Cytotoxic and antioxidant activities of flavonoids and diterpenoids from Macaranga involucrata (Roxb.) Baill

Alifia Muharram; Diah Ayu Rachmawati; Shola Mardhiyyah; Tjitjik Srie Tjahjandarie; Ratih Dewi Saputri; Norizan Ahmat; Mulyadi Tanjung

doi:10.7324/JAPS.2023.101645

Abstract

Two flavonols, macagigantin (1) and brussoflavonol E (2), and two diterpenoids, deheiculatin C (3) and poilaneic acid (4), were obtained from Macaranga involucrata (Roxb.) Baill. leaves. Their structures were fully detailed on high-resolution electrospray mass spectra, 1D NMR (1H, 13C), and 2D NMR (heteronuclear multiple quantum coherence, heteronuclear multiple bond coherence) spectra. The cytotoxic and antioxidant activities of compounds 1–4 were evaluated in murine leukaemia cancer cells (P-388) and DPPH radical assays, respectively. Compounds 1–3 showed moderate activity against P-388 cells with IC50 values of 26.3, 12.8, and 21.2 μM, respectively. Compounds 1–2 showed high activity against DPPH radical with IC50 values of 332.1 and 125.6 μM, respectively.

Keyword: Macaranga involucrata flavonoid diterpenoid cytotoxic antioxidant

Citation:

Muharram A, Rachmawati DA, Mardhiyyah S, Tjahjandarie TS, Saputri RD, Ahmat N, Tanjung M. Cytotoxic and antioxidant activities of flavonoids and diterpenoids from Macaranga involucrata (Roxb.) Baill. J Appl Pharm Sci, 2023. https://doi.org/10.7324/JAPS.2023.101645

Copyright: © The Author(s). This is an open-access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Reference

Aldin MF, Tjahjandarie TS, Saputri RD, Tanjung M. Macasiamenene V, a new stilbenoid from the leaves of Macaranga inermis. Nat Prod Sci, 2021; 27(1):45-8.

Aminah NS, Kristanti AN, Tanjung M. Antioxidant activity of flavonoid compounds from the leaves of Macaranga gigantea. J Chem Pharm Res, 2014; 6(6):688-92.

Klausmeyer P, Van QN, Jato J, McCloud TG, Beutler JA. Schweinfurthins I and J from Macaranga schweinfurthii. J Nat Prod, 2010; 73:479-81. https://doi.org/10.1021/np9006348

Le TNV, Truong BN, Le TP, Litaudon M, Tran DT, Chau VM, Mai HDT, Pham VC. Cytotoxic phenolic compounds isolated from the fruits of Macaranga denticulata. Nat Prod Res, 2021; 35(11):1861-8. https://doi.org/10.1080/14786419.2019.1639175

Marliana E, Astuti W, Kosala K, Hairani R, Tjahjandarie TS, Tanjung M. Chemical composition and anticancer activity of Macaranga hosei leaves. Asian J Chem, 2018; 30(4):795-8. https://doi.org/10.14233/ajchem.2018.21004

Pailee P, Sangpetsiripan S, Mahidol C, Ruchirawat S, Prachyawarakorn V. Cytotoxic and cancer chemopreventive properties of prenylated from Macaranga siamensis. Tetrahedron, 2015; 71:5562-71. https://doi.org/10.1016/j.tet.2015.06.058

Phommart S, Sutthivaiyakit P, Chimnoi N, Ruchirawat S, Sutthivaiyakit S. Constituents of the leaves of Macaranga tanarius. J Nat Prod, 2005; 68:927-30. https://doi.org/10.1021/np0500272

Qi WY, Shen Y, Wu Y, Leng Y, Gao K, Yue JM. Deheiculatins A-L, 20-oxygenated from Macaranga deheiculata. Phytochemistry, 2017; 136:101-7. https://doi.org/10.1016/j.phytochem.2017.01.009

Saputri RD, Tjahjandarie TS, Tanjung M. Two novel coumarins bearing acetophenone derivative from the leaves of Melicope quercifolia. Nat Prod Res, 2021; 35(8):1256-61. https://doi.org/10.1080/14786419.2019.1644634

Son KH, Keon SJ, Chang HW, Kim HP, Kang SS. Papyriflavonol A, a new prenylated flavonol from Broussonetia papyrifera. Fitoterapia, 2001; 72:456-8. https://doi.org/10.1016/S0367-326X(00)00329-4

Tanjung M, Juliawaty LD, Hakim EH, Syah YM. Flavonoid and stilbene derivatives from Macaranga trichocarpa. Fitoterapia, 2018; 126:74-7. https://doi.org/10.1016/j.fitote.2017.10.001

Tanjung M, Hakim EH, Elfahmi, Latif J, Syah YM. Dihydroflavonol and flavonol derivatives from Macaranga recurvata. Nat Prod Commun, 2012; 7(10):1309-10. https://doi.org/10.1177/1934578X1200701013

Tanjung M, Hakim EH, Mujahidin D, Hanafi M, Syah YM. Macagigantin, a farnesylated flavonol from Macaranga gigantea. J Asian Nat Prod Res, 2009; 11(11):929-32. https://doi.org/10.1080/10286020903302315

Tanjung M, Mujahidin D, Hakim EH, Darmawan A, Syah YM. Geranylated flavonoids from Macaranga rhizinoides. Nat Prod Commun, 2010; 5(8):1209-11. Tanjung M, Tjahjandarie TS, Saputri RD, Kurnia BD, Rachman MF, Syah YM. Calotetrapterins A-C, three new pyranoxanthones and their cytotoxicity from the stem bark of Calophyllum tetrapterum Miq. Nat Prod Res, 2021; 35(3):407-12. https://doi.org/10.1080/14786419.2019.1634714

Tanjung M, Tjahjandarie TS, Sentosa MH. Antioxidant and cytotoxic agent from the rhizomes of Kaempferia pandurata. Asian Pac J Trop Dis, 2013; 3(5):401-4. https://doi.org/10.1016/S2222-1808(13)60091-2

Tjahjandarie TS, Tanjung M, Saputri RD, Nadar PB, Aldin MF, Permadi A. Flavestin K, an isoprenylated stilbene from the leaves of Macaranga recurvata Gage. Nat Prod Sci, 2019; 25(3):244-7. https://doi.org/10.20307/nps.2019.25.3.244

Yang DS, Li ZL, Wang X, Yan H, Yang Y-P, Luo H-R, Liu K-C, Xiao WL, Li X-L. Denticulatins A and B: unique stilbene-diterpen heterodimers from Macaranga denticulata. RSC Adv, 2015; 5:13886-90. https://doi.org/10.1039/C4RA14805C

Yoder B, Cao S, Norris A, Miller JS, Ratovoson F, Razafitsalama J, Andriantsiferana R, Rasamison VE, Kingston DGI. Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest. J Nat Prod, 2007; 70(3):342-6. https://doi.org/10.1021/np060484y

Abstract

HTML Full Text

Reference

Article Metrics

Related Search

Citiaion Alert By Google Scholar

Similar Articles