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Table 4 Polyhydroxyphenols (polyphenols) as electron shuttles in plants

From: Polyphenolic compounds as electron shuttles for sustainable energy utilization

Model polyphenolsContents in plant speciesRefs.
A. Derivatives of phenylpropanoids
 Caffeic acid1.05–62.84 mg in 100 g dry samples of Echinacea purpurea[53]
773 mg phenolics (as caffeic acid) in 5 g sample of Ilex paraguariensis[54]
0.62 mg/g of Monarda fistulosa L.[55]
7.99–19.75 mg in 100 g dry samples of Salvia apiana[53]
1.98% in Salvia officinalis L.[56]
1.4% in Thymus vulgaris L.[56]
 Caffeoylquinic acid~ 11 mg/g dry sample of Akebia quinata[57]
0.740% in dry sample of Cynara scolymus[58]
773 mg phenolics (as caffeoylquinic acid)/5 g sample of Ilex paraguariensis[54]
723 mg/100 g fresh samples of Vallaris glabra[59]
 Monocaffeoyl tartaric acid223 μg caffeic acid (as monocaffeoyl tartaric acid)/g in fresh leaves of Cichorium intybus L.[60]
 Calceolarioside~1 mg/g dry sample of Akebia quinata[57]
 Chlorogenic acid566.5 μg of caffeic acid (as chlorogenic acid)/g fresh leaves of Cichorium intybus[60]
4.713% in dry sample of Cynara scolymus[58]
2.60% in dry samples of Eucommia ulmoides[61]
6.14% in dried plant samples of Lonicera japonica[62]
1.22% in Salvia officinalis L.[56]
0.22% in dry leaves weight of Taraxacum officinale Wigg[63]
1.02% in dry leaves weight of Vaccinum arctostaphylos L.[63]
 Cichoric acid (chicoric acid)1535 μg/g fresh leaves of Cichorium intybus[60]
0.41% in dry aerial parts weight of Chicorium intybus[63]
42.37–258.70 mg caffeic acid (as chicoric acid)/100 g dry samples of Echinacea purpurea[53]
88.5 mg in 100 g fresh weight of Ocimum basilicum L.[64]
0.77% in dry leaves weight of Taraxacum officinale Wigg[63]
 Cynarin1.689% in dry sample of Cynara scolymus[58]
 Danshensu24.8% in crude aqueous extract of Salvia miltiorrhiza[65]
 Echinacoside42.71% in 210 g crude phenyl ethanol glycosides extract from dried and sliced rhizomes of Cistanche tubulosa (6.0 kg)[66]
 Forsythiaside16.7 mg from 500 g Forsythia suspense[67]
 Gravolenic acidRuta graveolen[68, 69]
 Nordihydroguaiaretic acid (NDGA)0.0898% in the dried weight of Larrea divaricata[70]
 Orobanchoside3% from Orobanche rapum-genistae[71]
 Pedicularioside70 mg from 13.5 kg Buddleia lindleyan[72]
 Rosmarinic acid9.30 mg/g S. africana-lutea[55]
3.68% from dry weight basis in 40 Mentha × piperita Clones[73]
622.28 mg caffeic acid (as rosmarinic acid)/100 g dry samples of Melissa officinalis[53]
15.15% in Origanum majorana L.[56]
8% of rosemary extract from 50 g dried leaves of Rosmarinus officinalis L.[74]
4.8 g from dried roots of Salvia miltiorrhiza (32 kg)[75]
17.85% in Salvia officinalis L[56]
 Salvianolic acid A0.7 g from the dried roots of Salvia miltiorrhiza (32 kg)[75]
11.96 g residue from the dried roots of Salvia miltiorrhiza (30 kg)[76]
 Salvianolic acid B (lithospermic acid B)2.06 g from the dried roots of Salvia miltiorrhiza (32 kg)[75]
33.93 mg/g in Salvia miltiorrhiza (Danshen)[77]
 Salvianolic acid C0.4 g from dried roots of S Salvia miltiorrhiza (Danshen) (32 kg)[75]
 Tubuloside (A, B, C, D)Tubuloside A (II) 200 mg; Tubuloside B (VI) 100 mg; Tubuloside C (VII) 60 mg; Tubuloside D (VIII) 65 mg from fresh whole plants of Cistanche tubulosa (Schrenk) (22 kg)[78]
 Verbascoside (acteoside)0.009% (pure compound) from dried leaves (1 kg) of Buddleja globosa[79]
16 g isolated from dried and ground leaves of Buddleja cordata (2.3 kg)[80]
361.2 mg from the fresh whole plants (246 g) of Byblis liniflora Salisb.[81]
14.27% in 210 g crude phenyl ethanol glycosides extract from dried and sliced rhizomes of Cistanche tubulosa (6.0 kg)[66]
0.50 g from 35 g Lantana camara[82]
0.43 g from 35 g dry Lippia. javanica[82]
1.7% from dry weight of Olea europaea[83]
6% from the dried plant (Orobanche rapum-genistae)[71]
11.3 mg/mL (n-butanol extracts from dried and powdered leaves of Phlomis species (100 g))[84]
3–8% in Plantago lanceolata[85]
0.612 mg/g dry extract of Verbascum mallophorum[86]
0.18–3.03% of the dry weight Verbascum leaves[87]
30.31 mg/g dry weight of Verbascum nigrum[87]
~ 3.7% in MeOH extract from ground aerial parts (1.3 kg) of Verbena officinalis[88]
13.28 mg/g dry weight of Verbascum phoeniceum species[87]
15.79 mg/g dry weight of Verbascum xanthophoeniceum[87]
B-1. Quinones and derivatives
 Hydroxyechinofuran BHydroxyechinofuran B (15 mg) from 1 g of fresh hairy roots of Lithospermum erythrorbizon[89]
 6-(4,7-Hydroxy-heptyl) cyclohex-2,5-diene-ene-1,4-dione (6-(4,7-hydroxy-heptyl) quinone)the new quinone isolated from ten grams of crude ethyl acetate extract of 500 g Pergularia daemia leaves[90]
 Scabequinone~ 7 × 10−3 % from fresh Cyperus distans weight[91]
 2,6-Dimethoxyquinone~ 0.002% based on root of Rauwolfia vomitoria[92]
1.1% of aqueous methanol fraction from 15 g dried stems of Tibouchina pulchra[93]
 2,5-Dihydroxy-3-undecyl-para-benzoquinone (Embelin)1.9 g embelin from 100 g of Embelia ribes extracted using hexane[94]
B-2. Catechol and derivatives
 Catechol (1,2-dihydroxybenzene).0.1–0.2 g of crude catechol from 100 g of dry scales of pigmented onion scales (Allium cepa)[95]
 Protocatechuic acid (3,4-dihydroxybenzoic acid)~ 0.1 g/100 g dry scales of pigmented onion scales (Allium cepa)[96]
 Carnosic acid3.77% in Salvia officinalis L.[56]
7.57% in Thymus vulgaris L.[56]
 Dopaol beta-d-glucoside (2-(3,4-dihydroxyphenyl) ethyl β-d-gluco-pyranoside)~ 3 mg/g dry sample of Akebia quinata[57]
 Horminone0.4 g from about 1 kg of the dried whole plant (aerial parts and roots of Salvia lanata)[97]
B-3. Naphthoquinones and derivatives
 3′3-Biplumbagin~ 10% from the n-hexane extracts of stem bark (20 g) of Diospyros anisandra[98]
 Diosquinone120 μg from 5 kg of the dried root of Diospyros mespiliformis[99]
 Droserone~ 70% from the n-hexane extracts of stem bark (20 g) of Diospyros anisandra[98]
 Maritinone~ 5% from the n-hexane extracts of stem bark (20 g) Diospyros anisandra[98]
 Plumbagin~ 30% from the n-hexanic extracts obtained from Powdered stem bark (20 g) Diospyros anisandra[98]
34 mg from 5 kg of the dried root of Diospyros mespiliformis[99]
 Shikonin (derivatives)12.4% shikonin derivatives in cells corresponding to 3 g dry wt. inoculated on 1 L of the medium of Lithospermum erythrorhizon[100]
 Vitamin KSpinach, swiss chard, lettuce and Brassica vegetables (such as cabbage, kale, cauliflower, broccoli, and brussels sprouts), avocados, kiwifruit and grapes[101]
B-4. Anthraquinones and derivatives
1.9% free and 4.5% total anthaquinones in Cassia occidentalis roots[102]
hydroxyanthraquinones indicated in Cassia angustifolia Vahl, Cassia senna Linn. and Cassia tora[103]
0.04 to 3.8, 5.9 and 36 mg total anthraquinones per kg fresh weight in peas, cabbage, lettuce and beans, respectively[103]
Alizarin (1,2-dihydroxyanthraquinone)39 mg from Rubia cordifolia L. root powder (3 kg)[104]
147.9 and 216.8 μg/g dry weight of Rubia peregrina in roots and callus, respectively[105]
939.6 and 335.2 μg/g dry weight of Rubia tinctorum in roots and callus, respectively[105]
Chrysophanol140 mg from powdered roots of Rumex nepalensis (2 kg)[106]
1,3,8-Trihydroxy-6-methylanthracene-9,10-dione (Emodin, Emodol, Schuttgelb)0.1 g/8 kg (0.0012%) of Aster tataricus[107]
79 mg from Cassia obtusifolia seeds (4.9 kg)[108]
2.03 mg/g in Frangula alnus bark[109]
16.2 mg from 928 g of the ethanol extract (9% (g/g)) of the dried stem and roots of Polygonum hypoleucum Ohwi[110]
105 mg from powdered roots of Rumex nepalensis (2 kg)[106]
0.31% (w/w) from shade-dried plant samples of Ventilago madraspatana (500 g)[111]
Emodin-8-O-β-d-glucopyranoside17.4 mg from 928 g of the ethanol extract (9% (g/g)) of Polygonum hypoleucum Ohwi)[110]
35 mg from powdered roots of Rumex nepalensis (2 kg)[106]
Endocrocin7 mg from powdered roots of Rumex nepalensis (2 kg)[106]
Isomangiferin15 mg/g in Anemarrhena asphodeloides Bunge[112]
2 mg/g in Anemarrhenae Rhizoma)[112]
Mangiferin31 mg/g in Anemarrhena asphodeloides Bunge[112]
16 mg/g in Anemarrhenae Rhizoma[112]
Neomangiferin16 mg/g in Anemarrhena asphodeloides Bunge[112]
8 mg/g in Anemarrhenae Rhizoma[112]
MunjistinTwo major anthraquinones (munjistin and purpurin) representing 90% of the total anthraquinone yield from Rubia cordifolia L.calluses[113]
Physcion0.11 mg/g in Frangula rupestris bark (Scop.)[109]
8 mg from powdered roots of Rumex nepalensis (2 kg)[106]
0.22% (w/w) from shade-dried plant samples of Ventilago madraspatana (500 g)[111]
PurpurinTwo major anthraquinones (munjistin and purpurin) representing 90% of the total anthraquinone yield from Rubia cordifolia L.calluses[113]
C. Derivatives of flavonoids
  
 Azaleatin2 × 10−3 % from Plumbago indica[114]
 Catechin10.9 (mg/g) catechin from Abies pindrow[115]
75 (mg/g) in catechu resin chunks (Acacia catechu)[116]
2.67 (mg/g) from Cedrus deodara[115]
358 mg from 100 g dry matter in Chardonnay seeds[117]
127 mg from 100 g dry matter in Merlot seeds,[117]
12 mg from 100 g dry matter in Muscadine seeds[117]
the total catechins content in green tea ranges from 9 to 117 mg/g of dry weight of green tea leaves[118]
6.15(mg/g) from Pinus gerardiana[115]
13.3 (mg/g) from Pinus roxburghii[115]
5.78 (mg/g) from Pinus wallichiana[115]
12.7 mg isolated from 928 g of the ethanol extract (9% (g/g)) of Polygonum hypoleucum Ohwi[110]
21.8 (mg/g) from Taxus fuana[115]
3.6 mg/g (dry weight) of red wine wastes from Vitis vinifera[119]
56 mg/g (dry weight) of white wine wastes from Vitis vinifera[119]
total catechins, including EGCG, ECG, EC and EGC, accounted for 10.1 g/100 g dry longjing tea leaves[120]
 Cedeodarin3.23 (mg/g) from Cedrus deodara[115]
 Epicatechin15 (mg/g) in catechu resin chunks (Acacia catechu)[116]
421 mg in 100 g dry matter in Chardonnay seeds[117]
115 mg in 100 g dry matter in Merlot seeds[117]
96 mg in 100 g dry matter of Muscadine seeds[117]
3.1 mg/g dry weight of red wine wastes from Vitis Vinifera[119]
100 mg/g dry weight of white wine wastes from Vitis Vinifera[119]
7.5 mg isolated from 928 g of EP the ethanol extract (9% (g/g)) of Polygonum hypoleucum Ohwi)[110]
Epicatechin < 11 mg/g tea[121]
 Epicatechin-3-O-gallate21 (mg/g) in catechu leaves (Acacia catechu)[116]
 Eriocitrin14.98% (with a concentration range of 6.6–15.0%) in Mentha × piperita[73]
 Isomangiferin15 mg/g in Anemarrhena asphodeloides Bunge[112]
2 mg/g in Anemarrhenae rhizoma[112]
 Mangiferin31 mg/g in Anemarrhena asphodeloides Bunge)[112]
16 mg/g in Anemarrhenae Rhizoma[112]
 Luteolin-7-O-glucuronide1650 μg rutin (as luteolin-7-O-glucuronide)/g fresh leaves of Cichorium intybus[60]
Quercetin and luteolin glycosides up to 21% and 38% for radicchio di Chioggia and radicchio di Treviso respectively[60]
 Luteolin-7-O-rutinose0.420% in dry sample of Cynara scolymus L.[58]
9.38% in Origanum majorana L.[56]
8.61% in Salvia officinalis L.[56]
7.65% in Thymus vulgaris L.[56]
2.32% (dry Weight Basis) in 40 Mentha × piperita Clones[73]
 Quercetin9.3 mg from the air-dried and powered rhizomes of Alpinia officinarum (3.2 kg)[123]
Quercetin (1.6 g/8 kg) (0.02%) in Aster tataricus[107]
Quercetin and luteolin glycosides up to 21% and 38% for radicchio di Chioggia and radicchio di Treviso, respectively[60]
Rutin ~ 190 mg/g) and quercetin ~ 14 mg/g) from Sophora japonica L. buds[122]
 Quercetin 3-O-glucuronide1055 μg as rutin/g in fresh leaves of Cichorium intybus[60]
 Quercetin 7-O-glucoside2.52% in Salvia officinalis L.[56]
1.72% in Thymus vulgaris L.[56]
 Dihydroquercetin (taxifolin)5.98 (mg/g) in Cedrus deodara[115]
2.65 (mg/g) in Pinus roxburghii[115]
 Theaflavin1.58 g/100 g dry leaves of qimen black tea[124]
D. AnthocyanidinCyanidin and peonidin glycoside representing 37.1% of total anthocyanins in bilberries, and 17.6% in blueberries[125]
 CyanidinCyanidin and peonidin glycoside representing 37.1% of total anthocyanins in bilberries, and 17.6% in blueberries[125]
 Cyanidin 3-O-glucoside536 μg keracyanin (as cyanidin 3-O-glucoside)/g in fresh leaves of Cichorium intybus[60]
Red grapes, bilberry, blackberry, blueberry, cherry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry[125]
 Cyanidin 3-O-(6″malonyl)-glucoside4790 μg keracyanin (as cyanidin 3-O-(6″malonyl)-glucoside)/g in fresh leaves of Cichorium intybus[60]
 Petunidin (Petunidol; Myrtillidin)red grapes, bilberry, blackberry, blueberry, cherry, chokeberries, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry[125]
E. Tannin; ellagic acidStrawberries (630 μg/g dry wt), raspberries (1500 μg/g dry wt), blackberries (1500 μg/g dry wt), walnuts (590 μg/g dry wt), pecans (330 μg/g dry wt), cranberries (120 μg/g dry wt)[126]