Flavonoids and amides from Melodorum fruticosum L. stem bark and their a-glucosidase inhibitory activity
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https://doi.org/10.15625/2525-2518/18781Keywords:
Melodorum fruticosum L., flavonoid, amide, α-glucosidaseAbstract
Melodorum fruticosum Lour. (Annonaceae), a small tree or climber, is widely distributed in Central and Southern Vietnam. The leaves of M. fruticosum L. have been used as fork remedies for the treatment of digestive diseases and swelling of the breast, the roots of the plant were used to treat abdominal dyspepsia in women after giving birth. The dried powder of the stem of M. fruticosum L. collected in Lam Dong province was extracted with ethanol at room temperature and evaporated in the reduced pressure to yield an ethanol crude residue. From ethyl acetate extract, six compounds including eriodictyol (1), taxifolin (2), quercetin (3), paprazine (4), N-trans-caffeoyltyramine (5), and N-trans-feruloyltyramine (6) were isolated. The structures of these compounds were elucidated by NMR and ESI-MS as well as compared with data in the literatures. All isolated compounds, n-hexane, ethyl acetate and ethanol extracts were evaluated for their in vitro α-glucosidase inhibition, with acarbose as a positive control.
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References
1. Hongnak S., Jongaramruong J., Khumkratok S., Siriphong P., Tip-pyang S. - Chemical constituents and derivatization of Melodorinol from the roots of Melodorum fruticosum, Nat. Prod. Commun. 10 (2015) 633-636. https://doi.org/10.1177/1934578X1501000426.
2. Rachsawan M., Jittra P., Warinthorn C. - Chemical constituents from Melodorum fruticosum Lour. flowers against plant pathogenic fungi. Agri. Nat. Res. 50(4) (2016) 270–275. https://doi.org/10.1016/j.anres.2016.03.001.
3. Pripdeevech P., Chukeatirote E. - Chemical compositions, antifungal and antioxidant activities of essential oil and various extracts of Melodorum fruticosum L. flowers, Food Chem. Toxicol. 48 (10) (2010) 2754-2758. https://doi.org/10.1016/j.fct.2010.07.002.
4. Chaichantipyuth C., Tiyaworanan S., Mekaroonreung S., Ngamrojnavanich N., Roengsumran S., Puthong S., Petsom A., Ishikawa T. - Oxidized heptenes from flowers of Melodorum fruticosum, Phytochemistry 58 (8) (2001) 1311-1315. https://doi.org/10.1016/ S0031-9422(01)00215-1.
5. Tuchinda P., Udchachon J., Reutrakul V., Santisuk T., Taylor W. C., Farnsworth N. R., Pezzuto J. M., Kinghorn A. D. - Bioactive butenolides from Melodorum fruticosum, Phytochemistry 30(8) (1991) 2685-2689. https://doi.org/10.1016/0031-9422(91)85123-H.
6. Jung J. H., Pummangura S., Chaichantipyuth C., Patarapanich C., Fanwick P. E., Chang C. J., McLaughlin J. L. - New bioactive heptenes from Melodorum fruticosum (Annonaceae), Tetrahedron 46(15) (1990) 5043–5054. https://doi.org/10.1016/S0040-4020(01)87811-X.
7. Chan H. H., Hwang T. L., Thang T. D., Leu Y. L., Kuo P. C., Nguyet B. T. M., Wu T. S. - Isolation and synthesis of melodamide A, a new anti-inflammatory phenolic amide from the leaves of Melodorum fruticosum, Planta Med. 79 (2013) 288-294. http://dx.doi.org/ 10.1055/s-0032-1328131.
8. Pripdeevech P. - Analysis of odor constituents of Melodorum fruticosum flowers by solid-phase microextraction-gas chromatography-mass spectrometry, Chem. Nat. Compd. 47 (2011) 292-294. DOI:10.1007/s10600-011-9910-8.
9. Tanapichatsakul C., Monggoot S., Gentekaki E., Pripdeevech P - Antibacterial and antioxidant metabolites of Diaporthe sp. isolated from flowers of Melodorum fruticosum, Curr. Microbiol. 75 (2018) 476-483. https://doi.org/10.1007/s00284-017-1405-9.
10. Engels N.S., Waltenberger B., Michalak B., Huynh L., Tran H., Kiss A.K., Stuppner H. - Inhibition of pro-inflammatory functions of human neutrophils by constituents of Melodorum fruticosum leaves, Chem. Biodivers. 15(11) (2018) e1800269. DOI: 10.1002/cbdv.201800269.
11. Huber-Cantonati P., Mähr T., Schwitzer F., Kretzer C., Koeberle A., Mayr F., Engels N., Waltenberger B., Stuppner H., Werz O. - Benzylated dihydrochalcone MF-15 as a potent multitarget inhibitor of cancer cell growth, Planta Med. 87(15) (2021) 9-18. DOI: 10.1055/s-0041-1736947.
12. Sichaem J., Aree T., Lugsanangarm K., Tip-Pyang S. - Identification of highly potent α-glucosidase inhibitory and antioxidant constituents from Zizyphus rugosa bark: enzyme kinetic and molecular docking studies with active metabolites, Pharm. Biol. 55 (1) 1436-1441. doi:10.1080/13880209.2017.1304426.
13. Phu D. H., Tho L. H., Truong D. V. N., Hai N. X., Mai N. T. T., Nhan N. T. - Flavonoids from the stem barks of Swintonia griffithii Kurz (Anacadiaceae) and their tyrosinase inhibitory activities, Vietnam J. Chem. 57 (5) (2019) 581-584. DOI: vjch.201900080.
14. Lee S., Park Y., Moon B., Lee E., Hong S., Lim Y. - Substitution effect of hydroxyl groups on the 1H and 13C chemical shifts in hydroxyflavonols, Bull. Korean Chem. Soc. 29 (8) (2008) 1597-1600. doi: 10.5012/bkcs.2008.29.8.1597.
15. Matsuda H., Morikawa T., Toguchida I., Harima S., Yoshikawa M. - Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L.: Their inhibitory activities for rat lens aldose reductase, Chem. Pharm. Bull. 50 (7) (2002) 972-975. https://doi.org/10.1248/cpb.50.972.
16. Mostafa A. E., Amira S. W., Mohamed M. R., Nabil A. A., ElShahat S. T., Mahmoud A. E. - Chemical and biological studies of Cannabis sativa roots, Med. Cannabis Cannabinoids 1 (2) (2019). https://doi.org/10.1159/000495582.
17. Wu Y. C., Chang G. Y., Ko F. N. Ten C. M. - Bioactive constituents from the stems of Annona montana, Planta Med. 61 (2) (1995) 146-149. doi: 10.1055/s-2006-958035.
18. Tanaka H., Nakamura T., Ichino K. and Ito K. - A phenolic amide from Actinodaphne longifolia, Phytochemistry 28 (9) (1989) 2516-2511. https://doi.org/10.1016/S0031-9422(00)98022-1.
19. Su H., Ruan Y. T., Li Y., Chen J. G., Yin Z. P., Zhang Q. F. - In vitro and in vivo inhibitory activity of taxifolin on three digestive enzymes, Int. J. Biol. Macromol. 150 (2020) 31-37. https://doi.org/10.1016/j.ijbiomac.2020.02.027.
20. Luo Q. J., Zhou W. C., Liu X. Y., Li Y. J., Xie Q. L., Wang B., Liu C., Wang W. M., Wang W. Zhou X. D. - Chemical constituents and α-glucosidase inhibitory, antioxidant and hepatoprotective activities of Ampelopsis grossedentata, Molecules 28 (2023) 7956. https://doi.org/10.3390/molecules28247956.
21. Proença C., Freitas M., Ribeiro D., Oliveira E. F. T., Sousa J. L. C., Tomé S. M., Ramos M. J., Silva A. M. S, Fernandes P. A., Fernandes E. - α-Glucosidase inhibition by flavonoids: an in vitro and in silico structure–activity relationship study, J. Enzyme Inhib. Med. Chem. 32 (1) (2017) 1216-1228. https://doi.org/10.1080/14756366.2017.1368503.
22. Habtemariam S. - The anti-obesity potential of sigmoidin A, Pharm. Biol. 509 (12) (2012) 1519-1522. https://doi.org/10.3109/13880209.2012.688838.
23. Phat N. T., Dung L. T., Nhat M. P., Trong D. B, Tuyen P. N. K., Lien D. T. M, Tuyen N. D., Tri M. D. - A new dihydrofurocoumarin from the fruits of Pandanus tectorius Parkinson ex Du Roi, Nat. Prod. Res. 30(21) (2016) 2389-2395. https://doi.org/10.1080/14786419.2016.1188095.
24. Song Y. H., Kim D. W., Curtis-Long M. J., Park C., Son M., Kim J. Y., Yuk H. J., Lee K. W., Park K. H. - Cinnamic acid amides from Tribulus terrestris displaying uncompetitive α-glucosidase inhibition, Eur. J. Med. Chem. 114 (2016) 201-208. https://doi.org/10.1016/ j.ejmech.2016.02.044.
25. Zhang L., Tu Z. C., Yuan T., Wang H., Xie X., Fu Z. F. - Antioxidants and α-glucosidase inhibitors from Ipomoea batatas leaves identified by bioassay-guided approach and structure-activity relationships, Food Chem. 208 (2016) 61-67. https://doi.org/10.1016/ j.foodchem.2016.03.079.
26. Suthiphasilp V., Maneerat W., Andersen R. J., Phukhatmuen P., Pyne S. G., Laphookhieo S. - Dasymaschalolactams A-E, Aristolactams from a Twig Extract of Dasymaschalon dasymaschalum, J. Nat. Prod. 82 (11) (2019) 3176-3180. https://doi.org/10.1021/ acs.jnatprod.9b00506.
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