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DOI: 10.1055/s-0031-1298156
© Georg Thieme Verlag KG Stuttgart · New York
Spiranthenones A and B, Tetraprenylated Phloroglucinol Derivatives from the Leaves of Spiranthera odoratissima
Publication History
                     received	October 12, 2011
                     
                     revised	Dec. 13, 2011
                     
                     accepted	Dec. 15, 2011
                     
Publication Date:
23 January 2012 (online)

Abstract
Two new polyprenylated acylphloroglucinols, spiranthenones A (1) and B (2), a sesquiterpenoid, 6α-acetoxy,1β-hydroxyeudesm-4(15)-ene (3), along with sesamin and β-sitosterol, were isolated from the EtOAc extract of the leaves of Spiranthera odoratissima, and shown to display antiprotozoal activity. Their structures and relative stereochemistry were elucidated by NMR and mass spectrometry. These compounds exhibited moderate antiprotozoal activity, but without significant cytotoxicity against fibroblasts cell line NIH-3T3. Compound 3 was the most selective towards parasites.
Key words
Rutaceae - Spiranthera odoratissima - acylphloroglucinols - sesquiterpenoid - antiprotozoal activity
References
- 1 
            Matos L G, Pontes I S, Tresvenzol L M F, Paula J R, Costa E A. 
            Analgesic and anti-inflammatory activity of the ethanolic extract from Spiranthera odoratissima A. St. Hilaire (Manacá) roots. 
            Phytoter Res. 
            2004; 
            18 
            963-966 
            
            Reference Ris Wihthout Link
- 2 
            Freitas C M J, Lucchese A M, Silva F S, Velozo E S. 
            Coumarins, furoquinoline alkaloids and terpenes from Spiranthera odoratissima (Rutaceae). 
            Biochem Syst Ecol. 
            2003; 
            31 
            805-807 
            
            Reference Ris Wihthout Link
- 3 
            Ribeiro T A N, Ndiaye E A S, Velozo E S, Vieira P C, Ellena J, de Sousa P T. 
            Limonoids from Spiranthera odoratissima St. Hil. 
            J Braz Chem Soc. 
            2005; 
            16 
            1347-1352 
            
            Reference Ris Wihthout Link
- 4 
            Terezan A P, Rossi R A, Almeida R N A, Freitas T G, Fernandes J B, Silva M F G F, Vieira P C, Bueno O C, Pagnocca F C, Pirani J R. 
            Activities of extracts and compounds from Spiranthera odoratissima St. Hil. (Rutaceae) in leaf-cutting ants and their symbiotic fungus. 
            J Braz Chem Soc. 
            2010; 
            21 
            882-886 
            
            Reference Ris Wihthout Link
- 5 
            Albernaz L C, de Paula J E, Romero G A S, Silva M R R, Grellier P, Mambu L, Espindola L S. 
            Investigation of plant extracts in traditional medicine of the Brazilian Cerrado against
            protozoans and yeasts. 
            J Ethnopharmacol. 
            2010; 
            113 
            116-121 
            
            Reference Ris Wihthout Link
- 6 
            Mosmann T. 
            Rapid colorimetric assay for cellular growth and survival: application to proliferation
            and cytotoxicity assays. 
            J Immunol Methods. 
            1983; 
            65 
            55-63 
            
            Reference Ris Wihthout Link
- 7 
            Nan-Jun S, Ching-Jer C, Cassady J M. 
            A cytotoxic tetralone derivative from Pararistolochia flos-avis. 
            Phytochemistry. 
            1987; 
            26 
            3051-3053 
            
            Reference Ris Wihthout Link
- 8 
            Nes W D, Norton R A, Benson M. 
            Carbon-13 NMR studies on sitosterol biosynthesized from [13C] mevalonates. 
            Phytochemistry. 
            1992; 
            31 
            805-811 
            
            Reference Ris Wihthout Link
- 9 
            Ciochina R, Grossman R B. 
            Polycyclic polyprenylated acylphloroglucinols. 
            Chem Rev. 
            2006; 
            106 
            3963-3986 
            
            Reference Ris Wihthout Link
- 10 
            Fukuyama Y, Kaneshi A, Tani N, Kodama M. 
            Subellinone, a polyisoprenylated phloroglucinol derivative from Garcinia subelliptica. 
            Phytochemistry. 
            1993; 
            33 
            483-485 
            
            Reference Ris Wihthout Link
- 11 
            Verotta L, Appendino G, Jakupovic J, Bombardelli E. 
            Hyperforin analogues from St. John's wort (Hypericum perforatum). 
            J Nat Prod. 
            2000; 
            63 
            412-415 
            
            Reference Ris Wihthout Link
- 12 
            Tanaka N, Takaishi Y, Shikishima Y, Nakanishi Y, Bastow K, Lee K H, Honda G, Ito L, Takeda Y, Kodzhimatov O K, Ashurmetov O. 
            Prenylated benzophenones and xanthones from Hypericum scabrum. 
            J Nat Prod. 
            2004; 
            67 
            1870-1875 
            
            Reference Ris Wihthout Link
- 13 
            Winkelmann K, Heilmann J, Zerbe O, Rali T, Sticher O. 
            New prenylated bi- and tricyclic phloroglucinol derivatives from Hypericum papuanum. 
            J Nat Prod. 
            2001; 
            64 
            701-706 
            
            Reference Ris Wihthout Link
- 14 
            Bokesch H R, Groweiss A, McKee T C, Boyd M R. 
            Laxifloranone, a new phloroglucinol derivative from Marila laxiflora. 
            J Nat Prod. 
            1999; 
            62 
            1197-1199 
            
            Reference Ris Wihthout Link
- 15 
            Ohmoto T, Ikeda K, Nomura S, Shimizu M, Saito S. 
            Studies on the sesquiterpenes from Ambrosia elatior Linné. 
            Chem Pharm Bull. 
            1987; 
            35 
            2272-2279 
            
            Reference Ris Wihthout Link
- 16 
            Niwa M, Iguchi M, Yamamura S. 
            Biomimetic reactions of epoxygermacrene-D. 
            Tetrahedron Lett. 
            1978; 
            42 
            4043-4046 
            
            Reference Ris Wihthout Link
- 17 
            Chan J A, Shultis E A, Carr S A, DeBrosse C W, Eggleston D S, Francis T A, Hyland L J, Johnson W P, Killmer L B, Staiger D B, Westley J W. 
            Novel phloroglucinols from the plant Melicope sessiliflora (Rutaceae). 
            J Org Chem. 
            1989; 
            54 
            2098-2103 
            
            Reference Ris Wihthout Link
- 18 
            Verotta L. 
            Are acylphloroglucinols lead structures for the treatment of degenerative diseases?. 
            Phytochem Rev. 
            2002; 
            1 
            389-407 
            
            Reference Ris Wihthout Link
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