Anticancer Activities of Chemical Constituents from Leaves and Twigs of Mitrephora winitii

https://doi.org/10.22146/ijc.61085

Sukee Sukdee(1), Puttinan Meepowpan(2*), Narong Nantasaen(3), Siriporn Jungsuttiwong(4), Sarinya Hadsadee(5), Wilart Pompimon(6)

(1) Department of Chemistry, Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Graduate School, Chiang Mai University, 239 Huay Kaew Road, Chiang Mai 50200, Thailand
(2) Department of Chemistry, Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Graduate School, Chiang Mai University, 239 Huay Kaew Road, Chiang Mai 50200, Thailand
(3) The Forest Herbarium, Department of National Park, Wildlife and Plant Conservation, Ministry of Natural Resources and Environment, Bangkok, 10220, Thailand
(4) Center for Organic Electronic and Alternative Energy, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, 34190, Thailand
(5) Center for Organic Electronic and Alternative Energy, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, 34190, Thailand
(6) Laboratory of Natural Products, Faculty of Science and Center for Innovation in Chemistry, Lampang Rajabhat University, Lampang, 52100, Thailand
(*) Corresponding Author

Abstract


The genus Mitrephora has been investigated and its anti-inflammatory, anti-bacterial and anti-parasitical activities were examined along with its potential as an anti-cancer cell line and inhibitor for platelet aggregation. In this work, air-dried leaves and twigs of M. winitii were grounded and extracted with n-hexane, ethyl acetate and methanol, respectively. Chromatographic separations of these extracts led to the isolation of three known compounds and one new compound (compound 2). The chemical structures of these were identified using spectroscopic investigation of 1D- and 2D-NMR and the resulting data confirmed these as stigmasterol (1), (3,4-dimethoxyphenyl)(5-(3,4-dimethoxyphenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl)methanol (2), diayangambin (3), and methyl-L-inositol (4). The chemical constituents were reported the first time in M. winitii. Compound 2 showed anti-cancer cell lines with ED50 13.07 µg/mL against KB cells and then was tested for cytotoxicity against MCF-7 cells with ED50 11.77 µg/mL.

Keywords


Mitrephora winitii; anticancer; extraction; extract

Full Text:

Full Text PDF


References

[1] Florence, A.R., Joselin, J., Brintha, T.S.S., Sukumaran, S., and Jeeva, S., 2014, Preliminary phytochemical studies of select members of the family Annonaceae for bioactive constituents, Biosci. Discovery, 5 (1), 85–96.

[2] Mols, J.B., and Kessler, P.J.A., 2003, The genus Miliusa (Annonaceae) in the Austro-Malesian area, Blumea, 48 (3), 421–462.

[3] Rayanil, K., Limpanawisut, S., and Tuntiwachwuttikul, P., 2013, Ent-pimarane and ent-trachylobane diterpenoids from Mitrephora alba and their cytotoxicity against three human cancer cell lines, Phytochemistry, 89, 125–130.

[4] Lee, N.H.S., Xu, Y.J., and Goh, S.H., 1999, 5-Oxonoraporphines from Mitrephora cf. maingayi, J. Nat. Prod., 62 (8), 1158–1159.

[5] Zgoda, J.R., Freyer, A.J., Killmer, L.B., and Porter, J.R., 2001, Polyacetylene carboxylic acids from Mitrephora celebica, J. Nat. Prod., 64 (10), 1348–1349.

[6] Li, C., Lee, D., Graf, T.N., Phifer, S.S., Nakanishi, Y., Burgess, J.P., Riswan, S., Setyowati, F.M., Saribi, A.M., Soejarto, D.D., Farnsworth, N.R., Falkinham, J.O., Kroll, D.J., Kinghorn, A.D., Wani, M.C., and Oberlies, N.H., 2005, A hexacyclic ent-trachylobrane diterpenoid possessing an oxetane ring from Mitrephora glabra, Org. Lett., 7 (25), 5709–5712.

[7] Deepralard, K., Pengsuparp, T., Moriyasu, M., Kawanishi, K., and Suttisri, R., 2007, Chemical constituents of Mitrephora maingayi, Biochem. Syst. Ecol., 35 (10), 696–699.

[8] Li, C., Lee, D., Graf, T.N., Phifer, S.S., Nakanishi, Y., Riswan, S., Setyowati, F.M., Saribi, A.M., Soejarto, D.D., Farnsworth, N.R., Falkiham, J.O., Kroll, D.J., Kinghorn, A.D., Wani, M.C., and Oberlies, N.H., 2009, Bioactive constituents of the stem bark of Mitrephora glabra, J. Nat. Prod., 72 (11), 1949–1953.

[9] Husain, K., Jamal, J.A., and Jalil, J., 2012, Phytochemical study of Cananga odorata (Lam) Hook.F. & Thomson & Thoms (Annonaceae), Int. J. Pharm. Pharm. Sci., 4 (4), 465–467.

[10] Zgoda-Pols, J.R., Freyer, A.J., Killmer, L.B., and Porter, J.R., 2002, Antimicrobial diterpenes from the stem bark of Mitrephora celebica, Fitoterapia, 73 (5), 434–438.

[11] Mueller, D., Davis, R.A., Duffy, S., Avery, V.M., Camp, D., and Quinn, R.J., 2009, Antimalarial activity of azafluorenone alkaloids from the Australian tree Mitrephora diviversifolia, J. Nat. Prod., 72 (8), 1538–1540.

[12] Moharam, B.A., Jantan, I., Jalil, J., and Shaari, K., 2010, Inhibitory effects of phylligenin and quebrachitol isolated from Mitrephora vulpina on platelet activating factor receptor binding and platelet aggregation, Molecules, 15 (11), 7840–7848.

[13] Royal Botanic Gardens, 1922, “Mitrephora winitii” in Bulletin of Miscellaneous Information, Springer, Berlin/Heidelberg, 227–228.

[14] Graidist, P., Martla, M., and Sukpondma, Y., 2015, Cytotoxic activity of Piper cubeba extract in breast cancer cell lines, Nutrients, 7 (4), 2707–2718.

[15] Chaturvedula, V.S.P., and Prakash, I., 2012, Isolation of stigmasterol and β-sitosterol from the dichloromethane extract of Rubus suavissimus, Int. Curr. Pharm. J., 1 (9), 239–242.

[16] Russell, G.B., and Fenemore, P.G., 1973, New lignans from leaves of Macropiper excelsum, Phytochemistry, 12 (7), 1799–1803.

[17] Haasnoot, C.A.G., de Leeuw, F.A.A.M., de Leeuw, H.P.M., and Altona, C., 1981, The relationship between proton-proton NMR coupling constants and substituent electronegativities. II–Conformational analysis of the sugar ring in nucleosides and nucleotides in solution using a generalized Karplus equation, Org. Magn. Reson., 15 (1), 43–52.

[18] Jung, K.Y., Kim, D.S., Oh, S.R., Park, S.H., Lee, I.S., Lee, J.J., Shin, D.H., and Lee, H.K., 1998, Magnone A and B, Novel anti-PAF tetrahydrofuran lignans from the flower buds of Magnolia fargesii, J. Nat. Prod., 61 (6), 808–811.

[19] Tulake, A., Jiang, Y. and Tu, P.F., 2012, Nine lignans from Atemisia absinthium L., J. Chin. Pharm. Sci., 21, 360–364.

[20] Wang, T., Yuan, Y., Wang, J., Han, C., and Chen, G., 2012, Anticancer activities of constituents from the stem of Polyalthia rumphii, Pak. J. Pharm. Sci., 25 (2), 353–356.

[21] De León, E.J., Olmedo, D.A., Solis, P.N., Gupta, M.P., and Terencio, M.C., 2002, Diayagambin exerts immunosuppressive and anti-inflammatory effects in vitro and in vivo, Planta Med., 68 (12), 1128–1131.

[22] Júnior, H.V.N., Cunha, G.M.A., Moraes, M.O., Luciana, M.F.D., Oliveira, R.A., Maia, F.D., Nogueira, M.A.S., Lemos, T.L.G., and Rao, V.S., 2006, Quebrachitol (2-O-methyl-L-inositol) attenuates 6-hydroxydopamine-induced cytotoxicity in rat fetal mesencephalic cell cultures, Food Chem. Toxicol., 44 (9), 1544–1551.

[23] Sanseera, D., Niwatananun, W., Liawruangrath, B., Liawruangrath, S., Baramee, A., Trisuwan, K., and Pyne, S.G., 2012, Antioxidant and anticancer activities from aerial parts of Acalypha indica Linn, Chiang Mai Univ. J. Nat. Sci., 11(2), 157–168.

[24] Abraham, R.J., Byrne, J.J., Griffiths, L., and Koniotou, R., 2005, 1H chemical shifts in NMR: Part 22—Prediction of the 1H chemical shifts of alcohols, diols and inositols in solution, a conformational and solvation investigation, Magn. Reson. Chem., 43 (8), 611–624.

[25] Dewick, P.M., 2002, “The shikimate pathway: aromatic amino acids and phenylpropanoids” in Medicinal Natural Products: A Biosynthetic Approach, 2nd Ed., John Wiley & Sons, Ltd., 121–166.



DOI: https://doi.org/10.22146/ijc.61085

Article Metrics

Abstract views : 3111 | views : 1786


Copyright (c) 2021 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.