Skip to main content
Log in

Phenolic constituents of Acorus gramineus

  • Research Articles
  • Drug Design and Discovery
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

The purification of a MeOH extract from the rhizome of Acorus gramineus (Araceae) using column chromatography furnished two new stereoisomers of phenylpropanoid, acoraminol A (1) and acoraimol B (2). It also furnished 17 known phenolic compounds, β-asarone (3), asaraldehyde (4), isoacoramone (5), propioveratrone (6), (1′R,2′S)-1′,2′-dihydroxyasarone (7), (1′S,2′S)-1′,2′-dihydroxyasarone (8), 3′,4′-dimethoxycinnamyl alcohol (9), 3′,4′,5′-trimethoxycinnamyl alcohol (10), kaempferol 3-methyl ether (11), 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-propanediol (12), hydroxytyrosol (13), tyrosol (14), (2S,5S)-diveratryl-(3R,4S)-dimethyltetrahydrofuran (15), (7S,8R)-dihydrodehydrodiconiferyl alcohol (16), 7S,8S-threo-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan (17), 7S,8R-erythro-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8-O-4′-neolignan (18), and dihydroyashsbushiketol (19). The structures of the new compounds were elucidated by analysis of spectroscopic data including 1D and 2D NMR data. The absolute configurations of 1 and 2 were determined using the convenient Mosher ester procedure. Compounds 5–19 were isolated for the first time from this plant source. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamine B (SRB) bioassay.

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.

Similar content being viewed by others

References

  • Asakawa, Y., Chemical constituents of Alnus firma. Bull. Chem. Soc. Jpn., 43, 2223–2229 (1970).

    Article  CAS  Google Scholar 

  • Capasso, R., Cristinzio, G., Evidente, A., and Scognamiglio, F., Isolation, spectroscopy and selective phytotoxic effects of polyphenols from vegetable waste waters. Phytochemistry, 31, 4125–4128 (1992).

    Article  CAS  Google Scholar 

  • Chun, H. S., Kim, J. M., Choi, E. H., and Chang, N., Neuroprotective effects of several korean medicinal plants traditionally used for stroke remedy. J. Med. Food, 11, 246–251 (2008).

    Article  PubMed  CAS  Google Scholar 

  • de Silva Filho, A. A., Albuquerque, S., Silva, M. L., Eberlin, M. N., Tomazela, D. M., and Bastos, J. K., Tetrahydrofuran lignans from Nectandra megapotamica with trypanocidal activity. J. Nat. Prod., 67, 42–45 (2004).

    Article  PubMed  Google Scholar 

  • Feliciano, A. S., Medarde, M., Lopez, J. L., and Miguel del Corral, J. K., Two new cinnamyl isovalerate derivatives from Juniperus thurifera leaves. J. Nat. Prod., 49, 677–679 (1986).

    Article  Google Scholar 

  • Freire, F., Seco, J. M., Quinoa, E., and Riguera, R., Determining the absolute stereochemistry of secondary/secondary diols by 1H NMR: basis and applications. J. Org. Chem., 70, 3778–3790 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Greca, M. D., Monaco, P., Previtera, L., Aliotta, G., Pinto, G., and Pollio, A., Allelochemical activity of phenylpropanes from Acorus gramineus. Phytochemistry, 28, 2319–2321 (1989).

    Article  Google Scholar 

  • Herrera Braga, A. C., Zacchino, S., Badano, H., González Sierra, M., and Rúveda, E. A., 13C NMR spectral and conformational analysis of 8-O-4′ neolignans. Phytochemistry, 23, 2025–2028 (1984).

    Article  Google Scholar 

  • Joshi, B. P., Sharma, A., and Sinha, A. K., Microwave- and ultrasound-assisted semisynthesis of natural methoxylated propiophenones from isomeric mixture of phenylpropenes in minutes. Can. J. Chem., 83, 1826–1832 (2005).

    Article  CAS  Google Scholar 

  • Kouno, I., Yanagida, Y., Shimono, S., Shintomi, M., and Yang, C.-S., Phenylpropanoids from the barks of Illicium difengpi. Chem. Pharm. Bull., 40, 2461–2464 (1992).

    CAS  Google Scholar 

  • Kuang, H. X., Xia, Y. G., Yang, B. Y., Wang, Q. H., and Lü, S. W., Lignan constituents from Chloranthus japonicus sieb. Arch. Pharm. Res., 32, 329–334 (2009).

    Article  PubMed  CAS  Google Scholar 

  • Lee, J. Y., Lee, J. Y., Yun, B. S., and Hwang, B. K., Antifungal activity of β-asarone from rhizomes of Acorus gramineus. J. Agric. Food Chem., 52, 776–780 (2004).

    Article  PubMed  CAS  Google Scholar 

  • Liao, J. F., Huang, S. Y., Jan, Y. M., Yu, L. L., and Chen, C. F., Central inhibitory effects of water extract of Acori graminei rhizoma in mice. J. Ethnopharmacol., 61, 185–193 (1998).

    Article  PubMed  CAS  Google Scholar 

  • Matsuda, N. and Kikuchi, M., Studies on the constituents of Lonicera Species. X. Neolignan glycosides from the leaves of Lonicera gracilipes var. glandulosa MAXIM. Chem. Pharm. Bull., 44, 1676–1679 (1996).

    CAS  Google Scholar 

  • Nawamaki, K. and Kuroyanagi, M., Sesquiterpenoids from Acorus calamus as germination inhibitors. Phytochemistry, 43, 1175–1182 (1996).

    Article  CAS  Google Scholar 

  • Prasad, A. K., Tyagi, O. D., Wengel, J., Boll, P. M., Olsen, C. E., Bisht, K. S., Singh, A., Sarangi, A., Kumar, R., Jain, S. C., and Parmar, V. S., Neolignans and a lignan from Piper clarkii. Phytochemistry, 39, 655–658 (1995).

    Article  CAS  Google Scholar 

  • Patra, A. and Mitra, A. K., Constituents of Acorus calamus. J. Nat. Prod., 44, 668–669 (1981).

    Article  CAS  Google Scholar 

  • Santos, B. V. O. and Chaves, M. C. O., 2,4,5-trimetoxypropiophenone from Piper marginatum. Biochem. Sys. Ecol., 27, 539–541 (1999).

    Article  Google Scholar 

  • Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107–1112 (1990).

    Article  PubMed  CAS  Google Scholar 

  • Su, B. N., Park, E. J., Mbwambo, Z. H., Santarsiero, B. D., Mesecar, A. D., Fong, H. H., Pezzuto, J. M., and Kinghorn, A. D., New chemical constituents of Euphorbia quinquecostata and absolute configuration assignment by a convenient Mosher ester procedure carried out in NMR tubes. J. Nat. Prod., 65, 1278–1282 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Tang, W. and Eisenbrand, G., Chinese Drugs of Plant Origin. Springer, New York, pp. 45–46, (1992).

    Google Scholar 

  • Valesi, A. G., Methylated flavonols in Larrea cuneifolia. Phytochemistry, 11, 2821–2826 (1972).

    Article  CAS  Google Scholar 

  • Wang, H. Z., Cheng, Y. G., and Fan C. S., Review of studies on chemical constituents and pharmacology of genus Acorus. Acta Bot. Yunnanica, 5, 96–100 (1998).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Seung Young Lee.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Park, C.H., Kim, K.H., Lee, I.K. et al. Phenolic constituents of Acorus gramineus . Arch. Pharm. Res. 34, 1289–1296 (2011). https://doi.org/10.1007/s12272-011-0808-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-011-0808-6

Key words

Navigation