Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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3,7-Dihydroxy-2,4,6-trimethoxyphenanthrene, A New Phenanthrene from Bulbophyllum Odoratissimum

Bulbophyllum Odoratissimum에서 추출한 새로운 페난트렌, 3,7-Dihydroxy-2,4,6-trimethoxyphenanthrene

  • Chen, Ye-Gao (Department of Chemistry, Yunnan National University) ;
  • Xu, Jun-Ju (Department of Chemistry, Yunnan National University) ;
  • Yu, Hong (School of Life Science, Yunnan University) ;
  • Qing, Chen (Yunnan Key Laboratory of Pharmacology for Natural Products Research, Kunming Medical College) ;
  • Zhang, Yan-Li (Yunnan Key Laboratory of Pharmacology for Natural Products Research, Kunming Medical College) ;
  • Liu, Ying (Department of Chemistry, Yunnan National University) ;
  • Wang, Ji-Hua (Department of Chemistry, Yunnan National University)
  • Published : 2007.08.20
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Abstract

A new phenanthrene derivative 3,7-dihydroxy-2,4,6-trimethoxyphenanthrene was isolated from the all plant of Bulbophyllum odoratissimum, and its structure was elucidated by extensive spectral studies and chemical transformation. The compound displayed cytotoxicity against the growth of human leukemia cell lines K562 and HL-60, human lung adenocarcinoma A549, human hepatoma BEL-7402 and human stomach cancer cell lines SGC-7901 with IC50 values of 14.23, 10.02, 3.42, 15.36 and 1.13 mg/ml respectively.

Efficient stereoselective synthesis of α,β-Unsaturated acids, α-Cyanoacrylonitriles and α-Cyanoacrylates has been carried out in the presence of NaHSO4·SiO2 under solvent?free conditions with an E-geometry.

Keywords

EXPERIMENTAL SECTION

General Proceduces. MS were determined on an API Qstar Pulsa LC/TOF mass spectrometer. NMR spectra were measured on a Bruker DRX-500 spectrometer with TMS as internal standard. Silica gel (200-300 mesh) was used for column chromatography and silica gel GF254 for TLC (Qingdao Marine Chemical Co., China). Solvents were of industrial purity and distilled prior to use.

Plant materials. The whole plant of Bulbophyllum odoratissimum were collected from Simao County of Yunnan Province, China in February, 2004 and identified by one of the authors, Dr. Hong Wang, School of Life Science, Yunnan University, where a voucher specimen (No.0402017) was deposited.

Extraction and isolation. The air-dried powdered whole plant of B. odoratissimum (20 Kg) were extracted with 95% EtOH (20 liters × 4) at room temperature. The EtOH extract was concentrated in vacuo to yield a dark brown residue (1 Kg). H2O (2.5 L) was added to the residue, and the resultant solution was extracted with petroleum ether, EtOAc and n-BuOH successively (1.5 liters ×4). The EtOAc extract (350 g) was applied to a silica gel column, eluting with petroleum ether containing increasing amounts of acetone to obtain 6 fractions. Fr. 3 (77 g) was separated to two subfractions by silica gel column chromatography (petroleum ether-acetone 4:1, 7:3). The second subfraction (47 g) was subjected to repeated column chromatography, first on silica gel (CHCl3-acetone 80:1) and then on Sephadex LH-20 (MeOH-H2O 9:1) to obtain 1 (21 mg).

Compound 1: 1H-NMR (500 MHz, CD3OD) and 13C-NMR (125 MHz, CD3OD), see Table 1; EI-MS m/z (70 eV, ret. Int., %): 300 [M+] (100), 285 (63), 253 (17), 242 (22), 214 (33), 185 (11), 150 (16); HRESIMS m/z: 323.0889 [M+Na]+, requires 323.0895.

Methylation of 1: compound 1 (10 mg) was methylated with CH2N2 in Me2CO. Preparative TLC of the crude product (silica gel, petroleum ether-EtOAc 4:1) gave 2,3,4,6,7-pentamethoxyphenanthrene (1b, 6 mg) as a colorless amorphous powder. EI-MS m/z (70 eV, ret. Int., %): 328 [M+] (100); 1H-NMR (CD3COCD3): δ9.06 (1H, s, H-5), 7.61 (1H, d, J=9.0 Hz, H-9), 7.57 (1H, J=9.0 Hz, H-10), 7.34 (1H, s, H-1 or H-8), 7.27 (1H, s, H-8 or H-1), 4.04, 4.01, 3.99, 3.96, 3.96 (15H, each s, OMe ×5), identical to lit. values.4

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