PELTOPHORUM PTEROCARPUM: CHEMICAL AND PHARMACOLOGICAL ASPECTSHTML Full Text
Received on 17 August, 2013; received in revised form, 24 September, 2013; accepted, 15 December, 2013; published 01 January, 2014
PELTOPHORUM PTEROCARPUM: CHEMICAL AND PHARMACOLOGICAL ASPECTS
Shyamal K. Jash 1, Raj K. Singh 2, Sasadhar Majhi 3, Atasi Sarkar 4 and Dilip Gorai*5
Department of Chemistry, Saldiha College 1, Saldiha, Bankura-722173, West Bengal, India
Department of Botany, Jhargram Raj College 2, Jhargram, Paschim Medinipur-721507, West Bengal, India
Department of Chemistry, Patha Bhavana, Visva-Bharati 3, Santiniketan-731235, West Bengal, India
Department of Zoology, Kapastikuri S.S.K. Vidyapeeth 4, Sitapur-731235, Birbhum, West Bengal, India
Department of Chemistry, Kulti College 5, Kulti-713343, Burdwan, West Bengal, India
ABSTRACT: The present work offers a review addressing the detailed chemistry and pharmacology of Peltophorum pterocarpum (belonging to Fabaceae family) regarded as one of the most significant plant species in traditional system of medicine. The plant is used in different parts of the world for the treatment of several ailments like stomatitis, insomnia, skin troubles, constipation, ringworm, insomnia, dysentery, muscular pains, sores, and skin disorders and is the source of a diverse kind of chemical constituents such as aliphatic alcohols, fatty acids, amino acids, terpenoids, phenolics, flavonoids, alkaloids, steroids etc. The isolated phytochemicals as well as different extracts exhibited numerous biological activities including antimicrobial, antioxidant, cytotoxic, aldose reductase inhibition and antiglycaemic activities. Hence, up to-date information on the chemical and pharmacological knowledge on this plant may be helpful to guide researchers anticipating to undertake further investigations in these directions. The present review covers literature up to middle of 2013 and enlists 42 references.
Peltophorum pterocarpum, Fabaceae, Chemical constituents, Biological activity
INTRODUCTION:Peltophorum pterocarpum (Copperpod, Golden Flamboyant, Yellow Flamboyant, Yellow Flame Tree, Yellow Poinciana and Radhachura in Bangla; Synonyms: Peltophorum inermis and Peltophorum ferrugineum) is a family of Fabaceae native to tropical southeastern Asia and a popularly ornamental tree grown around the world. It is a deciduous tree growing to 15–25 m (rarely up to 50 m) tall, with a trunk diameter of up to 1 m.
The leaves are bipinnate, 30-60 cm long, with 16-20 pinnae, each pinna with 20-40 oval leaflets 8-25 mm long and 4-10 mm broad. The flowers are yellow, 2.5-4 cm in diameter, produced in large compound racemes up to 20 cm long. The fruit is a pod 5-10 cm long and 2.5 cm broad, red at first, ripening black, and containing one to four seeds. Trees begin to flower after about four years 1, 2.
The plant is native to tropical southeastern Asia and northern Australasia, in Sri Lanka, Thailand, Vietnam, Indonesia, Malaysia, Papua New Guinea, Philippines and the islands of the coast of Northern Territory, Australia 1,3. The plant is also found in different regions of India including Birbhum District, West Bengal. The wood of the plant is wide variety of uses, including cabinet-making 4 and the foliage is used as a fodder crop 1.
The taxonomical classification of Peltophorum pterocarpum is shown below:
|Binomial name||Peltophorum pterocarpum
(DC.) K. Heyne
Peltophorum pterocarpum (DC.) Baker ex Heyne is a deciduous tree commonly used for ornamental purpose and as an avenue tree. Different parts of this tree are used to treat many diseases like stomatitis, insomnia, skin troubles, constipation, ringworm and its flower extract is known to be a good sleep inducer and used in insomnia treatment 5-7. Its bark is used as medicine for dysentery, as eye lotion, embrocation for pains and sores. The traditional healers use the leaves in the form of decoction for treating skin disorders. Stem infusion of Peltophorum pterocarpum Baker ex K. Heyne used in dysentery, for gargles, tooth powder and muscular pain 8. Flowers are used as an astringent to cure or relieve intestinal disorders after pain at childbirth, sprains, bruises and swelling or as a lotion for eye troubles, muscular pains and sores 9.
MATERIALS AND METHODS: The chemical constituents isolated and identified from peltophorum pterocarpum, pharmacological activities exhibited by the isolated compounds as well as by the crude plant extracts were searched across the Medline (National Library of Medicine) and Science Direct databases. The data were updated in July 2013, using the search-terms Peltophorum pterocarpum, chemical constituents, biological activities, pharmacological activities or properties of Peltophorum pterocarpum as keywords. In addition, the reference lists of all papers identified were reviewed.
Chemical constituents: Chemical constituents (structures shown in Figure 1) isolated so far from this plant species are included in Table 1 and found that aliphatic alcohol, fatty acids, amino acids, terpenoids, phenolics, flavonoids, alkaloids, steroids are isolated as phytochemicals from this plant; eighty-three phytochemicals have been reported so far from this plant. Besides, some investigation regarding class of chemical constituents present in different extract of this plant has been studied 10.
TABLE 1: LIST OF PHYTOCHEMICALS ISOLATED FROM PELTOPHORUM PTEROCARPUM
|Compound (Str. No.)||Plant part||Reference|
|1-Ethyl-4,4-dimethylcyclohex-2-en-1-ol [Isosativen] (4)||Stem||8|
|Valerenic acid (11)||Stem||8|
|Megastigma-4,6E, 8E triene (12)||Stem||8|
|Hexadecanoic acid (13)||Stem||8|
|9,12-Octadecadienoic acid (14)||Stem||8|
|9-Octadecenoic acid ethyl ester (15)||Stem||8|
|Ethyl docosanoate (18)||Stem||8|
|Linoleic acid (21)||Seed oil||10|
|Linolenic acid (22)||Seed oil||10|
|Oleic acid (23)||Seed oil||10|
|Palmitic acid (24)||Seed oil||10|
|Stearic acid (25)||Seed oil||10|
|Lignoceric acid (26)||Seed oil||10|
|1,2-Benzenedicarboxylic acid (27)||Stem||8|
|Di-N-Octyl phthalate (28)||Stem||8|
|β-Sitosterol (29)||Stem, seed oil, flowers||8, 11-12|
|β- Sitosterol-3-O-β-glucopyranoside (30)||flowers||13|
|Cholesteryl propanoate (31)||Stem||8|
|Cholesta-4,6-dien-3-ol, benzoate (32)||Stem||8|
|Stigmasterol (35)||Seed oil||11|
|Ergost-5-en, 3-ol (37)||Seed oil||11|
|Campesterol-3-O- β-D- glucopyranoside (38)||flowers||13|
|Lupeol (39)||Stem, flowers||8,12|
|Phytol (40)||Seed oil||11|
|Vitamin E acetate (41)||Stem||8|
|Bergenin (42)||Flowers, sap wood||8, 14-17|
|5-Hydroxy-7-methoxy-2-(3,4-dihydroxy)- phenoxychromone (43)||Leaves||18|
|5-Hydroxy-7-methoxy-2-(3′-O-β-glucopyranosyl, 4′-hydroxy) phenoxychromone (44)||Leaves||18|
|7-Methoxy ophioglonin (48)||Leaves||18|
|Quercetin (56)||Fruits||18, 21|
|Rhamnetin (58)||Fruits||18, 21|
|Melanoxetin (59)||Fruits||18, 21|
|Meratin (60)||Fruits||18, 21|
|(-)-Epicatechin (61)||Sap wood||8, 16-17|
|Propelargonidin (62)||Fruits||18, 21|
|(+)-Leucocyanidin (63)||Bark, sap wood||8, 16-17, 22|
|Aspartic acid (67)||Seeds||25|
|Glutamic acid (68)||Seeds||25|
|Peltopterin (a protein)||Seeds||26|
Biological activities exhibited by the plant and plant constituents: Various biological activities exhibited by both the crude plant extracts and isolated chemical constituents are described categorically under the following sub-sections:
- Anti-microbial activity: Preliminary phytochemical screening of methanol extract of P. pterocarpum flower as investigated by Sukumaran et al 27 showed the presence of phenolic compounds, flavonoids, saponins, steroids, tannins, xanthoproteins, carboxylic acids, coumarins and carbohydrates. The investigators also reported that flower extract of this plant exhibited significant activity against four Gram-positive (Staphylococcus aureus, Bacillus cereus, Enterococcus faecalis and Streptococcus pyogenes) and three Gram-negative bacteria (Proteus mirabilis, Acinetobacter baumannii and Serratia marsecens), out of 12 pathogenic bacteria studied 27.
Bergenin (42), isolated from methanol fraction of P. pterocarpum flowers, is found to show antifungal activity against Trichophyton mentagrophytes, Epidermophyton floccosum, Trichophyton rubrum, Aspergillus niger and Botrytis cinerea having MIC value of 250, 500, 500 & 250 µg/mL, respectively. However, this compound (42) was unable to show any antibacterial activity 14.
Chew et al 28 reported that aqueous methanol and dichloromethane extract of flowers and leaves of P. pterocarpum exhibited antibacterial activity against two strains of methicillin resistant S. aureus with MID (Minimum inhibitory dose) values ranging between 100 μg/disc and 500 μg/disc. Nathan et al 10 investigated antibacterial activity of P. pterocarpum methanolic flower extract against the bacteria isolated from human infections like Salmonella typhi, Staphylococcus aureus, Proteus mirabilis, Bacillus subtilis and Escherichia coli following well diffusion method and found that the extract showed higher potency against P. mirabilis followed by Salmonella typhi. The methanolic extract of the plant showed promising antibacterial study against B. subtilis, P. vulgaris and K. pneumonia among the nine bacterial strains tested at concentrations 1.25, 2.5 and 5 mg/disc respectively 29. The extract was also found to show significant antifungal activity against the fungal strain, Candida albicans. Organic extracts (Petroleum ether, dichloromethane, ethylacetate and methanol) of stems of the plant exhibited antibacterial activity a number of Gram-positive and Gram-negative bacteria 8.
Maximum antimicrobial inhibition was demonstrated by ethyl acetate extract against B. subtilis, Pseudomonas aeruginosa and S. aureus having MIC of 31.25, 31.25 and 125 μg/mL, respectively 8. Flower extract at a dose of 200 μg/disc of the plant was found to show antimicrobial activity against a number of Gram-positive and Gram-negative bacteria 13. The highest zone of inhibition was found against E. coli and B. subtilis (18 ± 0.02 and 18 ± 0.11 mm, respectively), followed by Bacillus megatherium and Shigella boydii (zone of inhibition of both 15 and 17 mm, respectively) whereas the moderate activity was shown against Pseudomonas aeruginosa, Shigella flexneri, Bacillus cereus and Bacillus anthracis 13.
Ethanolic extract of the plant shows high bactereostatic and bactericidal activities as investigated by a research group 30. Vadlapudi reported 31 that methanol extract of the plant (whole plants) at a concentration of 100 mg/mL exhibited promising antimicrobial activity against a number of plant pathogens such as A. alternate, A. flavus, R. solani and X. compestries with zone of inhibition value 22, 15, 15 and 20 mm, respectively measured in agar well disc diffusion technique 31.
Organic extracts of P. pterocarpum flowers were found to show antibacterial as well as antifungal activity against a number of pathogens 32. The ethylacetate extract exhibited maximum antibacterial activity against S. aureus and E. aerogens with zone of inhabitation value 16.00 ± 0.57 and 15.33 ± 0.32 mm, respectively, while dichloromethane extract was active against R. planticola and E. aerogens with zone of inhabitation value 15.66 ± 1.19 and 14.66 ± 0.66 mm, respectively.
On the other hand, ethyl acetate extract was found to show appreciable antifungal activity against T. rubrum and P. crysogenum having equal zone of inhabitation value of 15 mm 32. A research group 33 suggested that ethanol and ethyl acetate extracts of P. pterocarpum can be used as herbal medicines in the control of E. coli and S. aureus induced medical diseases based on their investigation on antibacterial activity of organic extracts of the plant against such bacteria. The investigators also reported that organic extracts are also effective against the fungus, C. albicans 33.
Organic extracts of P. pterocarpum flowers and shoots in the concentration range of 1.25 to 2.5 mg/mL were reported to exhibit antibacterial activity against a number of Gram-positive and Gram-negative bacteria 34. The investigators also pointed out that flower part showed greater efficacy than shoot part and ethyl alcohol extract exhibited highest activity than the other extracts.
Terrestribisamide (65), isolated from methanol extract of flower part of the plant, showed moderate antimicrobial activity against a number of tested strains including fungi, Gram-positive and Gram-negative bacteria 24; the compound showed MIC value of 200 µg/mL for B. subtilis, S. epidermidis, M. luteus, E. coli (ESBL-3904), E. coli (ESBL-3984), M. pachydermatis, and C. albicans.
These experimental results get nice correlation with a previous investigation 30 where antimicrobial activity of methanol extract of P. pterocarpum flowers was found against B. subtilis, S. aureus, S. epidermidis, E. faecalis, E. coli, P. aeruginosa, K. pneumoniae, P. vulgaris, and C. albicans at the concentration of 5 mg/mL. Lam & Ng 26 isolated an amidase, peltopterin, from P. pterocarpum seeds and found its antifungal activity against Rhizotonia solani in the pH range 0–14 and temperature range of 25–100°C 26. This amidase impeded mycelial growth of this fungus with an IC50 of 0.65 μM.
- Anti-oxidant activity: Leave and flower extracts of P. pterocarpum are found to exhibit antioxidant activity against DPPH radical; leaf extract being more active than flower extract 28. Ethanolic and aqueous extracts of different parts of the plant are assessed for their antioxidant efficacies against DPPH, galvinoxyl and ABTS radicals and found that among the four plant parts investigated (leaf, bark, flower and pod), the free radical scavenging activity was the highest in the bark (EC50 value of 0.1 ± 0.04, 0.01 ± 0.02, 0.11 ± 0.04 mg/mL, respectively), whereas ethanolic extract being more active than aqueous extract 20.
Ethanolic and aqueous extracts of both bark and leaf were found to exhibit antioxidant activity against DPPH radical 35; ethanolic extract of leaf exhibited IC50 value of 0.17 ± 0.12 mg/mL. Methanolic extract of P. pterocarpum bark containing carbohydrates, proteins, amino acids, glycosides, triterpinoids, flavonoids and phenolics, is found to prevent significantly D-galactose induced oxidative stress and scopolamine induced memory impairment in rats 36.
The extract is also found to reduce AChE activity, serum biochemical parameter glucose, total cholesterol and reverse in the degenerative changes in the histopathological study of the rat brain and the increased activity of lipid peroxidation. Furthermore, the extract is found to increase activity of brain antioxidant enzymes such as catalase, super oxide dismutase, glutathione of the tested animal 36.
It was reported 20 that both the leaf and bark extract (ethanol and aqueous) exhibited lipid peroxidation inhibition activity; the ethanolic extract displayed 1.5-fold and aqueous extract 1.8-fold higher inhibition activity compared to the commercial grape seed extract. The presence of flavonoids in these plant parts may be responsible for exhibiting this activity 20.
Terrestribisamide (65), isolated from methanol extract of flower part of the plant, exhibited potent antioxidant activity at 1 mg/mL concentration against DPPH, cupric ion reducing antioxidant capacity (CUPRAC) assay, and ferric reducing antioxidant power (FRAP) assay 24.
- Cytotoxic activity: The alkaloid, Terrestribisamibe (65), showed prominent in vitro cytotoxic activity against COLO320 colorectal adenocarcinoma cell line. It showed 83.22 % activity at the dose of 200 µg/mL with an IC50 value of 50 µg/mL 24.
- Antiglycemic activity: It was reported 20 that the P. pterocarpum plant parts (leaf, bark, flower and pod) exhibited significant α-glucosidase inhibition activity in both the aqueous and ethanolic extracts compared to acarbose used as the positive control; ethanolic and aqueous extracts of leaf and bark showed the highest inhibition activities while the ethanolic extracts of flower and pod were more effective than aqueous extracts. All plant parts exhibited a far higher α-glucosidase inhibition activity compared to acarbose.
The investigators also reported that leaf and bark extracts exhibited higher α-amylase inhibitory activity compared to acarbose and the ethanolic extracts of the plant parts displayed both these activities higher compared to its aqueous extracts. The authors also found that the ethanolic extracts of bark exhibited both these activities greater compared to the other plant parts investigated in their study.
They are in opinion that the high content of tannins in bark may be responsible for this activity due to its non-specific absorption of proteins 20.
A research group 37 reported that methanol: ethyl acetate (1:9) of root extract of P. pterocarpum which includesdifferent types of compounds including flavonoids and steroids has significant activity in lowering fasting blood glucose level in alloxan and glucose induced diabetic mice.
- Aldose reductase (AR) inhibition activity: Inhibition of the aldose reductase activity has been reported to reduce the complication of diabetes such as retinopathy, neuropathy, nephropathy, and cataracts 38.
Ethanolic extracts of P. pterocarpum leaf and bark were found to be 28-fold and 56-fold more effective, respectively, in inhibiting aldose reductase activity compared to quercetin. Therefore, the plant may be used effectively in hyperglycemia management 20.
- Miscellaneous activity: A research group 18, using different model cell systems, revealed that ophioglonin (47) has estrogenic activity. They also reported that, although, 7-methoxy ophioglonin (48) is unable to stimulate the proliferation of breast and endometrial cancer cells but exhibited substantial estrogen receptor α-mediated activation of gene expression. This observation predicts the prospects of 48 as future anticancer drug 18.
Petroleum ether and ethanol extracts of P. pterocarpum flowerswere found to exhibit cardiotonic activity on frog heart 39; Petroleum ether extract produced significant positive inotropic and positive chronotropic actions (as adrenaline) by increasing force of contraction and the heart rate whereas, ethanol extract produced significant positive inotropic but slightly negative chronotropic effect (as digoxin) increasing force of contraction and decreasing in the heart rate.
The investigators are in opinion that this cardiotonic activity may be due to the presence of mixture of steroidal glycosides such as β-sitosterol-3-O-β-D-glucopyranoside (30), stigmasterol-3-O-β-D-glucopyranoside (36) and campesterol-3-O-β-D-glucopyranoside (38), reported to be present in the flower parts of the plant 39.
Taiwo et al 40 investigated cholinesterase inhibitory activity of methanolic extract of the leaves, root bark and stem bark of P. pterocarpum using eserin as reference and found that stem-bark gave the highest activity (68.85±3.53%) and better selectivity towards acetylcholinesterase (AChE) at a dose of 42.5 μg/mL followed by the root bark which inhibited both AChE and butyrylcholinesterase (BuChE) with inhibition percentage of 48.46±4.47 and 51.77±2.20, respectively and then the leaves (inhibition values of 47.50±2.41 and 48.91±0.71%, respectively).
The investigators also concluded that the plant may be used for the treatment of memory dysfunctions and neurodegenerative disorders such as Alzheimer’s disease 40. A research group 41 investigated anti-proliferative activity on HeLa cancer cell line of the aqueous extract of the plant by SRB assay and found significant activity compared to standard anticancer drug cis-platin. Biswas et al 42 reported that 70% ethanolic extract of P. pterocarpum leaves may have the potential therapeutic value in the treatment of paracetamol induced hepatic damage and some liver diseases of wister albino rats. They found that this extract at 100 mg/Kg and 200 mg/Kg doses significantly reduced the elevated levels (after administration of Paracetamol) of biochemical markers like SGPT, SGOT, ALP, bilirubin (total and direct), total cholesterol, triglycerides and depleted tissue GSH 42.
CONCLUDING REMARKS: The present article deals with an up-to-date review on the chemistry and pharmacology of Peltophorum pterocarpum, a useful medicinal plant from Fabaceae family finding applications in indigenous systems of medicine. The plant is used in different parts of the world for the treatment of stomatitis, insomnia, skin troubles, constipation, ringworm, insomnia, dysentery, muscular pains, sores, and skin disorders. Different class of chemical constituents including aliphatic alcohol, fatty acids, amino acids, terpenoids, phenolics, flavonoids, alkaloids, steroids are reported to be present in this plant.
The isolated phytochemicals as well as different extracts of the plant exhibited numerous biological activities. Hence, up-to-date information on the chemical and pharmacological knowledge on this plant may be helpful to guide researchers anticipating to undertake further investigations on this plant and we do anticipate that the present overview would boost the on-going development in this direction.
ACKNOWLEDGEMENTS: The authors are thankful to the Chemistry Department, Kulti College (Affiliated to The University of Burdwan) for providing infrastructural facilities. Financial support from the UGC (ER), Kolkata is also deeply acknowledged.
ABTS : 2, 2-Azobis-(3-ethylbenzothiozoline-6-sulphonic acid)
AChE : Acetylcholinesterase
ALP : Alkaline phosphatase
AR : Aldose Reductase
BuChE : Butyrylcholinesterase
COLO320 : Colorectal Adenocarcinoma Cell Line
CUPRAC : Cupric Ion Reducing Antioxidant Capacity
DPPH : Diphenylpicrylhydrazyl
FRAP : Fluorescence Recovery after Photo bleaching
GSH : Glutathione
MIC : Minimum Inhibitory Concentration
MID : Minimum Inhibitory Dose
SGOT : Serum Glutamic Oxalo acetic Transaminase
SGPT : Serum Glutamic-Pyruvic Transaminase
SRB : Sulforhodamine B
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How to cite this article:
Jash SK, Singh RK, Maji S, Sarkar A and Gorai D: Peltophorum pterocarpum: Chemical and Pharmacological aspects. Int J Pharm Sci Res 2013; 5(1): 26-36. doi: 10.13040/IJPSR. 0975-8232.5(1).26-36
All © 2013 are reserved by International Journal of Pharmaceutical Sciences and Research. This Journal licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Unported License
Shyamal K. Jash , Raj K. Singh , Sasadhar Majhi , Atasi Sarkar and Dilip Gorai*
Department of Chemistry, Kulti College 5, Kulti-713343, Burdwan, West Bengal, India
17 August, 2013
24 September, 2013
15 December, 2013
01 January, 2014