Abstract
A phytochemical investigation of the rhizomes of Curcuma zedoaria was carried out, leading to the isolation of a new diphenylheptanoid, zedoaroxane A (1), together with four known compounds (2–5). Their structures were elucidated based on NMR spectroscopic data. All isolated compounds possessed α-glucosidase inhibitory activity, with the IC50 values ranging from 35.2 to 89.0 µM, more potent than that of the positive control acarbose (IC50, 214.5 µM).
Acknowledgements
This research was supported by The Youth Incubator for Science and Technology Programe, managed by Youth Development Science and Technology Center – Ho Chi Minh Communist Youth Union and Department of Science and Technology of Ho Chi Minh City, the contract number is 30/2019/HĐ-KHCN-VƯ.
-
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: None declared.
-
Conflict of interest statement: No potential conflict of interest was reported by the authors.
References
1. Vo, VC. Dictionary of Vietnamese medicinal plants. Hanoi: Publishing House of Medicine; 2012:323 p.Search in Google Scholar
2. Do, LT. Vietnamese traditional medicinal plants and drugs. Hanoi: Publishing House of Medicine; 2001:235 p.Search in Google Scholar
3. Chen, IN, Chang, CC, Wang, CY, Shyu, YT, Chang, TL. Antioxidant and antimicrobial activity of Zingiberaceae plants in Taiwan. Plant Foods Hum Nutr 2008;63:15–20. https://doi.org/10.1007/s11130-007-0063-7.Search in Google Scholar
4. Gupta, R, Ali, M, Eranna, D, Setty, R. Evaluation of anti-ulcer effect of root of Curcuma zedoaria in rats. Indian J Tradit Knowl 2003;2:375–7.Search in Google Scholar
5. Lee, TK, Lee, D, Lee, S, Ko, YJ, Kang, KS, Chung, SJ, et al.. Sesquiterpenes from Curcuma zedoaria rhizomes and their cytotoxicity against human gastric cancer AGS cells. Bioorg Chem 2019;87:117–22. https://doi.org/10.1016/j.bioorg.2019.03.015.Search in Google Scholar
6. Singh, P, Singh, S, Kapoor, IPS, Singh, G, Isidorov, V, Szczepaniak, L. Chemical composition and antioxidant activities of essential oil and oleoresins from Curcuma zedoaria rhizomes, part-74. Food Biosci 2013;3:42–8. https://doi.org/10.1016/j.fbio.2013.06.002.Search in Google Scholar
7. Endo, K, Kanno, E, Oshima, Y. Structure of antifungal diarylheptanones, gingerones A, B, C and isogingerenone B, isolated from the rhizomes of Zingber officinale. Phytochemistry 1990;29:797–9. https://doi.org/10.1016/0031-9422(90)80021-8.Search in Google Scholar
8. Zeng, YC, Qiu, F, Liu, Y, Qu, G, Yao, X. Isolation and identification of phase 1 metabolites of demethoxycurcumin in rats. Drug Metab Dispos 2007;35:1564–73. https://doi.org/10.1124/dmd.107.015008.Search in Google Scholar
9. Portes, E, Gardrat, C, Castellan, A. A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids. Tetrahedron 2007;63:9092–9. https://doi.org/10.1016/j.tet.2007.06.085.Search in Google Scholar
10. Sonar, VP, Fois, B, Distinto, S, Maccioni, E, Meleddu, R, Cottiglia, F, et al.. Ferulic acid esters and withanolides: in search of Withania somnifera GABAA receptor modulators. J Nat Prod 2019;82:1250–7. https://doi.org/10.1021/acs.jnatprod.8b01023.Search in Google Scholar
11. Fuentes, RG, Toume, F, Arai, MA, Koyano, T, Kowithayakorn, T, Ishibashi, M. Constituents from the rhizomes of Curcuma comosa and their WNT signal inhibitory activities. Heterocycles 2014;88:1501–9.10.3987/COM-13-S(S)49Search in Google Scholar
12. Tormena, CF, Dias, LC, Rittner, R. Orbital interactions and their effects on 13C NMR chemical shifts for 4,6-disubstituted-2,2-dimethyl-1,3-dioxanes – a theoretical study. J Phys Chem A 2005;109:6077–82. https://doi.org/10.1021/jp052048a.Search in Google Scholar
13. Kim, KY, Nam, KA, Kurihara, H, Kim, SM. Potent α-glucosidase inhibitors purified from the red alga Grateloupia elliptica. Phytochemistry 2008;69:2820–5. https://doi.org/10.1016/j.phytochem.2008.09.007.Search in Google Scholar
14. Hiroyuki, F, Tomohide, Y, Kazunori, O. Efficacy and safety of Touchi extract, an α-glucosidase inhibitor derived from fermented soybeans, in non-insulin-dependent diabetic mellitus. J Nutr Biochem 2001;12:351–6. https://doi.org/10.1016/s0955-2863(01)00149-8.Search in Google Scholar
15. Fujisawa, T, Ikegami, H, Inoue, K, Kawabata, Y, Ogihara, T. Effect of two α-glucosidase inhibitors, voglibose and acarbose, on postprandial hyperglycemia correlates with subjective abdominal symptoms. Metabolism 2005;54:387–90. https://doi.org/10.1016/j.metabol.2004.10.004.Search in Google Scholar
16. Shibao, C. Primer on the autonomic nervous system, 3rd ed. Chapter 134: Acarbose. Elsevier Inc; 2012:639–41 pp. https://doi.org/10.1016/b978-0-12-386525-0.00134-7.Search in Google Scholar
Supplementary Material
Copies of spectroscopic data and HPLC chromatogram for 1 (Figures S1–S11).
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2021-0096).
© 2021 Walter de Gruyter GmbH, Berlin/Boston