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A New 1, 10-Secoguaianolide from the Aerial Parts of Artemisia Anomala

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A New 1, 10-Secoguaianolide from the Aerial Parts of Artemisia Anomala Chinese Journal of Natural Chinese Journal of Natural Medicines 2012, 10(5): 0358−0362 Medicines doi: 10.3724/SP.J.1009.2012.00358 A new 1, 10-secoguaianolide from the aerial parts of Artemisia anomala ZAN Ke1, CHEN Xiao-Qing2, TU Peng-Fei1* 1State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China; 2School of Traditional Chinese Medicine, Capital Medical University, Beijing 100069, China Available online Sep. 2012 [ABSTRACT] AIM: To study chemical constituents of the aerial parts of Artemisia anomala (Asteraceae). METHODS: The constituents were isolated with silica gel, ODS column chromatography and semi-preparative HPLC, and their structures were elucidated on the basis of physical characteristics and spectral data. RESULTS: Eight compounds were obtained, and their structures were identified as 3β-ethoxytanapartholide (1), (4S*, 5S*)-dihydro-5-[(1R*, 2S*)-2-hydroxy-2-methyl-5-oxo-3-cyclopenten-1-yl]-3-methylene-4-(3-oxobutyl)- 2(3H)-furanone (2), ligucyperonol (3), cyperusol C (4), santamarin (5), 1α, 2α, 3α, 4α, 10α -pentahydroxyguaia-11(13)-ene-12, 6α-olide (6), balanophonin (7), methyl 3-(2’-hydroxy-4’-methoxyphenyl) propanoate (8). CONCLUSION: Compound 1 was a new artifact, 4 and 8 were isolated from the genus Artemisia for the first time, and compounds 2–3, 5–7 were isolated from this plant for the first time. [KEY WORDS] Artemisia anomala; Chemical constituents; 1, 10-secoguaianolides; structure elucidation [CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2012)05-0358-05 1 Introduction 2 Experimental Artemisia anomala S. Moore (Chinese name ‘Nan-Liu- 2.1 Apparatus and reagents Ji-Nu’), a perennial herbaceous plant belonging to the As- Optical rotations were recorded on a Perkin-Elmer 243B teraceae family, has been commonly used in traditional Chi- digital polarimeter. NMR spectra were recorded on an Inova nese medicines as an analgesic, antibiotic, and as a wounds 500 spectrometer, operating at 500 MHz for 1H NMR and 13 healing agent [1]. Previous phytochemical investigations led 125 MHz for C NMR. The chemical shifts were given in δ to the isolation of flavonoids, coumarins, sesquiterpene lac- with TMS as internal standard. ESI-MS were measured on an tones and prostaglandin-like fatty acid derivatives from A. Agilent 6320 ion trap MS spectrometer. Semi-preparative anomala [2-13]. Compounds with antitumor and anti-inflam- HPLC was carried on a Waters 600 instrument with ODS matory activities were obtained from this plant by this labo- column (Agilent Technologies 250 mm × 9.4 mm, i.d., 5 μm) [6] ratory . As a continuation of this work, a systematically and C18 guard column with a 2996 photodiode array detector. phytochemical investigation on A. anomala has been carried Column chromatography was performed with silica gel (200–300 out. Herein, the isolation and structural elucidation of eight mesh, Qingdao Haiyang Chemical Works) and ODS (Merck). compounds from the aerial parts of A. anomala are reported. 2.2 Plant material The aerial parts of A. anomala were collected in Hang- zhou, Zhejiang Province, China in July, 2008. The plant ma- [Received on] 10-Oct.-2011 terial was authenticated by Prof. TU Peng-Fei. A voucher [Research funding] This project was supported by the National specimen (No. CM20071215) was deposited at the Herbar- Natural Science Foundation of China (No. 30973629), China Post- ium of the Peking University Modern Research Center for doctoral Science Foundation (No. 20110490251), Foundation of State Key Laboratory of Natural and Biomimetic Drugs in Peking Traditional Chinese Medicine. University (No. K20120213) and Capital TCM & Nursing Foun- 2.3 Extraction and isolation dation ( No.11ZYH08). Dried aerial parts (300 kg) of A. anomala were chopped [*Corresponding author] TU Peng-Fei: Prof., Tel: 86-10-82802750; and extracted three times with 95% EtOH. After evaporation E-mail: [email protected] of the solvent under reduced pressure, the residue was sus- These authors have no any conflict of interest to declare. pended in water and extracted with petroleum ether and chlo- 358 Chin J Nat Med Sep. 2012 Vol. 10 No. 5 2012 年 9 月 第 10 卷 第 5 期 ZAN Ke, et al. /Chinese Journal of Natural Medicines 2012, 10(5): 358−362 roform, successively. The residue of the CHCl3 layer (1 000 g) 1.24 (3H, t, J = 7.0 Hz) were displayed, which was confirmed was fractionated by silica gel column chromatography using by the 1H-1H COSY spectrum of 1. 1 a step-wise gradient of CHCl3 and MeOH to give 72 fractions. Apart from an ethoxyl, H NMR spectrum of 1 showed Fractions 25–29 (15 g) were subjected to ODS open column two methyl signals at δH 2.14 (s), 2.15 (s), a pair of olefinic chromatography (MeOH–H2O, 50 : 50 to 80 : 20) to afford protons at δH 6.34 (1H, d, J = 3.0 Hz), and 5.67 (1H, d, J = sub-fractions 1–5. Sub-fraction 2 was subjected to semi- 3.0 Hz) and a downfield signal of an O-substituted methine preparative HPLC eluted with MeOH–H2O(40 : 60) respec- proton at δH 4.98 (1H, d, J = 5.0 Hz). Complete analysis of tively, followed by repeated semi-preparative HPLC the 1H, 13C, and 1H-1H COSY spectra of 1 revealed the pres- (MeCN–H2O, 35 : 65) to yield 1 (10 mg) and 2 (5 mg). ence of a 2-oxo-butyl moiety in 1. The spectroscopic charac- Sub-fraction 3 was separated by semi-preparative HPLC teristics mention- ed above suggested that 1 might be a 1 13 (MeOH–H2O, 45 : 55) to give 3 (20 mg), 4 (9 mg) and 5 (18 secoguaianolide. Comparison of its H and C NMR data mg). Sub-fraction 4 was finally isolated by semi-preparative with those of the known compound 3-O-methyl-iso-seco- [14] HPLC (MeCN–H2O, 30 : 70) to afford 6 (9 mg). Sub-fraction tanapartholide revealed that they possessed a similar 5 was further purified by silica gel column chromatography skeleton, and that the difference between them was that the (CC) eluted with petroleum ether–acetone (3 : 1), repeatedly signal of the methoxyl group in the known compound disap- and finally affording 7 (15 mg) and 8 (30 mg). peared, replaced by an ethoxyl in 1. All of the protons and carbons were unambiguously assigned by analysis of 1H, 13C, 3 Results and Discussion 1H-1H COSY, HSQC spectra and confirmed by the HMBC Compound 1 was obtained as a colorless gum. The mo- spectrum (Fig. 2). The relative stereochemistry of 1 was es- lecular formula of C17H22O5 with seven degrees of unsatura- tablished by the NOESY spectrum. The relative configuration tion was deduced on the basis of HR-ESI-MS (m/z 329.137 0 of H-6 was assigned to be β, the same as the known com- + 13 13 [14] ([M + Na] ; (Calcd. for 329.136 5, C17H22O5Na). C NMR pound by detailed comparison of the C NMR data . In spectrum of 1 indicated 17 carbons including three carbonyl the NOESY spectrum, a weak effect was observed between carbons at δc 207.1, 202.6 and 169.9, four olefinic carbons at H-7 and H-3, whereas no NOEs could be discerned between δc 171.2, 138.4, 137.2 and 122.4, and two oxygen-bearing H-6 and H-7. These observations indicated that H-3 was carbons at δc 76.3 and 77.4. The 1H NMR revealed the pres- α-oriented. Thus, the structure of 1 was established and the ence of an ethoxy group at δH3.63 (2H, q, J = 7.0 Hz) and isolate named as 3β-ethoxytanapartholide. Fig. 1 Structures of compounds 1-8 Fig. 2 Significant 1H-1H COSY ( ), HMBC ( ) correlations for compound 1 4 Identification 22 Compound 1 Colorless gum. [α]D −38.5 (c 0.1, Fig. 3 Key NOESY ( ) of compound 1 2012 年 9 月 第 10 卷 第 5 期 Chin J Nat Med Sep. 2012 Vol. 10 No. 5 359 ZAN Ke, et al. /Chinese Journal of Natural Medicines 2012, 10(5): 358−362 MeOH); IR (KBr)νmax: 3 449, 2 925, 1 764, 1 711, 1 649, 1 2.52 (1H, m, H-7), 2.40 (1H, ddd, J = 3.5, 5.0, 17.0 Hz, 435, 1 346, 1 252, 1 203, 1 170, 1 113, 1 024, 818, 699 cm−1. H-2α), 2.35 (1H, d, J = 10.0 Hz, H-5), 2.09 (1H, m, H-8α), 1 13 H NMR spectral data (500 MHz, CDCl3) and C NMR 2.04 (1H, m, H-9β), 1.96 (1H, ddd, J = 3.5, 10.0, 17.0 Hz, spectral data (125 MHz, CDCl3), see Table 1; ESI-MS m/z H-2β), 1.83 (3H, s, H-15), 1.68 (1H, m, H-8β), 1.33 (1H, m, + + 13 329 [M + Na] ; HR-ESI-MS m/z: 329.137 0 [M + Na] H-9α), 0.88 (3H, s, H-14); C NMR (125 MHz, CDCl3) δ: (Calcd. for C17H22O5 Na, 329.136 5). 75.2 (C-1), 32.7 (C-2), 121.3 (C-3), 133.4 (C-4), 51.2 (C-5), Compound 2 Colorless gum (MeOH); positive ESI- 81.6 (C-6), 51.1 (C-7), 21.4 (C-8), 34.2 (C-9), 40.9 (C-10), + 22 1 MS m/z 301 [M + Na] . [α]D + 53° (c 0.2, CHCl3). H NMR 138.9 (C-11), 171.2 (C-12), 116.8 (C-13), 11.1 (C-14), 23.5 (500 MHz, CDCl3) δ: 7.44 (1H, d, J = 5.0 Hz, H-3), 6.31 (1H, (C-15).
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