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)

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.

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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 8 Bohlmann F, Misra L N, Jakupovic J. Pseudoguaianolides and carabrone derivatives from Loxothysanus sinuatus.  Phytochemistry. 1985;  24 1021-1026
  • 9 Romo J, Joseph-Nathan P, Diaz F A. Constituents of Helenium aromaticum. Structures of aromatin and aromaticin.  Tetrahedron. 1964;  20 79-85
  • 10 Maruyama M, Omura S. Carpesiolin from Carpesium abrotanoides.  Phytochemistry. 1977;  16 782-783
  • 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
  • 12 Wang F, Yang K, Ren F C, Liu J K. Sesquiterpene lactones from Carpesium abrotanoides.  Fitoterapia. 2009;  80 21-24
  • 13 Geissman T A, Matsueda S. Sesquiterpene lactones. Constituents of diploid and polyploid Ambrosia dumosa Gray.  Phytochemistry. 1968;  7 1613-1621
  • 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
  • 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
  • 16 Bohlmann F, Czerson H, Schoeneweiss S. New constituents of Inula viscosa Ait.  Chem Ber. 1977;  110 1330-1334
  • 17 Zdero C, Bohlmann F, King R M, Robinson H. Sesquiterpene lactones from Bedfordia arborescens.  Phytochemistry. 1987;  26 1207-1209
  • 18 Jakupovic J, Schuster A, Bohlmann F, King R M, Lander N S. Sesquiterpene lactones from Gnephosis species.  Phytochemistry. 1988;  27 3181-3185
  • 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
  • 20 Ito K, Iida T. Seven sesquiterpene lactones from Inula britannica var. chinensis.  Phytochemistry. 1981;  20 271-273
  • 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
  • 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
  • 23 Bohlmann F, Umemoto K, Jakupovic J. Pseudoguaianolides related to confertin from Stevia isomeca.  Phytochemistry. 1985;  24 1017-1019
  • 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
  • 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
  • 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
  • 27 Maruyama M, Karube A, Sato K. Sesquiterpene lactones from Carpesium abrotanoides.  Phytochemistry. 1983;  22 2773-2774
  • 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
  • 29 Stöchlin W, Waddell T G, Geissman T A. Circular dichroism and optical rotator dispersion of sesquiterpene lactones.  Tetrahedron. 1970;  26 2397-2410
  • 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
  • 31 Brito I, Bórquez J, Loyola L A, López-Rodríguez M. Aromaticine, a sesquiterpene lactone from Amblyopappus pusillus.  Acta Crystallogr. 2008;  E64 o529
  • 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
  • 33 Park E J, Kim J. Cytotoxic sesquiterpene lactones from Inula britannica.  Planta Med. 1998;  64 752-754

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