Flavonoid Components, Distribution, and Biological Activities in Taxus: A review
Abstract
:1. Introduction
2. Chemical Structure
3. Results
3.1. Chemical Components
3.1.1. Flavones
3.1.2. Biflavones
3.1.3. Flavonols or Flavonol Glycosides
3.1.4. Dihydroflavones, Dihydroflavonols, and Dihydroflavonol Glycosides
3.1.5. Flavanols and Biflavanols
3.1.6. Chalcones
3.2. Flavonoid Properties, Extraction, and Isolation
3.2.1. Physico-Chemical Properties of Flavonoids
3.2.2. Extraction and Isolation Methods
3.3. Flavonoid Distribution
3.4. Flavonoid Bioactivities
3.4.1. Antibacterial Activities
3.4.2. Antioxidant and Antiaging Activities
3.4.3. Anti-Alzheimer’s Activities
3.4.4. Antidiabetes Activities
3.4.5. Anticancer Activities
3.4.6. Antidepressant Activities
3.4.7. Neuronal Protective Activities
3.4.8. Antileishmaniasis Activities
3.4.9. Anti-Inflammatory, Antinociceptive, and Antiallergic Activities
3.4.10. Antivirus Activities
3.4.11. Antilipase Activities
3.4.12. Promotion of Melanogenesis
3.4.13. Hepatic-Protective Activities
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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No. | Type | Compound | Molecular Formula | Molecular Weight(Da) | Species (Part) | Bioactivity |
---|---|---|---|---|---|---|
1 | Flavone | Apigenin | C15H10O5 | 270.24 | T. fuana, T. yunnanensis (twigs); T. baccata (needles) [7,8] | Antioxidant, anticancer, antidepressant, anti-inflammatory activities [9,10,11] |
2 | Flavone | Luteolin | C15H10O6 | 286.24 | T. fuana, T. yunnanensis (twigs) [7] | Antioxidant, anticancer, anti-inflammatory activities [9,10] |
3 | Biflavone | Bilobetin | C31H20O10 | 552.48 | T. baccata, T. celebica (needles); T. chinensis, T. cuspidata, T. media (twigs, leaves) [12,13] | Antibacterial activities [12] |
4 | Biflavone | 4′′′-O-Methylamentoflavone(or podocarpusflavone-A) | C31H20O10 | 552.48 | T. baccata, T. media (needles) [9,14] | Anticancer activities [15] |
5 | Biflavone | Sciadopitysin | C33H24O10 | 580.54 | T. baccata, T. media, T. celebica (needles, leaves); T. cuspidata (twigs, bark, leaves, branches); T. brevifolia (leaves); T. canadensis (leaves, twigs); T. wallichiana (leaves); T. mairei (leaves); T. chinensis, T.media (twigs, leaves); T. cuspidate var. nana (leaves) [4,12,13,16,17,18,19,20,21,22,23,24,25,26] | Anti-Alzheimer’s disease, antibacterial, neuronal protective activities [12,27] |
6 | Biflavone | Ginkgetin | C32H22O10 | 566.51 | T. baccata (needles, leaves), T. cuspidata (twigs, bark, leaves, branches); T. canadensis (leaves, twigs); T. chinensis var. mairei, T. media (fruits); T. chinensis, T. media (twigs, leaves, fruits); T. wallichiana (leaves); T. fuana, T. yunnanensis (twigs); T. cuspidate var. nana (leaves) [4,7,12,13,16,17,18,19,20,22,23,24,26,28] | Antibacterial, anticancer activities [12,29] |
7 | Biflavone | Amentoflavone | C30H18O10 | 538.46 | T. baccata (needles); T. wallichiana(leaves); T. fuana, T. yunnanensis (twigs) [7,12,23,24] | Antibacterial, antileishmaniasis, antivirus activities [12,30,31] |
8 | Biflavone | Sequoiaflavone | C31H20O10 | 552.48 | T. baccata (needles, leaves); T. media (needles); T. wallichiana (leaves); T. canadensis (needles); T. mairei, T. chinensis (leaves) [4,12,14,16,23,24,25,32] | Antibacterial activities [12] |
9 | Biflavone | Isoginkgetin | C32H22O10 | 566.51 | T. chinensis, T. cuspidata, T. media (twigs, leaves); T. chinensis var. mairei (twigs) [13,33] | Anti-inflammatory activities [34] |
10 | Biflavone | Putraflavone | C32H22O10 | 566.51 | T. canadensis (needles); T. chinensis var. mairei (twigs) [32,33] | Anti-inflammatory activities [35] |
11 | Biflavone | Sotetsuflavone | C31H20O10 | 552.48 | T. baccata (not mentioned); T. cuspidata (leaves) [19,36] | Anticancer activities [37] |
12 | Biflavone | Kayaflavone | C33H24O10 | 580.54 | T. cuspidata (leaves); T. baccata (needles) [17,19,36] | Antivirus activities [31] |
13 | Biflavone | 4′,7,7″-Tri-O-methyl amentoflavone | C33H24O10 | 580.54 | T. baccata (leaves) [36,38] | Not reported |
14 | Biflavone | 4′,4″,7,7″-Tetra-O-methyl amentoflavone | C34H26O10 | 594.56 | T. baccata (needles, leaves) [36,38] | Not reported |
15 | Biflavone | 4′,7″-Di-O-methyl amentoflavone | C32H22O10 | 566.51 | T. baccata (needles) [36] | Not reported |
16 | Biflavone | 4″-O-methyl ginkgetin | C33H24O10 | 580.54 | T. chinensis var. mairei, T. media (fruits) [28] | Not reported |
17 | Biflavone | 3″-hydroxy-4″,7-dimethyl amentoflavone | C32H22O9 | 550.51 | T. canadensis (needles) [39] | Not reported |
18 | Flavonol | Kaempferol | C15H10O6 | 286.24 | T. brevifolia (leaves); T. baccata (needles); T. fuana, T. yunnanensis (twigs); T. mairei (twigs) [7,14,21,40] | Antioxidant, antivirus, anti-inflammatory activities [9,41] |
19 | Flavonol glycoside | Kaempferol-3-O-rutinoside | C27H30O15 | 594.52 | T. baccata (needles, twigs); T. chinensis var. mairei (twigs) [14,33,42] | Antioxidant activities [43] |
20 | Flavonol glycoside | Kaempferol-7-O-glucoside | C21H20O11 | 448.38 | T. baccata (needles); T. chinensis var. mairei (twigs) [14,33] | Antivirus activities [41] |
21 | Flavonol | Myricetin | C15H10O8 | 318.23 | T. baccata (needles) [14] | Antivirus activities [44] |
22 | Flavonol glycoside | Myricetin-3-O-rutinoside | C27H30O17 | 626.52 | T. baccata (needles) [14] | Not reported |
23 | Flavonol | Quercetin | C15H10O7 | 302.24 | T. brevifolia (leaves); T. cuspidate (bark, leaves); T. baccata (needles, twigs); T. fuana, T. yunnanensis (twigs); T. chinensis, T. cuspidata, T. media (twigs, leaves); T. mairei (twigs); T. chinensis var. mairei (twigs); T. cuspidate var. nana (leaves) [7,13,14,18,21,26,33,40,42] | Antioxidant, anti-inflammatory, antiallergic activities [9,45] |
24 | Flavonol glycoside | Quercetin-3-O-rutinoside (or rutin) | C27H30O16 | 610.52 | T. baccata (needles or leaves, twigs); T. chinensis var. mairei (twigs) [14,33,42] | Anticancer activities [46] |
25 | Flavonol glycoside | Quercetin-7-O-glucoside | C21H20O12 | 464.38 | T. baccata (needles) [14] | Antivirus activities [47] |
26 | Flavonol | Isorhamnetin | C16H12O7 | 316.26 | T. brevifolia (leaves); T. cuspidate (bark, leaves); T. cuspidate var. nana (leaves); T. baccata (needles) [8,18,21,26] | Antivirus activities [48] |
27 | Flavonol glycoside | Quercetin-3-O-α-L-arabinopyranosyl-(1′′′→6”)-β-D-glucopyranoside | C26H28O16 | 596.49 | T. cuspidata (needles) [49] | Antidiabetes activities [50] |
28 | Flavonol glycoside | Tricin-3-O-glucoside | C23H24O13 | 508.43 | T. chinensis var. mairei, T. media (fruits) [28] | Not reported |
29 | Flavonol glycoside | Quercetin-3-O-glucoside | C21H20O12 | 464.38 | T. cuspidata (branches, leaves); T. chinensis, T. cuspidata, T. media (twigs, leaves) [13,51] | Anticancer activities [51] |
30 | Flavonol glycoside | Quercetin 3-rhamnoside | C21H20O11 | 448.38 | T. chinensis, T. cuspidata, T. media (twigs, leaves) [13] | Antilipase activities [52] |
31 | Dihydroflavone | Pinocembrin | C15H12O4 | 256.25 | T. mairei (twigs) [53] | Antivirus activities [54] |
32 | Dihydroflavone | Eriodictyol | C15H12O6 | 288.25 | T. mairei (twigs) [53] | Antidiabetes activities [55] |
33 | Dihydroflavone | Butin | C15H12O5 | 272.25 | T. mairei (twigs) [53] | Antidiabetes activities [55] |
34 | Dihydroflavone | Naringenin | C15H12O5 | 272.25 | T. media, T. cuspidata (twigs); T. chinensis var. mairei (twigs) [33,53] | Anticancer, anti-inflammatory, antiallergic activities [45,56] |
35 | Dihydroflavone | Pinostrobin | C16H14O4 | 270.28 | T. media, T. cuspidata (twigs) [53] | Promotion of melanogenesis [57] |
36 | Dihydroflavone | Dihydrotricetin | C15H12O7 | 304.25 | T. media, T. cuspidata (twigs) [53] | Not reported |
37 | Dihydroflavonol | Taxifolin | C15H12O7 | 304.25 | T. baccata (needles) [8] | Antidiabetes activities [58] |
38 | Dihydroflavonol | Aromadendrin | C15H12O6 | 288.25 | T. chinensis var. mairei, T. media (fruits) [28] | Neuronal protective activities [59] |
39 | Dihydroflavonol glycoside | Aromadendrin-3-O-rutinoside | C27H32O15 | 596.53 | T. chinensis var. mairei, T. media (fruits) [28] | Not reported |
40 | Flavanol | 5-deoxyleucopelargonidin | C15H14O5 | 274.27 | T. media (twigs) [53] | Not reported |
41 | Flavanol | Leucopelargonidin | C15H14O6 | 290.27 | T. media (twigs); T. chinensis var. mairei, T. media (fruits) [24,53] | Not reported |
42 | Flavanol | Leucocyanidin | C15H14O7 | 306.27 | T. media (twigs) [53] | Not reported |
43 | Flavanol | (+)-Catechin | C15H14O6 | 290.27 | T. cuspidata (needles, wood, roots); T. fuana, T. yunnanensis (twigs); T. chinensis (leaves) [7,49,60,61] | Antioxidant, antidiabetes, anticanceractivities [3,51,60,61] |
44 | Flavanol | (-)-Epicatechin | C15H14O6 | 290.27 | T. cuspidata (needles, wood, roots); T. fuana, T. yunnanensis (twigs); T. chinensis (leaves) [7,49,60,61] | Antioxidant, antidiabetes, anticanceractivities [51,60,61,62,63] |
45 | Flavanol | Gallocatechin | C15H14O7 | 306.27 | T. chinensis (leaves) [61] | Antidiabetes, antivirus activities [61,64] |
46 | Flavanol | Epigallocatechin | C15H14O7 | 306.27 | T. chinensis (leaves) [61] | Antidiabetes activities [61] |
47 | Flavanol | (+)-Catechin pentaacetate | C25H24O11 | 500.45 | T. mairei (twigs) [40] | Not reported |
48 | Flavanol | (-)-Epicatechin pentaacetate | C25H24O11 | 500.45 | T. mairei (twigs) [40] | Not reported |
49 | Flavanol | Procyanidin B2 | C30H26O12 | 578.52 | T. chinensis (leaves) [61] | Antidiabetes activities [51,65] |
50 | Biflavanol | Procyanidin B-2 decaacetate | C50H46O22 | 998.89 | T. mairei (twigs) [40] | Not reported |
51 | Biflavanol | Procyanidin B-3-decaacetate | C50H46O22 | 998.89 | T. mairei (twigs) [40] | Not reported |
52 | Biflavanol | Procyanidin B-4-decaacetate | C50H46O22 | 998.89 | T. mairei (twigs) [40] | Not reported |
53 | Biflavanol | Afzelechin-(4α→8)-afzelechin | C30H26O10 | 546.52 | T. cuspidata (roots) [66] | Not reported |
54 | Biflavanol | Afzelechin-(4α→8)-afzelechin octaacetate | C46H42O18 | 882.81 | T. cuspidata (roots) [66] | Not reported |
55 | Chalcone | Pinocembrin chalcone(or 2′,4′,6′-trihydroxychalcone) | C15H12O4 | 256.25 | T. mairei (twigs) [53] | Antibacterial activities [67] |
56 | Chalcone | Isoliquiritigenin(or 2′,4′,4′-trihydroxy chalcone) | C15H12O4 | 256.25 | T. media (twigs) [53] | Hepatic-protective activities [68] |
57 | Chalcone | Butein | C15H12O5 | 272.25 | T. media (twigs) [53] | Anti-inflammatory, antinociceptive activities [69] |
58 | Chalcone | Homoeriodictyol chalcone | C16H14O6 | 302.28 | T. media (twigs) [53] | Not reported |
59 | Chalcone | Naringenin chalcone | C15H12O5 | 272.25 | T. media, T. cuspidata (twigs) [53] | Anti-inflammatory activities [45] |
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Wei, Q.; Li, Q.-Z.; Wang, R.-L. Flavonoid Components, Distribution, and Biological Activities in Taxus: A review. Molecules 2023, 28, 1713. https://doi.org/10.3390/molecules28041713
Wei Q, Li Q-Z, Wang R-L. Flavonoid Components, Distribution, and Biological Activities in Taxus: A review. Molecules. 2023; 28(4):1713. https://doi.org/10.3390/molecules28041713
Chicago/Turabian StyleWei, Qiang, Qi-Zhao Li, and Rui-Lin Wang. 2023. "Flavonoid Components, Distribution, and Biological Activities in Taxus: A review" Molecules 28, no. 4: 1713. https://doi.org/10.3390/molecules28041713