Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A New Lathyrane Diterpenoid from the Whole Plant of Euphorbia altotibetica

  • Zhang, Zhan-Xin (School of Pharmacy, Lanzhou University) ;
  • Qi, Feng-Ming (State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University) ;
  • Li, Hui-Hong (School of Pharmacy, Lanzhou University) ;
  • Dong, Le-Le (School of Pharmacy, Lanzhou University) ;
  • Hai, Yang (School of Pharmacy, Lanzhou University) ;
  • Fan, Gai-Xia (School of Pharmacy, Lanzhou University) ;
  • Fei, Dong-Qing (School of Pharmacy, Lanzhou University)
  • Received : 2013.09.12
  • Accepted : 2013.11.14
  • Published : 2014.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

Experimental Section

General Experimental Procedures. Optical rotations were measured on a Perkin Elmer 341 polarimeter. IR spectra were taken on a Nicolet NEXUS 670 FT-IR spectrometer. NMR spectra were recorded on a Bruker AVANVCE III-400 and a Varian Mercury-600BB NMR spectrometers with TMS as internal standard. LR-ESI-MS data were obtained on a Bruker Daltonics Esquire 6000 mass spectrometer. HR-ESI-MS data were recorded on a Thermo LTQ Orbitrap Elite mass spectrometer. Sephadex LH-20 were supplied by Amersham Pharmacia Biotech. Silica gel (200-300 mesh) used for column chromatography and silica gel GF254 (10-40 μM) used for TLC were supplied by the Qingdao Marine Chemical Factory, Qingdao, China. Spots were detected on TLC under UV light or by heating after spraying with 5% H2SO4 in C2H5OH (v/v).

Plant Material. The whole plant of E. altotibetica were collected from Qinghai Province, China, in August 2010 and identified by Prof. Hui-Yan Xiong, Qinghai University. A voucher specimen (No. 201008EA) was deposited at the School of Pharmacy, Lanzhou University.

Extraction and Isolation. The shade dried plant material (9.0 kg) was powdered and extracted three times (7 days in each case) with 95% EtOH at room temperature. After evaporation of solvent in vacuo, the residue (400 g) was suspended in H2O and partitioned with EtOAc and n-BuOH successively. The EtOAc-soluble fraction (293 g) was first subjected to column chromatography on silica gel eluted with petroleum ether-acetone (40:1 → 0:1) to afford seven fractions A–G according to TLC analysis. Fraction F (petro-leum ether-acetone, 1:1) was further CC on silica gel by gradient elution with CHCl3-acetone (20:1 → 1:1) to give five subfractions. Subfractions A (CHCl3-acetone, 20:1) was subjected to CC on Sephadex LH-20 (CHCl3-MeOH, 1:1) and silica gel (CHCl3-acetone, 3:1) to yield compound 1 (4 mg).

Altotibetol (1): Colorless oil; +6.25 (c 0.40, CHCl3); IR (film) νmax cm-1: 3414, 2953, 2924, 2870, 1740, 1646, 1615, 1454, 1371, 1266, 1063, 1046, 736; 1H-NMR and 13C-NMR (CDCl3) see Table 1; LR-ESI-MS m/z 399.4 [M + Na]+; HR-ESI-MS m/z 399.2140 [M + Na]+ (calcd. for C22H32O5Na, 399.2142)

Cytotoxicity Assay. Cytotoxicity against the K562, SGC-7901, and SMCC-7721 cell lines was evaluated by using the MTT method according to the protocols described in the previous literature.15

References

  1. Ferreira, A. M. V. D.; Carvalho, L. H. M.; Carvalho, M. J. M.; Sequeira, M. M.; Silva, A. M. S. Phytochemistry 2002, 61, 373. https://doi.org/10.1016/S0031-9422(02)00182-6
  2. Shi, Q. W.; Su, X. H.; Kiyota, H. Chem. Rev. 2008, 108, 4295. https://doi.org/10.1021/cr078350s
  3. Yang, Y. C. Handbook of Tibetan Medicine; Qinghai People's Press: Xining, China, 1991; p 145.
  4. Pan, L.; Zhang, X. F.; Deng, Y.; Wang, H.; Wu, D. G.; Luo, X. D. Helv. Chim. Acta 2003, 86, 2525. https://doi.org/10.1002/hlca.200390204
  5. Rondon, M.; Morales, A.; Amaro-Luis, J. M.; Bahsas, A.; Rojas, J.; Buitrago, D. Nat. Prod. Res. 2005, 19, 597. https://doi.org/10.1080/14786410412331280096
  6. Feng, W. S.; Gao, L.; Zheng, X. K.; Wang, Y. Z.; Chen, H. Chin. Chem. Lett. 2001, 21, 191.
  7. Appendino, G.; Prota, C. D.; Conseil, G.; Sterner, O.; Mercalli, E.; Dumontet, C.; Di Pietro, A. J. Nat. Prod. 2003, 66, 140. https://doi.org/10.1021/np0203537
  8. Ferreira, M. J. U.; Ascenso, J. R. Phytochemistry 1999, 51, 439. https://doi.org/10.1016/S0031-9422(98)00739-0
  9. Hohmann, J.; Evanics, F.; Vasas, A.; Dombi, G.; Jerkovich, G.; Mqthe, I. J. Nat. Prod. 1999, 62, 176. https://doi.org/10.1021/np980294q
  10. Appendino, G.; Belloro, E.; Tron, G. C.; Jakupovic, J.; Ballero, M. J. Nat. Prod. 1999, 62, 1399. https://doi.org/10.1021/np990209u
  11. Ferreira, A. M. V. D.; Carvalho, L. H. M.; Carvalho, M. J. M.; Sequeira, M. M.; Silva, A. M. S. Phytochemistry 2002, 61, 373. https://doi.org/10.1016/S0031-9422(02)00182-6
  12. Appendino, G.; Gravotto, G.; Jarevang, T.; Sterner, O. Eur. J. Org. Chem. 2000, 2000, 2933. https://doi.org/10.1002/1099-0690(200008)2000:16<2933::AID-EJOC2933>3.0.CO;2-J
  13. Itokawa, H.; Ichihara, Y.; Yahagi, M.; Watanabe, K.; Takeya, K. Phytochemistry 1990, 29, 2025. https://doi.org/10.1016/0031-9422(90)85062-K
  14. Liao, S. G.; Zhan, Z. J.; Yang, S. P.; Yue, J. M. Org. Lett. 2005, 7, 1379. https://doi.org/10.1021/ol050206a
  15. Huassain, R. F.; Nouri A .M. E.; Oliver, R. T. D. J. Immunol. Methods 1993, 160, 89. https://doi.org/10.1016/0022-1759(93)90012-V

Cited by

  1. vol.18, pp.12, 2016, https://doi.org/10.1021/acs.orglett.6b01093
  2. vol.14, pp.10, 2017, https://doi.org/10.1002/cbdv.201700327
  3. A novel spirocyclic triterpenoid and a new taraxerane triterpenoid from Teucrium viscidum vol.4, pp.1, 2017, https://doi.org/10.1039/C6QO00460A
  4. ChemInform Abstract: A New Lathyrane Diterpenoid from the Whole Plant of Euphorbia altotibetica. vol.45, pp.36, 2014, https://doi.org/10.1002/chin.201436197
  5. vol.16, pp.10, 2018, https://doi.org/10.1039/C7OB02991H
  6. Diterpenoids from Euphorbia helioscopia and their enhancement of NK cell-mediated killing of NSCLC cells vol.119, pp.None, 2014, https://doi.org/10.1016/j.bioorg.2021.105534