Download PDF
Planta Med 2013; 79(08): 693-696
DOI: 10.1055/s-0032-1328400
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

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

Shi-Xian Yang
1   Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Qian-Yun Sun
2   Key Laboratory of Chemistry for Natural Products, Guizhou Province and Chinese Academy of Sciences, Guiyang, Peopleʼs Republic of China
,
Fu-Mei Yang
2   Key Laboratory of Chemistry for Natural Products, Guizhou Province and Chinese Academy of Sciences, Guiyang, Peopleʼs Republic of China
,
Guang-Wan Hu
1   Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Ji-Feng Luo
1   Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Yue-Hu Wang
1   Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
,
Chun-Lin Long
1   Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peopleʼs Republic of China
3   College of Life and Environmental Sciences, Minzu University of China, Beijing, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 19 October 2012
revised 03 January 2013

accepted 04 March 2013

Publication Date:
10 April 2013 (online)

    Permissions and Reprints

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

Supporting Information

 

  • References

  • 1 Xia NH, Tseng YC, Gilbert MG. Flora of China, Volume 4. Beijing: Science Press; 1999: 110-129
    Google Scholar
  • 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
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    Google Scholar
  • 6 Stohr JR, Xiao PG, Bauer R. Isobutylamides and a new methylbutylamide from Piper sarmentosum . Planta Med 1999; 65: 175-177
    Article in Thieme ConnectPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 11 Masuda T, Inazumi A, Yamada Y, Padolina WG, Kikuzaki H, Nakatani N. Antimicrobial phenylpropanoids from Piper sarmentosum . Phytochemistry 1991; 30: 3227-3228
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 17 Santos BVO, Chaves EVL, Gray AI. Phenylalkanoids from Piper marginatum . Phytochemistry 1998; 49: 1381-1384
    CrossrefPubMedGoogle Scholar