Polyphenolic compounds as electron shuttles for sustainable energy utilization

Hsueh, Chung-Chuan; Wu, Chia-Chyi; Chen, Bor-Yann

doi:10.1186/s13068-019-1602-9

Biotechnology for Biofuels and Bioproducts

Table 4 Polyhydroxyphenols (polyphenols) as electron shuttles in plants

From: Polyphenolic compounds as electron shuttles for sustainable energy utilization

Model polyphenols	Contents in plant species	Refs.
A. Derivatives of phenylpropanoids
Caffeic acid	1.05–62.84 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 acid	223 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 acid	566.5 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]
Cynarin	1.689% in dry sample of Cynara scolymus	[58]
Danshensu	24.8% in crude aqueous extract of Salvia miltiorrhiza	[65]
Echinacoside	42.71% in 210 g crude phenyl ethanol glycosides extract from dried and sliced rhizomes of Cistanche tubulosa (6.0 kg)	[66]
Forsythiaside	16.7 mg from 500 g Forsythia suspense	[67]
Gravolenic acid	Ruta graveolen	[68, 69]
Nordihydroguaiaretic acid (NDGA)	0.0898% in the dried weight of Larrea divaricata	[70]
Orobanchoside	3% from Orobanche rapum-genistae	[71]
Pedicularioside	70 mg from 13.5 kg Buddleia lindleyan	[72]
Rosmarinic acid	9.30 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 A	0.7 g from the dried roots of Salvia miltiorrhiza (32 kg)	[75]
Salvianolic acid A	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]
Salvianolic acid B (lithospermic acid B)	33.93 mg/g in Salvia miltiorrhiza (Danshen)	[77]
Salvianolic acid C	0.4 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 B	Hydroxyechinofuran 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]
2,6-Dimethoxyquinone	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 acid	3.77% in Salvia officinalis L.	[56]
Carnosic acid	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]
Horminone	0.4 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]
Diosquinone	120 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]
Plumbagin	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 K	Spinach, 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]
Chrysophanol	140 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-glucopyranoside	17.4 mg from 928 g of the ethanol extract (9% (g/g)) of Polygonum hypoleucum Ohwi)	[110]
Emodin-8-O-β-d-glucopyranoside	35 mg from powdered roots of Rumex nepalensis (2 kg)	[106]
Endocrocin	7 mg from powdered roots of Rumex nepalensis (2 kg)	[106]
Isomangiferin	15 mg/g in Anemarrhena asphodeloides Bunge	[112]
Isomangiferin	2 mg/g in Anemarrhenae Rhizoma)	[112]
Mangiferin	31 mg/g in Anemarrhena asphodeloides Bunge	[112]
Mangiferin	16 mg/g in Anemarrhenae Rhizoma	[112]
Neomangiferin	16 mg/g in Anemarrhena asphodeloides Bunge	[112]
Neomangiferin	8 mg/g in Anemarrhenae Rhizoma	[112]
Munjistin	Two major anthraquinones (munjistin and purpurin) representing 90% of the total anthraquinone yield from Rubia cordifolia L.calluses	[113]
Physcion	0.11 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]
Purpurin	Two major anthraquinones (munjistin and purpurin) representing 90% of the total anthraquinone yield from Rubia cordifolia L.calluses	[113]
C. Derivatives of flavonoids
Azaleatin	2 × 10⁻³ % from Plumbago indica	[114]
Catechin	10.9 (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]
Cedeodarin	3.23 (mg/g) from Cedrus deodara	[115]
Epicatechin	15 (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-gallate	21 (mg/g) in catechu leaves (Acacia catechu)	[116]
Eriocitrin	14.98% (with a concentration range of 6.6–15.0%) in Mentha × piperita	[73]
Isomangiferin	15 mg/g in Anemarrhena asphodeloides Bunge	[112]
Isomangiferin	2 mg/g in Anemarrhenae rhizoma	[112]
Mangiferin	31 mg/g in Anemarrhena asphodeloides Bunge)	[112]
Mangiferin	16 mg/g in Anemarrhenae Rhizoma	[112]
Luteolin-7-O-glucuronide	1650 μg rutin (as luteolin-7-O-glucuronide)/g fresh leaves of Cichorium intybus	[60]
Luteolin-7-O-glucuronide	Quercetin and luteolin glycosides up to 21% and 38% for radicchio di Chioggia and radicchio di Treviso respectively	[60]
Luteolin-7-O-rutinose	0.420% 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]
Quercetin	9.3 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-glucuronide	1055 μg as rutin/g in fresh leaves of Cichorium intybus	[60]
Quercetin 7-O-glucoside	2.52% in Salvia officinalis L.	[56]
Quercetin 7-O-glucoside	1.72% in Thymus vulgaris L.	[56]
Dihydroquercetin (taxifolin)	5.98 (mg/g) in Cedrus deodara	[115]
Dihydroquercetin (taxifolin)	2.65 (mg/g) in Pinus roxburghii	[115]
Theaflavin	1.58 g/100 g dry leaves of qimen black tea	[124]
D. Anthocyanidin	Cyanidin and peonidin glycoside representing 37.1% of total anthocyanins in bilberries, and 17.6% in blueberries	[125]
Cyanidin	Cyanidin and peonidin glycoside representing 37.1% of total anthocyanins in bilberries, and 17.6% in blueberries	[125]
Cyanidin 3-O-glucoside	536 μg keracyanin (as cyanidin 3-O-glucoside)/g in fresh leaves of Cichorium intybus	[60]
Cyanidin 3-O-glucoside	Red grapes, bilberry, blackberry, blueberry, cherry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry	[125]
Cyanidin 3-O-(6″malonyl)-glucoside	4790 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 acid	Strawberries (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]

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