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A New Tricyclic Undecose Nucleoside from Streptomyces scopuliridis RB72
A New Tricyclic Undecose Nucleoside from Streptomyces scopuliridis RB72
Bulletin of the Korean Chemical Society. 2014. Apr, 35(4): 1215-1217
Copyright © 2014, Korea Chemical Society
  • Received : September 09, 2013
  • Accepted : December 10, 2013
  • Published : April 20, 2014
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About the Authors
Chun Whan Choi
Jung-Sup Choi
Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea
Young Kwan Ko
Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea
Chang-Jin Kim
Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-333, Korea
Young Ho Kim
College of Pharmacy, Chungnam National University, Daejeon 305-764, Korea
Joa Sub Oh
Shi Yong Ryu
Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea
Gyu Hwan Yon
Korea Research Institute of Chemical Technology, Daejeon 305-600, Korea

Abstract
Keywords
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Experimental Section
General Procedures . The high resolution electrospray ionization (HRESI) and electron impact (EI) mass spectra were obtained using a Q-Tof micro LC-MS/MS instrument (Waters, USA) and CP3800-1200L (Varian, USA) mass spectrometer, respectively. 1 H-NMR (nuclear magnetic re-sonance) and 13 C-NMR spectra were recorded on a Bruker (Rheinstetten, Germany) AM 300, AMX 500 and AMX 800 NMR spectrometer using TMS as an internal standard. Column chromatography was performed using a silica gel (Kieselgel 60, 70-230 mesh, Merck, Darmstadt, Germany) and Lichroprep RP-18 (40-63 mm, Merck). Thin layer chromatography (TLC) analysis was performed on Kieselgel 60 F254 plates (silica gel, 0.25 mm, Merck) and spots were detected by examination with a UV lamp Spectroline Medel ENF-240 C/F (Spectronics Corporation, Westbury, NY) followed by the addition of 10% H 2 SO 4 reagent. Solvents and reagents were obtained from commercial sources and used without further purification. Unless otherwise noted, all chemicals were purchased from Sigma.
Fermentation, Extraction and Isolation. The Strepto-myces scopuliridis RB72 was cultivated in Bennet’s medium 80 L, [160 × 500 mL: yeast extrac (0.5 g), beef extract (0.5 g), N-Z amine type A (Sigma C0626, 1.0 g), glucose (5.0 g), agar (7.5 g), distilled water (0.5 L), autoclave at 121 °C for 15 minutes] for 10 days at 27 °C and then filtered with celite 545 (from Samchun Pure Chemical Co., Ltd). The filtrates were concentrated (121.4 g), passed through a diaion HP-20 (Adsorbent resin from Mitsubish Co., Ltd) column (15 cm × 50 cm), and washed with H 2 O (5.0 L) followed by MeOH (5.0 L). The MeOH extract was evaporated to dryness in vacuo and then the crude extract (22.1 g) was subjected to reversed phase C-18 (from Merck) flash chromatography (5 cm × 50 cm) using the solvent systems of H 2 O and MeOH with a 10% increase of MeOH to yield six fractions (MeOH/H 2 O = 50/50, 60/40, 70/30, 80/20, 90/10, and 100/0). The 60% MeOH fraction was separated by reversed phase HPLC (25 × 4.6 mm, 5 μm, 2 mL/min) by eluting the 35% H 2 O and 65% MeOH solvents to produce a mixture at a retention time of 9 min. For purification, the mixture was rechromato-graphed by using the 40% ACN and 60% H 2 O solvents to give compound 1 (9 mg) and compound 2 (704 mg). Similarly, the 70% MeOH fraction was separated with the 30% H 2 O and 70% MeOH solvents to yield compound 3 (54 mg). Finally, compound 4 (14 mg) was isolated from the 80% MeOH subfraction by using the 25% H 2 O and 75% MeOH solvents
Herbicidin K (1): An amorphous powder
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: +0.13 ( C 0.2, CH 3 OH), has the molecular formula C 22 H 27 N 5 O 10 de-duced by a high-resolution electrosprayionization time-of-flight mass spectrometry (HRESITOFMS) experiment (found at m/z [M+H] + ) 522.1849, calculated for C 22 H 28 N 5 O 10 522.1836). 1 H and 13 C-NMR pectra data are presented in Table 1 .
Acknowledgements
This study was supported by the Rural Development Administration, Republic of Korea (PJ0068201002) and by the KRICT’s own project (KK-1304-B0).
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