Acorus calamus linn. : Chemistry and Biology

 

Arasan Elaya Raja1*, M Vijayalakshmi2 and Garikapati Devalarao1

1KVSR Siddhartha college of Pharmaceutical sciences, Vijayawada-520 010 India

2Department of Microbiology, Acharya Nagarjuna University, Guntur. India

*Corresponding Author E-Mail: elayaraja80@rediffmail.com

 

ABSTRACT:                         

Chemical constituents and biological activity of plant drug Acorus calamus Linn. (family:Araceae) was reviewed. Different parts of the plant showed the presence of large number of phenyl propanoids, sesquiterpenes and monoterpenes as well as xanthone glycosides, flavones, lignans, steroids and inorganic constituents. It is also reported to possess insecticidal, larvicidal, antibacterial, mutagenic, cytotoxic, hepatoprotective, anticonvulsant,neuroleptic,smooth muscle relaxant and smooth muscle stimulant activity.

 

KEY WORDS: Acorus calamus, Chemical constituents, Biological Activity

 


INTRODUCTION:

Acorus calamus Linn. commonly known as Sweet Flag, belongs to the family Araceae  (Adoraceae). It is also called as Acorus odoratus. The genus Acorus derived from Acoron (coreon = the pupil of the eye) and the species calamus is derived from the Greek word Calamos (a reed). The family Araceae comprises about 110 genera and more than 1,800 species. The members of the family are rhizomatous or tuberous herbs. Acorus calamus Linn. commercially occurs in both peeled and unpeeled forms. This perennial herb is common on the banks of streams and in damp marshy places. The sweet flag oil present in this plant is a unique source of oxygenated sesquiterpenes of great structural variety 1. Apart from this terpenes a few commonly occurring steroids and xanthones had also been reported. The rhizome of the plant has medicinal properties against bugs, moths, lice, emetic stomach in dyspepsia; etc2. Common names of Acorus calamus which are used in different parts in India are Bach (Hindi), Vashampu (Tamil), Baje (Kannada) and Vasa (Telugu).

 

Distribution

Acorus calamus is a native of eastern countries and also it is indigenous to the marshes of the mountains of India. It is cultivated throughout India, ascending to an altitude of about 2200 metres. It is also found in marshy tracts of Kashmir, Shirmaur (Himachal Pradesh), Manipur and in Naga Hills. It is regularly cultivated in the koratagere taluka of Karnataka state in peninsular India 3, 4.

 

DESCRIPTION

Acorus calamus Linn. is a herbaceous perennial with a long indefinite branched cylindrical rhizome which is about   3/4 inch in diameter, smooth, pinkish or pale green. Its leaf scars are brown, white and spongy. It possesses slender roots. Its leaves are few and distichously alternate 5.

 

Adulterants

The rhizomes of Althae officinalis and common yellow flag Iris pseudocorus Linn. are reported to be important adulterants which are mixed with that of the sweet flag rhizome. The powdered drug is reported to be adulterated with siliceous earth and cereal flours. However sweet flag is readily distinguished from its adulterants due to its darker, different structure and want of aromatic odour and taste 6, 7.

 

CHEMISTRY OF Acorus Calamus

Isolation Techniques of components in A.Calamus: -

A.calamus is a source of essential oil which is responsible for the medicinal and insecticidal properties 8.The essential oil of calamus was first isolated practically in Frankfurt in 1592 and in the dispensatorium Noricum in 15899 .But in recent years the isolation of various constituents from the oil has been enormously extended by the development of the techniques of Gas-Chromatography10.However, continuous solvent extraction by using Soxhlete apparatus is still be the usual procedure of extraction. Isocalamendiol11 was isolated by steam distillation of ethereal extract which is a colourless mobile liquid having a pleasant aromatic odour. During steam distillation of ethereal extract direct heating on a sand-bath should be avoided to prevent charring of the fibres 12.The chloroform extract residue was chromatographed over silica gel to yield asarone,the principle compound in different isomeric forms(γ,cis and trans forms)13 and acoradin which were got after evaporating the benzene and petrol-ether eluate 14.   Both acrogermacrone and preisocalamendiol were successfully separated by repeated preparative TLC using alumina [GF254 (Type-E)] in n-hexane-benzene (2:1) each in pure state 15.The sweet flag oil of European origin was rechromatographed on silica gel impregnated with AgNO3(15%) and elution with hexane-EtO2 (95:5)gave calamuseone in pure state (GLC,isothermal 160˚)16.In the isolation of Triterpenoid saponins and phenyl derivatives ,the ethanolic extract was chromatographed over silica gel column which gave compound 1 in Benzene-DCM(9:1,v/v) fraction, compound 2 in EtOAc-Methanol (8:2,v/v) fraction and phenyl derivatives in petrol eluate 17,18.Galangin,a dihydroxy flavanol was isolated from the ethanolic extract residue19. Different parts of the plant have been subjected to exhaustive extraction and the isolated constituents were reported in the literature, which includes Terpenoids, Steroids, Xanthones, Lignans, Flavones and presence of traces of alkaloids.

 

Phenylpropanoids

The aromatic constituents namely asarylaldehyde in roots and asarone in leaves are responsible for the smell of volatile oil 20.Most of the phenylpropanoids were isolated by steam distillation. An oily substance namely calamol was extracted which was found to be an allyl trimethoxy benzene derivative. It is isomeric with asarone.Many phenylpropanoids were extracted and isolated from chloroform extract, viz. isoeugenol methyl ether(1), γ-asarone(1,2,4 –trimethoxy-5(2- propenyl) benzene)(2), cis-asarone(cis-1,2,4 –trimethoxy-5(2- propenyl) benzene(3),Trans-asarone(trans-1,2,4 –trimethoxy-5(2-propenyl) benzene(4), Acoramone(1,2,4 –trimethoxy-5(2- propanoyl) benzene(or) 1(2,4,5-trimethoxyphenyl)-propan-2-one)(5) along with asarylaldehyde (2,4,5-trimethoxy benzaldehyde)(6). Also phenyl indene derivatives were isolated and their structures were derived. They were Z-3-(2,4,5-trimethoxy phenyl)-2-propenal (7) and 2,3-dihydro-4,5,7-trimethoxy-1- ethyl-2-methyl-3-(2,4,5-trimethoxy phenyl)indene(8).

 

STRUCTURES OF PHYTOCONSTITUENTS

 

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Sesquiterpenes

Acorus calamus showed the presence of a large number of sesquiterpenes which were extracted by steam distillation process. The fresh aerial parts yield about 0.123%, dried rhizomes yield about 0.62 per cent and dried roots yield about 2.50 per cent on distillation 21.Three monocyclic sesquiterpenes were isolated from rhizomes of the plant after extracting the essential oil using n-hexane and chromatographed with pet-ether-diethyl ether fraction (10:1). They were Shyobunone(9),Epishyobunone(10) and 2,6-diepishyobunone(11)22.In the subsequent fraction a new sesquiterpene bicyclic diol  namely Isocalamendiol(12) was isolated from pet-ether-diethyl ether fraction(3:1).On rapid elution with n-hexane afforded a mixture of Acoragermacrone(13) and Preisocalamendiol(14). Another two new guaiane sesquiterpenic ketones were isolated by gradient elution using hexane-Et2O mixtures from eastern European sweet flag oil. They were named as Calamusenone (15) and its isomer (16).

 

Monoterpenes

A number of monoterpenes have been reported in the plant. Some of the monoterpenes reported are as follows α and β-pinenes, myrcene, Cymene-Para, Terpinen-alpha, Phellandrene-beta, Terpinene-gamma, Terpinolene, Thujane (17) and Limonene (18).They were isolated by steam distillation from volatile oil.

 

Xanthone glycosides

A new xanthone glycoside was isolated from rhizome part from ethanolic extract by column chromatographed using benzene-DCM(9:1v/v) and on hydrolysis yield two sugar moieties as D-glucose and D-galactose.It was designated as 4, 5, 8-trimethoxyxanthone-2-O-β-D-glucopyranosyl (1→2)-O-β-D-galactopyranoside(19).

 

Flavones

The CHCl3 extract of the ethanolic residue afforded from CHCl3-MeOH (19:1) eluates yellow crystalline needles. All the physical and spectral data showed the conformity with the 5, 7-dihydroxyflavonol (Galangin) (20).

 

Lignans

A lignan was isolated from the rhizome part of the plant and it was designated as acoradin (21).It was eluated using benzene from chloroform extract of the Acorus calamus.

 

Steroids

β-Sitosterol 23 is isolated along with Galangin from petrol-benzene (1:1) eluate and forms like flaky substance. From the physical and spectral features it was conformed to be β-sitosterol (22).

 

Inorganic constituents

The oxalate and calcium content of Acorus calamus is about 2.00% and 0.078%.The oxalate is expressed as H2C2O4­.

Triterpenoid saponins

Two new triterpenoid saponins have been isolated and they are characterized as follows:

1) 1β, 2α, 3β, 19α-tetrahydroxyurs-12en-28-oicacid-28-O {-β-D-glucopyranosyl (1→2)} β- D- galactopyranoside (23).

2)  3β, 22α, 24, 29-tetrahydroxyolean-12-en-3-O-{-β-D-arabinosyl (1→3)}-β-D-

arabinopyranoside (24) 24.

 

BIOLOGY OF Acorus Calamus

Extractives of different parts of Acorus calamus and calamus oil are widely used now in pharmaceuticals, traditional systems of medicines for a number of ailments and in perfumes. Here it has generated a lot of interest amongst the scientist to evaluate the activity by using modern parameters too. The details are presented as under.

 

Anti-microbial

The alcoholic extract and essential oil (0.2%) exhibited high in vitro activity against some pathogenic and non-pathogenic fungi, gram -ve and gram +ve bacterias specifically effective against S.aureus, E.coli and A.niger but less effect on P.selinium. The essential oil (1:1000v/v) was found to be effective against citrus decay pathogens like P.digitatum, P.italicum, D.natalensis and A.tenuis and checked their growth. A.calamus as a constituent in AV/EPP/4(Herbal formulation) was found to be effective in controlling infestation of nymphus and infections by Chipicephalus sanguineus. Essential oils of a mixture including A.calamus oil had significant anti-bacterial anti fungal activities 25-32.

 

Anti-itching

Boiling water extract of A.calamus is used as bathing agent for skin diseases. A.calamus was used as one of the constituent in a poly herbal formulation namely, herbal multi action skin gel (AV/AAGD/14/), which was found to be effective against a variety of specific and non-specific dermatitis and maggot wounds 33, 34.

 

Anti-anxiety

Three drugs i.e.Brahmi, Vacha and Shankhapuspi used in combination as ratio 10:3.8:0.2 exhibits a significant anti-anxiety activity 35. Both the poly herbal formulations having A.calamus as an ingredient namely, Prasham (100mg) and P-tabs significantly provides a good relief against insominia, stress excitement and irritability 36, 37.

 

Anti-convulsant

A.calamus oil (100mg/kg) was ineffective against metrazol and minimal electro shock induced seizures in albino mice 38. Plant extract of Acorus calamus did not afford strychnine induced convulsion at 10-20mg/kg.It caused –ve ionotropic and chronotropic effects in frogs at 100μ/ml.It antagonized spontaneous motor activity and also amphetamine induced hyperactivity in mice 39.

 

Anti-viral and Anti-anginal activity

The alcoholic extract of A.calamus exhibited potent antiviral activity against herpes virus.i.e.HSV-1 and HSV-2 40. A. Calamus in dose of 1.5-3gm/day was found effective against ischaemic heart disease, improvement in chest pain, in stable angina, dyspnoae reduction of body weight, improving in ECG,decreasing serum cholesterol, decreasing SLDL and increasing SHDL41. A.calamus being a constituent in polyherbal drug namely Haritaki vati (HT)   ,which reduced the anginal frequency and decreases the serum cholesterol and serum triglyceride levels 42.

 

Anti-ulcer

The ethanolic extract of acorus rhizome is used as antiulcer agent which inhibits the gastric secretion and to protect gastrodudonal mucosa against the injuries caused by pyloric ligation in rat 43.

 

Anti-spasmodic

At a dose level of 10μg/ml, the β-asarone free oil (type-I) of A.Calamus had a pronounced spasmolytic activity 44, 45.

 

Anti-inflammatory

The aqueous extract of A.calamus showed a significant caraigeenan induced anti-inflammatory activity at a low dose 46 - 48.  

 

Anti-cancer

 α-asarone isolated from the volatile fraction of A.Calamus was found to exhibit anti-carcinogenic action on ED50 of SGC Cells at a dose level of 25mcg/ml 49.

 

Nootropic activity

α-asarone isolated from the volatile fraction of A.Calamus was found to exhibit anti-carcinogenic action on ED50 of SGC Cells at a dose level of 25mcg/ml 50.

 

Anti-sczhizophrenia

GK022, an herbal mixture containing A.calamus (100mg) as a constituent was reported to be significant in cases of Schizophrenia 51

 

Insecticide

Ethanolic extracts of A.calamus were most promising insecticides against mosquito and housefly 52. Also it is found to be very effective against larvae of root nematode 53.

 

Tranquilizer

The aqueous extract was also supposed to counteract the effect of mental stress by tranquilizing action as mentioned in ayurvedic texts 54.

 

Anti-asthmatic

Small pieces of rhizome (1kg) and an ayurvedic receipe namely Maduyashtyadi syrup in which A.Calamus as an ingredient, after administration showed a significant relief in bronchospasm without any side effect 55.

Anti-rheumatitis

Vachadi gana, which consists of six plants including A.Calamus was found to be effective in case of Rheumatoid arthritis with pain, swelling and functional disability 56.

 

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Received on 08.11.2008  Modified on 14.03.2009

Accepted on 21.04.2009  © RJPT All right reserved

Research J. Pharm. and Tech.2(2): April.-June.2009,;Page 256-261