An Update on Chemical Composition and Bioactivities of Acorus Species
Ashwani Kumar Srivastava
Medicinal and pharmacological significance of the Acorus species is steadily increasing. Several species mainly Acorus calamus, A. christophii, A. tatarinowii and A. gramineus have been investigated for their chemical compositions and bioactivities. Perhaps, A. calamus has been most extensively studied plant among others. A number of active constituents from leaves, rhizomes and essential oils of Acorus spp. have been isolated and characterized. The major active constituents identified were α-and β-asarones and held responsible for most of the bioactivities of Acorus species. Besides, more new active constituents possessing important bioactive properties are being isolated and identified from Acorus spp. A number of reports published have documented many new useful bioactivities of Acorus spp. whole plant extract, leaves and rhizome extracts, essential oils and α- and β-asarones such as, anti-inflammatory/ immunosuppressive, anti-adipogenic, antimicrobial, fungicidal, insulin sensitizing/anti-diabetic, neuro-protective, wound healing, mitogenic, insecticidal, anthelmintic, allelopathic, antiepileptic, antispasmodic activities and inhibitor of acetylcholine esterase. In the present article we have discussed recently recognized many newer bioactivities and chemical composition of Acorus spp. This study would be very useful for those conducting researches on bioactivity screening in Acorus spp. and similar other less studied species of the plants.
Received: March 12, 2011;
Accepted: April 18, 2011;
Published: July 28, 2011
The genus Acorus comprises 40 species, however, only few species like
Acorus calamus (Linn.), A. christophii A. tatarinowii (Schott.)
and A. gramineus (Solandin Ait.) have been investigated for their chemical
composition and bioactivities. Perhaps, A. calamus has been most extensively
investigated plant sp. among others. It is reported as a good source of active
constituents possessing several useful bioactive properties. Acorus calamus
(L.) commonly known as sweet flag is a native of Central Asia and Eastern Europe
(Gilani et al., 2006). The plant grows worldwide
wildly along swamps, rivers and lakes (Kim et al.,
2009). It is widely used in traditional folk medicine of America and Indonesia
for gastrointestinal disorders such as, colic pain, diarrhea and the radix in
the therapy of diabetes (Gilani et al., 2006;
Si et al., 2010). Also, A. calamus has
been an integral part of Indian and Chinese systems of medicine for hundreds
of years (Wu et al., 2009; Lee
et al., 2011). The other species A. gramineus is native to
eastern Asia and commonly known as Japanese sweet flag is an aquatic or wetland
perennial plant with semi evergreen grass like foliage. It has narrow, 6 to
14 in (15-35.6 cm) glossy leaves and looks like thick, lush grass.
Many previous studies have reported chemical compositions and bioactivities
of A. calamus whole plant, different parts like rhizome, leaves and essential
oil obtained from steam-distillation of rhizome material (Namba,
1993; Wang et al., 1998). Reports have revealed
that A. calamus rhizomes, roots and essential oils of rhizomes possess
important bioactivities viz., antimicrobial (McGaw
et al., 2002; Lee, 2005; Phongpaichit
et al., 2005; , Devi and Ganjewala, 2009),
allelopathic (Nawamaki and Kuroyanagi, 1996), anticellular
and immunosuppressive (McGaw et al., 2002). Essential
oils of A. calamus have been reported to demonstrate antigonadal activities
in insects (Mathur and Saxena, 1975; Koul
et al., 1977a, b; Saxena
et al., 1977; Schmidt and Streloke, 1994).
Aromatic oils obtained by alcoholic extraction of the rhizome are used in the
pharmaceutical and oenological industries (Du et al.,
2008). Studies of chemical composition of Acorus spp. have revealed
α- and β-asarones as the major active components in the extracts of
different plant parts and essential oils (Raina et al.,
2003; Venskutonis and Dagilyte, 2003; Lee
et al., 2010; Geng et al., 2010).
Some other constituents like caryophyllene, isoasarone, methyl isoeugenol and
safrol present in lesser amounts have also been identified in the extracts of
rhizomes and roots (Namba, 1993; Wang
et al., 1998). Geng et al. (2010)
have found that β-asarone showed beneficial effects in cognitive impairment
associated disorders such as, Alzheimers Disease (AD). The lectins found
in the rhizomes of A. calamus and A. gramineus have mitogenic
activity (Bains et al., 2005).
Until few years back the Acorus spp. comparatively less has been a studied species of the plant However, after realizing its pharmacology and medicinal significance a steadily increasing progress has been witnessed towards investigating chemical composition and bioactivities of this species and the present study discusses new developments on investigation of chemical compositions and bioactivity screening of Acorus spp. highlights its rapidly growing pharmacological and medicinal significance. The information complied in the present article have been derived from the analysis of the research articles and reports published on chemical composition and bioactivities of Acorus spp. during 2002-2011.
Chemical compositions: Chemical compositions of Acurus spp.
mainly of A. calamus have been investigated thoroughly. Several studies
and reviews have documented chemical compositions of Accorus spp. whole
plant, plant parts viz., leaves and rhizomes as well as of essential oils of
rhizomes. Du et al. (2008) have investigated
chemical composition of A. gramineus leaves and rhizome and found that
these materials were highly rich in methylchavicol (49%) which gives an unusual
anisic odor, whereas chemical investigation of A. christophii leaf and
rhizome have revealed β-asarone (43%) as the major compound. Twenty eight
chemical constituents were identified in A. calamus rhizome tissues.
Of the 28 compounds identified three were new sesquiterpenes (1 beta, 7 alpha
(H)-cadinane-4 alpha, 6 alpha, 10 alpha-triol, 1 alpha, 5 beta-guaiane-10 alpha-O-ethyl-4
beta, 6 beta-diol and 6 beta, 7 beta (H)-cadinane-1 alpha, 4 alpha, 10 alpha-triol
(Dong et al., 2010a). Dong
et al. (2010b) have also reported the presence of two new sesquiterpenes,
cadinane with a propan-2-ylidene in the ethanol extract of A. calamus
rhizome tissues. Seven new compounds namely, 1-hydroxy-7, 9-guaiadien-8-one,
calamenone, cis-asarone, chrysophanol, physcion, emodin, (+)-galbacin were isolated
and identified in the petroleum ether fraction of ethanolic extract of A.
tatarinowii (Zhu et al., 2010). Previously,
two novel spiroalkaloids namely acortatarins A and B with a naturally unusual
morpholine motif were reported from the rhizome of A. tatarinowii (Tong
et al., 2010a). A cortatarins-A has potential of inhibiting reactive
oxygen species production in high-glucose-stimulated mesangial cells in a dose-and
time-dependent manner (Tong et al., 2010a). Another
study by Tong et al. (2010b) has revealed the
presence of a new cadinane-type sesquiterpenoid, tatarinowin-A, two phenylpropanoids,
tatarinoids A and B and a trinorlignan, tatarinoid C along with other 15 known
compounds in the A. tatarinowii rhizome tissue. Chemical structures of
some of these compounds are presented in Fig. 1.
Anti-inflammatory and immunosuppressive activities: Anti-inflammatory
properties of many plants species have been known for a long time. The fact
that the plants and their products may be implicated in alleviating diseases
via modulation of immune responses has directed researchers for screening
of plants for anti-inflammatory properties. Several studies have recognized
anti-inflammatory potential of Acurus spp. A study by Mehrotra
et al. (2003) has revealed that ethanolic extract of A. calamus
rhizome display anticellular and immunomodulatory properties. The extract inhibits
proliferation of mitogen (phytohaemagglutinin; PHA) and antigen (purified protein
derivative; PPD)-stimulated human Peripheral Blood Mononuclear Cells (PBMCs).
Kim et al. (2009) have studied anti-inflammatory
activity of A. calamus leaf extract and elucidated the mechanism of action
of the extract using human keratinocyte HaCaT cells. The anti-inflammatory properties
of the extract have been studied using RT-PCR, ELISA, immunoblotting and immunofluorescence
staining techniques which revealed that A. calamus leaf extract inhibits
the production of pro-inflammatory cytokines through multiple mechanisms (Kim
et al., 2009).
Anti-adipogenic activity: Researchers investigating anti-adipogenic
properties of Accorus spp. for past few years have found that A. calamus
demonstrate hypolipidemic activity in rats (Parab and Mengi,
2002). The saponins found in ethanolic extract of A. calamus apparently
have hypolipidemic properties. The water extract of A. calamus at high
concentration have also demonstrated hypolipidemic activity (Parab
and Mengi, 2002).
Ethanol extract devoid of β-asarone has been reported to enhance differentiation
in adipocytes in mouse (Wu et al., 2007). Differentiations
in adipocytes were measured as a function of triglyceroids and protein expression
of the glucose transporter in adepocytes. The property of A. calamus
to enhance differentiations in adipocytes is most likely very useful in the
treatment of type 2 diabetes. Interestingly, β-asarone present in the essential
oil of A. calamus has shown inhibitory effect on adipogenesis in 3T3-L1
cells (Lee et al., 2011).
|| Structures of some chemical constituents isolated from Acorus
As a plausible mechanism of action it has been suggested that β-asarone
might have suppressed the expression of adipogenic transcription factors (Lee
et al., 2011). Earlier, this group has reported that asarones from
A. calamus have properties of inhibiting adipogenesis and stimulating
lipolysis in 3T3-L1 adipocytes (Lee et al., 2010).
Asarone tend to reduces intracellular triglyceride levels by stimulating the
phosphorylation of hormone-sensitive lipase which triggers lipolysis in adipocytes.
Antimicrobial and fungicidal properties: Comparatively, antimicrobial
properties of Acorus spp. have been studied in more detail. We have studied
antibacterial and antifungal properties of petroleum ether, chloroform, hexane
and ethyl acetate extract of leaf and rhizome tissues of A. calamus
as well as commercial α- and β-asarone. Results of the study have
shown that leaf and rhizome extract demonstrated marked antifungal activity
but no antimicrobial activity observed except against Escherichia coli
(Devi and Ganjewala, 2009). Moreover, commercial α-
and β-asarones were found to be more effective than the leaf and rhizome
extracts (Devi and Ganjewala, 2009). Anti-microbial
properties of A. calamus leaf and rhizome extracts have been attributed
to α- and β-asarone. Phongpaichit et al.
(2005) have reported significant antimicrobial activity of crude methanolic
extract of A. calamus. The active constituent β-asarone has also
possessed antibacterial as well as anthelmintic properties (McGaw
et al., 2002).
Lee et al. (2004) for the first time have reported
that β-asarone (cis-2,4,5-trimethoxy-1-propenylbenzene) isolated from A.
gramineus rhizomes demonstrated antifungal activity against phytopathogens
like Magnaporthe grisea and Cladosporium orbiculare. Further,
Lee (2007) has studied the fungicidal property of hexane
extract of A. gramineus rhizome-derived materials against Botrytis
cineria, Erysiphe graminis, Phytophthora infestans, Puccinia
recondita, Pyricularia grisea and Rhizoctonia solani and found
that β-asarone and asaronaldehyde present in rhizome has fungicidal properties
against selected pathogens.
The plant of A. calamus biosynthesizes and accumulates haem peroxidase
enzymes which serves as part of antifungal defense system during the pathogenesis
(Ghosh, 2006). Their synthesis, however, is triggered
by the pathogenesis. The haem peroxidase of A. calamus has been classified
as class III peroxidase and it significantly inhibits growth of phytopathogens
such as M. phaseolina, Fusarium moniliforme and Trichosporium
vesiculosum (Ghosh, 2006). Later, this enzyme was
isolated and purified from the leaf epidermal cells and lumen tissues of xylem.
Several reports published previously have reported that a number of plant species
synthesize and accumulate such types of enzymes/proteins to protect themselves
from the attack of phytopathogens. At present, knowledge of synthesis and accumulation
of the heam perxidase or similar proteins in other members of Acorus
spp. is completely lacking. Therefore, future studies in this direction may
provide further, details regarding the biosynthesis and regulation of defense
enzymes/proteins and their mechanism of action in Acorus sp. during the
Insulin sensitizing/Antidiabetic activities: Recent studies have shown
anti-diabetic potential of Acorus spp. For long time, the radix of A.
calamus is being used in the therapy of diabetes in traditional folk medicine
of America and Indonesia. A new study reports that A. calamus improves
postprandial hyperglycemia and cardiovascular complications (Si
et al., 2010). The study found that ethyl acetate fraction of A.
calamus had insulin releasing and α-glucosidase inhibitory activities
in vitro HTT-T15 cell line and in vivo fasted and glucose/amylum
challenged normal mice (Si et al., 2010). Certainly,
the hypoglycemic effects are due to insulin releasing and α-glucosidase
inhibitory properties of A. calamus extract. Previously, Wu
et al. (2009) have reported similar insulin sensitizing properties
of ethyl acetate fraction of A. calamus in vitro and in vivo.
Although these preliminary reports have clearly indicated the potential of A.
calamus for its application in the treatment of diabetes and cardiovascular
complications, more research efforts needed for the investigation of other members
of the species for their anti-diabetic or insulin sensitizing properties and
elucidation of exact mechanism of action.
Protective effects: Protective roles of Acorus spp. have been
studied against free radicals and other Reactive Oxygen Species (ROS). The protective
effects of Acorus spp. have augmented its implication in neurodegenerative
diseases. A. calamus leaves and rhizomes are already known for a long
time to be used for the treatment of various neurological disorders. Commercial
asarones as well as those isolated from A. gramineus have been evaluated
for their neuroprotective properties and their mechanism of action in the primary
cultured rat cortical cells (Cho et al., 2002).
Commercially obtained α- and β-asarone and asarone isolated have been
found to inhibit the excitotoxicity induced by the N-Methyl-D-Aspartate (NMDA)
in primary cortical cultures but the commercial α- and β-asarone exhibited
more potent inhibitions of the NMDA-induced excitotoxicity. Furthermore, the
excitotoxicity induced by glutamate has also been inhibited, but with much less
potency than the toxicity induced by NMDA (Cho et al.,
2002). The study based on the receptor-ligand binding using a use-dependent
NMDA receptor-channel blocker [3H]MK-801 revealed that asarone inhibited
the specific bindings in a concentration-dependent fashion (Cho
et al., 2002). Asarone exhibited neuroprotective action against the
NMDA- or Glu-induced excitotoxicity through the blockade of NMDA receptor function.
Acorus calamus rhizome extract prepared with ethanol:water (1:1) has
demonstrated neuroprotective effects in the middle cerebral artery occlusion-induced
ischaemia in rats (Shukla et al., 2006). Application
of A. calamus rhizome extract has resulted in a significant improvement
in neurobehavioural performances such as, rota-rod performance and grid walking
in the experimental rats.
Free radicals and other ROS have been recognized as an important causative
factor in the development of neurodegenerative disorders. In the past several
years, a number of reports have been published revealing antioxidant potential
of many medicinal plants which has been implicated in minimizing harmful effects
of free radicals. Several research groups have evaluated antioxidant potential
of plants of Acosrus spp. and validated their protective roles in free
radical and ROS generated disorders. In our recently published study we have
reported antioxidant activities of methanolic extract of A. calamus
leaves and rhizomes (Devi and Ganjwala, 2011). The properties
of scavenging free radical of A. calamus has been found to be useful
to overcome excess production of oxygen free radicals generated due to continuous
exposure to loud noise which pose a serious health problem (Manikandan
and Devi, 2005). Protective effect of ethyl acetate and methanolic extract
of A. calamus against noise stress induced changes in the rat brain have
also been reported (Manikandan et al., 2005).
These extracts have protected most of the changes induced by noise-stress in
the rat brain. The protective effects were substantiated by measurement of the
activities of enzymes superoxide dismutase, catalase, glutathione peroxidase,
reduced glutathione as well as the level of vitamin C, E, protein thiols and
lipid peroxidation (Manikandan et al., 2005).
The antioxidant property of β-asarone found in A. calamus is believed
to be responsible for counteracting the stress in the rat brain due to continuous
exposure to noise. Though these studies have favored implication of β-asarone
against noise-stress induced changes perhaps further studies involving clinical
trials would be required for validation of efficacy of β-asarone in noisy
environment in human subjects (Manikandan et al.,
2005). A study by Hazra et al. (2007) has
revealed that A. calamus helped preventing the development of ferric
chloride-induced epileptogenesis in rats by modulating antioxidant enzymes.
Thus, this property of A. calamus could be exploited for the development
of an effective anti-epileptic drug in future.
A recent study has provided preliminary insight into the radioprotecting potential
of A. calamus (Sandeep and Nair, 2010). The study
in vitro carried out has shown that extract of A. calamus safeguarded
DNA and membrane damages in murine cells and human peripheral blood leukocytes
caused due to γ-radiation (Sandeep and Nair, 2010).
The radioprotective effects were evaluated by measuring the degree of lipid
peroxidation caused using thiobarbituric acid reacting substances. In vitro
DNA damage was measured by assessing the radiation induced relaxation of supercoiled
plasmid DNA (pBR322) whereas alkaline single cell gel electrophoresis or comet
assay was used to monitor any damage to cellular DNA induced by γ-radiation
(Sandeep and Nair, 2010). The properties of A. calamus
extract scavenging free radicals have been attributed for radioprotective effects
Extract of A. calamus has also displayed protective effects on nickel
chloride induced renal oxidative stress, toxicity and cell proliferation response
in male Wistar rats (Prasad et al., 2006). Nickel,
is a major environmental pollutant known for its clastogenic, toxic and carcinogenic
properties. Beside protective roles of A. calamus against nickel chloride
induced renal oxidative stress, the rhizome extract of A. calamus are
reported to have protective roles against acrylamide induced neurotoxicity in
rats (Shukla et al., 2002).
In recent years search for new drugs for Alzheimers disease from medicinal
plants has been rapidly increased. In this context several research groups are
investigating Acorus spp. Geng et al. (2010)
have published first report describing anti-Alzheimers potential of the
β-asarone isolated from A. tatarinowii. Their study revealed that
the β-asarone suppressed neuronal apoptosis in the β-amyloid hippocampus
injection rats (Geng et al., 2010). They also
studied the mechanism of action of β-asarone which indicated that β-asarone
attenuates β-amino acid peptide (1-42 amino acid long) induced neuronal
apoptosis in hippocampus by reversal down-regulation of Bcl-2, Bcl-w, caspase-3
activation and c-Jun N-terminal kinase phosphorylation (Geng
et al., 2010).
Other useful bioactivities: The list of important bioactivities of the
Acorus spp. is steadily increasing. In this section we have discussed
several important but less studied bioactivities of Acorus species. Interestingly,
pharmacological as well as ecological significance of A. calamus and
its active chemical constituent α- and β-asarone and essential oil
obtained from rhizomes have been impressively increased in the past few years.
Ethanolic extracts of A. calamus leaves possess wound-healing activity
in an excision and incision-based wound model in both male and female rats (Jain
et al., 2010). Treatment of wound in male and female rats induced
by an excision and incision with ethanolic extract has been found to be promising
for healing. Novel lectins isolated from the rhizomes of A. calamus
and A. gramineus have shown potent mitogenic activity towards mouse splenocytes
and human lymphocytes whereas inhibitory activities towards murine cancer cell
lines (Bains et al., 2005). These lectins have
molecular weight 55-56 kDa and stable up to 55°C. They did not require metal
ions for their activity however affected by high concentrations of denaturants
like urea, thiourea and guanidine hydrochloric acid (Bains
et al., 2005).
Park et al. (2003) have studied insecticidal
activities of asarones present in A. gramineus rhizome against three
stored product pests Sitophilus oryzae, Callosobruchus chinensis
and Lasioderma serricorne. Two research groups have documented allelopathic
activities of A. tatarinowii and A. calamus on algae and water-bloom
forming algal species (He and Wang, 2001; Hu
et al., 2009a). The root system of A. tatarinowii excretes
some chemical substances which arrest the algal growth. These substances tend
to destroy some chlorophyll-A molecules thereby inhibit photosynthesis in algae.
Their effects on algae were dose dependent; at low concentration they promoted
algal growth whereas at high concentration they inhibited the algal growth (He
and Wang, 2001). Water extracts of A. calamus has also demonstrated
allelopathic effects on the growth of two water bloom-forming algal species
Microcystis aeruginosa and Chlorella pyrenoidosa (Hu
et al., 2009a). Shah and Gilani (2009) based
on their findings that A. calamus extract has properties of lowering
blood pressure and vascular modulator mediated through multiple pathways have
suggested their application for the treatment of cardiovascular disorders. Essential
oil of A. calamus rhizome is reported to cause injuries to Plasmatocytes
(Pls) and Granular hemocytes (GRs) and affects the hemogram of the tobacco armyworm,
Spodoptera litura (Sharma et al., 2008).
A study has shown beneficial effects of A. tatarinowii on ultra structure
and permeability of blood-brain barrier in rats (Hu et
al., 2009b) while another study has reported its antiepileptic effect
(Liao et al., 2005). The rhizome extract and
volatile oil of A. tatarinowii display anticonvulsive effects in pentylenetetrazol
kindling models. Also, both extracts prevents convulsion-related GABAergic neuron
damage in the brain in the prolonged pentylenetetrazol kindling model (Liao
et al., 2005). The essential oil of A. calamus and its major
constituent β-asarone has been found to inhibit activity of acetylcholine
esterase (Mukherjee et al., 2007). Extract of
A. calamus contains chemical constituents with properties to block calcium
channel which has been held responsible for spasmolytic activity (Gilani
et al., 2006). Crude extract and ethyl acetate and n-hexane fractions
of the extract have been evaluated for spasmolytic effects in the isolated rabbit
jejunum preparation (Gilani et al., 2006).
In recent times usefulness of A. calamus extract has been tested to
develop environment friendly control measures. A study by Ghosh
et al. (2010) has highlighted the efficacy of A. calamus extract
against cattle tick Rhipicephalus microplus. They have tested large number
of extracts prepared with ethanol, hydroethanol and hot water against the cattle
tick (Ghosh et al., 2010). These extract have
been found to be safe and did not show any reaction in animals treated even
with 50% of the concentration.
In the present study, we have discussed the chemical composition and bioactivities
of less studied Acorus spp. However, several recently published reports
on bioactive potential of the Acorus spp. have indicated their rising
pharmacological and medicinal significance. The genus Acorus comprises
40 species but only 3-4 species, A. calamus, A. christophii, A. tatarinowii
and A. gramineus have been considerably investigated for their chemical
composition and bioactivities. In the past few years many promising bioactivities
such as, anti-inflammatory/immunosuppressive, anti-adipogenic, antimicrobial,
fungicidal, insulin sensitizing/antidiabetic, neuroprotective of Acorus
spp. plants have been reported. The most striking activity realized is anti-Alzheimers
of β-asarone from A. tatarinowii. Also, for the first time bioactive
potential of Acorus species as wound healing, mitogenic, insecticidal,
anthelmintic, allelopathic, antiepileptic, antispasmodic and inhibitor ofacetylcholinesterase
have been realized. Of course it is due to these bioactive properties pharmacological
and medicinal significance of Acorus species is gradually increasing.
Perhaps, thorough studies involving clinical trials in human subject remains
to be performed. Therefore, these are high times for investigations of chemical
composition and bioactivities of unexplored plants of the Acorus and
devote more efforts towards understanding the mechanism of action of bioactive
constituents present therein.
Corresponding author of this article is grateful to Dr. Ashok Kumar Chauhan, Founder President and Mr. Atul Chauhan, Chancellor of Amity University, Uttar Pradesh, Noida, India for providing necessary support. I am also indebted to Dr. G. Viswanathan, Chancellor, Vellore Institute of Technology University, Vellore, Tamilnadu, India for providing necessary support and facilities to carry out research work in Acorus calamus.
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