Alkaloids and Styryllactones from Goniothalamus Cheliensis Wuttichai Jaidee Mae Fah Luang University

View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Research Online University of Wollongong Research Online Faculty of Science, Medicine and Health - Papers: Faculty of Science, Medicine and Health Part B 2019 Alkaloids and styryllactones from Goniothalamus cheliensis Wuttichai Jaidee 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] Chatchai Muanprasat Mahidol University See next page for additional authors Publication Details Jaidee, W., Andersen, R. J., Patrick, B. O., Pyne, S. G., Muanprasat, C., Borwornpinyo, S. & Laphookhieo, S. (2019). Alkaloids and styryllactones from Goniothalamus cheliensis. Phytochemistry, 157 8-20. Research Online is the open access institutional repository for the University of Wollongong. For further information contact the UOW Library: [email protected] Alkaloids and styryllactones from Goniothalamus cheliensis Abstract Eight previously undescribed compounds, including four alkaloids and five styryllactones together with 36 known compounds were isolated from the twig and leaf extracts of Goniothalamus cheliensis. Their trs uctures were elucidated by extensive analysis of their spectroscopic data. The bsa olute configuration of (−)- (4S,5S,6R,7S,8S)-goniochelienlactone and (−)-(4S,5S,6R,7S,8S)-7-acetylgoniochelienlactone were established from single crystal X-ray analysis using Cu Kα radiation. The bsa olute configurations of the other related compounds were identified by comparisons of their ECD spectra with those of related known compounds. Most of the isolated compounds were evaluated for their cytotoxicities against human colorectal cancer cells (HCT-116). Griffithazanone A was the most potent with an IC50 value of 2.39 μM. Publication Details Jaidee, W., Andersen, R. J., Patrick, B. O., Pyne, S. G., Muanprasat, C., Borwornpinyo, S. & Laphookhieo, S. (2019). Alkaloids and styryllactones from Goniothalamus cheliensis. Phytochemistry, 157 8-20. Authors Wuttichai Jaidee, Raymond J. Andersen, Brian O. Patrick, Stephen G. Pyne, Chatchai Muanprasat, Suparerk Borwornpinyo, and Surat Laphookhieo This journal article is available at Research Online: https://ro.uow.edu.au/smhpapers1/274 1 Alkaloids and styryllactones from Goniothalamus cheliensis 2 Wuttichai Jaidee a,b , Raymond J. Andersen c, Brian O. Patrick c, Stephen G. Pyne d, 3 Chatchai Muanprasat e,f , Suparerk Borwornpinyo g, Surat Laphookhieo a,b, * a 4 Center of Chemical Innovation for Sustainability (CIS), Mae Fah Luang University, 5 Chiang 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, 8 Vancouver, BC, Canada V6T 1Z1 9 d School of Chemistry, University of Wollongong, Wollongong, New South Wales, 10 2522, Australia 11 e Department of Physiology, Faculty of Science, Mahidol University, Rajathevi, 12 Bangkok 10400, Thailand 13 f Excellent Center for Drug Discovery, Faculty of Science, Mahidol University, 14 Rajathevi, Bangkok 10400, Thailand 15 g Department of Biotechnology, Faculty of Science, Mahidol University, Rajathevi, 16 Bangkok 10400, Thailand 17 * Corresponding author. 18 E-mail address : [email protected] (S. Laphookhieo) 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 1 42 ABSTRACT 43 Eight previously undescribed compounds, including four alkaloids and five 44 styryllactones together with 36 known compounds were isolated from the twig and 45 leaf extracts of Goniothalamus cheliensis . Their structures were elucidated by 46 extensive analysis of their spectroscopic data. The absolute configuration of (−)- 47 (4 S,5 S,6 R,7 S,8 S)-goniochelienlactone and (−)-(4 S,5 S,6 R,7 S,8 S)-7- 48 acetylgoniochelienlactone were established from single crystal X-ray analysis using 49 Cu K α radiation. The absolute configurations of the other related compounds were 50 identified by comparisons of their ECD spectra with those of related known 51 compounds. Most of the isolated compounds were evaluated for their cytotoxicities 52 against human colorectal cancer cells (HCT-116). Griffithazanone A was the most 53 potent with an IC 50 value of 2.39 µM. 54 Keywords: Goniothalamus cheliensis, Annonaceae, Alkaloids, Styryllactones 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 2 83 1. Introduction 84 Goniothalamus is the one of the largest genera of the family Annonaceae. It is 85 distributed throughout the world and is found predominately in Southeast Asia (Duc 86 et al., 2016). This genus includes about 160 species, of which 25 are found in 87 Thailand (Saunders et al., 2008). Some species have been used as traditional 88 medicines for the treatment of fever (Surivet and Vatèle, 1999), scabies (Heyne, 89 1950), edema, rheumatism (Jiang et al., 2011), tympanites (Quismbing, 1951), and 90 typhoid fever (Efdi et al., 2010). Goniothalamus cheliensis Hu is a large green tree 91 which is distributed throughout the forested slopes at 1500 m, in South Yunnan, 92 China (Saunders et al., 2008). This plant is found in the Northern parts of Thailand, 93 especially in Chiang Rai and Nan Provinces. Previous phytochemical investigations 94 of G. cheliensis , resulted in the isolation and identification of various types of 95 compounds, including styryllactones (Jiang et al., 2011; Wang et al., 2002; Zhu et al., 96 2012, Duc et al., 2016; Wang et al., 2003, Si et al., 2002), alkaloids (Jiang et al., 2008; 97 Duc et al., 2016), flavonoids (Wang et al., 2003, Sun et al., 2014), and acetogenins 98 (Duc et al., 2016). Many of these isolated compounds exhibited a variety of biological 99 activities such as antiproliferative (Sun et al., 2014), antifungal (Duc et al., 2016), 100 antimalarial (Duc et al., 2016) and cytotoxic activities (Wang et al., 2002; Zhu et al., 101 2012). In this study, we describe the isolation and identification of eight previously 102 undescribed compounds ( 1−3 and 5−9) and 36 known compounds (4 and 10 −44 ) 103 (Fig. 1) from the twig and leaf extracts of G. cheliensis collected from Doi Tung, 104 Chiang Rai Province, Thailand. Their cytotoxicities against the colon cancer cell line 105 HCT-116 are also reported. 106 2. Results and Discussion 107 The acetone extracts of the leaves and twigs of G. cheliensis were individually 108 subjected to separation by silica gel and Sephadex LH-20 column chromatography 109 (CC) followed by semipreparative RP-HPLC to afford eight previously undescribed 110 compounds (1−3 and 5−9) and 36 known compounds (4 and 10−44). The known 111 compounds were identified as 3-methyl-1H-benz[ f]indole-4,9-dione ( 4) (Efdi et al., 112 2010), (−)-goniobutenolide B ( 10) (Xu et al., 1994), 7-epi -(−)-goniobutenolide B ( 11) 113 (Popsavin et al., 2012), (+)-goniodiol ( 12) (Fang et al., 1991), goniodiol-8- 114 monoacetate ( 13) (Wu et al., 1992), (+)-7-O-acetylgoniodiol ( 14) (Kampong et al., 115 2013), 8-acetoxy goniofufurone ( 15) (Zhang et al., 1998), isoaltholactone ( 16) 116 (Colegate et al., 1990), (+)-glaberide I ( 17) (Wu et al., 2013), (−)-glaberide I ( 18 ) 117 (Chang et al., 2015), (+)-syringaresinol ( 19 ) (Rahman et al., 2007; Yamauchi et al., 118 2015), (+)-medioresinol ( 20) (Nakasone et al., 1996; Yamauchi et al., 2015), (+)- 119 episyringaresinol ( 21) (Chen et al., 1998), (−)-syringaresinol ( 22) (Rahman et al., 120 2007; Yamauchi et al., 2015), (−)-episyringaresinol ( 23) (Lui et al., 2015), (−)- 121 pinoresinol ( 24) (Ming et al., 2001; Yamauchi et al., 2015), griffithazanone A ( 25) 122 (Zhang et al., 1999 ), cleistopholine ( 26) (Waterman and Muhammad, 1985), vanillic 123 acid ( 27) (Wu et al., 2000), p-hydroxybenzoic acid ( 28 ) (Rukachaisirikul et al., 2010), 124 p-methylbenzoicacid ( 29 ) (Zhou et al., 2013), 4-hydroxy-3-methoxypropiophenone 125 (30) (Ito et al., 2001), 3,5-dimethoxy-4-hydroxypropiophenone ( 31) (Zdero et al., 126 1986), p-hydroxybenzaldehyde ( 32 ) (Zhou et al., 2013), ethyl-4-hydrozybenzoate ( 33) 3 127 (Fan et al., 2016), trans -ferulic acid ( 34) (Salum et al., 2010), (–)-(3 R)-mellein methyl 128 ether ( 35) (Li et al., 2017), derrusnin ( 36) (East et al., 1969), 5-hydroxy-7-methoxy- 129 3',4'-methylene dioxy isoflavone ( 37) (Liping et al., 1996), derrustone ( 38 ) (Singh and 130 Muthukrishnan, 2005), robustone methyl ether ( 39 ) (East et al., 1969), derrugenin 131 (40) (Ortega et al., 2015), robustigenin ( 41) (Pancharoen et al., 2008), methyl-BRM-5 132 (42) (Tahara et al., 1986), trans -N-coumaroyltyramine ( 43) (Holzbach and Lopes, 133 2010 ), and N-trans-feruloyl tyramine ( 44) (Holzbach and Lopes, 2010) by comparison 134 of their spectroscopic data with those published. 135 Compound 1, goniochelienic acid A, was obtained as yellow needles. The core 136 structure of compound 1 was a benzo[ f]indole-4,9-dinone (Efdi et al., 2010) which 137 was confirmed by a single-crystal X-ray diffraction analysis using Mo K α radiation 138 (Fig. 5). The HRESIMS spectrum showed a [M + Na] + ion peak at m/z 294.0379 139 (calcd. for C14 H9NO 5Na, 294.0378) which also supported this structural assignment. 140 The 1H NMR spectrum of 1 (Table 1) showed resonances for a hydroxy proton of a 141 carboxylic acid [ δH 13.68 (CO OH )], a H-bonded hydroxy proton [δH 12.20 (1H, s, 8- 142 OH)], aromatic protons of an ABC spin system [δH 7.82 (1H, d, J = 7.4 Hz, H-5)/δC 143 120.7, 7.64 (1H, dd, J = 7.8, 7.4 Hz, H-6)/δC 136.0, 7.32 (1H, d, J = 7.8 Hz, H-7)/δC 144 126.1], an olefinic proton [ δH 7.74 (1H, s, H-2)/δC 138.0], and a N-methyl group [δH 145 4.15 (3H, s, N-CH 3)/δC 37.5].

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