XylO-
GluO
HHOHHHRubia cordifolia [32]
60Ruberythric acid (1-hydroxy-2-[(6-O--D-xylopyranosyl--D-glucopyranosyl)oxy]-AQ)OHXylO-
GluO
HHHOHHHRubia cordifolia [32],  Rubia tinctorum [32], and  Rubia iberica [45]
61Lucidin primeveroside (1-hydroxy-2-(hydroxymethyl)-3-[(6-O--D-xylopyranosyl--D-glucopyranosyl)oxy]-AQ)OHHOCH2XylO-
GluO
HHOHHHRubia cordifolia [32],  Rubia tinctorum [32],  Rubia iberica [45], and Rubia yunnanensis  [43]
621-Acetyl-3-[(4-O-6-deoxy--D-mannopyranosyl--D-glucopyranosyl)oxy]-6-hydroxy-2-methyl-AQMeCOMe6-dManO-GluOHHOHHHRubia cordifolia [32]
632-[(6-O--D-Glucopyranosyl--D-glucopyranosyl)oxy]methyl-11-hydroxy-AQHHHHHHHGluO-GluORubia cordifolia [32] and  Rubia schumanniana [32]
643-[(2-O-6-Deoxy--D-mannopyranosyl--D-glucopyranosyl)oxy]-1-hydroxy-2-(methoxycarbonyl)-AQOHMeOOC6-dManO-GluOHHHHHRubia cordifolia [32]
653-(-D-Glucopyranosyloxy)-2-(hydroxymethyl)-AQHHOCH2GluOHHHHHRubia tinctorum [32]
663-(-D-Glucopyranosyloxy)-8-hydroxy-2-(hydroxymethyl)-AQHHOCH2GluOHHHHOHRubia tinctorum [32]
672-(-D-Glucopyranosyloxy)-1,3-dihydroxy-AQOHGluOOHHHHHHRubia tinctorum [32]
683-(-D-Glucopyranosyloxy)-1-hydroxy-2-(hydroxymethyl)-AQOHHOCH2GluOHHHHHRubia cordifolia [32]
69Emodin (1,3,8-trihydroxy-6-methyl-AQ)OHHMeHHOHHOHF. japonica [28, 52]
70Cascarin (emodin 6-O-rhamnoside)OHHMeHHRhaOHOHRhamnus sp. [28]
71Rhein (1,8-dihydroxy-3-carboxyl-AQ)OHHHOOCHHHHOHCassiasp. [28]
72Catenarin (1,4,6,8-tetrahydroxy-3-methyl-AQ)OHHMeOHHOHHOHHelminthosporium catenarium [28]
73Aloe-emodin (1,8-dihydroxy 3-hydroxy methyl anthraquinone)OHHCH2OHHHHHOHAloe vera [53], Cassiasp. [53], Rhamnus frangula,Cascara Sagrada  [53],  Rhamnus purshiana [53], and Rheum rhaponticum [53]
74Chrysophanol (1,8-dihydroxy-3-methyl-AQ)OHHMeHHMeOHOHCassia sp. [54]
75Rhein-8-glucosideOHHHOOCHHHHGluOCassia sp. [54]
76Alatinone (1,5,7-trihydroxy-3-methyl-AQ)OHHMeHOHHOHHCassia sp. [54]
77Diacerein (diacerhein)OAcHHOOCHHHHOAcCassia sp. [54]
78Fistulic acidOHMeHOOCOHHMeOMeOOHCassia sp. [54]
795-Hydroxy emodinOHHMeHOHOHHOHCassia sp. [54]
801,3-hihydroxy-6,8-dimethoxy-AQOHHOHHHMeOHMeOCassia sp. [54]
811,3,5,8-Tetrahydroxy-2-methyl-AQOHMeOHHOHMeOHOHCassia sp. [54]
821,2-Dihydro-1,3,8-trihydroxy-2-methyl-AQOHMeOHHHHHOHCassia sp. [54]
831,8-Dihydroxy-6-methoxy-2-methyl-AQOHMeHHHMeOHOHCassia sp. [54]
841,8-Dihydroxy-6-methoxy-3-methyl-AQOHHMeHHMeOHOHCassia sp. [54]
85Citreorosein (1,3,8-trihydroxy-6-hydroxymethyl-AQ)OHHCH2OHHHOHHOHCassia sp. [54]
86Emodic acid (1,6,8-trihydroxy-AQ-3-carboxylic acid)OHHHOOCHHOHHOHCassia sp. [54]
87Obtusifolin (2,8-dihydroxy-1-methoxy-3-methyl-AQ)MeOOHMeHHHHOHCassia sp. [54]
882-Formyl-1,3,8-trihydroxy-AQOHCHOOHHHHHOHCassia sp. [54]
893-Formyl-1-hydroxy-8-methoxy-AQOHHCHOHHHHMeOCassia sp. [54]

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

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