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Planta Med 2012; 78(5): 465-471
DOI: 10.1055/s-0031-1298147
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Sesquiterpene Lactones from Inula hookeri

Xiang-Rong Cheng1 , Wei-Wei Li1 , Jie Ren1 , Qi Zeng1 , Shou-De Zhang1 , Yun-Heng Shen2 , Shi-Kai Yan1 , Ji Ye2 , Hui-Zi Jin1 , Wei-Dong Zhang1 , 2
  • 1School of Pharmacy, Shanghai Jiao Tong University, Shanghai, PR China
  • 2School of Pharmacy, Second Military Medical University, Shanghai, PR China
Further Information

Publication History

received October 5, 2011 revised Nov. 16, 2011

accepted Dec. 12, 2011

Publication Date:
10 January 2012 (online)

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Abstract

Four new sesquiterpene lactones, (1S,5R,6S,7S,8R,9R,10S,11S)-6-acetoxy-9-hydroxy-4-oxo-pseudoguai-2(3)-en-12,8-olide (1), (1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-ethoxy-4-oxo-pseudoguai-11(13)-en-12,8-olide (2), (1S,2R,5R,6S,7R,8S,10R)-6-acetoxy-2-hydroxy-4-oxo-pseudoguai-11(13)-en-12,8-olide (3), and 14-acetoxy-1β,5α,7αH-4β-hydroxy-guai-9(10),11(13)-dien-12,8α-olide (4), along with 26 known sesquiterpene lactones, were isolated from the whole plants of Inula hookeri C. B. Clarke. Their structures were established based on spectroscopic methods including HRESIMS, 1D and 2D NMR, and CD techniques. All compounds were evaluated for their cytotoxic activities against HepG2, HeLa, PC-3, and MGC-803 cell lines by CCK-8 assay. Some of the isolates, especiallly pseudoguaianolides and guaianolides, exhibited significant cytotoxicities against these four examined cell lines.

Key words

Inula hookeri - Compositae - sesquiterpene lactones - cytotoxicity - CCK-8 assay

Supporting Information

References

  • 1 Zhao Y M, Zhang M L, Shi Q W, Hiromasa K. Chemical consitituents of plants from the genus Inula.  Chem Biodivers. 2006;  3 371-384
    Google Scholar
  • 2 Committee of Chinese Pharmacopoeia .Pharmacopoeia of the People's Republic of China. 2010 Chinese Edition, Volume 1 Beijing: China Medical Science and Technology Press; 2010: 15 202, 305
    Google Scholar
  • 3 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
    Google Scholar
  • 4 Qin J J, Jin H Z, Zhu J X, Fu J J, Qi Z, Cheng X R, Zhu Y, Shan L, Zhang S D, Pan Y X, Zhang W D. New sesquiterpenes from Inula japonica Thunb. with their inhibitory activities against LPS-induced NO production in RAW264.7 macrophages.  Tetrahedron. 2010;  66 9379-9388
    Google Scholar
  • 5 Cheng X, Zeng Q, Ren J, Qin J, Zhang S, Shen Y, Zhu J, Zhang F, Chang R, Zhu Y, Zhang W, Jin H. Sesquiterpene lactones from Inula falconeri, a plant endemic to the Himalayas, as potential anti-inflammatory agents.  Eur J Med Chem. 2011;  46 5408-5415
    Google Scholar
  • 6 Qin J J, Zhu J X, Zeng Q, Cheng X R, Zhu Y, Zhang S D, Shan L, Jin H Z, Zhang W D. Pseudoguaianolides and guaianolides from Inula hupehensis as potential anti-inflammatory agents.  J Nat Prod. 2011;  74 1881-1887
    Google Scholar
  • 7 Wang Q, Zhou B N, Zhang R W, Lin Y Y, Lin L Z, Gil R R, Cordell G A. Cytotoxicity and NMR spectral assignments of ergolide and bigelovin.  Planta Med. 1996;  62 166-168
    Google Scholar
  • 8 Bohlmann F, Misra L N, Jakupovic J. Pseudoguaianolides and carabrone derivatives from Loxothysanus sinuatus.  Phytochemistry. 1985;  24 1021-1026
    Google Scholar
  • 9 Romo J, Joseph-Nathan P, Diaz F A. Constituents of Helenium aromaticum. Structures of aromatin and aromaticin.  Tetrahedron. 1964;  20 79-85
    Google Scholar
  • 10 Maruyama M, Omura S. Carpesiolin from Carpesium abrotanoides.  Phytochemistry. 1977;  16 782-783
    Google Scholar
  • 11 Lee H T, Yang S W, Kim K H, Seo E K, Mar W. Pseudoguaianolides isolated from Inula britannica var. chinensis as inhibitory constituents against inducible nitric oxide synthase.  Arch Pharm Res. 2002;  25 151-153
    Google Scholar
  • 12 Wang F, Yang K, Ren F C, Liu J K. Sesquiterpene lactones from Carpesium abrotanoides.  Fitoterapia. 2009;  80 21-24
    Google Scholar
  • 13 Geissman T A, Matsueda S. Sesquiterpene lactones. Constituents of diploid and polyploid Ambrosia dumosa Gray.  Phytochemistry. 1968;  7 1613-1621
    Google Scholar
  • 14 Abdel-Mogib M, Jakupovic J, Dawidar A M, Metwally M A, Abou-Elzahab M. Sesquiterpene lactones and kaurane glycosides from Francoeuria crispa.  Phytochemistry. 1990;  29 2581-2584
    Google Scholar
  • 15 Bohlmann F, Mahanta P K, Jakupovic J, Rastogi R C, Natu A A. New sesquiterpene lactones from Inula species.  Phytochemistry. 1978;  17 1165-1172
    Google Scholar
  • 16 Bohlmann F, Czerson H, Schoeneweiss S. New constituents of Inula viscosa Ait.  Chem Ber. 1977;  110 1330-1334
    Google Scholar
  • 17 Zdero C, Bohlmann F, King R M, Robinson H. Sesquiterpene lactones from Bedfordia arborescens.  Phytochemistry. 1987;  26 1207-1209
    Google Scholar
  • 18 Jakupovic J, Schuster A, Bohlmann F, King R M, Lander N S. Sesquiterpene lactones from Gnephosis species.  Phytochemistry. 1988;  27 3181-3185
    Google Scholar
  • 19 Kupchan S M, Cassady J M, Kelsey J E, Schnoes H K, Smith D H, Burlingame A L. Structural elucidation and high-resolution mass spectrometry of gaillardin, new cytotoxic sesquiterpene lactone.  J Am Chem Soc. 1966;  88 5292-5302
    Google Scholar
  • 20 Ito K, Iida T. Seven sesquiterpene lactones from Inula britannica var. chinensis.  Phytochemistry. 1981;  20 271-273
    Google Scholar
  • 21 Jakupovic J, Zdero C, Grenz M, Tsichritzis F, Lehmann L, Hashemi-Nejad S M, Bohlmann F. Twenty-one acylphloroglucinol derivatives and further constituents from South African Helichrysum species.  Phytochemistry. 1989;  28 1119-1131
    Google Scholar
  • 22 Kim M R, Lee S K, Kim C S, Kim K S, Moon D C. Phytochemical constituents of Carpesium macrocephalum FR- et SAV-.  Arch Pharm Res. 2004;  27 1029-1033
    Google Scholar
  • 23 Bohlmann F, Umemoto K, Jakupovic J. Pseudoguaianolides related to confertin from Stevia isomeca.  Phytochemistry. 1985;  24 1017-1019
    Google Scholar
  • 24 Kuo Y H, Lin B Y. A new dinorxanthane and chromone from the root of Tithonia diversifolia.  Chem Pharm Bull. 1999;  47 428-429
    Google Scholar
  • 25 Ohno S, Tomita-Yokotani K, Kosemura S, Node M, Suzuki T, Amano M, Yasui K, Goto T, Yamamura S, Hasegawa K. A species-selective allelopathic substance from germinating sunflower (Helianthus annuus L.) seeds.  Phytochemistry. 2001;  56 577-581
    Google Scholar
  • 26 Lanzetta R, Lama G, Mauriello G, Parrilli M, Racioppi R, Sodano G. Ichthyotoxic sesquiterpenes and xanthanolides from Dittrichia graveolens.  Phytochemistry. 1991;  30 1121-1124
    Google Scholar
  • 27 Maruyama M, Karube A, Sato K. Sesquiterpene lactones from Carpesium abrotanoides.  Phytochemistry. 1983;  22 2773-2774
    Google Scholar
  • 28 Sondheimer F, Burstein S, Mechoulan R. Synthesis in the cardiac aglycone filed. 3. The conversion of a 14α- to a 14β-hydroxy group in the androstane series. The ultraviolet spectra of Δ 15-androsten-17-ones.  J Am Chem Soc. 1960;  82 3209-3214
    Google Scholar
  • 29 Stöchlin W, Waddell T G, Geissman T A. Circular dichroism and optical rotator dispersion of sesquiterpene lactones.  Tetrahedron. 1970;  26 2397-2410
    Google Scholar
  • 30 Chekholv A N. Crystal structure and absolute configuration of 6α-acetoxy − 4-oxo-(1αH,7αH,8βH,10βH)-15(4 → 5β)abeo-guaia-2, 11(13)-dien-8, 12-olide.  J Struct Chem. 2000;  41 1084-1087
    Google Scholar
  • 31 Brito I, Bórquez J, Loyola L A, López-Rodríguez M. Aromaticine, a sesquiterpene lactone from Amblyopappus pusillus.  Acta Crystallogr. 2008;  E64 o529
    Google Scholar
  • 32 Pal H C, Sehar I, Bhushan S, Gupta B D, Saxena A K. Activation of caspases and poly (ADP-ribose) polymerase cleavage to induce apoptosis in leukemia HL-60 cells by Inula racemosa.  Toxicol In Vitro. 2010;  24 1599-1609
    Google Scholar
  • 33 Park E J, Kim J. Cytotoxic sesquiterpene lactones from Inula britannica.  Planta Med. 1998;  64 752-754
    Google Scholar

Dr. Hui-Zi Jin
Wei-Dong Zhang

School of Pharmacy
Shanghai Jiao Tong University

Shanghai Dongchuan Rd 800

Shanghai 200240

PR China

Phone: +86 21 34 20 59 89

Fax: +86 21 34 20 59 89

Email: kimhz@sjtu.edu.cn

Email: wdzhangy@hotmail.com

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