Download PDF
Planta Med 2014; 80(08/09): 695-702
DOI: 10.1055/s-0034-1368505
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Aryltetralin Lignans from Fruits of Cleistanthus indochinensis

Van Trinh Thi Thanh
1   Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam
,
Van Cuong Pham
1   Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam
,
Huong Doan Thi Mai
1   Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam
,
Marc Litaudon
2   Institut de Chimie des Substances Naturelles, Gif-sur Yvette, France
,
Françoise Guéritte
2   Institut de Chimie des Substances Naturelles, Gif-sur Yvette, France
,
Van Hung Nguyen
1   Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam
,
Van Minh Chau
1   Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Cau Giay, Hanoi, Vietnam
› Author Affiliations
Further Information

Publication History

received 07 February 2014
revised 11 February 2014

accepted 22 April 2014

Publication Date:
04 June 2014 (online)

Also available at
    Permissions and Reprints

Abstract

Eight new aryltetralin lignans, cleisindosides A–F (1–6), picroburseranin (7), and 7-hydroxypicropolygamain (8), were isolated from the fruits of Cleistanthus indochinensis (Euphorbiaceae). The structures of the isolates were established on the basis of their one- and two-dimensional NMR spectral data, as well as their mass spectrometric data. Compound 7 was found to have potent cytotoxicity against oral epidermoid carcinoma cells with an IC50 value of 0.062 µM, whereas glycosylation to 3 (IC50 7.5 µM) and stereochemical changes to 8 (IC50 10.8 µM) led to marked decreases in biological activity. Thus, it was determined that the C-7 and C-8′ positions are critical for the biological activity of the lignans from this plant.

Key words

Euphorbiaceae - Cleistanthus indochinensis - lignans - glycosides - cytotoxicity

Supporting Information

 

  • References

  • 1 Pinho PMM, Kijjoa A. Chemical constituents of the plants of the genus Cleistanthus and their biological activity. Phytochem Rev 2007; 6: 175-182
    CrossrefPubMedGoogle Scholar
  • 2 Ramesh C, Ravindranath N, Ram TS, Das B. Arylnaphthalide lignans from Cleistanthus collinus . Chem Pharm Bull 2003; 51: 1299-1300
    CrossrefPubMedGoogle Scholar
  • 3 Eswarappa S, Chakraborty AR, Palatty BU, Vasnaik M. Cleistanthus collinus poisoning: case reports and review of the literature. J Toxicol Clin Toxicol 2003; 41: 369-372
    CrossrefPubMedGoogle Scholar
  • 4 Govindachari TR, Sathe SS, Viswanathan N, Pai BR, Srinivasan M. Chemical constituents of Cleistanthus collinus (Rox.). Tetrahedron 1969; 25: 2815-2821
    CrossrefPubMedGoogle Scholar
  • 5 Anjaneyulu ASR, Ramaiah PR, Row LR, Venkateswarlu R, Pelter A, Ward RS. New lignans from the heartwood of Cleistanthus collinus . Tetrahedron 1981; 37: 3641-3652
    CrossrefPubMedGoogle Scholar
  • 6 Sastry KV, Rao EV, Buchanan JG, Sturgeon RJ. Cleistanthoside B, a diphyllin glycoside from Cleistanthus patulus heartwood. Phytochemistry 1987; 26: 1153-1154
    CrossrefPubMedGoogle Scholar
  • 7 Pradheepkumar CP, Shanmugam G. Anticancer potential of cleistanthin A isolated from the tropical plant Cleistanthus collinus . Oncol Res 1999; 11: 225-232
    PubMedGoogle Scholar
  • 8 Prabhakaran C, Kumar P, Panneerselvam N, Rajesh S, Shanmugam G. Cytotoxic and genotoxic effects of cleistanthin B in normal and tumour cells. Mutagenesis 1996; 11: 553-557
    CrossrefPubMedGoogle Scholar
  • 9 Parasuraman S, Raveendran R. Effect of cleistanthin A and B on adrenergic and cholinergic receptors. Pharmacogn Mag 2011; 7: 243-247
    CrossrefPubMedGoogle Scholar
  • 10 Pham HH. An illustrated flora of Vietnam. 2nd ed. Volume II. Vietnam: NXB Tre, TP Ho CHi Minh; 2003: 231-235
    Google Scholar
  • 11 Thanh VT, Pham VC, Doan TMH, Litaudon M, Gueritte F, Retailleau P, Nguyen VH, Chau VM. Cytotoxic lignans from fruits of Cleistanthus indochinensis: synthesis of cleistantoxin derivatives. J Nat Prod 2012; 75: 1578-1583
    CrossrefPubMedGoogle Scholar
  • 12 Ishii T, Yanagisawa M. Synthesis, separation and NMR spectral analysis of methyl apiofuranosides. Carbohydr Res 1998; 313: 189-192
    CrossrefPubMedGoogle Scholar
  • 13 Kitagawa I, Hori K, Sakagami M, Hashiuchi F, Yoshikawa M, Ren J. Saponin and sapogenol. XLIX. On the constituents of the roots of Glycyrrhiza inflata Batalin from Xinjiang, China. Characterization of two sweet oleanane-type triterpene oligoglycosides, apioglycyrrhizin and araboglycyrrhizin. Chem Pharm Bull 1993; 41: 1350-1357
    CrossrefPubMedGoogle Scholar
  • 14 Nakanishi T, Inatomi Y, Murata H, Shigeta K, Iida N, Inada A, Murata J, Farrera MA, Iinuma M, Tanaka T, Tajima S, Oku N. A new and known cytotoxic aryltetralin-type lignans from stems of Bursera graveolens . Chem Pharm Bull 2005; 53: 229-231
    CrossrefPubMedGoogle Scholar
  • 15 Silva R, Heleno VCG, Albuquerque S, Bastos JK, Silva MLA, Donate PM, Silva GV. Spectral assignments and reference data. Magn Reson Chem 2004; 42: 985-989
    CrossrefPubMedGoogle Scholar
  • 16 Peraza-Sanchez SR, Pena-Rodriquez LM. Isolation of picropolygamain from the resin of Bursera simaruba . J Nat Prod 1992; 55: 1768-1771
    CrossrefPubMedGoogle Scholar
  • 17 Sheriha GM, Abouamer K, Elshtaiwi BZ, Ashour AS, Abed FA, Alhallaq HH. Quinoline alkaloids and cytotoxic lignans from Haplophyllum tuberculatum . Phytochemistry 1987; 26: 3339-3341
    CrossrefPubMedGoogle Scholar
  • 18 Klyne W, Stevenson R, Swan RJ. Optical rotatory dispersion. Part XXVIII. The absolute configuration of otobain and derivatives. J Chem Soc C 1966; 893-896
    CrossrefPubMedGoogle Scholar
  • 19 Zhao C, Nagatsu A, Hatano K, Shirai N, Kato S, Ogihara Y. New lignan glycosides from Chinese medicinal plant, Sinopodophillum emodi . Chem Pharm Bull 2003; 51: 255-261
    CrossrefPubMedGoogle Scholar
  • 20 Gu JQ, Park EJ, Totura S, Riswan S, Fong HH, Pezzuto JM, Kinghorn AD. Constituents of the twigs of Hernandia ovigera that inhibit the transformation of JB6 murine epidermal cells. J Nat Prod 2002; 65: 1065-1068
    CrossrefPubMedGoogle Scholar
  • 21 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Meth 1983; 65: 55-63
    CrossrefPubMedGoogle Scholar
  • 22 Evaristo IM, Leitao MC. Identification and quantification by DAD-HPLC of the phenolic fraction contained in the leaves of Quercus suber L. Silva Lusitana 2001; 9: 135-141
    PubMedGoogle Scholar