Chemical Constituents from the Rhizome of Acorus calamus L.

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
• 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
• 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
• 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
• 5 Nawamaki K, Kuroyanagi M. Sesquiterpenoids from Acorus calamus as germination inhibitors.  Phytochemistry. 1996;  43 1175-1182
• 6 Iguchi M, Niwa M, Nishiyama A. Isolation and structure of acoragermacrone.  Tetrahedron Lett. 1973;  29 2759-2762
• 7 Patra A, Mitra A K. Constituents of Acorus calamus Linn.  Indian J Chem. 1979;  17B 412-414
• 8 Rai R, Siddiqui I R, Singh J. Triterpenoid saponins from Acorus calamus.  Indian J Chem. 1998;  37B 473-476
• 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
• 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
• 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
• 12 Kamel A. 7-epi-Eudesmanes from Teucrium polium.  J Nat Prod. 1995;  58 428-431
• 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
• 14 Yamamura S, Iguchi M, Nishiyama A, Niwa M, Koyama H, Hirata Y. Sesquiterpenes from Acorus calamus L.  Tetrahedron. 1971;  27 5419-5431
• 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
• 16 Evans F E. Structure analysis of proximadiol (crypromeridiol) by ¹³C spectroscopy.  Phytochemistry. 1982;  21 937-938
• 17 Bruno M, De La Torre M, Rodriguez B, Omar A A. Guaiane sesquiterpenes from Teucrium leucocladum.  Phytochemistry. 1993;  34 245-247
• 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
• 19 Mahmoud A A. 7-Epi-eudesmanes, eudesmanoic acids, eudesmanolides and other sesquiterpenes from Pluchea dioscoridis.  Phytochemistry. 1997;  45 1633-1638
• 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
• 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
• 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
• 23 Monaco P, Previtera L. A steroid from Pistia stratiotes.  Phytochemistry. 1991;  30 2420-2422
• 24 Goswami P, Kotoky J, Chen Z N, Lu Y. A sterol glycoside from leaves of Clerodendron colebrookianum.  Phytochemistry. 1996;  41 279-281
• 25 Ahmad V U, Aliya R, Perveen S, Shameel M. A sterol glycoside from marine green alga Codium iyengarii.  Phytochemistry. 1992;  31 1429-1431
• 26 Guo Q, Fang H, Su W. Lignans in flower buds of Magnolia biondii.  Chin Tradit Herb Drugs. 2004;  35 849-851
• 27 Matsushita H, Miyase T, Ueno A. Lignan and terpene glycosides from Epimedium sagittatum.  Phytochemistry. 1991;  30 2025-2027
• 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
• 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
• 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
• 31 Poigny S, Guyot M, Samadi M. Total synthesis of maesanin and analogues.  Tetrahedron. 1998;  54 14791-14802
• 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
• 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
• 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
• 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
• 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