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Lawsonia Inermis (Henna): A Natural Dye of Various Therapeutic Uses - A Review

Jiny Varghese K1, Silvipriya KS1, Resmi S1, Jolly CI2

Abstract: The plant Lawsonia inermis (Lythraceae) commonly called as Henna or Mailanchi is known for its cosmetic properties. This hair care plant is reported to possess immunomodulatory, antiviral, antibacterial, antifungal, nootropic, antifertility, hepatoprotective, tuberculostatic activity, antimitotic, analgesic and anti-inflammatory, anticarcinogenic and antioxidant properties. Henna is an important source of phytochemicals of immense medicinal and pharmaceutical significance such as naphthoquinone derivatives, aliphatic components, triterpenes, sterols, phenolic derivatives, coumarins, xanthones, flavonoids, gallic acid, hennotannic acid and mannitol which are effective as immunomodulators and other allied agents. Hence, in view of the immense medicinal significance of the plant, this review is therefore an effort to compile all the information reported on its phytochemical and pharmacological activities, so that interest could be diverted towards this potential dye herb, for the treatment and relief from various ailments and diseases. Keywords: Lawsonia inermis, natural dye, phytochemistry, immunomodulatory, antimicrobial, antimitotic. INTRODUCTION Lawsonia is monotypic genus, represented by Lawsonia inermis, native of North Africa and south-west Asia, widely cultivated as an ornamental and dye plant throughout India [1]. Lawsonia inermis (Lythraceae) is commonly called as Henna (Figure 1) and the synonym is Lawsonia alba Linn. In India, it is known by various names in different languages viz., Mehndi in Hindi, Mendika, Rakigarbha in Sanskrit, Mailanchi in Malayalam, Maruthani in Tamil, Benjati in Oriya, Mayilanchi in Kannada, and Mehedi in Bengali [2]. It is a glabrous, much branched shrub or small tree and grows wild. The plant part used are bark, leaves, flowers and seeds. Henna (Figure 2) is cultivated in many tropical and warm temperate regions as a hedge plant [3]. The leaves that yield the dye are confined to India, mainly in Punjab and Gujarat and to a small extent in Rajasthan and Madhya Pradesh. It is used in cosmetic preparation in many ways as a colouring and cosmetic ingredient. It has been in use for nearly three millennia as a hair colour, nail colour, and in the Muslim society for the decoration of the soles of the feet and palm of hands. The drug is widely used in cosmetology for its dyeing properties due to the strong binding of lawsone, (which is a naphthoquinone) to hair, probably be attributed due to the reaction of thiol group with keratin. It is also used in the form of shampoo and hair lotion. Henna is used in Ayurvedic preparations for the treatment of

1Amrita

concentration of 1.0-1.4 %. The compound was extracted from the leaves and preparation of various derivatives of lawsone was reported [20]. Spectrophotometric method has been developed for determination of lawsone in Henna [21]. Colorimetric methods have been described for the estimation of lawsone in leaves [22]. A TLC system for identification of the natural red dye has been evaluated [23]. Resolution of chlorophyll, lawsone, 1, 3- dihydroxy naphthalene, 1,4- naphthoquinone and 1,2dihydroxy-4-glucosyloxynaphthalene has been isolated from water insoluble extract of Henna leaves. A new naphthoquinone derivative isoplumpagin has been isolated from the stem bark of Henna [24]. Aliphatic components, triterpenes, and sterols The structure of new phenolic glycosides, lawsoniaside and lalioside isolated from the leaves has been established as 1,2,4trihydroxynaphthalene 1,4di-Dglucopyranoside and 2,3,4,6tetrahydroxyacetoxy-2- -D-glucopyranoside [25]. An aliphatic ester n-tricontyl ntridecanoate, -sitosterol, lupeol (Figure 3), 30-norlupan-3 -ol-20-one, betulin (Figure 4) and betulinic acid (Figure 5) have been isolated from the bark of L.inermis [26]. A glucoside of -sitosterol (Figure 6) has been reported from the leaves [27]. Methanol extract of leaves of Henna also yielded -sitosterol and stigmasterol [28] (Figure 7). Two pentacyclic triterpenes isolated from the bark of Henna were identified as 3- -30-dihydroxylup-20 (29)-ene-one (hennadiol) and (20 S) - 3- , 30dihydroxylupane [29]. The seeds of the plants yielded 7.5 % viscous oil containing behenic, arachidic, stearic, palmitic, oleic and linolenic acids. Among the fatty acids the linolenic occurred in the predominant amount [30]. From the stem bark, an aliphatic constituent 3methyl-nonacosan-1-ol [31] and the sterols viz. lawsaritol [32] and lawsaritol A [33] have been reported. Bioassay guided fractionation of methanolic extract of the defatted seed led to isolation of two new triterpenoids, lawnermis acid and its methyl ester [34]. Phenolic derivatives, coumarins, xanthones and flavonoids The ethanolic extract of the whole of the aerial parts of Henna was found to be devoid of tannins [35]. Garlic acid has been reported in the leaves. The structure of coumarins, lacoumarin isolated from the whole plant, was established as 5-allyoxy-7-hydroxycoumarin [36]. Three new laxanthones, viz laxanthones I, II, and III which were characterized as 1, 3dihydroxy-6, 7-dimethoxy xanthone, 1hydroxy-3, 6-diacetoxy-7-methoxyxanthone and 1-hydroxy-6- acetoxy xanthone, respectively

skin ailments, burns and wounds. Mahaneela gritha (5-10 ml b.i.d), Madayanti churna (1-3 gms b.i.d), Juice (5-10 ml b.i.d) and leaf powder (locally as paste) are some of the formulations of Henna [4]. A decoction is used as gargle for relaxed sore throat. Lawsonia inermis has been claimed to have [5-6], [7], immunomodulatory antiviral antibacterial [8], antifungal [9], nootropic [10], antifertility [11-13], hepatoprotective [14], [15], antimitotic analgesic and antiinflammatory [16-18] properties. The main constituents reported are naphthoquinone derivatives, aliphatic components, triterpenes, sterols, phenolic derivatives, coumarins, xanthones, and flavonoids. TAXONOMICAL HIERARCHY OF LAWSONIA INERMIS [19] Kingdom: Plantae-Plants Division :Angiospermae Class: Dicotyledoneae Order: Myrtales Family: Lythraceae Genus: Lawsonia Species: inermis PHYTOCHEMISTRY Much work is done in the field of phytochemical investigation of the plant. The chemical constituents isolated from Henna are divided into the following categories: Naphthoquinone derivatives Aliphatic components, triterpenes, and sterols Phenolic derivatives, coumarins, xanthones and flavonoids Other Chemical Constituents Naphthoquinone derivatives The colouring matter in the leaves of Henna is lawsone and identified as 2-hydroxy-1, 4naphthoquinone (C10H6O3, m.p.1900 decomp.) which is present in dried leaves in a

School of Pharmacy, Amrita Vishwa Vidyapeetham ­ University, AIMS Healthcare Campus, AIMS Ponekkara P.O. Kochi, Kerala 682041, India. E-mail: [email protected], [email protected] 2Kerala Ayurveda Limited, Athani Post, Ernakulam, Kerala 683585, India. E-mail: [email protected]

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Figure 6. - sitosterol Figure 1. Henna plant

Figure 11. Luteolin

Figure 12. Cosmosiin have been reported [37-38]. Apigenin-7-glucoside, apigenin-4-glycoside, luteolin-7-glucoside and luteolin-3-glucoside were the flavonoids isolated from Henna [39]. Luteolin, luteolin-7-O-glucoside and acacetin-7O-glucoside have been isolated from the leaves. Other chemical constituents The leaves contain a brown substance of a resinoid fraction having the chemical properties, which characterize the tannins, and therefore named hennotannic acid. Tannin and chlorogenic acid are absent. The leaves also contain glucose but starch and pyrogallol absent. Gallic acid [40] is present to the extent of 5-6 %. The amino acid composition of Henna has been reported [41]. The presence of mannitol in Henna stem, flowers and roots has been investigated. An albumin inhibitable lectin was obtained from Henna. Trace elements in Henna powder were Cu, Ni, Mo, V, Mn, Sr, Ba, Fe and Al including mineral substances like Na2O, CaO and K2O. The essential oil of flowers of Henna contains ionone and -ionone as the chief constituents. The immunomodulatory bioassay-guided fractionation of the methanolic extract of henna leaves resulted in the isolation of seven compounds; three have been isolated for the first time from the genus, namely p-coumaric acid (Figure 8), 2-methoxy-3-methyl-1,4naphthoquinone (Figure 9) and apiin, along with the previously isolated compounds: lawsone (Figure 10), apigenin, luteolin (Figure 11), and cosmosiin [42] (Figure 12). PHARMACOLOGY In the indigenous system of medicine, Henna leaves are used as a prophylactic against skin diseases. It has been used for the treatment of boils, burns, bruises and skin inflammations. Although a lot of pharmacological investigations have been carried out based on

Figure 7. Stigmasterol

Figure 1. Aerial parts

Figure 8. p-coumaric acid Figure 3. Lupeol

Figure 9. 2-methoxy-3-methyl-1,4-naphthoquinone Figure 4. Betulin

Figure 5. Betulinic acid

Figure 10. Lawsone

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the ingredients present but a lot more can still be explored, exploited and utilized. Antiviral activity The ethanol soluble fraction of the fruits displayed highly potent activity against Semliki Forest Virus (SFV) in Swiss mice and chick embryo models exhibiting 65-100 % activity after 10-25 days of virus challenge [41]. Antibacterial activity The 50 % ethanolic extract of the whole aerial part did not show antibacterial activity against Bacillus subtilis, Staphylococcus aureus, Salmonella typhi, Escherichia coli and A. tumerfaciens. In another investigation, lawsone showed some inhibition against Proteus species and S. aureus. In another study, the leaf extract was active against a wide range of microbes such as Staphylococcus, Streptococcus, Brucella and Salmonella. The aqueous extract of the leaves of Henna was shown to possess reproducible activity in vitro against a wide variety of microorganisms. The effects of water and chloroform extracts of the leaves of Lawsonia inermis (henna plant) against the primary invaders of burnt wounds was investigated. Clinical isolates of Staphylococcus aureus, Streptococcus sp, Pseudemonas aeruginosa, Candida albicans, Fusarium oxysporum, and Aspergillus niger were treated with extracts of the leaves of L. inermis for antimicrobial activity using in vitro agar incorporation method and well diffusion methods respectively. The henna leaves extracts were able to inhibit the growth pattern of A. niger and F. oxysporum. Streptococcus sp. and S. aureus were also inhibited by the extracts. Inhibition of the microorganisms' growth suggests that henna may be valuable in the management of burnt wound infections [42]. Antifungal activity The ethanolic extract of the whole plant also showed Antifungal activity against Candida albicans, Cryptococcus neoformans, Trichophyton mentagrophytes, Microsporum canis and Aspergillus niger [43]. Alcoholic and aqueous extracts of Henna leaves and of lawsone were tested separately in vitro. No Antifungal activity was determined for the Henna solution in vitro. On the other hand, the lawsone aqueous solution showed a fungistatic activity. Bark decoction of Henna inhibited the activity of protopectinase and polygalactouronase [44]. Antiimplantation activity The alcoholic petroleum ether and aqueous extracts of Henna seeds at the doses of 100 and 500 mg/kg did not show any significant anti-implantation activity in female rats. Administration of the commercial preparation

`Avrodhak' which contained Henna leaves inhibited fertility in 40 % female rats with 30 mg dose whereas there was 60 % inhibition with 300 mg dose. The 50 % ethanolic extract of the bark of Henna at the dose of 250 and 500 mg/kg prevented CCl4 induced oxidative stress by significantly maintaining the levels of reduced glutathione, its metabolizing enzymes and simultaneously inhibiting the production of free radicals. Nootropic activity The acetone fraction of the petroleum ether extract of Henna inhibited prominent nootropic activity, potentiating clonidine induced hypodermia and decreased lithium induced head twitch. The fraction modified 5HT and NA mediated behaviour. However haloperidol induced catalepsy was not modified [45]. Immunomodulatory activity Methanolic extract of Henna leaves showed significant immunostimulant activity in mice [6]. Lawsone at a dose of 100 g/ml had suppressive effect on the induction of antibodies in lymphocytes in vitro. The naphthoquinone fraction at the dose of 5 mg/kg was shown to increase phagocytosis of carbon particle [46]. Lawnermis acid a triterpene derivative from the seeds showed significant anticomplementary activity in vitro. Anti-inflammatory activity An alcoholic extract of Henna leaves showed significant anti-inflammatory activity against carrageenan-induced edema in rats [47]. The extract also possessed antihyaluronidase activity in rats [48]. The extract at the dose of 10 mg/kg also possessed significant antiinflammatory activity in rats evidenced by Brodie's hind paw edema test, Granuloma pouch test and Lint pellet test. The antiinflammatory effect was found to be comparable to that of hydrocortisone. Isoplumbagin and lawsaritol (100 mg/kg, p.o.) have been screened for anti-inflammatory activity against carrageenan-induced paw edema. It was observed that isoplumpagin exhibited significant anti-inflammatory activity similar to that of phenylbutazone [49]. Luteolin, -sitosterol, lawsone and laxanthone II, isolated from the leaves were studied for their anti-inflammatory activity. Antimitotic activity In studies on the antimitotic actions of methanolic extracts of Henna and standard lawsone in onion root tips, it was discovered that Henna and standard lawsone inhibited mitosis in a concentration- dependent manner. The methanolic extract of Henna showed concentration-dependent inhibition of mitosis, which was less than that produced by the

standard lawsone at corresponding concentrations. The methanolic extract of Henna showed about 50 % mitotic inhibition, whereas standard lawsone showed about 60 % mitotic inhibition at 200 g/ml. Tuberculostatic activity of Henna The tuberculostatic activity of the herb henna (Lawsonia inermis Linn.) was tested in vitro and in vivo. On Lowenstein Jensen medium, the growth of tubercle bacilli from sputum and of Mycobacterium tuberculosis H37Rv was inhibited by 6 micrograms/ml of the herb. In vivo studies on guinea pigs and mice showed that the herb at a dose of 5 mg/kg body weight led to significant resolution of experimental tuberculosis following infection with M. tuberculosis H37Rv [50]. Modulatory effect of Henna leaf (Lawsonia inermis) on drug metabolising phase I and phase II enzymes, antioxidant enzymes, lipid peroxidation and chemically induced skin and forestomach papillomagenesis in mice The effect of 200 and 400 mg/kg body weight of 80% ethanolic extract of the fresh leaves of Lawsonia inermis were examined on drug metabolizing phase-I and phase-II enzymes, antioxidant enzymes, glutathione content, lactate dehydrogenase and lipid peroxidation in the liver of 7 weeks old Swiss albino mice. Also anticarcinogenic potential of Henna leaf extract was studied adopting the protocol of benzo(a)pyrene induced forestomach and 7,12 dimethylbenz(a)anthracene (DMBA)-initiated and croton oil-promoted skin papillomagenesis. Primary findings reveal the 'duel-acting' nature of henna leaf as deduced from its potential to induce only the phase-II enzyme activity, associated mainly with carcinogen detoxification in liver of mice and inhibit the phase I enzyme activities. The hepatic glutathione S-transferase and DTdiaphorase specific activities were elevated above basal level by Lawsonia inermis extract treatment. With reference to antioxidant enzymes the investigated doses were effective in increasing the hepatic glutathione reductase (GR), superoxide dismutase (SOD) and catalase activities significantly at both the dose levels. Reduced glutathione (GSH) measured as non-protein sulphydryl was found to be significantly elevated in liver and in all the extrahepatic organs studied Among the extrahepatic organs examined (forestomach, kidney and lung) glutathione S-transferase and DT-diaphorase level were increased in a dose independent manner. Chemopreventive response was measured by the average number of papillomas per mouse (tumor burden) as well as percentage of tumor bearing animals and tumor multiplicity. There was a significant inhibition of tumor burden in both the tumor model systems studied. Tumor

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incidence was also reduced by both the doses used in our experiment in both the model systems [51]. Anticarcinogenic properties and antioxidant activity The investigation was conducted to examine the anticarcinogenic properties of henna (Lawsonia inermis) extract (using chloroform as a solvent) by the microculture tetrazolium salt (MTT) assay on the human breast (dependent- hormone, MCF-7; non-dependent hormone, MDA-MB-231), colon (Caco-2), liver (HepG2) carcinoma cell lines and normal human liver cell lines (Chang Liver). The preliminary results showed that the henna extract displayed the cytotoxic effects against HepG2 and MCF-7 with IC -value of 0.3 and 24.85 µg mlG , respectively. However, no IC values were obtained from Caco-2 and MDAMB-231 cell lines at the concentration studied. This extract also did not show the IC value against normal human liver cell lines, Chang 50 Liver, indicated the selectivity of its cytotoxic properties. The antioxidative activities of this extract which could contribute to its cytotoxic properties were also studied. Antioxidant activity in henna was found to be the highest as compared to vitamin E or " tocopherol. The strong cytotoxic properties of this extract could be due to its high antioxidant activities [52]. Molluscicidal activity Leaf, bark and seed of henna against Lymnaea acuminata and Indoplanorbis exustus were studied. Seed powder was more toxic than leaf and bark against I. exustus. Binary combinations of henna seed with Cedrus deodara Roxh and Azadirachta indica A. Juss oil, or powdered Allium sativum, or Zingiber officinale rhizome oleoresin was more toxic to snails L. acuminata and I. exustus than their single treatment. The highest increase in the toxicity was observed when henna seeds powder and C.deodara oil (1:1) were tested against both the snails. The combination with neem oil was also more toxic than their individual components and other combinations [53]. Wound healing activity The ethanol extract of Lawsonia inermis (200 mg/kg/day) was used to evaluate the wound healing activity on rats using excision, incision and dead space wound models. The animals were divided into three groups of six each in the excision model and two groups of six each in the incision model and dead space models. The topical application was made in the case of excision wound model, whereas, oral treatment was done with incision and dead space wound models. The following differences were noted in the group of experimental animals which were treated with

an extract of L. inermis when compared with the control and reference standard animals: a high rate of wound contraction, a decrease in the period of epithelialization, high skin breaking strength, a significant increase in the granulation tissue weight and hydroxyproline content. The extract-treated animals showed 71% reduction in the wound area when compared with controls which was 58%. Histological studies of the tissue obtained on day 10 from the extract-treated group showed increased well organized bands of collagen, more fibroblasts and few inflammatory cells when compared with the controls which showed inflammatory cells, scanty collagen fibres and fibroblasts. Enhanced wound contraction, increased skin breaking strength, hydroxyproline and histological findings suggest the use of L. inermis in the management of wound healing [54]. CONCLUSION Henna, the potential medicinal plant is the unique source of various pharmacologically important compounds. Extensive investigation is needed to make the most of their Pharmaceutical and therapeutic utility to fight various diseases. A drug-development programme can be undertaken to develop novel drugs with the compounds isolated from henna. Although crude extracts from various parts of henna have therapeutic applications; modern drugs can be developed after extensive investigation of its biological activity, mechanism of action, pharmacotherapeutics, and toxicity and after proper standardization and clinical trials. As the global scenario is now changing towards the use of safer non toxic plant products having traditional medicinal use, development of modern drugs from henna should be emphasized for the control of various diseases. In fact, time has come to exploit the centuriesold knowledge on henna through modern approaches of drug development. For the last few years, there has been an increasing trend and awareness in herbal research. Significant numbers of research works have already been carried out during the past few decades in exploring the chemistry of different parts of henna. Several therapeutically and industrially useful preparations and compounds have also been marketed, which generates much interest among the scientists in exploring more information about this versatile herb. An extensive research and development work should be undertaken on henna and its products for their better economic and therapeutic utilization. REFERENCES

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