Planta Med 2004; 70(3): 234-238
DOI: 10.1055/s-2004-815540
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

New Lignans and Cytotoxic Constituents from Wikstroemia lanceolata

Ru-Wei Lin1 , Ian-Lih Tsai1 , Chang-Yih Duh2 , Kuo-Hsiung Lee3 , Ih-Sheng Chen1
  • 1Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan, Republic of China
  • 2Graduate Institute of Marine Resources, National Sun Yat-sen University, Kaohsiung, Taiwan, Republic of China
  • 3Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina, U.S.A.
This research was financially supported by the National Science Council of the Republic of China
Further Information

Publication History

Received: July 10, 2003

Accepted: November 22, 2003

Publication Date:
23 March 2004 (online)

Abstract

Two new lignans, (-)-aptosimon (1) and (-)-diasesamin-di-γ-lactone (2), together with twenty-two known compounds, have been isolated from the stems and roots of Wikstroemia lanceolata. The structures of the new compounds were determined through spectral analyses. The proton and carbon assignments of the known sesquiterpenoid, 1α,7α,10αH-guaia-4,11-dien-3-one (24) were revised by 2D NMR techniques. Among the isolates, three compounds, (+)-hinokinin (6), 2,6-dimethoxy-p-benzoquinone (17), and 1α,7α,10αH-guaia-4,11-dien-3-one (24) exhibited effective cytotoxicities (ED50 values < 4.0 μg mL-1) against P-388 and HT-29 tumor cell lines.

References

  • 1 Chang C E. Thymelaeaceae in Flora of Taiwan. 2nd Edition. Editorial Committee of the Flora of Taiwan Taipei, Taiwan; 1993 Vol. 3: 772-9
  • 2 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
  • 3 Kakisawa H, Chen Y P, Hsü H Y. Lignans in flowers buds of Magnolia fargesii .  Phytochemistry. 1972;  11 2289-93
  • 4 Yamauchi S, Yamauchi M. Synthesis of (+)-aptosimon, a 4-oxofurofuran lignan, by erythro selective aldol condensation and stereoconvergent cyclization as the key reactions.  Biosci Biotechnol Biochem. 2003;  67 838-46
  • 5 Stevens D R, Whiting D A. Synthetic methods for (exo,exo)- and (exo,endo)- 2,6-diarylbicyclo[3 : 3:0]octane lignans: syntheses of (±)-aptosimon, (±)-styraxin, (±)-asarinin, and (±)-pluviatilol.  Tetrahedron Lett. 1986;  27 4629-32
  • 6 Brieskorn C H, Huber H. Vier neue Lignane aus Aptosimum spinescens (Thunbg.) Weber.  Tetrahedron Lett. 1976;  26 2221-4
  • 7 Peterson J R, Peterson S, Baker J K, Rogers R D. Anticancer agent development. 5. X-ray structure and 1H nmr spectral analysis of (1α,2α,5α,6α)-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-4,8-dione.  J Crystallogr Spectrosc Res. 1990;  20 327-33
  • 8 Yu H J, Chen C C, Shieh B J. The constituents from the leaves of Magnolia coco .  J Chin Chem Soc. 1998;  45 773-8
  • 9 Lee K H, Tagahara K, Suzuki H, Wu R Y, Haruna M, Hall I H, Huang H C, Ito K, Iida T, Lai J S. Antitumor agents. 49. tricin, kaempferol 3-O-β-D-glucopyranoside and (+)-nortrachelogenin, antileukemic principles from Wikstroemia indica .  J Nat Prod. 1981;  44 530-5
  • 10 Ikeda R, Nagao T, Okabe H, Nakano Y, Matsunaga H, Katano M, Mori M. Anti-proliferative constituents in Umbelliferae plants. IV. Constituents in the fruits of Anthriscus sylvestris Hoffm.  Chem Pharm Bull. 1998;  46 875-8
  • 11 Lin Y L, Tasi W J, Chen I S, Kuo Y H. Chemical constituents from Mucuna membranacea .  J Chin Chem Soc. 1998;  45 213-7
  • 12 Wu T S, Jong T T, Tien H J, Kuoh C S, Furukawa H, Lee K H. Anaoquinone-A, an antimicrobial and cytotoxic principle from Annona montana .  Phytochemistry. 1987;  26 1623-5
  • 13 Chen C Y, Chang F R, Teng C M, Wu Y C. Cheritamine, a new n-fatty acyl tryptamine and other constituents from the stems of Annona cherimola .  J Chin Chem Soc. 1999;  46 77-86
  • 14 Dupont M P, Llabrés G, Delaude C, Tchissambou L, Gastmans J P. Sterolic and triterpenoidic constituents of stem bark of Drypetes gossweileri .  Planta Med. 1997;  63 282-4
  • 15 Chen J J. Ph. D. Dissertation. Kaohsiung Medical College Kaohsiung, Taiwan; 1997: 195-8
  • 16 Jiménez , Marcos M, Villaverde M C, Riguera R, Castedo L, Stermitz F. A chromone from Zanthoxylum species.  Phytochemistry. 1989;  28 1992-3
  • 17 Kisiel W, Jakupowic J. Long-chain alkyl hydroxycinnamates from Crepis taraxacifolia .  Planta Med. 1995;  61 87-8
  • 18 Lin Y L, Wang W Y, Kuo Y H, Chen C F. Nonsteroidal constituents from Solanum incanum L.  J Chin Chem Soc. 2000;  47 247-52
  • 19 Zdero C, Bohlmann F, Solomon J C, King R M, Robinson H. Ent-clerodanes and other constituents from Bolivian Baccharis species.  Phytochemistry. 1989;  28 531-42
  • 20 Blay G, Bargues V, Cardona L, García B, Pedro J R. Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaia-4,11-dien-3-one and hydrocolorenone from santonin.  Tetrahedron. 2001;  57 9719-25
  • 21 Chakrabarti R, Das B, Banerji J. Bis-coumarin from Edgeworthia gardneri .  Phytochemistry. 1986;  25 557-8
  • 22 Reisch J, Novák I, Szendrei K, Minker E. Über weitere C3-substituierte Cumarin-Derivate aus Ruta graveolens: Daphnoretin und Daphnoretin-Methyläther.  Planta Med. 1968;  16 372-6

Prof. Dr. I. S. Chen

Graduate Institute of Natural Products

Kaohsiung Medical University

Kaohsiung

Taiwan 807

Republic of China

Phone: +886-7-3121101 ext 2123

Fax: +886-7-3210683

Email: m635013@kmu.edu.tw