Sarmentosumols A to F, New Mono- and Dimeric Alkenylphenols from Piper sarmentosum

Abstract

Two new mono- and four new dimeric alkenylphenols, namely sarmentosumols A to F (1–6), were isolated from the aerial parts of Piper sarmentosum. The structures of these compounds were determined through a detailed analysis of NMR and MS data. Their antimicrobial activity against Escherichia coli, Staphyloccocus aureus, and Candida albicans, and their cytotoxic activity against human myeloid leukemia (K562) and human lung adenocarcinoma (A549) cell lines were also evaluated. Except for sarmentosumol A (1), whose MIC on S. aureus was reported to be 7.0 µg/mL, none of the other newly discovered compounds exhibited antimicrobial property. The studied compounds did not possess any cytotoxic property.

Key words

Piperaceae - Piper sarmentosum - alkenylphenols - antimicrobial activity

• References

• 1 Xia NH, Tseng YC, Gilbert MG. Flora of China, Volume 4. Beijing: Science Press; 1999: 110-129
• 2 Scott IM, Jensen HR, Philogene BJR, Arnason JT. A review of Piper spp. (Piperaceae) phytochemistry, insecticidal activity and mode of action. Phytochem Rev 2008; 7: 65-75
• 3 Parmar VS, Jain SC, Bisht KS, Jain R, Taneja P, Jha A, Tyagi OD, Prasad AK, Wengel J, Olsen CE. Phytochemistry of the genus Piper . Phytochemistry 1997; 46: 597-673
• 4 Orjala J, Mian P, Rali T, Sticher O. Gibbilimbols A–D, cytotoxic and antibacterial alkenylphenols from Piper gibbilimbum . J Nat Prod 1998; 61: 939-941
• 5 Editorial Board of ʼZhonghua Bencaoʼ, State Administration of Traditional Chinese Medicine of the Peopleʼs Republic of China. Zhonghua Bencao, Volume 3. Shanghai: Shanghai Scientific and Technical Publishers; 1999: 445-446
• 6 Stohr JR, Xiao PG, Bauer R. Isobutylamides and a new methylbutylamide from Piper sarmentosum . Planta Med 1999; 65: 175-177
• 7 Tuntiwachwuttikul P, Phansa P, Pootaeng-On Y, Taylor WC. Chemical constituents of the roots of Piper sarmentosum . Chem Pharm Bull 2006; 54: 149-151
• 8 Rukachaisirikul T, Siriwattanakit P, Sukcharoenphol K, Wongvein C, Ruttanaweang P, Wongwattanavuch P, Suksamrarn A. Chemical constituents and bioactivity of Piper sarmentosum . J Ethnopharmacol 2004; 93: 173-176
• 9 Sim KM, Mak CN, Ho LP. A new amide alkaloid from the leaves of Piper sarmentosum . J Asian Nat Prod Res 2009; 11: 757-760
• 10 Bokesch HR, Gardella RS, Rabe DC, Bottaro DP, Linehan WM, McMahon JB, McKee TC. A new hypoxia inducible factor-2 inhibitory pyrrolinone alkaloid from roots and stems of Piper sarmentosum . Chem Pharm Bull 2011; 59: 1178-1179
• 11 Masuda T, Inazumi A, Yamada Y, Padolina WG, Kikuzaki H, Nakatani N. Antimicrobial phenylpropanoids from Piper sarmentosum . Phytochemistry 1991; 30: 3227-3228
• 12 Pan L, Matthew S, Lantvit DD, Zhang X, Tran NN, Chai H, de Blanco EJC, Soejarto DD, Swanson SM, Kinghorn AD. Bioassay-guided isolation of constituents of Piper sarmentosum using a mitochondrial transmembrane potential assay. J Nat Prod 2011; 74: 2193-2199
• 13 Ee GCL, Lim CM, Lim CK, Rahmani M, Shaari K, Bong CFJ. Alkaloids from Piper sarmentosum and Piper nigrum . Nat Prod Res 2009; 23: 1416-1423
• 14 Likhitwitayawuid K, Ruangrungsi N, Lange GL, Decicco CP. Structural elucidation and synthesis of new components isolated from Piper sarmentosum (Piperaceae). Tetrahedron 1987; 43: 3689-3694
• 15 Tang GH, Chen DM, Qiu BY, Sheng L, Wang YH, Hu GW, Zhao FW, Ma LJ, Wang HA, Huang QQ, Xu JJ, Long CL, Li J. Cytotoxic amide alkaloids from Piper boehmeriaefolium . J Nat Prod 2011; 74: 45-49
• 16 Masaki ME, Hiro S, Usuki Y, Harumoto T, Terazima MN, Buonanno F, Miyake A, Iio H. Climacostol, a defense toxin of Climacostomum virens (protozoa, ciliata), and its congeners. Tetrahedron 2004; 60: 7041-7048
• 17 Santos BVO, Chaves EVL, Gray AI. Phenylalkanoids from Piper marginatum . Phytochemistry 1998; 49: 1381-1384