Bioactive Lupane and Hopane Triterpenes from Lepisanthes senegalensis

Pornwimon Lomchid; Pitak Nasomjai; Somdej Kanokmedhakul; Jaursup Boonmak; Sujittra Youngme; Kwanjai Kanokmedhakul

doi:10.1055/s-0042-116438

Planta Medica, Table of Contents

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

¹Natural 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

¹Natural 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

¹Natural 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

²Materials 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

²Materials 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

¹Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand

› Author Affiliations

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

Full Text

References

References
1 Smitinand T. Thai Plant Names, revised Edition. Bangkok: Prachachon Co. Limited; 2001: 317
2 Chuakul W, Saralamp P, Paonil W, Temsiririrkkul R, Clayton T. Medicinal Plants in Thailand, Vol. II. Bangkok: Amarin Printing and Publish; 1997: 145
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
4 Wutithamawech W, Tantirungkij M, Liangsakul P. Antibacterial potential of some Thai medicinal plants. Int J Pharm Bio Sci 2014; 5: 412-421
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
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
7 Tanaka R, Matsunaga S. Saturated hopane and gammacerane triterpene-diols from the stem bark of Abies veitchii . Phytochemistry 1992; 31: 3535-3539
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
9 Tinto W, Blair LC, Alli A. Lupane triterpenoids of Salacia cordata . J Nat Prod 1992; 55: 395-398
10 Ikuta A, Itokawa H. Triterpenoids of Paeonia japonica callus. Phytochemistry 1988; 27: 2813-2815
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
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
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
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
15 Bruker. APEX2, SAINT and SADABS. Madison, Wisconsin: Bruker AXS Inc; 2014
16 Sheldrick GM. Integrated space-group and crystal-structure determination. Acta Crystallogr Sect A 2015; A71: 3-8
17 Sheldrick GM. Crystal structure refinement with SHELXL. Acta Crystallogr Sect C 2015; C71: 3-8
18 Sheldrick GM. A short history of SHELX. Acta Crystallogr Sect A 2008; A64: 112-122
19 Hübschle CB, Sheldrick GM, Dittrich B. ShelXle: a Ot graphical user interface for SHELXL. J Appl Cryst 2011; 44: 1281-1284
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
21 Kuo YH, Chang CI, Kuo YH. Triterpene from Diospyros maritime. Phytochemistry 1997; 46: 1135-1137
22 Trager W, Jensen JB. Human malaria parasites in continuous culture. Science 1976; 193: 673-675
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
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
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

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