Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales
Abstract
:1. Introduction
2. Monomeric Ellagitannins
2.1. Simple Ellagitannins
2.2. C-Glycosidic Ellagitannins
2.3. Complex Tannins
3. Oligomeric Ellagitannins
3.1. Oligomers from the Combretaceae
3.2. Oligomers from the Lythraceae and Onagraceae
3.3. Oligomers from Myrtaceae
3.4. Oligomers from Melastomataceae
4. Structure Determination of the Oligomeric Ellagitannins
5. Biological Activities of Ellagitannins Found in the Myrtales
5.1. Casuarinin (20), Castalagin (21), and Related Tannins
5.2. Punicalagin (9) and Related Tannins
5.3. Lagerstroemin (29)
5.4. Oenothein B (54) and Related Macrocyclic Oligomers
5.5. Nobotanins
6. Conclusions
References and Notes
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Tannin | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Plant source [Ref] | |||||||||||||||
Trapaceae | |||||||||||||||
Trapa japonica [9] | + | + | + | + | |||||||||||
Melastomataceae | |||||||||||||||
Bredia tuberculata [10] | + | + | |||||||||||||
Heterocentron roseum [11] | + | + | |||||||||||||
Melastoma malabathricum [12] | + | + | + | ||||||||||||
M. normale [10] | + | + | + | ||||||||||||
Tibouchina semidecandra [13] | + | + | + | ||||||||||||
Myrtaceae | |||||||||||||||
Callistemon lanceolatus [14] | + | + | + | ||||||||||||
Eucalyptus alba [15] | + | + | + | + | |||||||||||
E. consideniana [16] | + | + | + | + | |||||||||||
E. globulus [17] | + | ||||||||||||||
E. rostrata [18] | + | ||||||||||||||
E. viminalis [16] | + | + | + | + | |||||||||||
Myrtus communis [19] | + | + | |||||||||||||
Pimenta dioica [20] | + | + | + | + | |||||||||||
Syzygium aqueum [21] | + | + | + | ||||||||||||
S. aromaticum [22] | + | + | + | + | + | ||||||||||
Onagraceae | |||||||||||||||
Epilobium angustifolium [23] | + | + | + | + | |||||||||||
Oenothera erythrosepala [24] | + | + | |||||||||||||
O. laciniata [25] | + | ||||||||||||||
O. tetraptera [26] | + | + | + | ||||||||||||
Combretaceae | |||||||||||||||
Combretum glutinosum [27] | + | + | + | ||||||||||||
C. molle [28] | + | + | |||||||||||||
Quisqualis indica [29] | + | + | + | + | + | + | |||||||||
Terminalia arborea [30] | + | + | + | + | + | ||||||||||
T. arjuna [31] | + | + | + | ||||||||||||
T. brachystemma [32] | + | ||||||||||||||
T. calamansanai [33] | + | + | + | + | + | ||||||||||
T. catappa [34] | + | + | + | + | + | + | + | + | + | ||||||
T. chebula [35] | + | + | + | + | + | + | |||||||||
T. citrina [36] | + | + | |||||||||||||
T. macroptera [37] | + | + | + | + | |||||||||||
T. myriocarpa [38] | + | + | |||||||||||||
T. triflora [39] | + | ||||||||||||||
Punicaceae | |||||||||||||||
Punica granatum [40] | + | + | + | + | + | + |
Family | Plant species | C-Glycosidic tannins | Ref. |
---|---|---|---|
Combretaceae | Anogeissus acuminata | 16, 17, 18, 19 | [43] |
Anogeissus leiocarpus | 16 | [44] | |
Lumnitzera racemosa | 16 | [45] | |
Terminalia arjuna | 16, 20, 22 | [31] | |
Terminalia macroptera | 27 | [37] | |
Terminalia arborea | 28 | [30] | |
Thiloa glaucocarpa | 16, 18, 20, 21 | [46] | |
Lythraceae | Lagerstroemia flos-reginea | 16, 18, 20, 21, 22, 23, 24, 29 | [47] |
Lagerstroemia speciosa | 16, 18, 19, 29 | [48] | |
Melastomataceae | Osbeckia chinensis | 20, 22, 25 | [49] |
Tibouchina semidecandra | 16, 18, 20 | [13] | |
Myrtaceae | Callistemon lanceolatus | 20 | [14] |
Eucalyptus alba | 21, 22 | [15] | |
Eugenia grandis | 16, 18 | [50] | |
Kunzea ambigua | 20 | [51] | |
Melaleuca squarrosa | 20, 21 | [52] | |
Pimenta dioica | 16, 18, 20, 22 | [20] | |
Siphoneugena densiflora | 16, 20 | [53] | |
Syzygium aqueum | 16, 18, 19 | [21] | |
Syzygium aromaticum | 20, 22 | [22] | |
Punicaceae | Punica granatum | 20, 22, 25, 26, 27, 28 | [40] |
Trapaceae | Trapa japonica | 20 | [9] |
Biological activity | Compound (source) | Ref. |
---|---|---|
Anti-Herpes simplex virus type 2 activity | casuarinin (20) (Terminalia arjuna) | [67] |
Apoptosis in human breast adenocarcinoma MCF-7 cells | casuarinin (20) | [68] |
Antileishmanial activity | casuarinin (20), castalagin (16) | [69] |
castalagin (16) (Anogeissus leiocarpus) | [44] | |
Antihypertensive activity (rats) | castalagin (16) (Lumnitzera racemosa) | [45] |
corilagin, chebulinic acid (15) | ||
α-Glucosidase inhibitor | casuarictin (7) (Syzygium aromaticum) | [70] |
chebulagic acid (14) (Terminalia chebula) | [71] | |
Dual inhibitor against COX and 5-LOX | chebulagic acid (14) (T. chebula) | [72] |
Anti-inflammation in LPS-induced RAW 264.7 cells | chebulagic acid (14) (T. chebula) | [73] |
Effect on carageenan-induced inflammation | punicalagin (9), punicalin (10) (T. catappa) | [74] |
Antioxidant and hepatoprotective effects on acetaminophen-induced liver damage in rats | punicalagin (9), punicalin (10) (T. catappa) | [75] |
Effect against bleomycin-induced genotoxicity in Chinese hamster ovary cells | punicalagin (9) (T. catappa) | [76] |
Chemopreventive effect on H-ras-transformed NIH3T3 cells | punicalagin (9) (T. catappa) | [77] |
Inhibitory effect on HIV-1 reverse transcriptase | punicalin (10), 2-O-galloylpunicalin (T. triflora) | [39] |
Inhibitory effect on CCl4-induced hepatotoxicity | punicalagin (9) (T. myriocarpa) | [38] |
Activators of glucose transport in fat cells | lagerstroemin (29), reginin A (49) (L. speciosa) | [78] |
Activation of insulin receptors | lagerstroemin (29) | [79] |
Insulin-like glucose uptake-stimulatory/inhibitory and adiposities differentiation inhibitory activity in 3T3-L1 cells | lagerstroemin (29) casuarinin (20), casuariin (22), stachyurin (21) | [80] |
Host-mediated antitumor effect | oenothein B (54) (Oenothera erythrosepala) | [24] |
Host-mediated antitumor | oenothein B (54) (Woodfordia fruticosa) | [56] |
woodfordins A-C (53) | ||
Inhibitor of deoxyribonucleic acid topoisomerase II | woodfruticosin [= woodfordin C (53)] | [81] |
EBV DNA polymerase inhibitory effect | oenothein B (54) (Eugenia uniflora) | [82] |
eugeniflorins D1, D2 (57) | ||
5α-reductase, aromatase inhibitory effect | oenotheins A (59), B (54) (Epilobium sp) | [59] |
Induction of neutral endopeptidase activity in PC-3 cells | oenothein B (54) (Epilobium angustifolium) | [83] |
In vitro immunomodulatory effect on human mononuclear cells | cuphiin D1 (55) (Cuphea sp) | [84] |
Induce apoptosis in HL-60 cells | cuphiin D1 (55) | [85] |
Poly (ADP-ribose) glycohydrolase inhibition | nobotanins B (70), K (72) (Tibouchina sp) | [86] |
© 2010 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
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Yoshida, T.; Amakura, Y.; Yoshimura, M. Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales. Int. J. Mol. Sci. 2010, 11, 79-106. https://doi.org/10.3390/ijms11010079
Yoshida T, Amakura Y, Yoshimura M. Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales. International Journal of Molecular Sciences. 2010; 11(1):79-106. https://doi.org/10.3390/ijms11010079
Chicago/Turabian StyleYoshida, Takashi, Yoshiaki Amakura, and Morio Yoshimura. 2010. "Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales" International Journal of Molecular Sciences 11, no. 1: 79-106. https://doi.org/10.3390/ijms11010079