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Planta Med 2017; 83(03/04): 334-340
DOI: 10.1055/s-0042-116438
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Bioactive Lupane and Hopane Triterpenes from Lepisanthes senegalensis

Pornwimon Lomchid
1   Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
,
Pitak Nasomjai
1   Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
,
Somdej Kanokmedhakul
1   Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
,
Jaursup Boonmak
2   Materials Chemistry Research Center, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
,
Sujittra Youngme
2   Materials Chemistry Research Center, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
,
Kwanjai Kanokmedhakul
1   Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
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Weitere Informationen

Publikationsverlauf

received 26. April 2016
revised 16. August 2016

accepted 29. August 2016

Publikationsdatum:
12. September 2016 (online)

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Abstract

Two lupane and hopane caffeates (1 and 4) and two hopane coumarates (2 and 3) along with eight known compounds (5–12) were isolated from stems and roots of Lepisanthes senegalensis. Their structures were established on the basis of spectroscopic techniques. The structure of compound 2 was confirmed by single-crystal X-ray diffraction analysis. Triterpenes 1 and 4–6 showed cytotoxicity against the NCI-H187 cell line with IC50 values of 31.5, 28.5, 16.2, and 4.0 µM, respectively. However, these compounds also showed cytotoxicity against Vero cells, with IC50 values of 75.5, 16.6, 8.9, and 5.0 µM, respectively. In addition, compound 6 exhibited a moderate antimalarial activity with an IC50 value of 4.5 µM.

Key words

Lepisanthase senegalensis - Sapindaceae-triterpene caffeate - hopane coumarate-antimalarial - cytotoxicity

Supporting Information

 

  • References

  • 1 Smitinand T. Thai Plant Names, revised Edition. Bangkok: Prachachon Co. Limited; 2001: 317
    Suche in Google Scholar
  • 2 Chuakul W, Saralamp P, Paonil W, Temsiririrkkul R, Clayton T. Medicinal Plants in Thailand, Vol. II. Bangkok: Amarin Printing and Publish; 1997: 145
    Suche in Google Scholar
  • 3 Quattrocchi U. CRC World Dictionaries of medicinal and poisonous Plants: common Names, scientific Names, Synonyms, and Etymology. Boca Raton: CRC Press; 2012: 2254-2255
    Suche in Google Scholar
  • 4 Wutithamawech W, Tantirungkij M, Liangsakul P. Antibacterial potential of some Thai medicinal plants. Int J Pharm Bio Sci 2014; 5: 412-421
    PubMedSuche in Google Scholar
  • 5 Patra A, Chaudhuri SK, Panda KS. Betulin-3-caffeate from Quercus suber. 13C-NMR spectra of some lupenes. J Nat Prod 1988; 51: 217-220
    CrossrefPubMedSuche in Google Scholar
  • 6 Chien NQ, Hung NV, Santarsiero BD, Mesecar AD, Cuong NM, Soejarto DD, Pezzuto JM, Fong HSS, Tan GT. New 3-O-acyl betulinic acids from Strychnos vanprukii Craib. J Nat Prod 2004; 67: 994-998
    CrossrefPubMedSuche in Google Scholar
  • 7 Tanaka R, Matsunaga S. Saturated hopane and gammacerane triterpene-diols from the stem bark of Abies veitchii . Phytochemistry 1992; 31: 3535-3539
    CrossrefPubMedSuche in Google Scholar
  • 8 Otsuka H, Fujioka S, Komiya T, Goto Y, Hiramatsu Y, Fujimura H. Studies on anti-inflammatory agents V. A new anti-inflammatory constituent of Pyracantha crenulata Roem. Chem Pharm Bull 1981; 29: 3099-3104
    CrossrefPubMedSuche in Google Scholar
  • 9 Tinto W, Blair LC, Alli A. Lupane triterpenoids of Salacia cordata . J Nat Prod 1992; 55: 395-398
    CrossrefPubMedSuche in Google Scholar
  • 10 Ikuta A, Itokawa H. Triterpenoids of Paeonia japonica callus. Phytochemistry 1988; 27: 2813-2815
    CrossrefPubMedSuche in Google Scholar
  • 11 Fotie J, Bohle DS, Leimanis ML, Georges E, Rukunga G, Nkengfack AE. Lupeol long-chain fatty acid ester with antimalarial activity from Holarrhena floribunda . J Nat Prod 2006; 69: 62-67
    CrossrefPubMedSuche in Google Scholar
  • 12 Forgo P, Kover KE. Gradient enhanced selective experiments in the H NMR chemical shift assignment of the skeleton and side-chain resonance of stigmasterol, a phytosterol derivative. Steroids 2004; 69: 43-50
    CrossrefPubMedSuche in Google Scholar
  • 13 Harasawa A, Tagashira A. Isolation of 2,6-dimethoxy-1,4-benzoquinone from Hydrangea (Hydrangena macrophylla Seringe var. Otaksa Makino) and its deodorant activity against methyl mercaptan. Biosci Biotech Biochem 1994; 58: 2073-2074
    CrossrefPubMedSuche in Google Scholar
  • 14 Fuchino H, Satoh T, Tanaka N. Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii . Chem Pharm Bull 1995; 43: 1937-1942
    CrossrefPubMedSuche in Google Scholar
  • 15 Bruker. APEX2, SAINT and SADABS. Madison, Wisconsin: Bruker AXS Inc; 2014
    Suche in Google Scholar
  • 16 Sheldrick GM. Integrated space-group and crystal-structure determination. Acta Crystallogr Sect A 2015; A71: 3-8
    PubMedSuche in Google Scholar
  • 17 Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr Sect C 2015; C71: 3-8
    PubMedSuche in Google Scholar
  • 18 Sheldrick GM. A short history of SHELX. Acta Crystallogr Sect A 2008; A64: 112-122
    CrossrefPubMedSuche in Google Scholar
  • 19 Hübschle CB, Sheldrick GM, Dittrich B. ShelXle: a Ot graphical user interface for SHELXL. J Appl Cryst 2011; 44: 1281-1284
    CrossrefPubMedSuche in Google Scholar
  • 20 Spek AL. PLATON SQUEEZE: a tool for the calculation of the disordered solvent contribution to the calculated structure factors. Acta Crystallogr Sect C 2015; C71: 9-18
    PubMedSuche in Google Scholar
  • 21 Kuo YH, Chang CI, Kuo YH. Triterpene from Diospyros maritime. Phytochemistry 1997; 46: 1135-1137
    CrossrefPubMedSuche in Google Scholar
  • 22 Trager W, Jensen JB. Human malaria parasites in continuous culture. Science 1976; 193: 673-675
    CrossrefPubMedSuche in Google Scholar
  • 23 Desjardins RE, Canfield CJ, Haynes JD, Chulay JD. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob Agents Chemother 1979; 16: 710-718
    CrossrefPubMedSuche in Google Scholar
  • 24 Brien JO, Wilson I, Orton T, Opognan F. Investigation of the alamar blue (resazurin) fluorescent for the assessment of mammalian cell cytotoxicity. Eur J Biochem 2000; 267: 5421-5426
    CrossrefPubMedSuche in Google Scholar
  • 25 Hunt L, Jordan M, De Jesus M, Wurm FM. GFP-expressing mammalian cells for fast, sensitive, noninvasive cell growth assessment in a kinetic mode. Biotechnol Bioeng 1999; 65: 201-205
    CrossrefPubMedSuche in Google Scholar