Download PDF
Planta Med 2010; 76(5): 454-457
DOI: 10.1055/s-0029-1186217
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Chemical Constituents from the Rhizome of Acorus calamus L.

Weiwei Dong2 , 3 , Dajian Yang2 , Runhua Lu1
  • 1Department of Applied Chemistry, College of Sciences, China Agricultural University, Beijing, P. R. China
  • 2State Key Laboratory of Chinese Medicine and Molecular Pharmacology, Shenzhen, P. R. China
  • 3Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, P. R. China
Further Information

Publication History

received August 28, 2009 revised Sept. 16, 2009

accepted Sept. 22, 2009

Publication Date:
21 October 2009 (online)

Also available at
    Permissions and Reprints

Abstract

Three new sesquiterpenes, 1β,7α(H)-cadinane-4α,6α,10α-triol (1), 1α,5β-guaiane-10α-O-ethyl-4β,6β-diol (2), and 6β,7β(H)-cadinane-1α,4α, 10α-triol (3), together with 25 known ones, were isolated from the rhizome of Acorus calamus L. Their chemical structures were established on the basis of interpretation of spectroscopic data and comparison with those of the related known compounds.

Key words

Acorus calamus L. - Araceae - sesquiterpenes - chemical structure - NMR

References

  • 1 Robert B, Henrey T. Medicinal plants. London; Churchill 1983
    PubMedSearch in Google Scholar
  • 2 Shoba F G, Thomas M. Study of antidiarrhoeal activity of four medicinal plants in castor-oil induced diarrhoea.  J Ethnopharmacol. 2001;  76 73-76
    CrossrefPubMedSearch in Google Scholar
  • 3 Zanoli P, Avallone R, Baraldi M. Sedative and hypothermic effects induced by β-asarone, a main component of Acorus calamus.  Phytother Res. 1998;  12 S114-S116
    CrossrefPubMedSearch in Google Scholar
  • 4 Wu H S, Li Y Y, Weng L J, Zhou C X, He Q J, Lou Y J. A Fraction of Acorus calamus L. extract devoid of β-asarone enhances adipocyte differentiation in 3T3-L1 cells.  Phytother Res. 2007;  21 562-564
    CrossrefPubMedSearch in Google Scholar
  • 5 Nawamaki K, Kuroyanagi M. Sesquiterpenoids from Acorus calamus as germination inhibitors.  Phytochemistry. 1996;  43 1175-1182
    CrossrefPubMedSearch in Google Scholar
  • 6 Iguchi M, Niwa M, Nishiyama A. Isolation and structure of acoragermacrone.  Tetrahedron Lett. 1973;  29 2759-2762
    PubMedSearch in Google Scholar
  • 7 Patra A, Mitra A K. Constituents of Acorus calamus Linn.  Indian J Chem. 1979;  17B 412-414
    PubMedSearch in Google Scholar
  • 8 Rai R, Siddiqui I R, Singh J. Triterpenoid saponins from Acorus calamus.  Indian J Chem. 1998;  37B 473-476
    PubMedSearch in Google Scholar
  • 9 Todorova M N, Ognyanov I V, Shatar S. Chemical composition of essential oil from Mongolian Acorus calamus L. rhizomes.  J Essent Oil Res. 1995;  7 191-193
    PubMedSearch in Google Scholar
  • 10 Tkachev A V, Gur'ev A M, Yusubov M S. Acorafuran, a new sesquiterpenoid from Acorus calamus essential oil.  Chem Nat Compd. 2006;  42 696-698
    CrossrefPubMedSearch in Google Scholar
  • 11 He K, Zeng L, Shi G, Zhao G X, Kozlowski J F, Mclaughlin J L. Bioactive compounds from Taiwania cryptomerioides.  J Nat Prod. 1997;  60 38-40
    CrossrefPubMedSearch in Google Scholar
  • 12 Kamel A. 7-epi-Eudesmanes from Teucrium polium.  J Nat Prod. 1995;  58 428-431
    CrossrefPubMedSearch in Google Scholar
  • 13 Battaglia R, Bernardi M D, Fronza G, Mellerio G, Vidari G, Finsi P V. Fungal metabolites. VIII: Structures of new sesquiterpenes from Lactarius scrobiculatus.  J Nat Prod. 1980;  43 319-328
    CrossrefPubMedSearch in Google Scholar
  • 14 Yamamura S, Iguchi M, Nishiyama A, Niwa M, Koyama H, Hirata Y. Sesquiterpenes from Acorus calamus L.  Tetrahedron. 1971;  27 5419-5431
    CrossrefPubMedSearch in Google Scholar
  • 15 Perales A, Martinez-Ripoll M, Fayos J, Savona G, Bruno M, Rodriguez B. Sesquiterpenoid constituents of Meriandra benghalensis (Labiatae). X-ray structure analysis.  J Org Chem. 1983;  48 5318-5321
    CrossrefPubMedSearch in Google Scholar
  • 16 Evans F E. Structure analysis of proximadiol (crypromeridiol) by 13C spectroscopy.  Phytochemistry. 1982;  21 937-938
    CrossrefPubMedSearch in Google Scholar
  • 17 Bruno M, De La Torre M, Rodriguez B, Omar A A. Guaiane sesquiterpenes from Teucrium leucocladum.  Phytochemistry. 1993;  34 245-247
    CrossrefPubMedSearch in Google Scholar
  • 18 Nagashima F, Tanaka H, Toyota M, Hashimoto T, Kan Y, Takaoka S, Tori M, Asakawa Y. Sesqui- and diterpenoids from Plagiochila species.  Phytochemistry. 1994;  36 1425-1430
    CrossrefPubMedSearch in Google Scholar
  • 19 Mahmoud A A. 7-Epi-eudesmanes, eudesmanoic acids, eudesmanolides and other sesquiterpenes from Pluchea dioscoridis.  Phytochemistry. 1997;  45 1633-1638
    CrossrefPubMedSearch in Google Scholar
  • 20 Kuo Y H, Cheng Y S, Kao S T, Lin Y T. Two new saturated sesquiterpene diolscadinan-3β,9β-diol and cadinan-3β,9α-diol from Taiwania cryptomerioides Hayata.  J Chin Chem Soc. 1973;  20 83-86
    PubMedSearch in Google Scholar
  • 21 Pettit G R, Numata A, Cragg G M, Herald D L, Takada T, Iwamoto C, Riesen R, Schmidt J M, Doubek D L, Goswami A. Isolation and structures of schleicherastatins 1–7 and schleicheols 1 and 2 from the teak forest medicinal tree Schleichera oleosa.  J Nat Prod. 2000;  63 72-78
    CrossrefPubMedSearch in Google Scholar
  • 22 Riccardis F, Minale L, Iorizzi M, Debitus C, Lévi C. Marine sterols, side-chain-oxygenated sterols, possibly of abiotic origin, from the new caledonian sponge Stelodoryx chlorophylla.  J Nat Prod. 1993;  56 282-287
    CrossrefPubMedSearch in Google Scholar
  • 23 Monaco P, Previtera L. A steroid from Pistia stratiotes.  Phytochemistry. 1991;  30 2420-2422
    CrossrefPubMedSearch in Google Scholar
  • 24 Goswami P, Kotoky J, Chen Z N, Lu Y. A sterol glycoside from leaves of Clerodendron colebrookianum.  Phytochemistry. 1996;  41 279-281
    CrossrefPubMedSearch in Google Scholar
  • 25 Ahmad V U, Aliya R, Perveen S, Shameel M. A sterol glycoside from marine green alga Codium iyengarii.  Phytochemistry. 1992;  31 1429-1431
    CrossrefPubMedSearch in Google Scholar
  • 26 Guo Q, Fang H, Su W. Lignans in flower buds of Magnolia biondii.  Chin Tradit Herb Drugs. 2004;  35 849-851
    PubMedSearch in Google Scholar
  • 27 Matsushita H, Miyase T, Ueno A. Lignan and terpene glycosides from Epimedium sagittatum.  Phytochemistry. 1991;  30 2025-2027
    CrossrefPubMedSearch in Google Scholar
  • 28 Jin X Q, Xu D M, Xu Y J, Cui D B, Xiao Y W. The structure identification of zhepiresionol.  Acta Pharm Sin. 1993;  28 212-215
    PubMedSearch in Google Scholar
  • 29 Sinha A K, Acharya R, Joshi B P. A mild and convenient procedure for the conversion of toxic β-asarone into rare phenylpropanoids: 2,4,5-trimethoxycinnamaldehyde and γ-asarone.  J Nat Prod. 2002;  65 764-765
    CrossrefPubMedSearch in Google Scholar
  • 30 Patra A, Mitra A K. Constituents of Acorus calamus: structure of acoramone. carbon-13 NMR spectra of cis- and trans-asarone.  J Nat Prod. 1981;  44 668-669
    CrossrefPubMedSearch in Google Scholar
  • 31 Poigny S, Guyot M, Samadi M. Total synthesis of maesanin and analogues.  Tetrahedron. 1998;  54 14791-14802
    CrossrefPubMedSearch in Google Scholar
  • 32 Yang X Y, Chen F K, Wu L J. Studies on chemical constituents of Acorus tatarinowii decoction.  Chin Tradit Herb Drugs. 1998;  29 730-731
    PubMedSearch in Google Scholar
  • 33 Ma C Y, Liu W K, Che C T. Lignanamides and nonalkaloidal components of Hyoscyamus niger seeds.  J Nat Prod. 2002;  65 206-209
    CrossrefPubMedSearch in Google Scholar
  • 34 Chen Y, Yang G Z, Li Y C. Studies on the chemical constituent of Tripterygium wilfordill Hook. F.  Nat Prod Res Dev. 2005;  17 301-302
    PubMedSearch in Google Scholar
  • 35 Zhang J F, Li Y B, Qian S H, Li C L, Jiang J Q. Studies on chemical constituents in root tuber of Cynanchum auriculatum.  China J Chin Mater Med. 2006;  31 814-816
    PubMedSearch in Google Scholar
  • 36 Fu H Z, Yang X W, Cai S Q. Studies on chemical constituents of Siegesbeckia pubescens.  Chin Tradit Herb Drugs. 1997;  28 259-262
    PubMedSearch in Google Scholar

Prof. Dr. Runhua Lu

Department of Applied Chemistry
College of Sciences
China Agricultural University

17# Qinghua East Road

100094 Beijing

P. R. China

Phone: + 86 10 62 73 69 57

Fax: + 86 10 62 73 67 77

Email: rhlu@cau.edu.cn

    www.thieme-connect.de/ejournals/toc/plantamedica