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Oliveramine: An Isolated Alkaloid from Fagraea fragrans (Tembesu) Bark

1Department of Chemistry, Faculty of Sciences, Sriwijaya University, Inderalaya 30662, Ogan Ilir, Indonesia

2Department of Parasitology, Faculty of Medicine, Sriwijaya University, Palembang, Indonesia

Received: 13 Jun 2022; Revised: 22 Jul 2022; Accepted: 9 Aug 2022; Published: 31 Aug 2022.
Open Access Copyright 2022 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

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Abstract
This paper described the progress of phytochemical, especially alkaloids, work on Fagraea fragrans species (tembesu), Loganiaceae. A dimeric-pyridine alkaloid with molecular formula C20H20O4N2 has been successfully isolated from diethyl ether extracts from this plant’s barks. The alkaloid was explored from diethyl ether extracts using sulphuric acid (2%), then basified with ammonium hydroxide (25%) until the solution had a pH of 10.5. The later solution was extracted again with chloroform. The alkaloid residue was subjected to column chromatography and eluted with 10% acetone in chloroform. The chemical structure of the isolated dimeric-pyridine alkaloid was determined by LCMS/MS, 13C-NMR, and 1H-NMR spectroscopies. As a result, the isolated dimeric-pyridine alkaloid was closely similar to the oliveramine alkaloid, and this is also the first report about oliveramine from Fagraea fragrans (F. Fragrans).
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Keywords: Fagraea fragrans; bark; dimeric; pyridine; alkaloid

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  1. Suwaibah Madmanang, Naseebah Cheyeng, Sareefah Heembenmad, Wilawan Mahabusarakam, Jongkon Saising, Markus Seeger, Sasitorn Chusri, Suda Chakthong, Constituents of Fagraea fragrans with antimycobacterial activity in combination with erythromycin, Journal of Natural Products, 79, 4, (2016), 767-774 https://doi.org/10.1021/acs.jnatprod.5b00691
  2. Marie-Caroline Jonville, Marie Capel, Michel Frederich, Luc Angenot, Georges Dive, Robert Faure, Nadine Azas, Evelyne Ollivier, Fagraldehyde, a secoiridoid isolated from Fagraeafragrans, Journal of Natural Products, 71, 12, (2008), 2038-2040 https://doi.org/10.1021/np800291d
  3. Dasril Basir, Miksusanti Miksusanti, Dian Dwita Maizur, Susilawati Susilawati, Alkaloids of Fagraea fragrans (Tembesu) Fruits, IJFAC (Indonesian Journal of Fundamental and Applied Chemistry), 6, 3, (2021), 64-68 http://dx.doi.org/10.24845/ijfac.v6.i3.64
  4. D. Basir, Harmida, Julinar, Secondary metabolite profile of Fagraea fragrans fruits identified with LCMS/MS: The fruits for herbal cosmetic, AIP Conference Proceedings, 2020 https://doi.org/10.1063/5.0001088
  5. S. Rattanaburi, K. Kaikaew, R. Watanapokasin, S. Phongpaichit, W. Mahabusarakamb, A new lignan from the stem bark of Fagraea fragrans Roxb, Natural Product Research, 36, 7, (2022), 1851-1856 https://doi.org/10.1080/14786419.2020.1821020
  6. Watchara Sangsopha, Ratsami Lekphrom, Florian T. Schevenels, Brendan Byatt, Stephen G. Pyne, Nattakarn Sridadom, Kanlayanee Sawanyawisuth, A new secoiridoid glycoside and other constituents from the roots and flowers of Fagraea fragrans Roxb.(Gentianaceae), Natural Product Research, 35, 21, (2021), 3908-3917 https://doi.org/10.1080/14786419.2020.1749611
  7. Lynette K. Lambert, Benjamin P. Ross, Myrna A. Deseo, Mary J. Garson, Phytochemical study of fagraea spp. Uncovers a new terpene alkaloid with anti-inflammatory properties, Australian Journal of Chemistry, 64, 4, (2011), 489-494 https://doi.org/10.1071/CH10421
  8. Jinfeng Zhang, Yunqing Li, Yi Wang, The complete chloroplast genome sequence of Fagraea fragrans, Mitochondrial DNA Part B, 5, 1, (2020), 711-712 https://doi.org/10.1080/23802359.2020.1714504
  9. Alfred S. C. Wan, Y. L. Chow, Alkaloids of Fagraea fragrans Roxb, Journal of Pharmacy and Pharmacology, 16, 7, (1964), 484-486 https://doi.org/10.1111/j.2042-7158.1964.tb07497.x
  10. Nitin Chandel, Amit Chaudhary, Diksha Choudhary, Kapil Kumar Verma, The Potential and Outgoing Trends in Traditional, Phytochemical, and Ethnopharmacological Activity of Gentiana olivieri : A Comprehensive Review, International Journal of Pharmacy & Pharmaceutical Research, 22, 1, (2021), 272-279
  11. Karimjan Tayjanov, Nilufar Z. Mamadalieva, Michael Wink, Diversity of the mountain flora of Central Asia with emphasis on alkaloid-producing plants, Diversity, 9, 1, (2017), 11 http://dx.doi.org/10.3390/d9010011
  12. Prastyono Prastyono, Liliek Haryjanto, Estimasi Komponen Varian Semai Tembesu (Fagraea fragrans Roxb.) pada Umur 6 Bulan, Proceeding Biology Education Conference: Biology, Science, Enviromental, and Learning, 2017
  13. Evayusvita Rustam, Agus Astho Pramono, Morfology and development of flowering-fruiting of tembesu (Fragraea fragrans), Prosiding Seminar Nasional Masyarakat Biodiversitas Indonesia, 2018 https://doi.org/10.13057/psnmbi/m040102
  14. K. M. Wong, M. Sugumaran, Studies in Malesian Gentianaceae III: Cyrtophyllum reapplied to the Fagraea fragrans alliance, Gardens’ Bull Singapore, 64, 2, (2012), 497-510
  15. Zheng Pan, Feng Xiong, Yi-Long Chen, Guo-Guo Wan, Yi Zhang, Zhi-Wei Chen, Wen-Fu Cao, Guo-Ying Zhou, Traceability of geographical origin in Gentiana straminea by UPLC-Q exactive mass and multivariate analyses, Molecules, 24, 24, (2019), https://doi.org/10.3390/molecules24244478
  16. Dilfuza Egamberdieva, Dilfuza Jabborova, Medicinal plants of Uzbekistan and their traditional uses, Vegetation of Central Asia and environs, (2018), 211-237 https://doi.org/10.1007/978-3-319-99728-5_8
  17. T. U. Rakhmatullaev, S. Yu Yunusov, Alkaloids of Gentiana olivieri, Chemistry of Natural Compounds, 9, 1, (1973), 56-58 https://doi.org/10.1007/BF00563746
  18. Jun-Li Yang, Lei-Lei Liu, Yan-Ping Shi, Phytochemicals and biological activities of Gentiana species, Natural Product Communications, 5, 4, (2010), 649-664 https://doi.org/10.1177%2F1934578X1000500432
  19. Yu Pan, Yan-Li Zhao, Ji Zhang, Wan-Yi Li, Yuan-Zhong Wang, Phytochemistry and pharmacological activities of the genus Gentiana (Gentianaceae), Chemistry & Biodiversity, 13, 2, (2016), 107-150 https://doi.org/10.1002/cbdv.201500333
  20. Sayeed Ahmad, Sultan Zahiruddin, Bushra Parveen, Parakh Basist, Abida Parveen, Rabea Parveen, Minhaj Ahmad, Indian medicinal plants and formulations and their potential against COVID-19–preclinical and clinical research, Frontiers in Pharmacology, 11, 578970, (2021), 1-34 https://doi.org/10.3389/fphar.2020.578970
  21. Dwi Rahmasari Fatmawati, Danny Nur Wahyu Hidayat, Diah Kartika Sari, Rizky Riyami Putri, Jumina Jumina, Yehezkiel Steven Kurniawan, Potential of C-Phenylcalix[4]Resorcinarene Epoxide Compound as Drug Delivery Agent in Breast Cancer Cells MCF-7, Jurnal Kimia Sains dan Aplikasi, 25, 3, (2022), 7 https://doi.org/10.14710/jksa.25.3.123-129
  22. Michael Heinrich, Jeffrey Mah, Vafa Amirkia, Alkaloids Used as Medicines: Structural Phytochemistry Meets Biodiversity—An Update and Forward Look, Molecules, 26, 7, (2021), 1-18 https://doi.org/10.3390/molecules26071836

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