Download PDF
Planta Med 2012; 78(2): 166-171
DOI: 10.1055/s-0031-1280294
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Sesquiterpenoids from Inula racemosa Hook. f. Inhibit Nitric Oxide Production

Shou-De Zhang1 , Jiang-Jiang Qin1 , Hui-Zi Jin1 , Yin-Hua Yin2 , Hong-Lin Li3 , Xian-Wen Yang4 , Xia Li2 , Lei Shan2 , Wei-Dong Zhang1 , 2
  • 1School of Pharmacy, Shanghai Jiao Tong University, Shanghai, China
  • 2Department of Natural Product Chemistry, School of Pharmacy, Second Military Medical University,Shanghai, China
  • 3Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, China
  • 4Key Laboratory of Marine Bio-Resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China
Further Information

Publication History

received June 30, 2011 revised August 2, 2011

accepted Sept. 19, 2011

Publication Date:
14 October 2011 (online)

Also available at
    Permissions and Reprints

Abstract

A novel trinorsesquiterpene (1), three new (2–4), and 10 known sesquiterpenes were isolated from the roots of Inula racemosa Hook. f. The structures and absolute configurations of the new sesquiterpenes were elucidated by extensive spectroscopic and computational methods. All compounds were evaluated for their inhibition of LPS-induced nitric oxide production in RAW264.7 macrophages, and the results indicated that compounds 9, 12, and 13 moderately inhibited nitric oxide production with IC50 values of 7.39 ± 0.36, 6.35 ± 0.26, and 5.39 ± 0.18 µM, respectively.

Key words

Inula racemosa Hook. f. - Compositae - sesquiterpenes - density functional theory - nitric oxide

Supporting Information

References

  • 1 Zhao Y M, Zhang M L, Shi Q W, Hiromasa K. Chemical constituents of plants from the genus Inula.  Chem Biodivers. 2006;  3 371-384
    CrossrefPubMedGoogle Scholar
  • 2 Dictionary of Traditional Chinese Materia Medica, Vol. 2. Shanghai: Shanghai People's Press; 1977: 2216-2219
    Google Scholar
  • 3 Kobayashi T, Song Q H, Hong T, Kitamura H, Cyong J C. Preventative effects of the flowers of Inula britannica on autoimmune diabetes in C57BL/KsJ mice induced by multiple low doses of streptozotocin.  Phytother Res. 2002;  16 377-382
    CrossrefPubMedGoogle Scholar
  • 4 Cho S. Prophylactic/therapeutic preparation for diabetes and prophylactic/therapeutic method for diabetes using the same. JP Patent 2001039882 2001
    Google Scholar
  • 5 Song Q H, Kobayashi T, Hong T, Cyong J C. Effects of Inula britannica on the production of antibodies and cytokines and on T cell differentiation in C57BL/6 mice immunized by ovalbumin.  Am J Chin Med. 2002;  30 297-305
    CrossrefPubMedGoogle Scholar
  • 6 Song Q H, Kobayashi T, Iijima K, Hong T, Cyong J C. Hepatoprotective effects of Inula britannica on hepatic injury in mice.  Phytother Res. 2000;  14 180-186
    CrossrefPubMedGoogle Scholar
  • 7 Bai N, Lai C S, He K, Zhou Z, Zhang L, Quan Z, Zhu N, Zheng Q Y, Pan M H, Ho C T. Sesquiterpene lactones from Inula britannica and their cytotoxic and apoptotic effects on human cancer cell lines.  J Nat Prod. 2006;  69 531-535
    CrossrefPubMedGoogle Scholar
  • 8 Zhou B N, Bai N S, Lin L Z, Cordell G A. Sesquiterpene lactones from Inula salsoloides.  Phytochemistry. 1994;  36 721-724
    CrossrefPubMedGoogle Scholar
  • 9 Qin J J, Jin H Z, Fu J J, Hu X J, Wang Y, Yan S K, Zhang W D. Japonicones A-D, bioactive dimeric sesquiterpenes from Inula japonica Thunb.  Bioorg Med Chem Lett. 2009;  19 710-713
    CrossrefPubMedGoogle Scholar
  • 10 Nie L Y, Qin J J, Huang Y, Yan L, Liu Y B, Pan Y X, Jin H Z, Zhang W D. Sesquiterpenoids from Inula lineariifolia inhibit nitric oxide production.  J Nat Prod. 2010;  73 1117-1120
    CrossrefPubMedGoogle Scholar
  • 11 Wu Z Y, Hong D Y. Flora Reipublicae Popularis Sinicae (Flora of China). Tomus 7 Beijing: Science Press; 1989: 254-255
    Google Scholar
  • 12 Qin J J, Jin H Z, Zhu J X, Fu J J, Hu X J, Liu X H, Zhu Y, Yan S K, Zhang W D. Japonicones E-L, dimeric desquiterpene lactones from Inula japonica Thunb.  Planta Med. 2010;  76 278-283
    Article in Thieme ConnectPubMedGoogle Scholar
  • 13 Schmidt H H H W, Kelm M. Methods in nitrix oxide research. chapter 33. London: John Wiley & Sons, Ltd.; 1996: 491-497
    Google Scholar
  • 14 Denizot F, Lang R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability.  J Immunol Methods. 1986;  89 271-277
    CrossrefPubMedGoogle Scholar
  • 15 Konishi T, Shimada Y, Nagao T, Okabe H, Konoshima T. Antiproliferative sesquiterpene lactones from the roots of Inula helenium.  Biol Pharm Bull. 2002;  25 1370-1372
    CrossrefPubMedGoogle Scholar
  • 16 Bohlmann F, Mahanta P K, Jakupovic J, Rastogi R C, Natu A A. New sesquiterpene lactones from Inula species.  Phytochemistry. 1978;  17 1165-1172
    CrossrefPubMedGoogle Scholar
  • 17 Diedrich C, Grimme S. Systematic investigation of modern quantum chemical methods to predict electronic circular dichroism spectra.  J Phys Chem A. 2003;  107 2524-2539
    CrossrefPubMedGoogle Scholar
  • 18 Crawford T D, Tam M C, Abrams M L. The current state of Ab Initio calculations of optical rotation and electronic circular dichroism spectra.  J Phys Chem A. 2007;  111 12057-12068
    CrossrefPubMedGoogle Scholar
  • 19 Stephens P J, Devlin F J, Gasparrini F, Ciogli A, Spinelli D, Cosimelli B. Determination of the absolute configuration of a chiral oxadiazol-3-one calcium channel blocker, resolved using chiral chromatography, via concerted density functional theory calculations of its vibrational circular dichroism, electronic circular dichroism, and optical rotation.  J Org Chem. 2007;  72 4707-4715
    CrossrefPubMedGoogle Scholar
  • 20 Ding Y Q, Li X C, Ferreira D. Theoretical calculation of electronic circular dichroism of the rotationally restricted 3,8-biflavonoid morelloflavone.  J Org Chem. 2007;  72 9010-9017
    CrossrefPubMedGoogle Scholar
  • 21 Berova N, Bari L D, Pescitelli G. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds.  Chem Soc Rev. 2007;  36 914-931
    CrossrefPubMedGoogle Scholar
  • 22 Frisch M J, Trucks G W, Schlegel H, Scuseria G E, Robb M A, Cheeseman J R, Montgomery J A J, Vreven T, Kudin K N, Burant J C, Millam J M, Iyengar S S, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson G A, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox J E, Hratchian H P, Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R C, Pomelli R, Ochterski J, Ayala P Y, Morokuma K, Voth G A, Salvador P, Dannenberg J J, Zakrzewski V G, Dapprich S, Daniels A D, Strain M C, Farkas O, Malick D K, Rabuck A D, Raghavachari K, Foresman J B, Ortiz J V, Cui Q, Baboul A G, Clifford S, Cioslowski J, Stefanov B B, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin R L, Fox D J, Keith T, Al-Laham M A, Peng C Y, Nanayakkara A, Challacombe M, Gill P M W, Johnson B G, Chen W, Wong M W, Gonzalez C, Pople J A. GAUSSIAN 03 (Revision B.05). Wallingford: Gaussian, Inc.; 2004
    Google Scholar
  • 23 Mohamadi F, Richards N, Guida W, Liskamp R, Lipton M, Caufield C, Chang G, Hendrickson T, Still W C. Macromodel: an integrated software system for modeling organic and bioorganic molecules using molecular mechanics.  J Comput Chem. 1990;  11 440-467
    CrossrefPubMedGoogle Scholar
  • 24 Klamt A, Schüürmann G. COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient.  J Chem Soc [Perkin II]. 1993;  2 799-805
    PubMedGoogle Scholar
  • 25 Klamt A. Conductor-like screening model for real solvents: a new approach to the quantitative calculation of solvation phenomena.  J Phys Chem. 1995;  99 2224-2235
    CrossrefPubMedGoogle Scholar
  • 26 Yang C, Zhu Q X, Zhang Q, Wang Q, Jia Z J. A new eudesmanolide and a new aromatic derivative from Carpesium cernuun.  Chin Chem Lett. 2001;  12 597-600
    PubMedGoogle Scholar
  • 27 Guerreiro E, Kavka J, Giordano O S, Gros E G. Sesquiterpenoids and flavonoids from Flourensia oolepis.  Phytochemistry. 1979;  18 1235-1237
    CrossrefPubMedGoogle Scholar
  • 28 Greger H, Zdero C, Bohlmann F. Eudesman-12,8β-olides and other terpenes from Artemisia species.  Phytochemistry. 1986;  25 891-897
    CrossrefPubMedGoogle Scholar
  • 29 Kalsi P S, Goyal R, Talwar K K, Chhabra B R. Stereostructures of two biological active sesquiterpene lactones from Inula racemosa.  Phytochemistry. 1989;  28 2093-2096
    CrossrefPubMedGoogle Scholar
  • 30 Huo Y, Shi H M, Wang M Y, Li X B. Complete assignments of 1H and13CNMR spectral data for three sesquiterpenoids from Inula helenium.  Magn Reson Chem. 2008;  46 1208-1211
    CrossrefPubMedGoogle Scholar
  • 31 Rustaiyan A, Habibi Z, Saberi M, Jakupovic J. A nor-guaianolide and a glaucolide-like eudesmanolide from pulicaria undulata.  Phytochemistry. 1991;  30 2405-2406
    CrossrefPubMedGoogle Scholar
  • 32 Herz W, Sumi Y, Sudarsanam V, Raulais D. Contituents of Iva species. X. Ivangulin, a novel seco-eudesmanolide from Iva angustifolia.  Nutt J Org Chem. 1967;  32 3658-3662
    PubMedGoogle Scholar
  • 33 Fraga B M. ChemInform abstract: natural sesquiterpenoids.  Nat Prod Rep. 2010;  27 1681-1708
    CrossrefPubMedGoogle Scholar

Lei Shan

Department of Natural Product Chemistry
School of Pharmacy
Second Military Medical University

325 Guohe Road

Shanghai 200433

China

Phone: +86 21 34 20 59 89

Fax: +86 21 34 20 59 89

Email: shanleish@yahoo.com.cn

Wei-Dong Zhang

Department of Natural Product Chemistry
School of Pharmacy
Second Military Medical University

325 Guohe Road

Shanghai 200433

China

Phone: +86 21 34 20 59 89

Fax: +86 21 34 20 59 89

Email: wdzhangy@hotmail.com