1Akson college of Health Sciences, Mirpur University of Science and Technology Mirpur A. .J. .K& Kashmir, Pakistan, 2Department of Pharmacy, BahauddinZakariya University Multan, Pakistan, 3School of Pharmacy, The University of Faisalabad, Faisalabad, Pakistan, 4Lahore Pharmacy College (A project of LMDC), Lahore, Pakistan.
Received: 10 Aug 2014 Revised and Accepted: 15 Sep 2014
Aphelandra belong to family Acanthaceae. We have reviewed traditional uses, pharmacological potential and phytochemical study of family Acanthaceae and genus Aphelandra. Traditionally the most important part use in Acanthaceae is the leaves and they are used externally for wounds. We have found that Acanthaceae possess antifungal, cytotoxic, anti-inflammatory, anti-pyretic, anti-oxidant, insecticidal, hepatoprotective, immunomodulatory, Anti- platelet aggregation and anti-viral potential. Phytochemical reports on family Acanthaceae are glycosides, flavonoids, benzonoids, phenolic compounds, naphthoquinone and triterpenoids. We have also document genus Aphelandra, its phytochemical and pharmacological potential.
Keywords: Acanthaceae, Aphelandra, Ethnomedicinal, Phytochemistry, Wound healing potential,
Majority of the population in developing world is struggling to raise living standards and improvement of health care delivery due to increasing poverty and population. According to an estimate, 70-80% of rising world is dependent on conventional plants obtained remedies as pharmaceuticals are high priced. From this reality, it can be retrieved that by data assembling and experimentation, valuable plus economical medicaments can be separated from different flora to satisfy requirements of evolving world. Hence requirements of officinal plants cannot be neglected. .Databases used to search for the literature were: Google scholar,PubMed, Tropicos (for plant taxonomy). Bold numeral in the text refers to chemical structures reported in Fig. 1. .All the structures were reported from the literature and drawn by ChemDraw.
Ethnomedicinal importance of family acanthaceae
Ground leaves of Adhatoda vesica Nees. (Acanthaceae) are used in treatment of bronchial diseases. Ground fresh leaves of Andrographispaniculata are used to alleviate bites of poisonous insects and reptiles.
Infusions of leaves of Aystasiaschimperi, Dyschoristeradicans, Acanthus eminens, Dyschoristethumbergiiflora, Lepidagathisscariosa and Thunbergiaalata (Family: Acanthaceae) are used for cough, skin diseases, wounds, eye infections, anti-diarrhea, edema, pneumonia and backache. Paste of leaves of Barberiagrandicalyx (Acanthaceae) is used for snake bites. Ash of leaves of Justiciabetonica, Acanthus pubescens and Justiciaflava is used for dry cough, anti-diarrhea, flu and ulcers .
Leaves of Blepharismaderaspatensis belonging to family Acanthaceae are mixed with onion bulbs to form paste. This paste is applied externally for cuts and wounds. Leaves of Hygrophilaauriculata (Acanthaceae) are used to relieve from cough. Leaves of Justiciatranquebariensis (Acanthaceae) are used for poisonous bites .
Leaves of Andrographispaniculata Nees. And Justiciagendrarussa L. Which belongs to family Acanthaceae, are used for fever, headache, vertigo and wounds .
Powder of leaves of Andrographispaniculata (Acanthaceae) is used internally for diabetes. Juice of leaves of Blepharismaderaspatensis (Acanthaceae) is used externally for wounds. Paste of leaves of Elytrariaacualis (Acanthaceae) is used externally for hip pain. Decoction of whole plant of Rungialinifolia which belongs to family Acanthaceae is used internally for ulcers .
Leaves of Justiciaadhatoda which belongs to family Acanthaceae are used for rheumatism, fever, chest diseases, pneumonia, asthma, tuberculosis, antispasmodic, expectorant, diuretic, antiseptic and to reduce swelling .
Andrographispaniculata, Hygrophilaspinosa, Barleriaprionitis and Adhatoda vasica are members of the Acanthaceae family, which are used traditionally as antiviral, antipyretic, antiasthmatic and in respiratory diseases .
Pharmacological reports on family acanthaceae
Aqueous extract of Andrographispaniculata belonging to family Acanthaceae showed significant antibacterial activity against Bacillus subtilis, Staphylococcus aereus, Escherichia coli and Pseudomonas aeruginosa in comparison to some known antibiotics.
Methanolic extract of Asteracanthalongifolia L. belonging to family Acanthaceae showed the most promising results against Burkholderiapseudomallei strain1and strain 2 and Staphylococcus aureuss.
Acetone crude extract of Andrographisaffinis Nees belongs to family Acanthaceae showed higher degree of inhibition against Staphylococcus aureus, Proteus vulgaris, Escherichia coli, Klebsiellapneumoniae, and Pseudomonas aeruginosa.
Chloroform crude extract of Andrographispaniculata (Acanthaceae) showed antibacterial activity against S. .aereus, E. coli,B. .subtilis and P. vulgaris. The effect produced by the extract was comparable with benzyl penicillin.
A large number of gram positive and gram negative bacteria exhibited vulnerability when exposed to extract ofRhinacanthusnasutus (Acanthaceae) .
The dichloromethane extract of the leaves of Hypoestesserpens (Acanthaceae) showed antifungal activity against Cladosporiumcucumerinum and Candida albicans. .Fusicoserpenol A and dolabeserpenoid acid A were isolated responsible for this activity .
The chloroform extract of Androgrphispaniculata (Acanthaceae) exhibited activity against Aspergillusnigerand Penicillium chrysogenum. The activity was found to be effective against all the organisms tested .
Antifungal activity was reported by aqueous extract of Andrographispaniculata belonging to family acanthaceae against Candida albicans in comparison to Nystatin. Anti-fungal activity has been exhibited by the extract of Rhinacanthusnasutus (Acanthaceae) against Aspergillusniger, Pyriculariaoryzae, Cryptococcus neoformans, Saccharomyces spp., Epidermophytesfloccosum, Candida albicans, Trichophytonrubrum, Tricophytonmentagagrophytes, Microsporumcanis and Microsporumgypeseum.
Elenoside(1) was reported in Justiciahyssopifolia belonging to family Acanthaceae. Elenoside showed cytotoxic activity to human cancer cell lines in range concentrations from 10-5 to10-4M. It has an LD50 in mice, of 305mg/kg and central depression properties at doses of 25, 50, and 100mg/kg. Thus elenoside appears to be sedative with broad spectrum cytotoxicity .
Table 1: Traditional uses of family Acanthaceae
|Species||Part use||Traditional uses|
|Adhatoda vesica Nees||Leaves||Treatment of bronchial diseases2|
|Andrographispaniculata||Leaves||Alleviate bites of poisonous insects and reptiles 2|
|Aystasiaschimperi, Dyschoristeradicans, Acanthus eminens, Dyschoristethumbergiiflora, Lepidagathisscariosa
|Leaves||Used for cough, skin diseases, wounds, eye infections, anti-diarrhea, edema, pneumonia and backache3.|
|Barberiagrandicalyx||Paste of leaves||Paste of leaves of (Acanthaceae) is used for snake bites.3|
|Justiciabetonica, Acanthus pubescens and Justiciaflava||Ash of leaves||Ash of leaves of are used for dry cough, anti-diarrhea, flu and ulcers3|
|Blepharismaderaspatens||Mixed with onion bulbs to form paste||This paste is applied externally for cuts and wounds.4|
|Hygrophilaauriculata||Leaves||Leaves of Hygrophilaauriculata (Acanthaceae) are used to relieve from cough. 4|
|Justiciatranquebariensis||Leaves||Leaves of Justiciatranquebariensis(Acanthaceae) are used for poisonous bites 4|
|Andrographispaniculata Nees. and Justiciagendrarussa L||Leaves||Leaves of Andrographispaniculata Nees. and Justiciagendrarussa L. which belongs to family Acanthaceae, are used for fever, headache, vertigo and wounds 5|
|Andrographispaniculata||Powder of leaves||Powder of leaves of Andrographispaniculata (Acanthaceae) is used internally for diabetes.|
|Blepharismaderaspatensis||Juice of leaves||Juice of leaves of Blepharismaderaspatensis (Acanthaceae) is used externally for wounds.6|
|Elytrariaacualis||Paste of leaves||Paste of leaves of Elytrariaacualis (Acanthaceae) is used externally for hip pain6|
|Rungialinifolia||Decoction of whole plant||Decoction of whole plant of Rungialinifolia which belongs to family Acanthaceae is used internally for ulcers 6|
|Justiciaadhatoda||Leaves||Leaves of Justiciaadhatoda which belongs to family Acanthaceae are used for rheumatism, fever, chest diseases, pneumonia, asthma, tuberculosis, antispasmodic, expectorant, diuretic, antiseptic and to reduce swelling 7|
|Andrographispaniculata, Hygrophilaspinosa, BarleriaprionitisAdhatoda vasica||Leaves||Andrographispaniculata, Hygrophilaspinosa, Barleriaprionitis and Adhatoda vasica are members of Acanthaceae family, which are used traditionally as antiviral, antipyretic, antiasthmatic and in respiratory diseases 8|
Justiflorinol(2), justicinol(3), patentiflorin A (4), patentiflorin B (5), 4”-O-acetylpatentiflorin B (6) and 4”-O-acetylmanathoside B (7) were separated from leaves and stems of Justiciapatentiflora (Acanthaceae) by bioassay-guided purification. These compounds display significant cytotoxic activity against cancer cell lines and arrest the cell cycle .
Methanol extract of Andrographispaniculataexhibited anti-cancer activity. Andrographolide(8), 14-deoxyandrographolide (9) and 14-deoxy-11, 12-didehydroandrographolide (10) were separated from this extract . .Andrographolide(8) from the plant Andrographispaniculata (Acanthaecae) and its derivative 8, 17 -epoxy andrographolide(11) showed cytotoxic activity . .Rhinacanthin-A (12), rhinacanthin-B (13), rhinacanthin-C (14), rhinacanthin-D (15), rhinacanthin-G, rhinacanthin-H, rhinacanthin-I, rhinacanthin-K,rhinacanthin-M, rhinacanthin-N (16), rhinacanthin-Q (17) and wogonin(18)separated from the roots of Rhinacanthusnasutus (Acanthaceae) showed cytotoxic activity. .The leaf and root extract of Rhinacanthusnasutus (Acanthaceae) showed antiproliferative activity against human cervix adenocarcinomaand other types of cancers .
Anti-inflammatory and antipyretic activity
Leaves extracts of Hygrophilaspinosa (Acanthaceae) exhibited anti-pyretic and anti-inflammatory activity .
Alcoholic extract of Lepidegathisanobrya of family acanthaceae showed analgesic and anti-inflammatory activities.
Anti-inflammatory and analgesic activities were reported by the methanol extract of Diclipteraverticillata (Acanthaceae). Ethanol extract of Justciagendrarussa (Acanthaceae) exhibitedanalgesic activity and anti-inflammatory activity.
The aqueous extract of roots of Barleriaprionitis L. (Acanthaceae) showed anti-inflammatory activity by using caragennan-induced rat paw edema method.
The methanol extract of leaves of Andrographispaniculata (Acanthaceae) was tested on inhibition of lipopolysaccharide induced and calcimycin induced mediators in diverse cell models. The results showed that extract was fairly potent in attenuating pro-inflammatory, inflammatory and allergic mediators.
Rhinacanthin-E and rhinacanthin-F separated from the aerial parts of Rhinacanthusnasutus (Acanthaceae) exhibited antiviral activity .
Methanol and aqueous extracts of aerial parts of Justiciaspicigera of family acanthaceae exhibited antioxidant activity. DPPH radical scavenge method was used. Water extract has lower activity than that of methanol .
Methanol extracts (at 100µg/ml) of Ruelliakerrii and Strobilanthesauriculata showed antioxidant activity. Methanolextracts of Barleriacristata, Justiciaprocumbens, Ruelliakerrii and Strobilanthesaureculata showed antioxidant activity .
The extract of Rhinacanthusnasutus (Acanthaceae) exhibited antioxidant activity. Anti-aging effect was produced by the cosmetics containing this extract. The mechanism involved is the removal of superoxide from the human body .
Antioxidant activity of the methanol fraction of Blepharisedulis (Forssk.) Pers. Family Acanthaceae was determined using the DPPH radical test .
The extract of Andrographispaniculata(Acanthaceae) was examined for hepatoprotective effect by administration to male mice. Andrographolide(8) and its derivativesexhibited hepatoprotective activity .
Rhinacanthusnasutus root extracts showed hepatoprotective effect in rats treated with aflatoxin-B1.
The alcoholic extract of the aerial parts of Acanthus montanus Nees (Family: Acanthaceae) exhibited a significant activity against adult Aedesaegypti. Phytochemical study of the plant has resulted in isolation of compounds which exhibit variable degrees of insecticidal activity. Β-sitosterol-3-O-β-D-glucoside(19) exhibited mosquitocidal activity (100% mortality) against adult Aedesaegypti at 1.25µg/mg concentration, followed by palmitic acid (20) (90%), linaroside(21) (80%) and acetoside(22) (70%) respectively .
The extract of Rhinacanthusnasutus of family Acanthaceae exhibited immunomodulatory activity .
Anti- platelet aggregation activity
The Rhinacanthusnasutus (Acanthaceae) plant extract showed the anti-platelet aggregation effect. Rhinacanthin-A (12), rhinacanthin-B (13), rhinacanthin-C (14), rhinacanthin-G,rhinacanthin-H, rhinacanthin-I, rhinacanthin-K, rhinacanthin-M and rhinacanthin-Q (17) separatedfrom the roots of Rhinacanthusnasutus. These compounds showed inhibition of rabbit platelet aggregation induced by arachidonic acid .
Phytochemical reports on family acanthaceae
From the aerial parts of Acanthus ilicifolicus, which is a member of Acanthaceae family, (2R)-2-O-β-D-gluco-pyranosyl-2H-1,4-benzoxazin-3(4H)-one (23), (2R)-2-O-β-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)–one (24), (2R)-2-O-β- D-glucopyranosyl-7-hydroxy-2H-1,4-benzoxazin-3(4H)-one (25), 7-chloro-(2R)-2-O-β-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (26) and (2R)-2-O-β-D-glucopyranosyl-5-hydroxy-2H-1,4-benzoxazin-3(4H)-one(27) have been isolated .
Salidroside(28),benzyl β-D-glucopyranoside(29), (6S,9R)-roseoside(30), asysgangoside(31), ajugol(32), apigenin 7-O-β-D-glucopyranoside(33), apigenin 7-O-neohesperidoside (34) and apigenin 7-O-β-Dglucopyranosy (1→ 6)-β-D-glucopyranoside(35) have been reported in Asystasiagangeticawhich belongs to family Acanthaceae .
Olean-12-ene-1β,3β,11α,28-tetraol-28-O-β-D-glucopyranosyl-(1→2) -β-D-glucopyranoside (36), olean-12-ene-1β,3β,11α,28-tetraol-28-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-gluco pyranoside(37), 11α-methoxy-olean-12-ene-1β,3β,28-triol-28-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside(38) and 11α-methoxy-olean-12-ene-1β, 3β, 28-triol 28-O-β-Dglucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (39) were reported from JusticiabetonicaL. .belonging to family Acanthaceae . Three phenylethnoid glycosides, desrhamnosylacteoside(40), acteoside (41) and poliumoside(42) were separated and identified from the callus cultures of Barleriacristata L. of family Acanthaceae .
New phenylethanoid glycoside namely acanmontanoside(43) together with eight known compounds, identified as decaffeoylverbascoside,verbascoside(44), isoverbascoside(45), leucosceptoside A (46), (2R)-2-O-β-D-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one,(2R)-2-O-β-D-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one (47), (3R)-1-octen-3-ol-3-O-β-D-xylopyranosyl-(1→6)-O-β-D-glucopyranoside (48) and ebracteatoside B (49) have been reported from the methanol extract of aerial portion of Acanthus montanus.
From the genus Asystasia of Acanthaceae family following compounds have been reported: 6β-hydroxyantirrhide (50),angeloside(51),ajugol(32), 6-O-α-L-rhamnopyranosyl-catapol (52), 6-O-α-(3’’-O-trans-caffeoyl)-L-rhamnopyranosyl-catapol(53), 6-O-α-(3’’-O-trans-p-coumaroyl)-L-rhamnopyranosyl-catapol(54), sinuatol (55), luteolin7-O-β-D-glucopyranoside(56), luteolin 7-O-rutinoside(57), apigenin 7-O-rutinoside (58) and apigenin 7-O-β-D-glucuronide(59) .
Ethanol extract of leaves of Barleriacristata gave two iridoidal glycosides like barlerin(60) and shanshide methyl ester (61).
Chemical investigation of the methanol fraction of the aerial parts of Blepharisedulis (Forssk.) Pers. Family Acanthaceae revealed the presence of phenylethnoids namely verbascoside(44), cis-verbascoside, isoverbascoside(45) and leucosceptoside A (46) . Glycoside compounds; sitosterol-β-D-glucopyranoside(62), stigmasterol-β-D-glucopyranoside(63), 3, 4-dimethylphenol-β-D-glucopyranoside(64) and 3, 4, 5-trimethylphenol-β-D-glucopyranoside(65) were isolated from leaves and stems of Rhinacanthusnasutus plant of family Acanthaceae .
The preliminary phytochemical screening of Dipteracanthuspatulus Jacq. Nees (Acanthaceae) revealed the presence of flavonoids .
From the crude ethanol extract of Brillantaisiapalisatii (Acanthaceae) 3-epi-ursolic acid (66), verbascoside(44) and lespedin(67) were isolated. Following compounds were reported from Andrographispaniculata (Acanthaceae); β-sitosterol(68), andrographolide(8),14-deoxy-ll,12-dedihydro andrographolide,14-deoxyandrographolide (69), 7-O-methyldihydrowogonin (70), (2S)-5,7,2’,3’-tetramethoxyflavanone (71), dihydroskullcapflavone I (72), 7-O-methylwogonin (73), 5-hydroxy-7,8,2’,5’-tetramethoxy-flavone (74), 5-hydroxy-7,8,2’,3’-tetramethoxyflavone (75), 5-hydroxy-7,2’,6’-trimethoxyflavone(76), 5-hydroxy-7,2’,3’-trimethoxyflavone(77), skullcapflavone12’-methylether (78), cinnamic acid(79), caffeic acid (80), ferulic acid (81), chlorogenic acid (82), 7-O-methylwogonin 5-glucoside (83), skullcapflavone I 2’-glucoside (84), 14-deoxy- 15-isopropylidene-11,12-didehydro-andrographolide(85), 14-deoxy-11-hydroxyandro grapholide (86), neoandrographolide(87) and andro graphoside(88) . Chromatographic resolution of ethyl acetate extract of leaves of Barleriacristata furnished two flavonoid compounds, which were further identified and characterizes as luteoline(89) and 7-methoxy luteoline(90). Coumarins, (+)-pracruptorin, umbelliferone(91) and 2, 6-dimethoxy benzoquinone (92)derivedfrom the whole plant of Rhinacanthusnasutus plant of family Acanthaceae .
Petroleum ether extract of leaves of Barleriacristata furnished two phenolic compounds, which were characterized as p-coumaric acid (93) and α-tocopherol(94) .
Rhinacanthin-A (12), rhinacanthin-B (13), rhinacanthin-C (14), rhinacanthin-D (15), rhinacanthin-G, rhinacanthin-H, rhinacanthin-I,rhinacanthin-J, rhinacanthin-K, rhinacanthin-L, rhinacanthin-M, rhinacanthin-N (16), rhinacanthin-O, rhinacanthin-P and rhinacanthin-Q (17) were isolated aerial parts of Rhinacanthusnasutus plant of family Acanthaceae .
The benzonoids compounds p-hydroxy-benzaldehyde(95), vanillic acid (96), syringic acid (97), 2-methoxy-propionolphenol (98), methyl valinate(99) and syringaldehyde(100) were isolated from leaves, roots and stems of Rhinacanthusnasutus plant of family Acanthaceae .
The triterpenoids compounds β-amyrin(101), glutinol(102) and lupeol(103) were derived from roots of Rhinacanthusnasutus plant of family Acanthaceae .
Pharmacological reports on genus Aphelandra
Antibacterial activity and Antifungal activity
From the roots of genus Aphelandra2-benzoxazolinones (104) and 6-methoxy-2-benzoxazolinone (105) were separated. These compound and their related synthetic derivatives showed antibacterial and antifungal activity . Plants belonging to genus Aphelandra (Acanthaceae)showed antimicrobial activity against E. coli, P. .aeruginosa, S. aureus, and C. .albicans. The methanol extracts of Aphelandra squarrosashowed antibacterial activity against at least one of the following test organisms, Staphylococcus aureus, Escherichia coli, Proteus vulgaris andPseudomonas aeruginosa using the tube dilution and plate diffusion methods .
2-benzoxazolinone (104) and 2-hydroxy-1, 4-benzoxazin-3-one (106) were isolated from Aphelandra tetragona. These were bio transformed into 2-amino-3-H-phenoxazine-3-one (107) by endophytic fungi.2-amino-3-H-phenoxazine-3-one (107) has potent anti-inflammatory and immunoregulatory properties. These properties may provide a promising therapeutic strategy for the treatment of T cell-mediated inflammatory auto immune diseases as well as for bacteria induced chronicinflammatory diseases.
Both 2-benzoxazolinone (104) and 2-hydroxy-1, 4-benzoxazin-3-one (106) are compounds calledphytoanticipins and present in healthy plants as substances toovercome microbial diseases and herbivore.
Phytochemical reports on genus Aphelandra
Macrocyclic polyamine alkaloid aphelandarine(108) was isolated from the roots of Aphelandra tetragona, which consists of spermine and two units of 4-hydroxycinnamic acid .
N1,N5-Di-p-coumaroylspermidine (109), N5,N-di-p-coumaroylspermidine (110), and N1,N5,N-tri-p-coumaroylspermidine (111) were isolated from anthers of Aphelandratetragonaand A. .chamissoniana.
18-O-Methylchaenorpine and iso-18-O-methylchaenorpine two novel stereo-isomeric spermine alkaloids were separated from Aphelandratetragona.
Macrocyclicspermine alkaloids namely 6-hydroxy-aphelandrine (112) and 6-acetoxy-aphelandrine (113) were isolatedfrom the roots of Aphelandra fuscopunctata.
Benzoxazinoids-cyclic hydroxamic acids and their correspondingglucosides
From roots of Aphelandra squarrosa and Aphelandra fuscopunctata following compounds were separated; 2,4-dihydroxy-1,4-benzoxazin-3(H)-one (114), 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3(H)-3one (115), 2-hydroxy-1,4-benzoxazin-3(2H)-one (116), 2-hydroxy-7-methoxy-1,4-benzoxazin-3(2H)-one (117), and their corresponding glycosides as well as bezoxazolinones
In Aphelandra squarrosaglycosides are present in the roots .
Flavonoids and Isoflavones
Several compounds were isolated and identified from the leaves and stems of Aphelandra aurantiaca which consists of scopoletin(118), chrysin(119), eucalyptin(120), gnaphalin(121), nevadensin(122) and p-coumaric acid (123) in the form of ester with glucose .
Fig. 1: Structure of compounds present
Literature actually reports chemical investigations of a large family of nearly 250 genera and 2500 species, distributed mainly in the tropics and extending to Mediterranean, Australia and Southern U. .S. .A. In Pakistan it is represented by 18 genera and 60 specific and infraspecific taxa; of which 44 are native. There are no published data concerning either the toxicity of the whole remedies and their isolated compounds. Further investigations on phytochemical discovery and subsequent screening are needed for opening new opportunities to develop pharmaceuticals based on Family Acanthaceae and genus Aphelandra.
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