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Advances in Pharmacology & Clinical Trials Research Article 13 min read

Comparative Assessment of Compounds in Lawsonia Inermis L. - A Potent Antileishmanial Plant

Kashif Iqbal
ISSN: 2474-9214  10.23880/apct-16000230  Received: December 08, 2023  Published: December 28, 2023
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Keywords
Lawsonia inermis L Leishmaniasis Anti-leishmanial Active Compounds Natural Compounds
Abstract

Lawsonia Inermis L. plant, traditionally known as henna, played a svital role in the daily lives of ancient cultures, offering medicinal and psychological benefits, in addition to being used for personal beautification. The medicinal role of Lawsonia Inermis L. plant was known since ages and several isolated compounds from this plants plays an important role in the treatment of several tropical disease including Leishmaniasis. A large number of active compounds are present in this plant which could be used for the efficient treatment of this disease. Active compounds were collected from data bank of The Royal library/Copenhagen University library, PubMed, Scifinder, Reaxys, and Google Scholar etc. More than 161 compounds are identified, well-studied along with their molecular characterization from Lawsonia inermis L. plant out of which 20 compounds possess antileishmanial activity whereas 12 compounds were similar between Lawsonia inermis L and other plants that have Antileishmanial activities.. Although many studies reported the pharmacological activities of compounds isolated from Lawsonia Inermis L. plant in several diseases but the anti-leishmanial roles of compounds have not been widely investigated. The goal of present study was to evaluate the potential of the isolated compounds from Lawsonia Inermis L. plant in terms of their anti-leishmanial activity. The present review provides valuable information about compounds isolated from the Lawsonia Inermis L. plant, which could be considered in the future experimental and clinical trials for the treatment of leishmaniasis and other diseases.

Introduction

Leishmaniasis is an infectious neglected parasitic disease, caused by the intracellular parasite which is transmitted via the bite of female sand fly and belong to the genus Leishmania. It has been extended in five continents with high endemicity in developing countries [1]. The disease has widespread clinical spectrums ranging from self- limiting cutaneous to fatal visceral form which depends on the parasite strain and host immune response. World Health Organization (WHO) highlights on leishmaniasis as one of the seven significant diseases [2]. Approximately, 1.5 million new cases of leishmaniasis are reported annually and 12 million people are affected. Moreover, nearly 350 million people are at the risk of disease in 98 countries. Almost, 90% cases of leishmaniasis occur in Saudi Arabia, Iran, Afghanistan, Syria, Peru, Iraq and Brazil [3]. Pentavalent antimonials are mostly used for leishmaniasis from 1959 but it is a toxic drug with life-threatening side effects and needs prolong injections. The emergence of resistance has further decreased the efficacy of antimonials and limits their usage [4]. Other drugs including pentamidine and amphotericin B are used as second line agents, but have severe side effects. The absence of vaccines further deteriorates the situation due to complexity of immunity to parasites and technical challenges. Therefore, there is an urgent need for the supplementation or replacement of current drugs with new and more effective anti-leishmanial drugs. WHO suggests the use of traditional medicine for neglected diseases in societies with poor health facilities. Plant extracts or biochemical active compounds isolated from plants are likely to offer a beneficial source of new medicinal drugs. The crucial requisite for substituting medications has led to screening of natural compounds in leishmaniasis. The data acquired from reviewing isolated active compounds from plants could result in the emergence of safer and effective natural compounds with valuable anti- leishmanial activity. Moreover, it could also be an efficient approach for the production of new synthetic compounds [5]. Lowsonia inermis L pant (commonly known as Mehndi or Henna) belongs to the family Lythraceae. It is widely cultivated in tropical and subtropical areas, and native to the Southern-western Asia and Northern Africa. It is chemically well explored and many active compounds have been reported [6], including napthalenes, flavonoids, coumarins, naphthoquinones, terpenes (both volatile and non-volatile), alkylphenones, alkaloids and aliphatic hydrocarbons. It is extensively used for various medicinal purposes, and preserve a variety of pharmacological activities, including antibacterial, antioxidant, antiviral, antifungal, antiparasitic, cytotoxic, antidiabetic and anti-leishmanial efficacy [5]. Dichloromethane and methanol extracts acquired from the leaves displayed antiparacidal activity against Trypanosoma brucei, plasmodium falciparum, Nematoda and Leishmania donovani [7].

The present study attempts to offer a summary on the bioactive compounds isolated from the Lawsonia Inermis L. plant and the assessment with other plants, which could offer a valuable treatment option compound against Leishmania parasites. To best of our knowledge, the present study is first to summarize potential of active compounds isolated from Lawsonia Inermis L. plant for leishmaniasis.

Methods

Search method

An exclusive search was executed through all major scientific databases from 1976 to December, 2017 including five English databases, including Scopus, PubMed, Google Scholar, SciFinder and Reaxys. All articles which are related to the Lawsonia Inermis L plant and leishmaniasis were selected having at least GC-MS and/or NMR data. Moreover, the bibliography lists of all the articles were assessed for prevention of missing pertinent data. The search terms were: “medicinal plants”, “Lawsonia Inermis L”, “Leishmaniasis”, “anti-leishmanial agents”, “natural and synthetic compounds” “herbal extract”, “phytopharmaceuticals” and “isolated active compounds” alone or in combination together. Other relevant topics including Leishmania parasite, half-maximal inhibitory concentration (IC50) values, chemical name, class, structure of isolated compound, part of Lawsonia Inermis L plant and in vitro/in vivo evaluation of isolated active compounds were also evaluated and incorporated if the appropriate outcomes were recovered.

Paper selection

The papers selected for inclusion were reviewed thoroughly. The studies with poor methodology, papers on plants other than Lawsonia Inermis L and repetitive studies were excluded. The following data were obtained: parasite species, the structure of pure isolated compound, GC-MS, NMR data, chemical name, phytochemical class, part of plant used for extraction and research outcomes. Two referees individually examined studies recognized for inclusion and established study eligibility (Kapp index displayed an agreement 91% between two referees). Disagreements were settled by the third party interpretation.

Phytochemicals

Almost a hundred of phytochemical compounds, demonstrating a number of classes, have been recognized from all parts of Lawsonia Inermis L. plant. This abundance of pharmacologically active compounds suggests that this plant has could have active compounds which can be used for the treatment of several ailments including Leishmaniasis. Previous literature is lacking the in-depth details of anti- leishmanial compounds present in Lawsonia Inermis L.

Antileishmanial Compounds Isolated from Lawsonia Inermis L.Leishmania StrainReferences
1Lawsone (2-hydroxy-1,4-naphthoquinone)L. Mexicana[8]
2ScopoletinL. donovani,[9,10]
2ScopoletinL. amazonensis,[9,10]
2ScopoletinL. infantum and[9,10]
2ScopoletinL. braziliensia,[9,10]
3tannic acidL. donovani[11]
44-methoxyapigenin (linarisenin, acacetine or linarigenin)L. donovani[10]
5luteolin-7-O-glucosideL. donovani[12,13]
67-hydroxyflavoneL. donovani[3]
7diosmetin-7-rutinosideL. donovani[3]
8BetulinL. donovani[14]
9LupeolL. donovani[14]
10isocaryophlleneL. donovani[15]
11ethyl hexadecanoateL. donovani[15]
12HarmalineL. donovani[16]
13HarmineL. donovani[16]
1424-ethylcholest-olL. major[6]
15ApigeninL. tropica[5]
16LuteolinL. tropica[5]
17LaliosideL. tropica[5]
18Luteolin-4-O-beta-D-glucopyranosideL. tropica[5]
19Apigenin-4-O-beta-D-glucopyranosideL. tropica[5]
20ApigeninL. tropica[5]

Table 1: Antileishmanial activities of compounds from Lawsonia Inermis L.

S/No.Antileishmanial Compounds Isolated from other Plants (also existed
in Lawsonia Inermis L.)		Leishmania StrainReferences
1LinaloolL. amazonensis[17]
2ApigeninL. donovani[10]
3Apigenin 7-O-glucosideL. donovani[10]
4Luteolin 7-O-glucosideL. donovani[10]
5QuercetinL. donovani[10]
6CatechinL. donovani[10]
7Gallic acidL. donovani[10]
8p-Coumaric acidL. donovani[10]
9p-cymeneL. major[18]
10Beta-pineneL. major[18]
11Alpha-pineneL. major[18]
121,8-cineoleL. major[18]

Table 2: Similar Compounds between Lawsonia Inermis L. and other Plants having Antileishmanial activities.

The anti-leishmanial compounds reportedly produced by the plant have been characterized according to main classes as following:

Phenolic compounds

Napthoquinones: A number of naphthoquinones are present in the leaves of the Lawsonia Inermis L. including 2-hydroxy- 1,4-naphthoquinone (lawsone). This compound is the dyeing principle of this plant and is particularly found in the leaf petioles [19]. Moreover, this compound is unstable when exposed to light or high temperature, making it necessary to use appropriate means to dry it. The anti-leishmanial activity of lawsone has been reported and displayed that this compound is active against L. mexicana parasites [8].

Coumarins: In the case of coumarins, scopoletin was identified in the leaves part of the Lawsonia Inermis L. plant [20, 21]. It was displayed in several studies that scopoletin is active against different types of Leishmania parasites, including L. donovani, L. amazonensis, L. infantum and L. braziliensia, whereas IC50 values were reported to be 30, 41, 44 and >50 μg/ml, respectively [9, 10].

Tannins: The hairy root of Lawsonia Inermis L. yields tannic acid which is one of the main constituents of this plant and show good efficacy for Leishmaniasis [11].

Flavonoids: A large number of flavonoids have been isolated from the aerial parts of the Lawsonia Inermis L plant. These include 4-methoxyapigenin also known as linarisenin, acacetine or linarigenin. This compound is shown to be active against L. donovani, having IC50 value of 19 μg/ml [10]. The other compounds included luteolin-7-O-glucoside and several studies indicated the anti-lesihmanial activity this compound [12, 13]. This compound displayed most potent anti-lesihmanial activity (IC50 0.8 μg/ml) when tested in vitro against L. donovani promastigotes. 7-hydroxyflavone and diosmetin-7-rutinoside are compounds is isolated from the leaves of the plant and exhibited efficacy against L. donovani, having IC50 value of 4.1 and 2.6 μg/ml, respectively [3].

Terpenes

Non-volatile terpenoids: Betulin and lupeol are the two- known non-volatile terpenoids that have been identified in the seeds of Lawsonia inermis [21]. These compounds show anti-leishmanial activity when evaluated against the intra- macrophage model of amastigotes [14].

Volatile terpenes: A clear essential oil with deep fragrance is isolated from the flowers. The smell of this oil resembles a combination of roses, chocolate and cigars. The oil comprises mainly isocaryophllene and ethyl hexadecanoate, which are active against the Leishmania parasites [16].

Alkaloids

Harmaline and harmine are the two major alkaloids which are isolated from the extract of seeds of Lawsonia inermis. A study displayed that when administered in experimental model of leishmaniasis, it decreased the parasitic load and could be used in combination with other anti-leishmanial synthetic compounds [16].

Steroids

Till now, only one steroid, 24-ethylcholest-ol has been isolated from the roots of the plant and a study shows that it could be effective when used against the promastigotes of L. major parasites [6].

Miscellaneous

Many other constituents are known anti-leishmanial compounds which are isolated from leaves and stems of this plant including oleamide and 2-butoxysuccininc acid [22]. (Supplementary material)

Conclusion

To summarize, the present review it is the first time to present complete information about isolated compounds, antileishmanial activity and compounds similar between Lawsonia Inermis L. and other plants, this offers a valuable evidence about the biologically active compounds present in the Lawsonia inermis L. plant having anti-leishmanial activities and could be used alone or in combination with marketed synthetic compounds for clinical and experimental therapy studies. There is a need to exploit and explore more anti-leishmanial compounds, and potential adverse effects that would lead to developing safe and well-tolerated drugs for leishmaniasis. This serves a valid statement that Lawsonia inermis L. is a potent antileishmanial plant.

S/NoName of CompoundReferences
1Harmine[16]
2Harmaline[16]
31,2,4-trihydroxynapthalene-1-O-beta-D-glycopyranoside[23]
4D-glucopyranose[23]
5D-Mannitol[23]
6Methyl pheophorbide[23]
7Oleamide[23]
82-Butoxysuccinic acid[23]
9Geistein[23]
10Lawsochylin A[23]
11Lawsonaphthoate A[23]
12Lawsonaphthoate B[23]
13Lawsonaphthoate C[23]
14Luteolin[23]
15Luteolin 7-O-beta-D-glucopyranoside[23]
16Luteolin 4-O-beta-D-glucopyranoside[23]
17Apigenin 7-O-beta-D-glucopyranoside[23]
18Apigenin 4-O-beta-D-glucopyranoside[23]
19Apigenin[23]
20Luteolin 7-O-rutinoside[23]
21Diosmetin 7-O-rutinoside[23]
223-Amino-2-methoxycarbonyl-1,4-naphthoquinone[23]
23(4S)-4hydroxy-alpha-tetralone[23]
243alpha,4alpha-dihydroxy-alpha-tetralone[23]
259-hydroxy-4-megostigmen-3-one[23]
26(+)-dihydrodehydrodiconiferyl alcohol[23]
274-dihydroxybenzaldehyde[23]
28Isoplumbagin[24]
29p-coumaric acid[25]
302-methoxy-3-methyl-1.4-naphthoquinone[25]
31Apiin[25]
32Cosmosin[25]
33Lalioside[26]
34Lawsoniaside[26]
352,4,6-trihydroxyacetophenone-2-O-beta-D-glucopyranoside[26]
361,2,4,-trihydroxynaphthalene-1-O-beta-D-glucopyranoside[26]
37Lawsochrysin[27]
39Lawsochrysinin[27]
40Lawsonaringenin[27]
413’,4’-dimethoxyflavone[27]
427-hydroxyflavone[27]
433,3’,4’,7-tetrahydroxyflavonone[27]
44Dodecane[28]
45Tridecane[28]
461-(1,5-dimethyl-4-hexenyl-4methyl-benzene[28]
47Tetradecane[28]
482-methyl-decane[28]
493-methyl-decane[28]
503-methyl-hexasecane[28]
51Heptodecane[28]
522-methyldodecane[28]
53Pentadecane[28]
54Hexadecane[28]
55Octadecane[28]
56Hexahydropseudoionone[28]
57Eicosane[28]
582-hexyle-1-decanol[28]
59Isophytol[28]
60Dibutyl phthalate[28]
61Heptafluorobutyric acid, n-tetradecyl ester Phytol[28]
62Isoctyl phthalate[28]
638-heptyl pentadecane[28]
64Dotriacontane[28]
65Octacosane[28]
667-hexyl-eicosane[28]
67Linalool[29]
68Alpha-terpineol[29]
69Etherphenylvinyl[29]
701.3-indandione[29]
71Eugenol[29]
72Cis-hexahydro-8a-methyl18[2H,8H]naphthalenedione[29]
73Oxirane-tetradecyl[29]
74Hexadecanoic acid[29]
75Phytol[29]
76Acacetin[30]
77Acacetin 7-glucoside[30]
78Laxanthone I[30]
79Laxanthone II[30]
80Lawsone[30]
81Beta-sitosterol (-Glucoside)[30]
82D-mannitol[31]
83Benzaldehyde[15]
842-heptanone[15]
85Amyl isobutyrate[15]
86Undecane[15]
87Naphthalene[15]
88Methyl salicylate[15]
89Decane[15]
90(Z)-alpha-damascenone[15]
91Alpha-copaene[15]
92Beta-elemene[15]
93Isocaryiphyllene[15]
94(E)-alpha-ionone[15]
95Neryl acetone[15]
96(E),-beta-famesene[15]
97Gamma-muurolene[15]
98Alpha-pinene[32]
99Beta-pinene[32]
100Alpha-phellandrene[32]
101p-cymene[32]
102Limonene[32]
1031,8-cineole[32]
104Alpha-terpineol[32]
105Beta-caryophyllene[32]
106Aromadendrene[32]
107Alpha-humulene[32]
108alloaromadendrene[32]
1092H-Pyran-2,6(3H)-Dione[33]
1104H-Pyran-4-one,2,3 dihydro 3,5-dihydroxy-6-methyl-[33]
111Benzene[33]
1121.4-Naphthalenedione,2-hydroxy (Henna)[33]
113Methyl alpha-D-Glucopyranoside[33]
114n-hexadecanoic acid[33]
115Lawsoniasides A[34]
116Lawsoniasides B[34]
117Dihydroxylupene[35]
118Dihydroxylupane[35]
119Gallic acid[36]
1202-hydroxy-1,4-naphthoquinone[36]
1211,3-hydroxy-naphthoquinone[36]
1221,4-naphthoquinone[36]
1231,2-DIhydroxy-4-Glucosyloxynaphthalene[37]
124Lacoumarin[38]
125Lawnermis acid[39]
126Lawsaritol[40]
127Catechin[41]
128Antocyanins[41]
129Quercetin[41]
1301-hydroxy-3,7-dimethoxy-6-acetoxy xanthone[42]
131Bicoumarin A[43]
132Biflavonoid A[43]
133Biquinone A[43]
134Lawsonicin[44]
135Lawsonadeem[44]
136Vomifoliaol[44]
1371,2,4-trIhydroxynaphthalene-4,4-di beta-D-glucopyranoside[45]
1382,3,4,6-tetrahydroxyacetophenone-2- beta-D-glucopyranoside[45]
139n-triacontyl n-tridecanoate[46]
140n-triacontanol[46]
141Beta-sitosterol[46]
142Lupeol[46]
1433o-norlupan-3-beta-ol-20-one[46]
144Betulinic acid[46]
145Betulin[46]
146Rosamutin[47]
147Euscaphic acid[47]
1481beta,2beta,3beta,19alpha-tetrahydroxyurs-12-en-28-oic acid[47]
149Ursolic acid[47]
150Arjunic acid[47]
15112-[2’-(1’.4’-doxin-5’.6’-dione)]-8”E-undecenyl-dodecanoate[48]
1525-[1’-(docosa-2’E.5’E-dienyl)]-1.4-doxin-2,3-dione[48]
153Lawsorosemarinol[49]
154Lawsofructose[49]
1552-(beta-D-glucopyranosyloxy)-1,4-naphthoquinone[49]
1563-(4-hydroxyphenyl)-tricontyl-(Z)-propenoate[49]
1574-hydroxy coumarine[49]
1583-(4-hydroxy-3-methoxyphenyl)-tricontyl-(Z)-propenoate[49]
1594-hydroxy-4-methyl coumarine[49]
1601,3-dihydroxy-6,7-dimethyoxyxanthione[50]
1611,hydroxy-3,6-diacetoxy-7-methyoxyxanthione[50]

Table 3: Supplementary material: Complete list of Isolated Compounds from Lawsonia Inermis L.

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@article{kashif2023,
  title   = {Comparative Assessment of Compounds in Lawsonia Inermis L. - A Potent Antileishmanial Plant},
  author  = {Kashif Iqbal},
  journal = {Advances in Pharmacology & Clinical Trials},
  year    = {2023},
  volume  = {8},
  number  = {4},
  doi     = {10.23880/apct-16000230}
}
Kashif Iqbal (2023). Comparative Assessment of Compounds in Lawsonia Inermis L. - A Potent Antileishmanial Plant. Advances in Pharmacology & Clinical Trials, 8(4). https://doi.org/10.23880/apct-16000230
TY  - JOUR
TI  - Comparative Assessment of Compounds in Lawsonia Inermis L. - A Potent Antileishmanial Plant
AU  - Kashif Iqbal
JO  - Advances in Pharmacology & Clinical Trials
PY  - 2023
VL  - 8
IS  - 4
DO  - 10.23880/apct-16000230
ER  -