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. 2020 Mar 13;11:229. doi: 10.3389/fgene.2020.00229

TABLE 1.

Bioactive and nutritional compounds identified in pigmented rice.

Compound PubChem CID Compound class Figure 2a References
Cyanine 3-glucoside 197081 Anthocyanin Pereira-Caro et al., 2013;
Peonidin-3-glucoside 443654 Anthocyanin Zhang et al., 2015;
Cyanidin 128861 Anthocyanin Tantipaiboonwong et al., 2017;
Cyanidin-3,5-diglucoside 44256718 Anthocyanin Shao et al., 2018
Cyanidin-3-O-(6”-O-p-coumaroyl)glucoside Anthocyanin
Pelargonidin-3-O-glucoside 443648 Anthocyanin
Peonidin-3-O-(6”-O-p-coumaroyl)glucoside Anthocyanin
Cyanidin-3-O-arabidoside Anthocyanin

Flavone 10680 Flavone
Luteolin-6/8-C-pentoside-6/8-C-hexoside (2 isomers) Flavone Pereira-Caro et al., 2013;
Apigenin-6/8-C-pentoside-8/6-C-hexoside (three isomers) Flavone glycoside Kim et al., 2014;
Apigenin-6-C-glucosyl-8-C-arabinoside Flavone Ghasemzadeh et al., 2018;
Tricin-O-rhamnoside-O-hexoside Flavone Poulev et al., 2019
Tricin 5281702 Flavone
Chrysoeriol 5280666 Flavone
Luteolin 5280445 Flavone
Apigenin 5280443 Flavone

Caffeic acid 689043 Hydrocinnamic acid Gunaratne et al., 2013;
p-Coumaric acid 637542 Hydrocinnamic acid Zhang et al., 2015;
Ferulic acid 445858 Hydrocinnamic acid Irakli et al., 2016;
Sinapic acid 637775 Hydrocinnamic acid Tantipaiboonwong et al., 2017;
Isoferulic acid 736186 Hydrocinnamic acid Chiou et al., 2018;
Chlorogenic acid 1794427 Hydrocinnamic acid Ghasemzadeh et al., 2018; Shao et al., 2018

2,5-Dihydroxybenzoic acid 3469 Hydroxybenzoic acid Kim et al., 2014;
p-Hydroxybenzoic acid 135 Hydroxybenzoic acid Valarmathi et al., 2014;
Gallic acid 370 Hydroxybenzoic acid Suwannakul et al., 2015;
Vanillic acid 8468 Hydroxybenzoic acid Huang and Lai, 2016;
Syringic acid 10742 Hydroxybenzoic acid Irakli et al., 2016;
Protocatechuic acid 72 Hydroxybenzoic acid Tantipaiboonwong et al., 2017;
Salicylic acid 338 Hydroxybenzoic acid Ghasemzadeh et al., 2018;
β-Resorcylic acid 1491 Hydroxybenzoic acid Shao et al., 2018

Protocatechualdehyde 8768 Phenolic aldehyde Huang and Lai, 2016
8-5′-Coupled diferulic acid Phenolic dehydrodimer Zhang et al., 2015
5-5′-Coupled diferulic acid Phenolic dehydrodimer
8-8′-Coupled diferulic acid benzofuran form Phenolic dehydrodimer

Proanthocyanidin dimer Proanthocyanin Gunaratne et al., 2013
Proanthocyanidin trimer Proanthocyanin

Catechin 73160 Flavanonol Tantipaiboonwong et al., 2017;
Epicatechin 72276 Flavanonol Ghasemzadeh et al., 2018

Quercetin 5280343 Flavonol Pereira-Caro et al., 2013;
Quercetin-3-O-glucoside Flavonol Valarmathi et al., 2014;
Quercetin-3-O-rutinoside Flavonol Chiou et al., 2018;
Isorhamnetin-3-O-glucoside 5318645 Flavonol Ghasemzadeh et al., 2018;
Myricetin 5281672 Flavonol Poulev et al., 2019
Rutin 5280805 Flavonol
Kaempferol 5280863 Flavonol
Kaempferide 5281666 Flavonol
Naringenin 932 Flavanone Chiou et al., 2018
Cycloartenol ferulate 134695320 γ-Oryzanol Chakuton et al., 2012;
24-Methylenecycloartenol ferulate 9920169 γ-Oryzanol Gunaratne et al., 2013;
Campesteryl ferulate 15056832 γ-Oryzanol Pereira-Caro et al., 2013
β-Sitosteryl ferulate 9938436 γ-Oryzanol
Δ7-Campesteryl ferulate γ-Oryzanol
Campestanyl ferulate 13786591 γ-Oryzanol
Sitostanyl ferulate 11227138 γ-Oryzanol

Phytic acid 890 Phytic acid Chakuton et al., 2012; Insuan et al., 2017

Tocotrienols (α-, β-, γ-, δ-forms) 9929901 Vitamin E Zubair et al., 2012;
Tocopherols (α-, β-, γ-, δ-forms) 14986 Vitamin E Gunaratne et al., 2013; Irakli et al., 2016

Riboflavin 493570 Vitamin B2 Valarmathi et al., 2014

Nicotinic acid 938 Vitamin B3 Kim et al., 2014

Lutein 5281243 Carotenoid Pereira-Caro et al., 2013;
Zeaxanthin 5280899 Carotenoid Valarmathi et al., 2014;
β-Carotene 5280489 Carotenoid Irakli et al., 2016;
Lycopene 446925 Carotenoid Melini and Acquistucci, 2017
β-Carotene-4,4′-dione Carotenoid
all-trans-3,3’,4,4’-Tetrahydrospirilloxanthin 5366411 Carotenoid
10′-Apo-β-carotenoic acid Carotenoid
24-Methylene-ergosta-5-en-3β-ol Phytosterol Suttiarporn et al., 2015
24-Methylene-ergosta-7-en-3β-ol Phytosterol
Fucosterol 5281326 Phytosterol
Gramisterol 5283640 Phytosterol
Campesterol 173183 Phytosterol
Stigmasterol 5280794 Phytosterol
β-Sitosterol 222284 Phytosterol

Cycloeucalenol 101690 Triterpenoid Suttiarporn et al., 2015
Lupenone 92158 Triterpenoid
Lupeol 259846 Triterpenoid
24-Methylenecycloartanol 94204 Triterpenoid
LysoPC 14:0 460604 Phospholipid Kim et al., 2014
LysoPC 18:2 11005824 Phospholipid
LysoPC 16:0 460602 Phospholipid
LysoPC 18:1 53480465 Phospholipid
Histidine 6274 Essential amino acid Kim et al., 2014;
Threonine 6288 Essential amino acid Thomas et al., 2015
Valine 6287 Essential amino acid
Methionine 6137 Essential amino acid
Lysine 5962 Essential amino acid
Isoleucine 6306 Essential amino acid
Leucine 6106 Essential amino acid
Phenylalanine 6140 Essential amino acid

L-Aspartate 5460294 Non-essential amino acid Kim et al., 2014;
Serine 5951 Non-essential amino acid Valarmathi et al., 2014;
Glutamine 5961 Non-essential amino acid Thomas et al., 2015
Glycine 750 Non-essential amino acid
Arginine 6322 Non-essential amino acid
Alanine 602 Non-essential amino acid
Proline 614 Non-essential amino acid
Tyrosine 6057 Non-essential amino acid
α-Aminobutyric acid (AABA) 6657 Non-essential amino acid
Potassium (K) 5462222 Mineral Valarmathi et al., 2014;
Calcium (Ca) 5460341 Mineral Thomas et al., 2015;
Magnesium (Mg) 5462224 Mineral Raghuvanshi et al., 2017;
Sodium (Na) 5360545 Mineral Shozib et al., 2017;
Chromium (Cr) 23976 Mineral Hurtada et al., 2018
Iron (Fe) 23925 Mineral
Manganese (Mn) 23930 Mineral
Zinc (Zn) 23994 Mineral
Copper (Cu) 23978 Mineral
Phosphorus (P) 5462309 Mineral

Caproic acid 8892 Fatty acid Valarmathi et al., 2014;
Caprylic acid 379 Fatty acid Thomas et al., 2015
Capric acid 2969 Fatty acid
Lauric acid 3893 Fatty acid
Tridecanoic acid 12530 Fatty acid
Myristic acid 11005 Fatty acid
Pentadecanoic acid 13849 Fatty acid
Palmitic acid 985 Fatty acid
Stearic acid 5281 Fatty acid
Arachidic acid 10467 Fatty acid
9-Octadecanoic acid 965 Fatty acid
Undecanoic acid 8180 Fatty acid
Oleanolic acid 10494

Myristoleic acid 5281119 Mono-unsaturated fatty acid Valarmathi et al., 2014;
cis-10-Pentadecenoic acid 5312411 Mono-unsaturated fatty acid Thomas et al., 2015
Oleic acid 445639 Mono-unsaturated fatty acid
cis-Vaccenic acid 5282761 Mono-unsaturated fatty acid
Erucic acid 5281116 Mono-unsaturated fatty acid

Hexadecadienoic acid Polyunsaturated fatty acid Valarmathi et al., 2014;
Hexadecatrienoic acid 6506600 Polyunsaturated fatty acid Thomas et al., 2015
Linoleic acid 5280450 Polyunsaturated fatty acid
Octadecatetraenoic acid 11778225 Polyunsaturated fatty acid
cis-11,14,17-Eicosatrienoic acid 5312529 Polyunsaturated fatty acid
cis-5,8,11,14-Eicosatetraenoate acid Polyunsaturated fatty acid
Eicosatetraenoic acid 21863049 Polyunsaturated fatty acid
Pinellic acid 9858729 Oxylipin Kim et al., 2014
Succinic acid 1110 Carboxylic acid
Maleic acid 444266 Carboxylic acid
Malonic acid 867 Carboxylic acid
Citric acid 311 Carboxylic acid
Cinnamic acid 444539 Carboxylic acid
D-Xylose 135191 Sugar Kim et al., 2014;
D-Fructose 2723872 Sugar Valarmathi et al., 2014
D-Glucose 5793 Sugar
Maltose 439341 Sugar
myo-Inositol 892 Sugar

aCompounds present in Figure 2.