Synthesis of Nd-Pheophytin Complex and Its Hydrolysis into Nd-Pheophorbide from Katuk Leaves (Sauropus androgynous (L.) Merr)

Fadia Novayanti; Adhitiyawarman Adhitiyawarman; winda rahmalia

doi:10.21009/JRSKT.112.02

Authors

Fadia Novayanti Jurusan Kimia, Fakultas Matematika Dan Ilmu Pengetahuan Alam, Universitas Tanjungpura
Adhitiyawarman Adhitiyawarman Jurusan Kimia FMIPA Universitas Tanjungpura
winda rahmalia Jurusan Kimia, Fakultas Matematika Dan Ilmu Pengetahuan Alam, Universitas Tanjungpura

DOI:

https://doi.org/10.21009/JRSKT.112.02

Keywords:

Lanthanide, Neodimium, pheophytin complex, pheophorbide complex, synthesis

Abstract

Pheophorbide, as a chlorophyll derivative, has potential as a complexing ligand for heavy metals, including lanthanides. The synthesis of Nd-pheophytin complex and its more polar Nd-pheophorbide (pheophytin’s hydrolyzed product) were investigated using pheophytin isolated from Katuk’s (Sauropus androgynus L. Merr.) leaves. This study aims to determine the optimal reaction conditions and the complex characteristics. Pheophytin ligand and Nd were complexed under two different reaction conditions: room temperature and reflux at 65 °C for 10 hours. The pheophytin starting material was obtained by preparative thin-layer chromatography (PTLC), yielding 0.02 g. UV-vis analysis revealed characteristic absorption bands at 404 nm (Soret band) and 666 nm (Q band) in methanol, while FTIR spectra confirmed the presence of functional groups corresponding to pheophytin. The Nd-pheophytin complex formation was indicated by hypsochromic shifts in UV-vis spectra, suggesting the Nd³⁺ complexing. Fluorescence spectra between pheophytin and Nd-pheophytin showed distinct emission patterns, with pheophytin exhibiting peaks at 662 and 722 nm, while Nd-pheophytin displayed peaks with shoulders at 654 and 714 nm. Hydrolysis of Nd-pheophytin using 1 M NaOH at pH 10 produced Nd-pheophorbide. TLC analysis showed a decrease in the Rf value of Nd-pheophytin to Nd-pheophorbide from 0.95 to 0.43, with tailing, attributed to the higher polarity of pheophorbide. These findings confirm the successful synthesis and hydrolysis of the Nd-pheophytin complex.

References

Adhamatika, A., & Murtini, S. E. (2021). Pengaruh Metode Pengeringan Dan Persentase Teh Kering Terhadap Karakteristik Seduhan Teh Daun Bidara (Ziziphus mauritiana L.). Jurnal Pangan Dan Agroindustri, 9(4), 196–207. https://doi.org/https://doi.org/10.21776/ub.jpa.2021.009.04.1

Adhitiyawarman, & Lowe, M. P. (2018). A New Zinc(II) Responsive MRI Contrast Agent. Research Journal of Chemistry and Environment, 22(Special Issue II), 22–30.

Anjelia, R., Silalahi, I. H., & Gusrizal. (2019). Sintesis Dan Transisi Elektronik Senyawa Kompleks Klorofil Dengan Logam (M = Co2+, Fe3+). Indonesian Journal of Pure and Appled Chemistry, 2(3), 102–111. https://doi.org/https://doi.org/10.26418/indonesian.v2i3.36891

Choi, C.-S. (2019). The Design of Photobiological Active Molecular Model For Photodynamic Therapy.

Das, D., Patil, S., & Gajbhiye, A. (2022). Heme-Mimetic Potential of Iron Conjugated Pheophytin-I in Attenuating Oxidative Stress-Induced Cellular and Vascular Toxicity. Journal of Pharmacy and Bioallied Sciences, 14(Suppl 1), S115–S122. https://doi.org/10.4103/jpbs.jpbs_654_21

Erzunov, D. A., Bontar, A. A., Futerman, N. A., Vashurin, A. S., & Pukhovskaya, S. G. (2022). A simple Way To Obtain Stable Mono-decker Porphyrin Complexes With Heavy Metal Atoms. Inorganic and Nano-Metal Chemistry, 52(2), 181–184. https://doi.org/10.1080/24701556.2021.1884712

Jin, G.-Q., Chau, C. V., Arambula, J. F., Gao, S., Sessler, J. L., & Zhang, J.-L. (2022). Lanthanide Porphyrinoids as Molecular Theranostics. Chemical Society Reviews, 51(14), 6177–6209. https://doi.org/10.1039/D2CS00275B

Kang, Y. R., Park, J., Jung, S. K., & Chang, Y. H. (2018). Synthesis, characterization, and functional properties of chlorophylls, pheophytins, and Zn-pheophytins. Food Chemistry, 245, 943–950. https://doi.org/10.1016/j.foodchem.2017.11.079

Kusmita, L., Puspitaningrum, I., & Limantara, L. (2015). Identification, Isolation and Antioxidant Activity of Pheophytin from Green Tea (Camellia Sinensis (L.) Kuntze). Procedia Chemistry, 14, 232–238. https://doi.org/10.1016/j.proche.2015.03.033

Lopes, C. R. B., & Courrol, L. C. (2023). Evaluation of Steady-State and Time-Resolved Fluorescence Spectroscopy as a Method for Assessing the Impact of Photo-Oxidation on Refined Soybean Oils. Foods, 12(9). https://doi.org/10.3390/foods12091862

Majid, T. S., & Muchtaridi, M. (2018). Aktivitas Farmakologi Ekstrak Daun Katuk (Sauropus androgynus (L.) Merr). Farmaka, 16(2), 398–405.

Mohammed, H. A., Al-Omar, M. S., El-Readi, M. Z., Alhowail, A. H., Aldubayan, M. A., & Abdellatif, A. A. H. (2019). Formulation of Ethyl cellulose Microparticles Incorporated Pheophytin a Isolated From Suaeda Vermiculata for Antioxidant and Cytotoxic Activities. Molecules, 24(8). https://doi.org/https://doi.org/10.3390/molecules24081501

Nandiyanto, A. B. D., Oktiani, R., & Ragadhita, R. (2019). How To Read and Interpret FTIR Spectroscope of Organic Material. Indonesian Journal of Science and Technology, 4(1), 97–118. https://doi.org/10.17509/ijost.v4i1.15806

Notonegoro, H., Djamaludin, H., Setyaningsih, I., & Tarman, K. (2022). Fraksinasi Flavonoid Spirulina platensis dengan Metode Kromatografi Lapis Tipis dan Aktivitas Inhibisi Enzim α-Glukosidase. Jurnal Kelautan Tropis, 25(3), 299–308. https://doi.org/10.14710/jkt.v25i3.13905

Nurdin, Kushart, C. M., Tanziha, I., & Januwat, M. (2009). Kandungan Klorofil Berbagai Jenis Daun Tanaman Dan Cu-Turunan Klorofil Serta Karakteristik Fisiko-Kimianya. Jurnal Gizi Dan Pangan, 4(1), 13–19. https://doi.org/https://doi.org/10.25182/jgp.2009.4.1.13-19

Orzeł, Waś, J., Kania, A., Susz, A., Rutkowska-Zbik, D., Staroń, J., Witko, M., Stochel, G., & Fiedor, L. (2017). Factors Controlling The Reactivity of Divalent Metal Ions Towards Pheophytin a. Journal of Biological Inorganic Chemistry, 22(6), 941–952. https://doi.org/10.1007/s00775-017-1472-1

Pasaribu, M. N., Pramesti, R., & Sedjati, S. (2025). Pembentukan Zona Hambat Patogen Staphylococcus aureus dan Escherichia coli terhadap Pigmen Fukosantin Ekstrak Sargassum polycystum C. Agardh. Journal of Marine Research, 14(1), 72–78. https://doi.org/10.14710/jmr.v14i1.47898

Pesang, M. D., Ngginak, J., Kase, A. G. O., & Bisilissin, C. L. B. (2020). Komposisi Pigmen pada Ulva sp., Padina australis dan Hypnea sp. dari Pantai Tablolong Provinsi Nusa Tenggara Timur. Jurnal Kelautan Tropis, 23(2), 225–233. https://doi.org/10.14710/jkt.v23i2.5912

Pratiwi, R., Wahyuni, N., Hairil Alimuddin, A., & Hadari Nawawi, J. H. (2015). Uji Fotostabilitas TiO2-Klorofil Dari Mikroalga (Chlorella sp.). Jurnal Kimia Khatulistiwa, 4(3), 59–64.

Quach, H. T., Steeper, R. L., & William Griffin, G. (2004). An Improved Method for the Extraction and Thin-Layer Chromatography of Chlorophyll a and b from Spinach. Journal of Chemical Education, 81(3), 385–387. https://doi.org/https://doi.org/10.1021/ED081P385

Resita, D., Merdekawati, Susanto, AB., & Limantara, L. (2010). Kandungan dan Komposisi Pigmen Sargassum sp. pada Perairan Teluk Awur, Jepara dengan Perlakuan Segar dan Kering. Jurnal Perikanan (Journal of Fisheries Sciences), XII(1), 11–19. https://www.researchgate.net/publication/337621101

Riansyah, H., Maulidya Maharani, D., Nugroho, A., Teknologi Industri Pertanian, J., Pertanian, F., Lambung Mangkurat Jalan Yani Km, U. A., & Selatan, K. (2021). Intensitas Dan Stabilitas Warna Ekstrak Daun Pandan, Suji, Katuk, Dan Kelor Sebagai Sumber Pewarna Hijau Alami. Nal Riset Teknologi Industri, 15(1), 103–112. https://doi.org/https://doi.org/10.26578/jrti.v15i1.6549

Saide, A., Lauritano, C., & Ianora, A. (2020). Pheophorbide A: State of the art. Marine Drugs, 18(5), 257. https://doi.org/10.3390/md18050257

Saleh, I., & Halidun, W. O. N. S. (2022). Identifikasi Pigmen Klorofil Dan Celah Energi Pada Daun Cincau (Cyclea Barbata) Sebagai Fotosensitizer Alami Untuk Aplikasi DSSC. Jurnal Kumparan Fisika, 5(1), 31–36. https://doi.org/10.33369/jkf.5.1.31-36

Sandiningtyas, R. D., & Suendo, V. (2010). Isolation of Chlorophyll a From Spinach and Its Modification Using Fe2+ In Photostability Study. The International Conference on Mathematics and Natural Sciences. https://www.researchgate.net/publication/265490978

Sekali, E. E. K., Wartini, N. M., & Suhendra, L. (2020). Karakteristik Ekstrak Aseton Pewarna Alami Daun Singkong (Manihot Esculenta C.) pada Perlakuan Ukuran Partikel Bahan dan Lama Maserasi. Jurnal Ilmiah Teknologi Pertanian Agrotechno, 5(2), 49–58. https://doi.org/https://doi.org/10.24843/jitpa.2020.v05.i02.p02

Sumiati. (2021). Penggunaan Pelarut Etanol dan Aseton pada Prosedur Kerja Ekstraksi Total Klorofil Daun Jati (Tectona grandis) dengan Metode Spektrofotometri. Indonesian Journal of Laboratory, 4(1), 30–35. https://doi.org/https://doi.org/10.22146/ijl.v4i1.65418

Suria, Y., Ali, N. F. M., & Masrida, W. ode. (2024). Karakterisasi Senyawa Antibakteri Dari Ekstrak Biji Labu Kuning (Cucurbita Moschata Duch). Jurnal Penelitian Sains Dan Kesehatan Avicenna, 3(3), 214–226. https://doi.org/https://doi.org/10.69677/avicenna.v3i3.106

Syahadat, A., Siregar, N., Studi, P., Program, F., Fakultas, S., Universitas, K., Royhan, A., & Kotapadangsidimpuan, D. (2020). Skrining Fitokimia Daun Katuk (Sauropus androgynus) Sebagai Pelancar ASI. Jurnal Kesehatan Ilmiah Indonesia, 5(1), 85–89. https://doi.org/https://doi.org/10.51933/health.v5i1.246

Syahputri, Y., Sutanto, Mahmudin, M. D., & Ramadhan, M. R. I. (2024). Detection of Pb(II) and Cr(III) Using Dy(III) Ion with Pyrazoline Derivatives Ligand. Jurnal Sains Natural, 14, 135–141. https://doi.org/https://doi.org/10.31938/jsn.v14i3.733

Tao, Y., Zhao, G., Yang, J., Ikeda, S., Jiang, J., Hu, T., Chen, W., Wei, Z., & Hong, F. (2001). Determination of double decker sandwich structured La-substituted chlorophyll a by EXAFS. J. Synchrotron Radiat, 8, 996–997. https://doi.org/https://doi.org/10.1107/s0909049500019543

Usman, Fitri, I. A., & Suryani, C. L. (2022). Pengaruh Jenis Medium Sumber Zn2+ dan Lama Blanching Terhadap Aktivitas Antioksidan Bubuk Simplisia Sambiloto (Andrographis Paniculata). Prosiding Seminar Nasional Mini Riset Mahasiswa, 1(2), 54–66.

Utami, W. W., & Anjani, G. (2016). Yogurt Daun Katuk Sebagai Salah Satu Alternatif Pangan Berbasis Laktogenik. Journal of Nutrition College, 5(4), 513–519. https://doi.org/https://doi.org/10.14710/jnc.v5i4.16467

Wahyuni, I. T., & Setiarso, P. (2022). Karakterisasi Elektrokimia Ekstrak Klorofil dari Daun Salam (Syzgium polyanthum) pada pH Basa sebagai Sensitizer pada Dye Sensitized Solar Cell (DSSC). Alchemy: Journal Of Chemistry, 10(2), 41–47. https://doi.org/https://doi.org/10.18860/al.v10i2.14109

Wihenti, A. I., Supriyadi, & Santoso, U. (2021). Karakteristik Fisik dan Kimia Kelobot Jagung (Zea mays) Sebagai Bahan Pengemas. Warta IHP, 38(1), 46–53. https://doi.org/https://doi.org/10.32765/wartaihp.v38i1.6416

Yusprianto, M., Zaharah, T. A., & Silalahi, I. H. (2021). Bandgap Energy of TiO₂/M-Chlorophyll Material (M=Cu2+, Fe3+). Jurnal Kimia Sains Dan Aplikasi, 24(4), 126–135. https://doi.org/10.14710/jksa.24.4.126-135