Planta Med 2007; 73(12): 1292-1297
DOI: 10.1055/s-2007-990217
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Eremophilane-Type Sesquiterpenes from Senecio nemorensis

Dong-Qing Fei1 , Zhan-Xin Zhang1 , Jian-Jun Chen1 , Kun Gao1
  • 1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, People’s Republic of China
Further Information

Publication History

Received: June 26, 2007 Revised: July 17, 2007

Accepted: July 23, 2007

Publication Date:
13 September 2007 (online)

Abstract

Three new highly oxygenated eremophilane-type sesquiterpenes, 1β,10β(8,12)-diepoxy-7β,11β-dihydroxy-8β,12α-dimethoxyeremophilane (1), 1β,10β-epoxy-7β-hydroxy-8α-methoxyeremophil-11αH-12,8β-olide (2), and 6β-isobutyryloxy-8α-hydroxy-1-oxoeremophil-7(11),9-dien-12,8β-olide (3), together with nine known compounds (4 - 12) were isolated from the roots and aerial parts of Senecio nemorensis L. (Compositae). Structures of compounds 1 - 3 were elucidated on the basis of spectroscopic evidence including IR, HR-ESI-MS, 1D and 2D NMR techniques and were unequivocally confirmed by single-crystal X-ray diffraction experiments. The antimicrobial activity of the isolated compounds 1 - 3 and 8 - 12 was tested against Staphylococcus aureus and Candida albicans.

References

  • 1 Institute of Botany, the Chinese Academy of Sciences. Flora of China. Vol. 77 (1) Beijing; Science Press 1999: 225-33.
  • 2 Jiangsu College of New Medicine. A dictionary of traditional Chinese medicines. Shanghai; Shanghai Science and Technology Press 1977: 213-5.
  • 3 Bohlmann F, Ziesche J. New sesquiterpenes from Senecio species.  Phytochemistry. 1980;  19 1851-3.
  • 4 Bohlmann F, Knoll K, Zdero C, Mahauta P K, Grenz M, Suwita A. et al . Terpen-derivate aus Senecio-arten.  Phytochemistry. 1977;  16 965-85.
  • 5 Jiangsu College of New Medicine. A dictionary of traditional Chinese medicines. Shanghai; Shanghai Science and Technology Press 1977: 2040-1.
  • 6 Cheng D L, Gao J J, Yang L. Studies on the chemical constituents of Senecio nemorensis L.  Gaodeng Xuexiao Huaxue Xuebao. 1992;  13 781-3.
  • 7 Chu Y L, Lo S Y. Studies on pyrrolizidine alkaloids. I. The alkaloids of Senecio nemorensis .  Yao Xue Xue Bao. 1963;  10 536-42.
  • 8 Fei D Q, Li S G, Liu C M, Wu G, Gao K. Eremophilane-type sesquiterpene derivatives from the roots of Ligularia lapathifolia .  J Nat Prod. 2007;  70 241-5.
  • 9 Fei D Q, Wu G, Liu C M, Gao K. A novel benzofuran derivative, a new olean-type triterpene and other constituents from Ligularia odontomanes .  Chem Pharm Bull. 2007;  55 577-9.
  • 10 Liu C M, Fei D Q, Wu Q H, Gao K. Bisabolane sesquiterpenes from the roots of Ligularia cymbulifera .  J Nat Prod. 2006;  69 695-9.
  • 11 Li E W, Pan J, Gao K, Jia Z J. New eremophilenolides from Cacalia pilgeriana .  Planta Med. 2005;  71 1140-4.
  • 12 Han Y F, Zhang Q, Gao K, Jia Z J. New sesquiterpenes from Sonchus transcaspicus .  Planta Med. 2005;  71 543-7.
  • 13 Li X, Yang M, Han Y F, Gao K. New sesquiterpenes from Erigeron annus .  Planta Med. 2005;  71 268-72.
  • 14 Han Y F, Pan J, Gao K, Jia Z J. Sesquiterpenes, nortriterpenes and other constituents from Ligularia tongolensis .  Chem Pharm Bull. 2005;  53 1338-41.
  • 15 Li X Q, Gao K, Jia Z J. Eremophilenolides and other constituents from the roots of Ligularia sagitta .  Planta Med. 2003;  69 356-60.
  • 16 Wang W S, Gao K, Jia Z J. New eremophilenolides from Ligulariopsis shichuana .  J Nat Prod. 2002;  65 714-7.
  • 17 Demetzos C, Stahl B, Anastassaki T, Gazouli M, Tzouveleki L S, Rallis M. Chemical analysis and antimicrobial activity of the resin Ladano, of its essential oil and of the isolated compounds.  Planta Med. 1999;  65 76-8.
  • 18 Harmatha J, Samek Z, Novotny L, Herout V, Sorm F. The structure of adenostylone and isoadenostylone - two furoeremophilanes from adenostyles alliariae (Gouan) kern.  Tetrahedron Lett. 1968;  9 1409-12.
  • 19 Bohlmann F, Zdero C. Neue C10-Säureamide, Furanoeremophilane und andere Inhaltsstoffe aus bolivianischen Senecio-Arten.  Phytochemistry. 1979;  18 125-8.
  • 20 Jia Z J, Chen H M. Benzofuranosesquiterpenes from Ligularia virgaurea .  Phytochemistry. 1991;  30 3132-4.
  • 21 Zhao Y, Peng H R, Jia Z J. Six new eremophilane derivatives from two Ligularia species.  J Nat Prod. 1994;  57 1626-30.
  • 22 Wu Q X, Shi Y P, Yang L. Eremophilane sesquiterpene lactones from Ligularia virgaurea ssp. oligocephala .  Planta Med. 2004;  70 479-82.
  • 23 Glauco M B, Jorge B R, Arlett M P, Samuel P T, Luis A. An eremophilanolide from Senecio rosmarinus .  Phytochemistry. 1986;  25 2412-4.
  • 24 Mohamed A H, Ahmed A A. Eremophilane-type sesquiterpene derivatives from Senecio aegyptius var. discoideus .  J Nat Prod. 2005;  68 439-42.
  • 25 Jia Z J, Zhao Y, Tan R X, Yang L. Eremophilanolides from the roots of Ligularia veitchiana .  Phytochemistry. 1992;  31 2785-7.
  • 26 Zdero C, Bohlmann F. Eremophilanolides, eudesmanolides, guaianolides and other constituents from Ondetia linearis .  Phytochemistry. 1989;  28 1653-60.
  • 27 Naya K, Matsuura T, Makiyama M, Tsumura M. The conversion of furanoeremophilanes to epieremophilenolides.  Heterocycles. 1978;  10 177-82.
  • 28 Naya K, Nogi N, Makiyama Y, Takashina H, Imagawa T. The photosensitized oxygenation of furanoeremophilanes. II. The preparation and stereochemistry of the isomeric hydroperoxides and the corresponding lactones from furanofukinin and furanoeremophilane.  Bull Chem Soc Jpn. 1977;  50 3002-6.
  • 29 Yang S P, Yue J M. Two novel cytotoxic and antimicrobial triterpenoids from Pseudolarix kaempferi .  Bioorg Med Chem Lett. 2001;  11 3119-22.
  • 30 Yang S P, Dong L, Wang Y, Wu Y, Yue J M. Antifungal diterpenoids of Pseudolarix kaempferi, and their structure-activity relationship study.  Bioorg Med Chem. 2003;  11 4577-84.

Prof. Kun Gao

State Key Laboratory of Applied Organic Chemistry

College of Chemistry and Chemical Engineering

Lanzhou University

Lanzhou 730000

People’s Republic of China

Phone: +86-931-891-2592

Fax: +86-931-891-2582

Email: npchem@lzu.edu.cn

    >