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Amide Alkaloids from Scopolia Tangutica

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Amide Alkaloids from Scopolia Tangutica 1124 Original Papers Amide Alkaloids from Scopolia tangutica Authors Zhen Long 1*, Yan Zhang2*, Zhimou Guo 1, Lien Wang 2, Xingya Xue1, Xiuli Zhang1, Shisheng Wang3, Zhiwei Wang2, Olivier Civelli2, Xinmiao Liang 1 Affiliations 1 Key Laboratory of Separation Science for Analytical Chemistry, Key Lab of Natural Medicine, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Peopleʼs Republic of China 2 Department of Pharmacology, University of California, Irvine, California, United States 3 School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian, Peopleʼs Republic of China Key words Abstract gesia in mice. The analgesic effect was recorded l" Scopolia tangutica ! using the tail-flick assay and was reversed by na- l" Solanaceae Four new hydroxycinnamic acid amides, scotan- loxone. l" alkaloid amines A–D(1–4), and seven known alkaloids, in- l" hydroxycinnamic acid amide cluding N1,N10-di-dihydrocaffeoylspermidine (5), l" µ‑opioid receptor scopolamine (6), anisodamine (7), hyoscyamine Abbreviations (8), anisodine (9), caffeoylputrescine (10), and ! N1-caffeoyl-N3-dihydrocaffeoylspermidine (11), FLIPR: fluorometric imaging plate reader were obtained from the roots of Scopolia tanguti- assay ca. The present study represents the first recogni- HCA: hydroxycinnamic acid tion of hydroxycinnamic acid amides containing IR: infrared putrescine or spermidine in S. tangutica.Com- SCX: strong cation exchange pound 1, in particular, contains a moiety resulting SPE: solid-phase extraction from the condensation of nortropinone and pu- TCM: traditional Chinese medicine received February 22, 2014 revised July 3, 2014 trescine. Compound 2 exhibited moderate agonist accepted July 9, 2014 activity at the µ-opioid receptor (EC50 = 7.3 µM). Supporting information available at Compound 2 was tested in vivo and induced anal- http://www.thieme-connect.de/products Bibliography DOI http://dx.doi.org/ 10.1055/s-0034-1382961 Published online August 15, Introduction a better understanding of the pharmaceutical ef- 2014 ! fects of S. tangutica and in pursuit of the discovery Downloaded by: University of California. Copyrighted material. Planta Med 2014; 80: Alkaloids and alkaloid-producing plants are well of novel analgesics, a systematic investigation was 1124–1130 © Georg Thieme – Verlag KG Stuttgart · New York · known for their broad range of bioactivities [1 carried out on this herb. We describe herein the ISSN 0032‑0943 6]. As a part of our ongoing work on identifying purification and structure determination of four new analgesic compounds from TCMs, we re- new hydroxycinnamic acid (HCA) amides (1–4) Correspondence – Xinmiao Liang cently became interested in Scopolia tangutica and seven known alkaloids (5 11) from S. tangu- Key Laboratory of Separation Maxim (Solanaceae), a TCM that has been used tica. Given that opioid receptor agonists are well Science for Analytical Chemistry for centuries as an analgesic by the native people known to induce analgesia, all alkaloids obtained Dalian Institute of Chemical Physics on the Qinghai-Tibetan Plateau of mainland Chi- in this study were tested for their ability to inter- Chinese Academy of Sciences na. This herb produces high levels of tropane alka- act with the opioid receptors. 457 Zhongshan Road loids [1,7–10], including hyoscyamine [11], ani- Dalian 116023 – Peopleʼs Republic of China sodine [12], anisodamine [12 14], and scopola- [email protected] mine [15]. These compounds primarily affect the Results and Discussion parasympathetic nervous system and act as anti- ! Correspondence Xiuli Zhang cholinergic agents. In recent years, several studies The air-dried roots of S. tangutica were extracted Key Laboratory of Separation have been conducted on the tropane alkaloid with a mixture of EtOH and H2O (95/5, v/v). The Science for Analytical Chemistry components of this plant [16,17], while studies resulting alkaloids were enriched by SPE and then Dalian Institute of Chemical Physics on the other constituents and their potential an- purified by reverse-phase liquid chromatography Chinese Academy of Sciences algesic properties remain scarce. In order to foster and ion exchange liquid chromatography. Four 457 Zhongshan Road new (1–4; l" Fig. 1) and seven known alkaloids Dalian 116023 – l" Peopleʼs Republic of China (5 11; Fig. 1) were subsequently isolated and [email protected] * These authors contributed equally to this work. characterized. The known alkaloids were identi- Long Z et al. Amide Alkaloids from… Planta Med 2014; 80: 1124–1130 Original Papers 1125 Fig. 1 Structures of compounds from the roots of S. tangutica. 1 13 Table 1 H (600 MHz) and C NMR (150 MHz) spectroscopic data for compound 1 formate salt (DMSO-d6). Position δH (J in Hz) δC, type Position δH (J in Hz) δC, type 1/5 3.67, m 58.8, CH 14 165.8, C a 2a/4a 2.13 46.7, CH2 15 6.36 d (15.6) 119.1, CH 2b/4b 2.76a 3 208.2, C 16 7.22 d (15.6) 139.4, CH 7a/8a 2.03, m 27.4, CH2 17 126.8, C 7b/8b 1.54, m a 9 2.73 49.3, CH2 18 6.98 d (1.8) 114.3, CH 10 1.61, m 25.2, CH2 19 146.0, C 11 1.54, m 27.5, CH2 20 147.7, C 12 3.20, dd (12.6, 6.6) 38.8, CH2 21 6.74 d (8.4) 116.2, CH 13 8.07, t (6.0) NH 22 6.82 dd (8.4, 1.8) 120.8, CH Downloaded by: University of California. Copyrighted material. a Signal partially overlapped fied as N1,N10-di-dihydrocaffeoylspermidine (5) [18], scopola- three aromatic methine carbons, two nitrogen-bearing methy- mine (6) [19], anisodamine (7) [19], hyoscyamine (8) [20], aniso- lene carbons, two nitrogen-bearing methine carbons, one ole- dine (9) [21], caffeoylputrescine (10)[22–24], and N1-caffeoyl- finic bond, and six methylene carbons. The 1H NMR data revealed N3-dihydrocaffeoylspermidine (11) [2], based on their spectro- a typical ABX-type coupling pattern for the aromatic protons H- scopic data. The structures of these alkaloids are shown in 18 (δH 6.98, d, J = 1.8 Hz), H-21 (δH 6.74, d, J = 8.4 Hz), and H-22 " l Fig. 1. (δH 6.82, dd, J = 8.4, 1.8 Hz), indicating the presence of a 1,2,4-tri- Compound 1, a white powder, was obtained as the corresponding substituted benzene ring. The HMBC spectrum revealed the pres- 1 13 formate. Its molecular formula was determined as C20H26 N2O4 ence of long-range H- C couplings from H-16 (δH 7.22, d, 13 by C NMR spectroscopic and HRESIMS data in the positive ion J = 15.6 Hz) to C-17 (δC 126.8), C-18 (δC 114.3), and C-22 (δC + mode, which gave an m/z ion, 359.1954 for [M + H] (calcd. for 120.8), as well as correlations between H-21 and C-19 (δC 146.0) [M + H]+ = 359.1971). Consideration of the 13C NMR and DEPT and C-17. Correlations were also observed from H-18 and H-22 to spectra of 1 indicated that the compound contained nine indices C-20 (δC 147.7). Collectively, these findings indicated the pres- of hydrogen deficiency. The IR spectrum indicated the presence ence of a 4-substituted catechol moiety, as shown in l" Fig. 2. of hydroxyl (3390 cm−1), carbonyl (1727 cm−1), and amide The HMBC spectrum revealed correlations from the mutually −1 13 " (1656 cm ) groups. The C NMR and DEPT data (l Table 1) re- coupled H-16 and H-15 (δH 6.36, d, J = 15.6 Hz) to the C-14 amide vealed the presence of 20 carbon resonances in total (three of carbonyl carbon (δC 165.8), establishing the connection between which were equivalent), including two carbonyl carbons, two C-15 and C-14. 1H-1H COSY interactions were observed between oxygenated aromatic carbons, one aromatic quaternary carbon, H2-9 (δH 2.73), H2-10 (δH 1.61), H2-11 (δH 1.54), and H2-12 (δH Long Z et al. Amide Alkaloids from… Planta Med 2014; 80: 1124–1130 1126 Original Papers Fig. 2 Key 1H-1HCOSY(—) and HMBC (H→C) cor- relations of 1–4. (Color figure available online only.) Fig. 3 Key NOESY (↔) correlations of 1–4. (Color figure available online only.) −1 1 13 3.20, dd, J = 12.6, 6.6 Hz). HMBC correlations from H2-12 to C-14 (1633 cm ) groups. The tabulated Hand C assignments re- " 13 and from H2-9 to C-1/C-5 (δC 58.8) were observed. A comparison vealed by HSQC are listed in l Table 2.The C NMR and DEPT da- of the 1Hand13C NMR data of 1 with those of caffeoylputrescine ta (l" Table 2) revealed 26 carbon signals, including 12 aromatic [25] revealed that the two compounds were structurally similar, carbons, ten methylene carbons (including four nitrogen-bearing except for the substituted amino terminus. The molecular formu- methylene carbons), two carbonyl carbons, one oxygenated la of 1 suggested that its remaining moiety contained three indi- methine carbon, and one methoxy carbon. The 1H NMR spectrum ces of hydrogen deficiency. The 1Hand13C NMR data indicated exhibited two sets of ABX-type spin coupling interactions be- that this portion of the molecule contained seven carbon atoms, tween H-3 (δH 6.68, d, J = 1.8 Hz), H-5 (δH 6.54, dd, J =8.4, including one carbonyl group (δC 208.2), one set of equivalent 1.8 Hz), and H-6 (δH 6.61, d, J = 8.4 Hz), and H-24 (δH 6.57, d, Downloaded by: University of California. Copyrighted material. methines (δC 58.8; δH 3.67), and two sets of methylenes (δC 46.7; J = 1.8 Hz), H-27 (δH 6.71, d, J = 7.8 Hz), and H-28 (δH 6.42, dd, 1 1 δH 2.13 and 2.76, and δC 27.4; δH 2.03 and δH 1.54).
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