Skip to main content
Log in

Potent cytotoxicity against human small cell lung cancer cells of the heptenes from the stem bark of Xylopia pierrei Hance

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

Abstract

Phytochemical investigation of the stem bark of Xylopia pierrei Hance led to the isolation of one triterpene, polycarpol (1), three heptenes, (7R)-acetylmelodorinol (2), (7R)-melodorinol (3), and melodienone (8), and four flavonoids, pinocembrin (4), isochamanetin (5), chrysin (6), and dichamanetin (7). All compounds were isolated for the first time from this plant species. The structures of the isolated compounds were characterized by spectroscopic techniques and by comparison of the spectroscopic data with the literature values and the stereochemistry at the asymmetric carbon was determined by the modified Mosher’s method. Among them, compound 2 displayed potent cytotoxic activity against human small cell lung cancer (NCI-H187) cells with an IC50 value of 6.66 μM and it was 2.3-fold higher than that of the reference anticancer drug, ellipticine. In addition, compound 2 was also evaluated against the non-cancerous Vero cells and showed high selectivity index of 8.89, which is 59-fold greater than that of ellipticine. The findings suggest that compound 2 should be further developed as a potential lead molecule for anticancer drug development.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  • Achenbach H, Hohn M, Waibel R, Nkunya MHH, Jonker SA, Muhie S (1997) Oxygenated pyrenes, their potential biosynthetic precursor and benzylated dihydroflavones from two african Uvaria species. Phytochemistry 44:359–364

    Article  CAS  Google Scholar 

  • Andrade NC, Jose Maria BF, Marcelo SS, Emidio VLC, Jose Guilherme SM (2004) Diterpenes and volatile constituent from the leaves of Xylopia cayennensis Maas. Biochem Syst Ecol 32:1055–1058

    Article  Google Scholar 

  • Asekun OT, Adeniyi BA (2004) Antimicrobial and cyctoxic activities of the fruit essential oil of Xylopia aethiopica from Nigeria. Fitoterapia 75:368–370

    Article  CAS  PubMed  Google Scholar 

  • Brien JO, Wilson I, Orton T, Pognan F (2000) Investigation of the alamar blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur J Biochem 267:5421–5426

    Article  Google Scholar 

  • Da Silva FMA, Hector HFK, Andersson B, Afonso DLDS, Maria LBP (2012) Steroids and triterpene from the bark of Unonopsis guatterioides R. E. FR. (Anonnaceae). Int J Pharm Pharm Sci 4:522–523

    Google Scholar 

  • Dale JA, Dull DL, Mosher HS (1969) α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J Org Chem 34:2543–2549

    Article  CAS  Google Scholar 

  • Jung JH, Pummangura S, Chaichantipyuth C, Patarapanich C, Fanwick PE, Chang CJ, Mclaughlin JL (1990) New bioactive heptanes from Melodorum fruticosum (Annonaceae). Terahedron 46:5043–5054

    Article  CAS  Google Scholar 

  • Hunt L, Jordan M, De Jesus M, Wurm FM (1999) GFP-expressing mammalian cells for fast, sensitive, noninvasive cell growth assessment in a kinetic mode. Biotechnol and Bioeng 65:201–205

    Article  CAS  Google Scholar 

  • Kamperdick C, Phuong MN, Adam G, Sung TV (2003) Guaiane dimers from Xylopia vielana. Phytochemistry 64:811–816

    Article  CAS  PubMed  Google Scholar 

  • Kamperdick C, Phuong NM, Sung TV, Adam G (2001) Guaiane dimers from Xylopia vielana. Phytochemistry 56:335–340

    Article  CAS  PubMed  Google Scholar 

  • Lu X, Chen G, Xia L, Guo G (1997) Total synthesis of both enantiomers of melodorinol. Redetermination of their absolute configurations. Terahedron Asym 8:3067–3072

    Article  CAS  Google Scholar 

  • Martins D, Eliane O, Nidia FR, Vered M, Hugo EG (1998) A sesquiterpene dimer from Xylopia aromatica. Phytochemistry 48:677–680

    Article  CAS  Google Scholar 

  • Martins D, Hamerskib L, Alvarengac SAV, Roqued NF (1999) Labdane dimers from Xylopia aromatic. Phytochemistry 51:813–817

    Article  CAS  Google Scholar 

  • Moreira IC, Joao Henrique GL, Nidia FR (2005) Sequiterpenes diterpenes, steroids and alkaloid from branches of Xylopia brasiliensis Spreng (Annonaceae). Biochem Syst Ecol 33:948–951

    Article  CAS  Google Scholar 

  • Moreira IC, Lago JHG, Young MCM, Roque NF (2003) Antifungal aromadendrane sesquiterpenoids from the Leaves of Xylopia brasiliensis. J Braz Chem Soc 14:828–831

    Article  CAS  Google Scholar 

  • Moreira IC, Nidia FR, Joao HGL (2006) Diterpene adducts from branches of Xylopia emarginata. Biochem Syst Ecol 34:833–837

    Article  CAS  Google Scholar 

  • Nishiyama Y, Moriyasu M, Ichimaru M, Iwasa K, Kato A, Mathenge SG, Mutiso PBC, Juma FD (2004) Quaternary isoquinoline alkaloids from Xylopia parviflora. Phytochemistry 65:939–944

    Article  CAS  PubMed  Google Scholar 

  • Nishiyama Y, Moriyasu M, Ichimaru M, Iwasa K, Kato A, Mathenge SG, Mutiso PBC, Juma FD (2006) Secondary and tertiary isoquinoline alkaloids from Xylopia parviflora. Phytochemistry 67:2671–2675

    Article  CAS  PubMed  Google Scholar 

  • Nishiyama Y, Moriyasu M, Ichimaru M, Iwasa K, Kato A, Mathenge SG, Mutiso PBC, Juma FD (2010) Antinociceptive effects of the extracts of Xylopia parviflora bark and its alkaloidal components in experimental animals. J Nat Med 64:9–15

    Article  CAS  PubMed  Google Scholar 

  • Ohtani I, Kusumi T, Kashman Y, Kakisawa H (1991) High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids. J Am Chem Soc 113:4092–4096

    Article  CAS  Google Scholar 

  • Smitinand T (2014) Thai Plant Names (revised edition). Forest Herbarium, Royal Forest Department, Bangkok, Thailand

    Google Scholar 

  • Suksamrarn A, Ponglikitmongkol M, Wongkrajang K, Chindaduang A, Kittdanarirak S, Jankam A, Yingyongnarongkul B, Kittpanumat N, Chokchaisiri R, Khetkam P, Piyachaturawat P (2008) Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation. Bioorg Med Chem 16:6891–6902

    Article  CAS  PubMed  Google Scholar 

  • Tavares JF, Karine FQ, Marianna VBS, Margareth FFMD, Jose MBF, Emidio VLC, Carlos Alberto S, Joao XAJ, Patricia SM, Marcela H, Marcelo SS (2006) ent-Trachylobane diterpenoids from Xylopia langsdorffiana. J Nat Prod 69:960–962

    CAS  PubMed  Google Scholar 

  • Tuchinda P, Udchachon J, Reutrakul V, Santisuk T, Taylor WC, Farnsworth NR, Pezzuto JM, Kinghorn AD (1991) Bioactive butenolides from Melodorum fruticosum. Phytochemistry 30:2685–2689

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We acknowledge financial support from University of Phayao (grant no. R020057216002). Supports from The Thailand Research Fund (grant no. DBG5980003) and the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Office of the Higher Education Commission are gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ratchanaporn Chokchaisiri.

Ethics declarations

Conflict of interest

The authors declare that they have no competing interests.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chokchaisiri, R., Kunkaewom, S., Chokchaisiri, S. et al. Potent cytotoxicity against human small cell lung cancer cells of the heptenes from the stem bark of Xylopia pierrei Hance. Med Chem Res 26, 1291–1296 (2017). https://doi.org/10.1007/s00044-017-1843-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-017-1843-8

Keywords

Navigation