Senyawa Isoflavonoid Terisoprenilasi dari Ranting Flemingia macrophylla
DOI:
https://doi.org/10.15575/ak.v8i1.8711Keywords:
Flemingia macrophylla, isoflavonoid, 8-(1.1-dimethyl-prop-2-enyl) genistein, osajin, anticancer.Abstract
Flemingia macrophylla merupakan tumbuhan perdu yang termasuk keluarga Fabaceae. Senyawa fenolik Flemingia mengandung senyawa flavonoid dan isoflavonoid. Penelitian ini bertujuan untuk menentukan aktivitas sitotoksik senyawa isoflavonoid dari Flemingia macrophylla terhadap sel kanker payudara T47D. Ekstraksi dan isolasi senyawa isoflavonoid menggunakan metanol pada suhu kamar. Dua senyawa isoflavonoid terisoprenilasi, 8-(1.1-dimetil-prop-2-enil) genistein (1) dan osajin (2) telah berhasil dipisahkan dari ranting Flemingia macrophylla. Penentuan struktur senyawa isoflavonoid menggunakan data spektroskopi ultraviolet (UV), inframerah (IR), 1D dan 2D NMR. Sitotoksik 8-(1.1-dimetil-prop-2-enil) genistein (1) dan osajin (2) terhadap sel kanker payudara T47D memperlihatkan nilai IC50 sebesar 10,91 ± 0,17 dan 3,72 ± 0,23 µg/mL.
References
H. Li, F. Zhai, M. Yang, X. Li, P. Wang, X. Ma, "A new benzofuran derivative from Flemingia philippinensis Merr, et, Rolfe", Molecules, vol. 17, no. 7, pp 7637-7644, 2012.
I. Gumula, J.P. Alao, I.O. Ndiege, P. Sunnerhagen, A. Yenesew, and M. Edelyi, "Flemingins G-O, cytotoxic and antioxidant constituents of the leaves of Flemingia grahamiana", Journal of Natural Products, vol. 77, no. 9, pp. 2060 – 2067, 2014.
W-J. Kang, D-H. Li, T. Han, L. Sun, Y-B. Fu, C-M. Sai, Z-L. Li, and H-M. Hua, "New chalcone and pterocarpoid derivates from the roots of Flemingia philippinensis with antiproliferative activity and apoptosis-inducing property", Fitoterapia, vol. 112, pp 222-228, 2016.
G. Xie, B. Lin, X. Qin, G. Wang, Q. Wang, J. Yuan, C. Li, and M. Qin, "New flavonoids with cytotoxicity from the roots of Flemingia latifolia", Fitoterapia, vol. 104, pp 97-101, 2015.
W-C. Lai, Y-T. Tsui, A.N.B. Singab, M. El-Shazly, Y-C. Du, T-L. Hwang, C-C. Wu, M-H. Yen, C-K. Lee, M-F. Hou, Y-C. Wu, and F-R. Chang, "Phyto-SERM constitutes from Flemingia macrophylla", International Journal of Molecular Science, vol. 14, no. 8, pp 15578–15594, 2013.
S-Y. Jeong, M. Chang, S-H. Choi, S-R. Oh, H-H. Wu, Y. Zhu, X-M. Gao, X. Wang, B. Zhang, D-S. Lim, J.Y. Lee, S-D. Kim, and Y.S. Kim, "Estrogenic effects of phytoestrogens derived from Flemingia strobilifera in MCF-7 cells and immature rats", Achives of Pharmacal Research, vol. 41, no. 5, pp 519–529, 2018.
J.Y. Kim, Y. Wang, Y.H. Song, Z. Uddin, Z.P. Li, Y.C. Ban, and K.H. Park, "Antioxidant activities of phenolic metabolites from Flemingia philippinensis merr. et rolfe and their application to DNA damage protection", Molecules, vol. 23, no. 4, pp 1–13, 2018.
T.S. Tjahjandarie, M. Tanjung,R.D. Saputri, M.F. Aldin, R.A. Susanti, N.P. Pertiwi, R.S. Wibawa, and I.N. Halizah, “Cytotoxicity evaluation of two new chalcones from the leaves of Flemingia macrophylla (Willd.) Merrâ€, Phytochemistry Letters, 44, pp. 78-81, 2021.
M.F. Aldin, R.D. Saputri, T.S. Tjahjandarie, and M. Tanjung, “Aktivitas antikanker senyawa stilbenoid dari daun Macaranga aleuritoidesâ€, Pharmacy Medical Journal, vol. 2, no. 1, pp. 1-7, 2019.
R.D. Saputri, T.S. Tjahjandarie, M. Tanjung, “Meliglabrin, a new flavonol derivative from the leaves of Melicope glabra (Blume) T.G. Hartleyâ€, Natural Product Sciences, 24, no. 3, pp. 155-158, 2018.
R.D. Saputri, T.S. Tjahjandarie, and M. Tanjung, “Two novel coumarins bearing an acetophenone from the leaves of Melicope quercifoliaâ€, Natural Product Research, 35, no. 8, pp. 1256-1261, 2021.
M. Tanjung, T.S. Tjahjandarie, R.D. Saputri, D. K. Baharrani, M. F. Rachman, and Y. M. Syah. “Calotetrapterins A-C, three new pyranoxanthones and their cytotoxicity from the stem bark of Calophyllum tetrapterum Miqâ€, Natural Product Research, 35, no. 18, pp. 407-412, 2021.
T.S. Tjahjandarie, M. Tanjung, R.D. Saputri, P. B. Nadar, M. F. Aldin, E. Marliana, and A. Permadi. “Flavestin K, an isoprenylated stilbene from the leaves of Macaranga recurvat Gageâ€, Natural Product Sciences, 25, no 3, pp. 244-247, 2019.
T.S. Tjahjandarie, and M. Tanjung, “Phenolic compounds from the stem bark of Erythrina orientalis and their cytotoxic and antioxidant activitiesâ€, Der Pharma Chemica, vol. 7, no. 1, pp. 206-211, 2015.
Y. Wang, M. J. Curtis-Long, H. J. Yuk, D. W. Kim, X. F. Tan, and K. H. Park. “Bacterial neuraminidase inhibitory effects of preylated isoflavones from the roots of Flemingia philippinensisâ€. Bioorganic and Medicinal Chemistry, vol. 21, no. 21, pp. 6398-6404, 2013.
Y-C. Shiao, C-N. Wang, W-Y. Wang, and Y-L. Lin. “Neuroprotective flavonoids from Flemingia macrophyllaâ€, Planta Medic, vol. 71, no. 9, pp. 835-840, 2005.
C. Peterson, A. Fristad, R. Tsao, and J. R. Coats, “Osajin and pomiferin, two isoflavones purified from osage orange fruits, tested for repellency to the maize weevil (Coleoptera: Curculionidae)â€, Physiological and Chemical Ecology, vol. 29, no. 6, pp. 1133-1137, 2000.
M.F. Aldin, T.S. Tjahjandarie, R.D. Saputri, and M. Tanjung, “Macasiamenene V, a new stilbenoid from the leaves of Macaranga inermisâ€, Natural Product Sciences, 27, no. 1, pp. 45-48, 2021.
J.S. Iffah, M. Tanjung, T.S. Tjahjandarie, R.D. Saputri, and M.F. Aldin, “Senyawa santon terisoprenilasi dari kulit batang Cratoxylum arborescens dan aktivitas sitotoksiknya terhadap sel HeLaâ€, Chimica et Natura Acta, vol 8, no. 2, pp. 72-76, 2021.
E. Marliana, W. Astuti, K. Kosala, R. Hairani, T.S. Tjahjandarie, and M. Tanjung, “Chemical composition and anticancer activity of Macaranga hosei leaves, Asian Journal Chemistryâ€, vol 30, no. 4, pp. 795–798, 2018.
T.S. Tjahjandarie, R.D. Saputri, N.A. Putri, B.K. Dewi, and M. Tanjung, “Dua isomer senyawa flavonoid dari batang Sesbaniaa grandifloraâ€, Jurnal Farmasi Medica, vol 3, no. 1, pp. 35-39, 2020.
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