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Antioxidant Neolignans from the Twigs and Leaves of Mitrephora Wangii HU Wuttichai Jaidee Mae Fah Luang University

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Antioxidant Neolignans from the Twigs and Leaves of Mitrephora Wangii HU Wuttichai Jaidee Mae Fah Luang University University of Wollongong Research Online Faculty of Science, Medicine and Health - Papers: Faculty of Science, Medicine and Health Part B 2018 Antioxidant neolignans from the twigs and leaves of Mitrephora wangii HU Wuttichai Jaidee Mae Fah Luang University Wisanu Maneerat Mae Fah Luang University Raymond J. Andersen University of British Columbia Brian O. Patrick University of British Columbia Stephen G. Pyne University of Wollongong, [email protected] See next page for additional authors Publication Details Jaidee, W., Maneerat, W., Andersen, R. J., Patrick, B. O., Pyne, S. G. & Laphookhieo, S. (2018). Antioxidant neolignans from the twigs and leaves of Mitrephora wangii HU. Fitoterapia, 130 219-224. Research Online is the open access institutional repository for the University of Wollongong. For further information contact the UOW Library: [email protected] Antioxidant neolignans from the twigs and leaves of Mitrephora wangii HU Abstract Two new compounds, odoratisol E (1) and decurrenal A (2), together with 12 known compounds were isolated from the twig and leaf extracts of Mitrephora wangii HU (Annonaceae). All structures were elucidated by spectroscopic methods. The trs ucture of compound (+)-6 was also confirmed by X-ray diffraction analysis. The bsa olute configurations of odoratisol E and decurrenal A were determined by comparison of their electronic circular dichroism (ECD) spectra with those of related known compounds. Most of the isolated compounds were evaluated for their antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assays. Compounds 4 and (+)-6 displayed potent ABTS radical scavenging activity with IC50 values of 11.9 ± 1.8 and 10.8 ± 1.7 μM, respectively, which is better than that of standard compound, ascorbic acid, (IC50 = 19.3 ± 0.1 μM). Compound 9 showed moderate DPPH radical scavenging activity with an IC50 value of 38.7 ± 0.8 μM. Publication Details Jaidee, W., Maneerat, W., Andersen, R. J., Patrick, B. O., Pyne, S. G. & Laphookhieo, S. (2018). Antioxidant neolignans from the twigs and leaves of Mitrephora wangii HU. Fitoterapia, 130 219-224. Authors Wuttichai Jaidee, Wisanu Maneerat, Raymond J. Andersen, Brian O. Patrick, Stephen G. Pyne, and Surat Laphookhieo This journal article is available at Research Online: https://ro.uow.edu.au/smhpapers1/194 1 Antioxidant neolignans from the twigs and leaves of Mitrephora wangii HU 2 Wuttichai Jaidee a,b , Wisanu Maneerat a,b , Raymond J. Andersen c,d , Brian O. Patrick c, Stephen 3 G. Pyne e, Surat Laphookhieo a,b,* 4 a Center of Chemical Innovation for Sustainability (CIS), Mae Fah Luang University, Chiang 5 Rai 57100, Thailand 6 b School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand 7 c Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, 8 Canada V6T 1Z1 9 d Department of Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036 10 Main Mall, Vancouver, BC, Canada V6T 1Z1 11 e School of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, 12 Australia 13 14 15 16 17 18 19 20 21 22 23 * Corresponding author. 24 E-mail address : [email protected] (S. Laphookhieo) 1 25 ABSTRACT 26 Two new compounds, odoratisol E (1) and decurrenal A (2), together with 12 known 27 compounds were isolated from the twig and leaf extracts of Mitrephora wangii HU 28 (Annonaceae). All structures were elucidated by spectroscopic methods. The structure of 29 compound (+)-6 was also confirmed by X-ray diffraction analysis. The absolute 30 configurations of odoratisol E and decurrenal A were determined by comparison of their 31 electronic circular dichroism (ECD) spectra with those of related known compounds. Most of 32 the isolated compounds were evaluated for their antioxidant activity using the 2,2-diphenyl-1- 33 pikrylhydrazyl (DPPH) and 2,2 ′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) 34 assays. Compounds 4 and (+)-6 displayed potent ABTS radical scavenging activity with IC 50 35 values of 11.9 ± 1.8 and 10.8 ± 1.7 µM, respectively, which is better than that of standard 36 compound, ascorbic acid, (IC 50 = 19.3 ± 0.1 µM). Compound 9 showed moderate DPPH 37 radical scavenging activity with an IC 50 value of 38.7 ± 0.8 µM. 38 Keywords : Mitrephora wangii , Annonaceae, lignan, neolignan, antioxidant activity 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 2 57 1. Introduction 58 Free radicals, especially oxygen derived radicals produced from exogenous and 59 endogenous metabolic processes in the human body, are the cause of various diseases 60 including cirrhosis, arteriosclerosis, rheumatoid arthritis, cancer, inflammatory diseases, and 61 neurodegenerative diseases associated with aging [1‒4]. An imbalance between the formation 62 and neutralization of free radicals results in diseases and the acceleration of aging [1, 2]. 63 Normally, the human body has several mechanisms to protect cells, including enzymes such 64 as superoxide dismutase or catalase or antioxidant compounds such as ascorbic acid, 65 tocopherol, and glutathione [1 ‒3]. There are several literature reports that natural antioxidants 66 play crucial roles in the prevention or reduction of the risks of chronic diseases as well as in 67 the maintenance or promotion of a state of well-being or health [5 ‒7]. Plant secondary 68 metabolites such as flavonoids, neolignans, and terpenoids also play an important role in the 69 defense against free radicals. In addition, benzofuran-type neolignans exhibit a significant 70 inhibitory effect against lipid peroxidation [8]. Therefore, the discovery of active antioxidants 71 from natural resources has received much attention. 72 Mitrephora belongs to the Annonaceae family and approximately 48 species are 73 distributed throughout Asia and Australia. In Thailand, twelve species are found and some of 74 these have been used in Thai traditional medicine as health tonics [9,10]. Previous 75 phytochemical investigations of Mitrephora wangii HU twigs and leaves resulted in the 76 isolation and identification of neolignans, alkaloids, phenolic amides, and steroids, and 77 allantoin. Some of these compounds showed antifungal, cytotoxic, and antioxidant activities 78 [11 ‒17]. The objective of the present study was to evaluate the antioxidant potential and to 79 establish phytochemical characterization of the secondary metabolites isolated from the twig 80 and leaf extracts of M. wangii . Herein, we report two new compounds (1 and 2) together with 3 81 12 known compounds (3‒14 ) from the twig and leaf extracts of M. wangii . The antioxidant 82 activities, DPPH and ABTS assays, of most of these compounds are also reported. 83 2. Results and discussion 84 The EtOAc extract of the leaves of M. wangii was separated by column 85 chromatography (CC) using various stationary phases to yield two previously undescribed 86 compounds (1 and 2) together with four known compounds ( 11 ‒14 ). While the separation of 87 the EtOAc extract of the twigs yielded eight known compounds ( 3‒10 ). 88 Compound 1 was obtained as a colorless oil with a molecular formula of C 19 H22 O3 + 89 based on the [M + Na] ion peak at m/z 321.1469 (calcd for C 19 H22 O3Na, 321.1469) from 90 HRESITOFMS. The 1H NMR spectroscopic data of 1 (Table 1) displayed resonances for the 91 presence of two benzylic oxymethines [ δH 5.13 (1H, d, J = 8.7 Hz, H-7), 4.37 (1H, d, J = 9.3 92 Hz, H-7ʹ)], two methines [ δH 2.23 (1H, m, H-8), 1.74 (1H, m, H-8ʹ)], two methyl groups [ δH 93 1.02 (3H, d, J = 6.5 Hz, H-9ʹ), 0.63 (3H, d, J = 6.9 Hz, H-9)], two aromatic rings having an 94 AA ʹBB ʹ spin system [δH 7.37 (2H, d, J = 8.4 Hz, H-2ʹ/6ʹ), 7.31 (2H, d, J = 8.4 Hz, H-2/6), 95 6.88 (2H, d, J = 8.4 Hz, H-3/5), 6.85 (2H, d, J = 8.4 Hz, H-3ʹ/5ʹ)] and a methoxy group [ δH 96 3.81 (3H, s, OMe-4)]. The 13 C NMR spectroscopic data revealed resonances, representing 19 97 carbons including, 12 aromatic carbons, four methine carbons, and three methyl carbons. The 98 NMR spectroscopic data of 1 were similar to those of (7 S,8 R,7 ʹR,8 ʹS)-4ʹ-hydroxy-4-methoxy- 99 7,7 ʹ-epoxylignan ( 15 ) isolated from Terminalia superba by Wansi et al. in 2007 (Table 1). 100 The major differences between these two compounds were observed from the following 101 NMR spectroscopic data of the furan. The two methyl groups of 15 have a syn relationship 102 with resonances at δH 0.55 (3H, d, J = 5.7 Hz, Me-9)/ δC 11.8 and δH 0.57 (3H, d, J = 5.7 Hz, 103 Me-9′)/ δC 11.8 [18], whereas in compound 1 the methyl groups are anti and resonate at δH 104 0.63 (3H, d, J = 6.9 Hz, Me-9)/δC 14.4 and 1.02 (3H, d, J = 6.5 Hz, Me-9ʹ)/δC 14.4. The 105 protons and carbons at C-7 and C-7′ of compound 15 are magnetically equivalent and 4 1 13 106 resonance at δH 5.10 (2H, d, J = 5.8 Hz, H-7 and H-7′)/ δC 82.6, while the H and C NMR 107 spectra of compound 1 displayed two set of resonances, δH 5.13 (1H, d, J = 8.7 Hz, H-7)/ δC 108 82.3 and δH 4.37 (1H, d, J = 9.3 Hz, H-7′)/ δC 86.7. The cis/trans relationship of the 109 tetrahydrofuran substituents were determined from the resonances of oxymethine (H-7/7 ʹ) 110 and methyl protons as described by Giang et al .
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