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New Dibenzocyclooctadiene Lignan from Kadsura induta and Their Cytotoxic Activities
New Dibenzocyclooctadiene Lignan from Kadsura induta and Their Cytotoxic Activities
Bulletin of the Korean Chemical Society. 2014. Jun, 35(6): 1859-1862
Copyright © 2014, Korea Chemical Society
  • Received : January 03, 2014
  • Accepted : February 18, 2014
  • Published : June 30, 2014
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About the Authors
Pham Thi Hong Minh
Do Tien Lam
Nguyen Quyet Tien
Nguyen Ngoc Tuan
Vu Phuong Nhung
Institute of Genome Research, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Vietnam
Nong Van Hai
Institute of Genome Research, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Vietnam
Phan Van Kiem
Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Vietnam
Nguyen Xuan Nhiem
Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Vietnam
Chau Van Minh
Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Vietnam
SeonJu Park
College of Pharmacy, Yonsei Institute of Pharmaceutical Sciences, Yonsei University, Incheon 406-840, Korea
Seung Hyun Kim
College of Pharmacy, Yonsei Institute of Pharmaceutical Sciences, Yonsei University, Incheon 406-840, Korea

Abstract
Keywords
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Experimental
General. Optical rotations were determined on a Jasco DIP-370 automatic polarimeter. The NMR spectra were recorded using a Bruker DRX 500 spectrometer ( 1 H, 500 MHz; 13 C, 125 MHz), and the FAB-MS using a JEOL JMS-HX/HX110A tandem mass spectrometer. The HR-ESI-mass spectra were obtained using an AGILENT 6550 iFunnel Q-TOF LC/MS system. Column chromatography was perform-ed using a silica-gel (Kieselgel 60, 70-230 mesh and 230-400 mesh, Merck) or YMC RP-18 resins (30-50 μm, Fujisilisa Chemical Ltd.), and thin layer chromatography (TLC) using a pre-coated silica-gel 60 F254 (0.25 mm, Merck) and RP-18 F 254S plates (0.25 mm, Merck)
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Important NOESY correlations of compound 1.
Plant Material. The leaves of K . induta were collected in Tamdao National Botanical Park, Vietnam during July 2012, and identified by Dr Bui Van Thanh, Institute of Ecology and Biological Resources, VAST. A voucher specimen (KI1207) was deposited at the Herbarium of the Institute of Chemistry, VAST.
Extraction and Isolation. The leaves of K . induta (1.5 kg) were extracted with MeOH by the sonication for 3 times at room temperature to yield 56.0 g of a dark solid extract, which was then suspended in water and successively parti-tioned with n -hexane and ethyl acetate (EtOAc) to obtain the n -hexane (KI1), EtOAc (KI2), and water (KI3) layers. KI1 was chromatographed on a silica gel column and eluted with gradient elution of n -hexane–acetone (40:1, 20:1, 10:1, 5:1, and 1:1) to obtain fractions, KI1A–KI1E. KI1B was chromato-graphed on a silica gel column eluting with n -hexane–EtOAc (15:1) to yield 2 (0.5 g). KI2 was chromatographed on a silica gel column eluting with CHCl 3 –MeOH (100:1, 50:1, 25:1, 10:1, and 5:1) to obtain fractions KI2A–KI2E. KH2B was chromatographed on an YMC column eluting with acetone–water (2:1) to yield 1 (8.8 mg). KH2C was chromatographed on an YMC column eluting with MeOH–water (5:1) to yield 3 (8.0 mg) and 4 (6.0 mg). KH2D was chromatographed on an YMC column eluting with acetone–water (2:1) to yield 5 (120.0 mg) and 6 (100.0 mg). KH2E was chromatographed on a silica gel column eluting with CHCl 3 –MeOH (6:1) to yield 7 (117.0 mg).
Schizanrin O (1): A white amorphous powder, [α] D 25 −56 ( c 0.1, CHCl 3 ), CD ( c 1 × 10 −3 M, MeOH) ∆ε 245 = –3.4, ∆ε 212 = +1.8, HR-ESI-MS found at m/z 631.2172 (Calcd C 33 H 37 O 11 for 631.2150), 1 H- and 13 C-NMR: see Table 1 .
Cytotoxicity Assay. The effect of compounds 1-7 on the growth of human cancer cells was determined by measuring the cytotoxic activity using a 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assay. 11 The A-549 (human lung cancer), HT-29 (human colon cancer) and OVCAR (human ovarian cancer) cell lines were obtained from the Korea Cell Line Bank (KCLB) and were grown in RPMI 1640 medium supplemented with 10% fetal bovine serum and penicillin/streptomycin (100 U/mL and 100 g/ mL, respectively) at 37 °C in a humidified 5% CO 2 atmosphere. The MTT assays were performed as follows: human cancer cells (1.5-2.5 × 10 5 cells/mL) were treated for 3 days with 1, 10, 50 and 100 µM of the isolated compounds. Mitoxantrone was used to final concentrations of 1, 3, 10 and 20 µM as a reference. After incubation, 0.1 mg (50 µL of a 2 mg/mL solution) MTT (Sigma, Saint Louis, MO, USA) was added to each well and the cells were then incubated at 37 °C for 4 h. The plates were centrifuged at 1000 rpm for 5 min at room temperature and the media was then carefully aspirated. Dimethylsulfoxide (150 µL) was then added to each well to dissolve the formazan crystals. The plates were read im-mediately at 540 nm on a microplate reader (Amersham Pharmacia Biotech., USA). All the experiments were performed three times and the mean absorbance values were calculated. The results are expressed as the percentage of inhibition that produced a reduction in the absorbance by the treatment of crude extract or solvent fractions compared to the untreated controls. A dose-response curve was generated and the inhibitory concentration of 50% (IC 50 ) was deter-mined for each compound as well as each cell line.
Acknowledgements
Declaration of Interest.The authors report no conflicts of interest.
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