TABLE 3.
Major polyphenol, flavonoid, and phenylpropanoids compounds in Chinese olive.
| Type | Name | Molecular formula | Extract solvent | References |
|---|---|---|---|---|
| Polyphenol | Brevifolin (1) | C12H8O6 | Acidic ethylacetate | Ito et al. (1990) |
| Brevifolin carboxylic acid (2) | C13H8O8 | 80% acetone | He and Xia (2007a) | |
| Chebulagic acid (3) | C41H30O27 | Water | Chang et al. (2017) | |
| Digallic acid (4) | C14H10O9 | Ethyl acetate | Yeh et al. (2020) | |
| 3,4-dihydroxybenzoic acid ethy ether (5) | C9H10O4 | 80% ethanol | Xiang et al. (2010) | |
| 3, 3′-dimethoxy-2, 2′, 4, 4′-tetrahydroxy-diphenylformic acid (6) | N/A | Water | Wei et al. (1999) | |
| 3, 4-dihydroxybenzoic acid (7) | C7H6O4 | Chloroform | Yang et al. (2018) | |
| 3,3′-Di-O-methylellagic acid (8) | C16H10O8 | acidic ethylacetate | Ito et al. (1990) | |
| 3-((8E,11E)-pentadeca-8,11,14-pentadecatrien-1-yl) phenol (9) | C21H30O | 70% ethanol | Zhang et al. (2019) | |
| Ellagic acid (10) | C14H6O8 | 80% acetone | He and Xia. (2007b) | |
| Ellagic acid-4-O-α-L-rhamnpyranoside (11) | C20H16O12 | Chloroform | Yang et al. (2018) | |
| Ellagic acid-4-O-β-D-glucopyranoside (12) | N/A | Water | Chang et al. (2017) | |
| Ellagic acid-4-O-β-D-xylopyranoside (13) | N/A | Water | Chang et al. (2017) | |
| Ethyl gallate (14) | C9H10O5 | 80% aqueous acetone | He et al. (2008) | |
| Gallic acid (15) | C7H6O5 | 80% aqueous acetone | He et al. (2008) | |
| Geraniin (16) | C41H28O27 | Water | Chang et al. (2017) | |
| 4-hydroxybenzaldehyde (17) | C7H6O2 | 70% ethanol | Zhang (2019) | |
| 4′-hydroxy-3′-methoxy-phenol-β-D-[6-O-(4″-hydroxy-3″,5″-dimethoxybenzoate)]glucopyranoside (18) | C22H26O12 | 70% ethanol | Zhang et al. (2019) | |
| Isocorilagin (19) | C27H22O18 | Water | Chang et al. (2017) | |
| Methyl brevifolincarboxylate (20) | C14H10O8 | ethyl acetate | Chen et al. (2020) | |
| Methyl gallate (21) | C8H8O5 | 80% aqueous acetone | He et al. (2008) | |
| Methyl vanillate (22) | C9H10O4 | 70% ethanol | Zhang et al. (2019) | |
| Octyl gallate (23) | C15H22O5 | Ethyl acetate | Yeh et al. (2020) | |
| 3-O-galloylquinic acid (24) | N/A | Water | Chang et al. (2017) | |
| 3-O-galloyl quinic acid butyl ester (25) | C18H24O10 | 80% aqueous acetone | He et al. (2009) | |
| 3-(8-pentadecenyl) phenol (26) | C21H34O | 70% ethanol | Zhang et al., 2019 | |
| Protocatechuic acid (27) | C7H6O4 | Ethyl acetate | Kuo et al. (2019) | |
| Propyl gallate (28) | C10H12O5 | Ethyl acetate | Yeh et al. (2020) | |
| Pyrogallic acid (29) | C6H6O3 | 80% ethanol | Wu and Xiang (2017) | |
| Salicylic acid (30) | C7H6O3 | 80% ethanol | Xiang et al. (2010) | |
| Sinapic acid (31) | C11H12O5 | 80% acetone | He and Xia (2007a) | |
| Urolithin M5 (32) | C13H8O7 | Water | Xiao et al. (2022a) | |
| Vanillic acid (33) | C8H8O4 | Ethyl acetate | Yeh et al. (2020) | |
| Flavonoid | Amentoflavone (34) | C30H18O10 | 80% aqueous acetone | He et al. (2008) |
| Astragalin (35) | C21H20O11 | Ethyl acetate | Yeh et al. (2020) | |
| Hyperin (36) | C21H20O12 | 80% aqueous acetone | He et al. (2008) | |
| Isoquercitrin (37) | C21H20O12 | 80% ethanol | Xiang et al. (2010) | |
| Kaempferol (38) | C15H10O6 | 80% ethanol | Xiang et al. (2010) | |
| Kaempferol-3-O-β-D-glucopyranoside (39) | N/A | 80% aqueous acetone | He et al. (2008) | |
| Luteolin (40) | C15H10O6 | 80% ethanol | Xiang et al. (2010) | |
| Luteolin-7-O-β-D-glucoside (41) | C21H20O11 | 80% ethanol | Xiang et al. (2010) | |
| Naringin (42) | C27H32O14 | Methanol | Wu and Xiang (2017) | |
| Quercetin (43) | C15H10O7 | 80% ethanol | Xiang et al., 2010 | |
| Quercetin-3-O-β-D-glucoside (44) | C21H19O12 | 80% ethanol | Xiang et al. (2010) | |
| Sitoindoside I (45) | C51H90O7 | Ethyl acetate | Kuo et al. (2019) | |
| Tetrahydroamentoflavone (46) | C30H22O10 | Ethyl acetate | Kuo et al. (2019) | |
| 3′,4′,7,8-tetrahydroxyflavanone (47) | C15H12O6 | 80% ethanol | Xiang et al. (2010) | |
| 3,5,7,3′-Tetrahydroxy-4′-methoxyflavanonol (48) | C16H14O8 | 80% ethanol | Xiang et al. (2010) | |
| Rutin (49) | C27H30O16 | Water/ethanol | Kuo et al. (2015) | |
| Phenylpropanoids | Aesculetin (50) | C9H6O4 | Ethyl acetate | Yeh et al. (2020) |
| Balanophonin (51) | C20H20O6 | 70% ethanol | Zhang et al. (2019) | |
| Cinnamic acid (52) | C9H8O2 | 70% ethanol | Zhang et al. (2019) | |
| (+)-(7S,8R,7′S,8′R)-Cinncassin D (53) | C28H28O9Na | 70% ethanol | Li et al. (2022) | |
| (−)-(7R,8S,7′R,8′S)-Cinncassin D (54) | C28H28O9Na | 70% ethanol | Li et al. (2022) | |
| (+)-(7S,8R,7′R,8′S)-Cinncassin D (55) | C28H28O9Na | 70% ethanol | Li et al. (2022) | |
| (−)-(7R,8S,7′S,8′R)-Cinncassin D (56) | C28H28O9Na | 70% ethanol | Li et al. (2022) | |
| Curcasinlignan C (57) | C18H18O6 | 70% ethanol | Zhang et al. (2019) | |
| Dihydroconiferyl alcohol (58) | C10H14O3 | 70% ethanol | Zhang et al. (2019) | |
| 3-ethoxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (59) | N/A | 70% ethanol | Zhang et al. (2019) | |
| (7R,8S)-erythro-7,8-bis (4-hydroxy-3-methoxyphenyl)-9-acetyl-7,9-propanediol (60) | C19H22O7 | 70% ethanol | Zhang et al. (2019) | |
| (+)-Erythro-(7S,8R)-canariol A (61) | C29H30O9Na | 70% ethanol | Li et al. (2022) | |
| (−)-Erythro-(7R,8S)-canariol A (62) | C29H30O9Na | 70% ethanol | Li et al. (2022) | |
| (+)-erythro-7-O-ethylguaiacylglycerol (63) | C12H18O5 | 70% ethanol | Zhang et al. (2019) | |
| (7R,8S)-erythro-guaiacylethoxyglycerol-β-O-4′-coniferyl aldehyde ether (64) | C22H26O7 | 70% ethanol | Chen et al. (2021) | |
| (7R,8R)-erythro-guaiacylethoxyglycerol-β-O-4′-guaiacyl aldehyde ether (65) | C20H24O7 | 70% ethanol | Zhang (2019) | |
| (7S,8R)-erythro-guaiacylglycerol-β-coniferyl aldehyde ether (66) | C20H22O7 | 70% ethanol | Zhang (2019) | |
| (7S,8R)-erythro-3-hydroxyl-4-methoxyl-balanophonin (67) | C20H20O6 | 70% ethanol | Zhang (2019) | |
| (7R,8S)-erythro-3-methoxy-4-hydroxy-7- methoxy-8-O-(2′-methoxy-4′-aldehyde-phenyl)-phenylpropanol (68) | C19H22O7 | 70% ethanol | Zhang (2019) | |
| (+)-epipinoresinol (69) | C20H22O6 | 70% ethanol | Zhang (2019) | |
| Evofolin-B (70) | C17H18O6 | 70% ethanol | Zhang (2019) | |
| Ferulic aldehyde (71) | C10H10O3 | 70% ethanol | Zhang (2019) | |
| Ficusal (72) | C18H18O6 | 70% ethanol | Zhang (2019) | |
| 4-hydroxycinnamic acid methyl ester (73) | C10H10O3 | 70% ethanol | Zhang (2019) | |
| β-hydroxypropiovanilone (74) | N/A | 70% ethanol | Zhang (2019) | |
| Lycocer-nuaside B (75) | N/A | 70% ethanol | Zhang (2019) | |
| (7S)-3-methoxy-4-hydroxy-7-hydromethyl-phenylacetic acid-8-O-(3′-methoxyl-4′-hydroxy) phenyl ester (76) | C17H18O7 | 70% ethanol | Zhang (2019) | |
| P-hydroxyphenylferulate (77) | C16H14O5 | 70% ethanol | Zhang (2019) | |
| (+)-(7R,8R,7′S,8′R)-Picrasmalignan (78) | C30H30O9Na | 70% ethanol | Li et al. (2022) | |
| (−)-(7S,8S,7′R,8′S)-Picrasmalignan (79) | C30H30O9Na | 70% ethanol | Li et al. (2022) | |
| (+)-(7R,8S,7′S,8′R)-Picrasmalignan (80) | C30H30O9Na | 70% ethanol | Li et al. (2022) | |
| (−)-(7S,8R,7′R,8′S)-Picrasmalignan (81) | C30H30O9Na | 70% ethanol | Li et al. (2022) | |
| (+)-(7S,8R,7′S,8′R)-Picrasmalignan (82) | C30H30O9Na | 70% ethanol | Li et al. (2022) | |
| (−)-(7R,8S,7′R,8′S)-Picrasmalignan (83) | C30H30O9Na | 70% ethanol | Li et al. (2022) | |
| (+)-(7S,8R,7′S,8′S)-Picrasmalignan (84) | C30H30O9Na | 70% ethanol | Li et al. (2022) | |
| (−)-(7R,8S,7′R,8′R)-Picrasmalignan (85) | C30H30O9Na | 70% ethanol | Li et al. (2022) | |
| (+)-pinoresinol (86) | C20H22O6 | 70% ethanol | Zhang et al. (2019) | |
| Scoparone (87) | C11H10O4 | Water | Wei et al. (1999) | |
| Scopoletin (88) | C10H8O4 | Chloroform | Yang et al. (2018) | |
| 8-O-1 system neolignan (89) | C19H22O7Na | 70% ethanol | Zhang et al. (2019) | |
| (7S,8R)-threo-balanophonin (90) | C20H20O6 | 70% ethanol | Zhang (2019) | |
| (+)-Threo-(7R,8R)-canariol A (91) | C29H30O9Na | 70% ethanol | Li et al. (2022) | |
| (−)-Threo-(7S,8S)-canariol A (92) | C29H30O9Na | 70% ethanol | Li et al. (2022) | |
| (+)-Threo-(7R,8R)-canariol B (93) | C29H28O9Na | 70% ethanol | Li et al. (2022) | |
| (−)-Threo-(7S,8S)-canariol B (94) | C29H28O9Na | 70% ethanol | Li et al. (2022) | |
| (7R,8R)-threo-guaiacylethoxyglycerol-β-O-4′-coniferyl aldehyde ether (95) | C22H26O7 | 70% ethanol | Zhang et al. (2019) | |
| (7R,8S)-threo-guaiacylethoxyglycerol-β-O-4′-guaiacyl aldehyde ether (96) | C20H24O7 | 70% ethanol | Chen et al. (2021) | |
| (7S,8R)-threo-1'-[3′-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-8-hydro-xymethyl-7,8 dihydrobenzofuran] acrylaldehyde (97) | C19H18O6 | 70% ethanol | Zhang et al. (2019) | |
| Threo-1-(4-hydroxy-3-methoxyphenyl)-1-methoxy-2-{4-[1-formyl-(E)-vinyl]-2-methoxyphenoxy}-3-propanol (98) | C21H24O7 | 70% ethanol | Zhang et al. (2019) | |
| (7S,8R)-threo-lycocernuaside B (99) | C19H20O6 | 70% ethanol | Zhang (2019) | |
| (7R,8S)-threo-3-methoxyl-4-hydroxyl-balanophonin (100) | C20H20O6 | 70% ethanol | Zhang (2019) | |
| (7S,8S)-threo-3-methoxy-4-hydroxy-7- methoxy- 8-O-(2′-methoxy-4′-aldehyde-phenyl)-phenylpropanol (101) | C19H22O7 | 70% ethanol | Chen et al. (2021) | |
| Vladinol-D (102) | C20H22O7 | 70% ethanol | Zhang et al. (2019) | |
| Triterpenoid | α-Amyrin (103) | C30H50O | Ethanol | Tamai et al. (1989) |
| β-amyrin (104) | C30H50O | Ethanol | Tamai et al. (1989) | |
| 3-epi-α-amyrin (105) | C30H50O | Ethanol | Tamai et al. (1989) | |
| 3-epi-β-amyrin (106) | C30H50O | Ethanol | Tamai et al. (1989) | |
| Olean-12-ene-3α,16β-diol (107) | — | Ethanol | Tamai et al. (1989) | |
| Urs-12-ene-3β,16α-diol (108) | C30H50O2 | Ethanol | Tamai et al. (1989) | |
| Urs-12-ene-3α,16β-diol (109) | C30H50O2 | Ethanol | Tamai et al. (1989) | |
| Other types | CPS1 (110) | — | Water | Zeng et al. (2015) |
| CPS2 (111) | — | Water | Zeng et al. (2015) | |
| CPS3 (112) | — | Water | Zeng et al. (2015) | |
| Myo-inositol (113) | C6H12O6 | Chloroform | Yang et al. (2018) | |
| (1′R, 3′S, 5′R, 8′R, 2Z, 4E)-dihydrophaseic acid-3′-O-β-D-glucopyranoside (114) | C21H32O10 | Chloroform | Yang et al. (2018) | |
| (1′S, 3′R, 5′S, 8′R, 2Z, 4E)-dihydrophaseic acid-3′-O-β-D-glucopyranoside (115) | C21H32O10 | Chloroform | Yang et al. (2018) |