Table 1.
Complexes of plant phenolic ligands with metal(loid) ions.
| Phenolic Ligand | Metal(loid) Ion | Number of Metal Ions | References |
|---|---|---|---|
| Phenolic acid | |||
| Hydroxybenzoic acids | |||
| Protocatechuic acid 1 | Al(III), U(VI) | 2 | [83,84] |
| Vanillic acid 2 | Zn(II), Y(III), La(III), Ce(III), Pr(III), Nd(III), Sm(III), Eu(III), Gd(III), Tb(III), Dy(III), Ho(III), Er(III), Tm(III), Yb(III), Lu(III), Np(V) |
17 | [85,86,87] |
| Gallic acid 3 | Fe(II), Zn(II), Fe(III), Eu(III) | 4 | [88,89,90,91] |
| Syringic acid 4 | Li(I), Na(I), K(I), Rb(I), Cs(I), Fe(II), Fe(III), Y(III), La(III), Ce(III), Pr(III), Nd(III), Sm(III), Eu(III), Gd(III), Tb(III), Dy(III), Ho(III), Er(III), Tm(III), Yb(III), Lu(III) |
22 | [92,93,94] |
| Hydroxycinnamic acids | |||
| Cinnamic acid 5 | Li(I), Na(I), K(I), Rb(I), Cs(I), Hg(I), Ca(II), Co(II), Ni(II), Cu(II), Zn(II), Ru(II), Cd(II), La(III), Eu(III), Tb(III), VO(IV), Th(IV) |
19 | [95,96,97,98,99,100,101,102] |
| p-Coumaric acid 6 | Li(I), Na(I), K(I), Rb(I), Cs(I), Co(II), Ni(II), Cu(II), Zn(II),Al(III) | 10 | [82,103,104] |
| Caffeic acid 7 | Li(I), Na(I), K(I), Rb(I), Cs(I), Cu(II), Pb(II), Pt(II), Al(III), Fe(III), Cr(III), Eu(III) |
12 | [82,105,106,107,108] |
| Ferulic acid 8 | Ca(II), Mn(II), Cu(II), Zn(II), Cd(II), Al(III), VO(IV), V(V) | 8 | [61,82,97,109] |
| Isoferulic acid 9 | Na(I), Mg(II), Mn(II) | 3 | [110] |
| Sinapic acid 10 | Cu(II), Pt(II), V(V) | 3 | [106,111] |
| Chlorogenic acid 11 | Li(I), Na(I), K(I), Rb(I), Cs(I), Ca(II), Zn (II), Fe(III), VO(IV) |
9 | [112,113,114,115,116] |
| Rosmarinic acid 12 | Li(I), Na(I), K(I), Rb(I), Cs(I), Ca(II), Cu(II) | 7 | [115,117,118] |
| Chicoric acid 13 | Co(II), Ni(II), Cu(II), Zn(II) | 4 | [119] |
| Coumarins | |||
| Coumarin 14 | La(III), Ce(III), Nd(III), Sm(III), Dy(III) | 5 | [108] |
| Umbellipherone 15 | Ce(III) | 1 | [120] |
| Daphnetin 16 | Cu(II), Zn(II), Ge(IV) | 3 | [121] |
| Chalcones | |||
| Butein 17 | Cu(II), Zn(II) | 2 | [122] |
| Dihydrochalcones | |||
| Phloretin 18 | Ru(III) | 1 | [123] |
| Flavanones | |||
| Naringenin 19, naringin 20 |
Fe(II), Cu(II), Ni(II), Zn(II), Pt(II), Fe(III), Cr(III), La(III), Y(III), Eu(III), Ce(IV), VO(IV), V(V) | 12 | [76,77,106,124,125,126] |
| Eriodictyol 21 | Fe(II), Fe(III) | 2 | [127] |
| Hesperitin 22, hesperidin 23 |
Ni(II), Cu(II), Zn(II), Al(III), VO(IV), | 5 | [76] |
| Flavanonols | |||
| Taxifolin 24 | Fe(II), Ni(II), Cu(II), Zn(II), Fe(III) |
5 | [77,124,128,129,130] |
| Dihydromyricetin 25 | Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II) | 6 | [131,132] |
| Flavonols | |||
| Kaempferol 26 | Fe(II), Cu(II), Zn(II), Pb(II), Fe(III), VO(IV) | 6 | [76,77,81,133] |
| Quercetin 27, rutin 28, quercitrin 29, isoquercitrin 30 |
Mg(II), Ca(II), Sc(II), Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), Mo(II), Pd(II), Cd(II), Hg(II), Sn(II), Pb(II), Al(III), Cr(III), Fe(III), Ga(III), Y(III), Rh(III), Sb(III), La(III), Pr(III), Nd(III), Eu(III), Gd(III), Tb(III), Dy(III), Tm(III), Au(III), Ge(IV), Zr(IV), Ru(IV), Sn(IV), Os(IV), Cr(VI), Mo(VI), W(VI), Tc(VII), Os(VIII), VO(IV), UO2(II), |
43 | [76,77,78,81,134,135,136,137,138,139,140] |
| Isorhamnetin 31 | Fe(II), Cu(II) | 2 | [141] |
| Tamarixetin 32 | Fe(II), Cu(II) | 2 | [141] |
| Fisetin 33 | Fe(II), Cu(II), Zn(II), Fe(III), VO(IV) | 4 | [77,142] |
| Morin 34 | Mg(II), Ca(II), Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Sr(II), Pd(II), Cd(II), Ba(II), Sn(II), Pt(II), Al(III), Cr(III), Fe(III), Au(III), La(III), Eu(III), Gd(III), Lu(III), Zr(IV), VO(IV), Mo(VI), W(VI), Ti(COO)2 2+ |
26 | [76,77,78,143] |
| Myricetin 35, myricitrin 36 |
Cu(II), Zn(II), Al(III), Fe(III) | 4 | [76,78,136] |
| Galangin 37 | Fe(II), Cu(II), Zn(II), Al(III) | 4 | [133] |
| Flavan-3-ols | |||
| (+)-Catechin 38, (-)-epicatechin 39 |
Fe(II), Cu(II), Zn(II), Hg(II), Al(III), Fe(III), Cr(III), La(III), Yb(III), Gd(III) |
10 | [77,144,145,146,147,148,149,150,151] |
| (+)-Epigallocatechin 40 | Fe(II) | 1 | [148] |
| (-)-Epicatechin 3-gallate 41 |
Fe(II), Cu(II), Zn(II), Al(III), Fe(III) |
3 | [80,146] |
| (-)-Epigallocatechin 3-gallate 42 |
Fe(II), Mn(II), Cu(II), Zn(II), Pt(II), Al(III), Fe(III) |
7 | [80,146,148,152,153] |
| Theaflavin 43 | Al(III), Fe(III) | 2 | [154,155] |
| Flavones | |||
| Primuletin 44 | Zn(II), Cu(II); Pb(II), Al(III), Fe(III) |
5 | [77,133] |
| Chrysin 45 | Cu(II), Pd(II), Al(III), Fe(III), La(III), Ho(III), Er(III), Yb(III), Ce(IV), VO(IV) | 10 | [76,77,133] |
| Apigenin 46 | Cu(II), Pb(II), VO(IV) | 3 | [76,133,156] |
| Luteolin 47 | Mn(II), Fe(II), Cu(II), Al(III), Fe(III), Y(III), Ho(III), Yb(III), Lu(III), VO(IV) | 10 | [76,77,81,156,157] |
| Tricetin 48 | Fe(II), Fe(III) | 2 | [127] |
| Baicalein 49, baicalin 50 |
Fe(II), Cu(II), Fe(III), VO(IV) | 4 | [76,77,156] |
| Acacetin 51 | Fe(III) | 1 | [158] |
| Isoflavones | |||
| Daidzein 52 | Ce(IV) | 1 | [77] |
| Genistein 53 | Cu(II), Fe(III) | 2 | [76,159] |
| Biochanin A 54 | Cu(II), Fe(III) | 2 | [159] |
| Anthocyanidins | |||
| Cyanidin 55 and its glycosides | Cs(I), Mg(II), Ca(II), Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Sr(II), Zn(II), Cd(II), Sn(II), Ba(II), Hg(II), Pb(II), B(III), Al(III), V(III), Cr(III), Fe(III), Ga(III), As(III), Bi(III), Ge(IV), VO3−, MoO42−, WO42− |
27 | [13,160,161,162,163] |
| Delphinidin 56 and its glycosides | Mg(II), Zn(II), Sn(II), Al(III), Cr(III), Fe(III), Ga(III) |
7 | [13,163,164] |
| Petunidin 57 and its glycosides | Mg(II), Sn(II), Al(III), Cr(III), Fe(III), Ga(III) | 6 | [164,165] |
| Xanthonoids | |||
| Mangiferin 58 | Fe(II), Cu(II), Zn(II), Fe(III), Se(IV), Ge(IV) |
6 | [121,166,167] |
| Stilbenes | |||
| Resveratrol 59 | Fe(II), Cu(II), Zn(II), Al(III), Fe(III) |
5 | [80,130,168,169] |
| Curcuminoids | |||
| Curcumin 60 | Mg(II), Ca(II), Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), Se(II), Pd(II), Cd(II), Sn(II), Hg(II), Pb(II), Al(III), Cr(III), Fe(III), Ga(III), Y(III), Ru(III), In(III), Re(III), Sm(III), Eu(III), Dy(III), Au(III), VO(IV), Nb(V) |
28 | [130,170,171,172] |
| Lignans | |||
| Secoisolariciresinol diglucoside 61 | Ag(I), Ca(II), Fe(II), Ni(II), Cu(II), Pb(II) | 6 | [173] |
| Flavonolignans | |||
| Silibinin(silybin) 62 | Ni(II), Cu(II), Zn(II), Fe(III), Ga(III), VO(IV) | 6 | [156,174,175,176] |
| Lignins | |||
| Ligno-cellulosic substrate | Mn(II), Cu(II), Fe(III) | 3 | [177] |
| Tannins | |||
| Condensed tannins | Fe(II), Cu(II), Zn(II), Al(III) | 4 | [178,179] |
| Oenothein B 63 | Al(III) | 1 | [180] |
| Ellagic acid 64 | Mg(II), Ca(II), Mn(II), Fe(II), Co(II), Cu(II), Fe(III) |
7 | [181] |
| Tannic acid 65 | Mg(II), Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), Mo(II), Cd(II), Al(III), V(III), Cr(III), Fe(III), Ru(III), Rh(III), Ce(III), Eu(III), Gd(III), Tb(III), Ti(IV), Zr(IV) |
21 | [153,182,183,184,185] |