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Xanthoangelol, geranilated chalcone compound, isolation from pudau leaves (Artocarpus kemando Miq.) as antibacterial and anticancer

  • Tati Suhartati EMAIL logo , Novita Andriyani , Yandri Yandri and Sutopo Hadi ORCID logo
Published/Copyright: March 28, 2023
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Abstract

From the leaves of Artocarpus kemando Miq, locally known as pudau plant, a flavonoid has been isolated and identified. The compound was then tested as antibacterial agent against Bacillus subtillis and Escherichia coli. The first step of isolation was extraction by maceration using methanol as solvent, and then followed by fractionation using partition treatment and vacuum liquid chromatography. Finally, the compound was purified using column chromatography method. The purity of the compound was evaluated using thin layer chromatography and melting point measurement, and the compound was subsequently characterized using UV–Vis, IR, and NMR spectroscopy. A total of 66.2 mg of the compound was obtained, in the form of yellow needle crystals with a melting point of 142.8–144 °C, which is a compound of geranylated chalcone, xanthoangelol. Xanthoangelol was the first chalcone compound isolated from A. kemando. Antibacterial tests were carried out at varied doses of 0.5; 0.4; and 0.3 mg/disk, and revealed that the compound exhibits high inhibitory power against B. subtillis, but has no activity against E. coli. The anticancer activity of xanthoangelol on MCF-7 cells indicated that the compound has an IC50 value of 7.79 μg/mL, suggesting that the compound possesses an active cytotoxic activity.


Corresponding author: Tati Suhartati, Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Lampung, Bandar Lampung 35145, Indonesia, E-mail:

Award Identifier / Grant number: 027/E5/PG.02.00/PT/2022 dated 16 March 2022 and 21

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The author would like to thank the Ministry of Education, Culture, Research and Technology, for funding support in the form of Basic Research, fiscal year 2022 with contract number 027/E5/PG.02.00/PT/2022 dated 16 March 2022 and 2143/UN26.21/PN/2022 29 April, 2022.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Nayak, M, Nagarajan, A, Majeed, M. Pharmacognostic evaluation of leaf and stem wood extracts of Artocarpus hirsutus Lam. Pharmacogenom J 2017;9:887–94. https://doi.org/10.5530/pj.2017.6.139.Search in Google Scholar

2. Suhartati, T, Epriyanti, E, Borisha, I, Yandri, Y, Suwandi, JF, Yuwono, SD, et al.. In vivo antimalarial test of artocarpin and in vitro antimalarial test of artonin M isolated from Artocarpus. Rev Chim 2020;71:400–8. https://doi.org/10.37358/rc.20.5.8150.Search in Google Scholar

3. Hidayati, AR, Widyawaruyanti, A, Ilmi, H, Tanjung, M, Widiandani, T, Siswandono, S, et al.. Antimalarial activity of flavonoid compound isolated from leaves of Artocarpus altilis. Pharmacogenom J 2020;12:835–42. https://doi.org/10.5530/pj.2020.12.120.Search in Google Scholar

4. Buddhisuharto, AK, Pramastya, H, Insanu, M, Fidrianny, I. An updated review of phytochemical compounds and pharmacology activities of Artocarpus genus. Biointerface Res Appl Chem 2021;11:14898–905.10.33263/BRIAC116.1489814905Search in Google Scholar

5. Suhartati, T. Phenol compounds of several plant species of Indonesian cempedak [Dissertation]. Bandung: ITB; 2001.Search in Google Scholar

6. Seo, EK, Lee, D, Shin, YG, Chai, HB, Navarro, HA, Kardono, LB, et al.. Bioactive prenylated flavonoids from the stem bark of Artocarpus kemando. Arch Pharm Res 2003;26:124–7. https://doi.org/10.1007/bf02976656.Search in Google Scholar PubMed

7. Ee, GCL, Teo, SH, Rahmani, M, Lim, CK, Lim, YM, Go, R. Artomandin, a new xanthone from Artocarpus kemando (Moraceae). J Nat Prod Res 2011;25:995–1003. https://doi.org/10.1080/14786419.2010.534471.Search in Google Scholar PubMed

8. Andini, V. Isolation, characterization, and anticancer and antibacterial activity test of artonin E compound from the polar fraction of the branch bark of the Pudau plant (Artocarpus kemando Miq.) [Thesis]. Bandar Lampung: Chemistry FMIPA University of Lampung; 2017.Search in Google Scholar

9. Borisha, I. Isolation, characterization, and antibacterial activity test of flavonoid compounds from the semi polar fraction of root bark of Pudau plant (Artocarpus kemando Miq.) [Thesis]. Bandar Lampung: Chemistry FMIPA University of Lampung; 2017.Search in Google Scholar

10. Fatimah, N. Isolation, characterization, and antibacterial activity test of flavonoid compounds from root wood of Pudau plant (Artocarpus kemando Miq.) [Thesis]. Bandar Lampung:Chemistry FMIPA University of Lampung; 2017.Search in Google Scholar

11. Yulia, H. Isolation, characterization, and antibacterial activity test of flavonoid compounds from branch wood of the Pudau plant (Artocarpus kemando Miq.) [Thesis]. Bandar Lampung: Chemistry FMIPA University of Lampung; 2019.Search in Google Scholar

12. Aliero, A, Aliero, BL, Buhari, U. Preliminary phytochemical and antibacterial screening of Scadoxus multiflorus. Int J Pure Appl Sci 2008;2:13–7.Search in Google Scholar

13. Saiful, S. Isolation and identification of antimicrobial compounds from galingggung leaves (Cassia alata Linn) [Thesis]. Yogyakarta: Gajah Mada University; 2005.Search in Google Scholar

14. Dewick, PM. Medicinal natural products: a biosynthetic approach, 2nd ed. Chichester: John Wiley; 2011.Search in Google Scholar

15. Bauer, AW, Kirby, WM, Sherris, JC, Turck, M. Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 1966;45:493–6. https://doi.org/10.1093/ajcp/45.4_ts.493.Search in Google Scholar

16. Zainudin, NHM, Razak, KA, Abidin, SZ, Abdullah, R, Rahman, WN. Influence of bismuth oxide nanoparticles on bystander effects in MCF-7 and hFOB 1.19 cells under 10 MV photon beam irradiation. Radiat Phys Chem 2020;177:109143. https://doi.org/10.1016/j.radphyschem.2020.109143.Search in Google Scholar

17. Markham, KR. How to identify flavonoids. Translate Kosasih Padmawinata. Bandung: ITB Press; 1988.Search in Google Scholar

18. Breitmair, E. Structure elucidation by NMR in organic chemistry: practical guide. Chicaster: John Wiley and Son, LTD; 2002.10.1002/0470853069Search in Google Scholar

19. Kimura, Y, Baba, K. Antitumor and antimetastatic activities of Angelica keiskei roots, part 1: isolation of an active substance, xanthoangelol. Int J Cancer 2003;106:429–37. https://doi.org/10.1002/ijc.11256.Search in Google Scholar PubMed

20. Davis, WW, Stout, TR. Disc plate method of microbiological antibiotik assay. Appl Microbiol 1971;22:659–65. https://doi.org/10.1128/am.22.4.659-665.1971.Search in Google Scholar PubMed PubMed Central

21. Inamori, Y, Baba, K, Tsujibo, H, Taniguchi, M, Nakata, K, Kozawa, M. Antibacterial activity of two chalcones, xanthoangelol and 4-hydroxyderricin, isolated from the root of Angelica keiskei KOIDZUMI. Chem Pharm Bull 1991;39:1604–5. https://doi.org/10.1248/cpb.39.1604.Search in Google Scholar PubMed

22. Miller, SI. Antibiotic resistance and regulation of the gram-negative bacterial other membrane barrier by host innate immune molecules. mBio 2016;7:e01541–16.10.1128/mBio.01541-16Search in Google Scholar PubMed PubMed Central

23. Hadi, S, Lestari, S, Suhartati, T, Qudus, HI, Rilyanti, M, Herasari, D, et al.. Synthesis and comparative study on the antibacterial activity organotin (IV) 3-hydroxybenzoate compounds. Pure Appl Chem 2021;93:623–8. https://doi.org/10.1515/pac-2020-1103.Search in Google Scholar

24. Annissa, Suhartati, T, Yandri, HS. Antibacterial activity of diphenyltin(IV) and triphenyltin(IV) 3-chlorobenzoate against Pseudomonas aeruginosa and Bacillus subtilis. Orient J Chem 2017;33:1133–9. https://doi.org/10.13005/ojc/330310.Search in Google Scholar

25. Hadi, S, Hermawati, E, Noviany, N, Suhartati, T, Yandri. Antibacterial activity test of diphenyltin(IV) dibenzoate and triphenyltin(IV) benzoate compounds against Bacillus substilis and Pseudomonas aeruginosa. Asian J Microbiol Biotechnol Environ Sci 2018;20:113–9.Search in Google Scholar

26. Susangka, AL, Hadi, S, Noviany, N, Kiswandono, AA, Nurhasanah, Pandiangan, KD, et al.. Characterization, and comparison of disinfectant bioactivity test of two triphenyltin(IV) compounds. J Turk Chem Soc A Chem 2022;9:1047–5.10.18596/jotcsa.1097465Search in Google Scholar

27. Hadi, S, Suhartati, T, Noviany, N, Pandiangan, KD, Yandri, Y, Simanjuntak, W, et al.. Disinfecting activity of some diphenyltin(IV) benzoate derivative compounds. Pure Appl Chem 2022;94:799–807. https://doi.org/10.1515/pac-2021-1106.Search in Google Scholar

28. Samsuar, S, Simanjuntak, W, Qudus, HI, Yandri, Y, Herasari, H, Hadi, S. Vitro antimicrobial activity study of some organotin(IV) chlorobenzoates against Staphylococcus aureus and Escherichia coli. J Adv Pharm Educ Res 2021;11:17–22. https://doi.org/10.51847/kaijzkafco.Search in Google Scholar

29. Atjanasuppat, K, Wongkham, W, Meepowpan, P, Kittakoop, P, Sobhon, P, Bartlett, A, et al.. In vitro screening for anthelmintic and antitumour activity of ethnomedicinal plants from Thailand. J Ethnopharmacol 2009;123:475–82. https://doi.org/10.1016/j.jep.2009.03.010.Search in Google Scholar PubMed

30. Jiang, C-H, Sun, T-L, Xiang, D-X, Wei, S-S, Li, W-Q. Anticancer activity and mechanism of xanthohumol: a prenylated flavonoid from hops (Humulus lupulus L.). Front Pharmacol 2018;9:530. https://doi.org/10.3389/fphar.2018.00530.Search in Google Scholar PubMed PubMed Central

Received: 2022-11-02
Accepted: 2023-01-31
Published Online: 2023-03-28

© 2023 Walter de Gruyter GmbH, Berlin/Boston

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