Pithecellobium Dulce Benth - A Review

M.Sugumaran

Pithecellobium species (leguminosae) are widely distributed in the tropics, chiefly in Asia and America.

Pithecellobium dulce Benth is one of the familiar species among them, native of Mexico extensively used for number of treatment in traditional medicines. Here the compounds isolated from different parts of P.dulce and biological activities of their extracts or the chemical constituents as reported in the literature since 1962 to 2007 have been reviewed.

Introduction

The Leguminosae is one of the largest families of flowering plants with 12000 species classified into around 600 genera. The family is usually divided in to three sub families: Papilionoidae, caesalpinioideae and mimosoideae, contain, respectively, about 377,40,and 133 genera ¹. Pithecellobium is one of 100-200 species in this genus under the subfamily of mimosoideae and distributed in the tropics, chiefly in Asia and America About 10 species, P. clypearia , P. dulce, P. monadelphum, P. globosum, P. unguiscati, P. arboreum, P.flexicaule, P. jiringa,P. parviflorum and P. mart etc² commonly occur in India

Pithecellobium dulce Benth is one of the familiar species among them, commonly referred as manila tamarind, as its sour taste resembles tamarind. The generic name is derived from the Greek word ‘pithekos’ meaning an ape and lobos referring to a pod and the species name ‘dulce’ in Latin means sweet in allusion to the edible pulp of the pod. Because of the resemblance of the fruits to the Indian sweet jalebi, the plant also given the name jungli jalebi. The vernacular name of this plant known as in Hindi: vilayati babul; Tamil:Kodukkapuli; Kannada:Kottampuli, Seemae Hunase; Bengali:Dekhani Babul; Marathi:Vilayati hinch; Telugu: Simachinta ; Malayalam: Korukkapuli etc ^2,3.

Plant Description

It is a small to medium sized , evergreen ,spiny tree up to 18 m height. They are broad-spreading with irregular branches. The bark is grey, becoming rough, furrowed and then peeling. Leaves are bipinnate, and leaflets oblong to 4 cm in length. The spines are in pairs at the base of leaves, and rang from 2 to 15 mm in length. The flowers are in small white heads 1 cm in diameter. Each flower has a hairy corolla and calyx surrounding about 50 thin stamens united in a tube at the base. Flowering begins in 3-4 years and is seasonal (January to March) and the fruits ripen from April to July. The pods are curved or twisted, constricted,pinkish, 1-1.5 cm wide, about 12 cm long, and become spiral as they mature.Seeds are about 10 per pod, black and shiny, hanging on a reddish thread from the pod. The pod splits along both margin. Bark smooth, grey with yellowish white lenticles ². The scientific classification of this plant is given in Table 1.

Ethano Medical Uses

Leaves can be used as a plaster to allay pain even from veneral sores, and can relieve convulsions. The leaves together with salt can cure indigestion and also induce abortion. An insulin –like principle has been reported in the leaves. In Mexico, the aril is reported to be used in the preparation of a beverage similar to lemonade. The saline extract of the seeds showed a haemolytic agglutinating reaction with human blood. The bark of the root is good for dysentery, and as a febrifuge in Guiana .The decoction is given as an enema. The plant is reported to be a folk remedy for ear ache, leprosy, peptic ulcer and tooth ache. It also act as emollient, anodyne and larvicide in folk medicine. Infusions of different parts have been used traditionally to treat diseases, such as skin of the stem for dysentery, leaves for intestinal disorders, and seeds for ulcer, among others ^3-10.

Chemical investigation on the different parts of the plant has resulted in the isolation (Fig.1) of a large number of novel and interesting metabolites. Some of the compounds have been screened for bioactivity. Here we discuss on the reported chemical constituents and biological activities of this plant.

Phytochemical Studies

Seven saponins named pithedulosides A-G (1 – 7) were isolated from the seeds of Pithecellobium dulce. Their structures were established through spectral analysis as echinocystic acid 3-0-a-L-arabinopyranosyl-(l®6)b-D-glucopyranoside, echinocystic acid and oleanolic acid 3-o-a-L-­ arabinopyranosyl-( 1®2)-a-L-arabinopyranosyl-( 1®6)-b-D- glucopyranosides and 3-o-b-D-xylopyranosyl-(l®2)-a-L­- arabinopyranosyl -(l®6)-b-D- glucopyranosides, oleanolic acid 3-o-a-L-arabinopyranosy-( 1®2)-a-L- arabinopyranosyl-( 1®6)-[b-D­-glucopyranosyl- (l®2)]-b- D-glucopyranoside, and 3-o-b-D-­xylopyranosyl-( 1®2)-a- L-arabinopyranosyl-( 1®6)-[b-D­- glucopyranosyl-( 1® 2) ]--b- D-glucopyranoside ^11.

Four new oleanane-type triterpene glycosides , Pithedulosides H-K, were further isolated from the seeds of Pithecellobium dulce. Their structures were established by extensive NMR experiments and chemical methods. Pithedulosides H, I, J comprised acacic acid (18) as the aglycon and either monoterpene carboxylic acid and its xyloside or monoterpene carboxylic acid as the acyl moiety at C-21. The oligosaccharide moieties linked to C-3 and C-28 were determined as µ-L-arabinopyranosyl-(1®2)-µ-L-arabinopyranosyl- (1®6)- [b-D-glucopyranosyl-(1®2)]­ b-D-glucopyranosyl and a-L-arabinofuran osyl l-(1®4)-[b-D­-glucopyranosyl-(1®3)]-a-rhamnopyranosyl-( 1® 2)-b- D­ glucopyranosyl ester, respectively. Pitheduloside K was established as an echinocystic acid 3-o-glycoside having the same sugar sequences as in the first three compounds. Also obtained in this investigation was the known compound, which was identified as echinocystic acid 3-o-b-D-xylopyranosyl- (1®2)-a-L­ - arabinopyranosyl- (1®6)- [b- D-glucopyranosy 1-(1®2)]- b- D—glucopyranoside ^12.

A new bisdesmodic triterpenoid saponin, dulcin (11) was isolated from the seeds and was identified as 3-o-[b-D-­glucopyranosyl ( 1®2 )-a- L-arabinopyranosyl] - 28-O-[b-D-­xylopyranosyl (1®6)-b- D-glucopyranosyl]-echinocystic acid. The known oleanolic acid saponin P_E, (10) oleanolic acid 3-O-b-D­- glucopyranosyl (l®2)-a-L-arabinopyranoside was also obtained. The structural features were elucidated by a combination of spectroscopic methods and some chemical transformations. The more polar glycoside, dulcin on acid hydrolysis furnished an aglycone identified as echinocystic acid (9) and monosaccharides from the acid hydrolysate were D-glucose, D-xylose and L-arabinose etc ^13.

A novel acylated triterpenoid saponin, designated pithecelloside, is isolated from the seeds and characterized as 3- O- [a-L-arabinopyranosyl-(1®2)-a-L-arabinopyranosyl-(1®6)-b-D-glucopyranosyl]-21b-O-[(2’E)-6’-hydroxy-2’,6’-dimethylocta-2’,7’-dienoyl] acacic acid ¹⁴ .

Seed fatty acid profile and alkylated resin has been worked out by Khatri, Hosamani & Anup Banerjee respectively ^{15,16 &17}. But Kulkarni et al studied the fatty acids distribution by GLC in total lipids, phospholipids and glycolipids of this plant.The major fatty acids present are palmitic , stearic ,oleic , linoleic , myristic , linolenic and arachidic acids. Total lipids from P.dulce seeds had a significant content of arachidic acid (16%) but the phospholipid and glycolipid did not contain appreciable amounts of the same acid ^18.

The cyclitol , dulcitol (16) was reported from acetone leaf extract of this plant by adinarayana et al ¹⁹. Novel isoflavonoidal glycoside, genistein 4’-O-µ-L- rhamnopyranoside (12) has been isolated from the ethanolic root extract of this plant ^20.

A new flavonoid, (17) 3’- prenyl apigenine -7-O- rutinoside, ( m.p. 128°c) from pithecellobium dulce stem have been reported by saxena et al ²¹. The alcoholic extract of the leaves of P.dulce on solvent segregation and chromatography of the different fractions yield octacosanol , b- D- glucoside of a- spinasterol (19) , a- spinasterol (20) and kaempferol-3- rhamnoside ²². The seed flavonoid was found to be a mixture of Kaempferol and quercetin ^23. The sterol glucoside-A ( m.p. 282-286°c), from the fruit pulp reported was a mixture of glucoside of – b sitosterol (13) , campesterol (14) and stigmasterol (15) ^24.

The bark contains tannin of a catechol type, which varies according to the age of the plant. Acetone extract of the bark is reported to consist mostly of 3, 4,7,3’,4’- pentahydroxy flavan -a compound which combines the properties of both leucoanthocyanidin and phlobotannin . The antitumour compound, b-sitosterol²⁴, and campesterol, stigmasterol and a-spinasterol were reported in the heart wood of this plant. The methanolic extract of P.dulce afforded a series of compounds exhibiting both 2, 3 – trans and 2,3- cis relative configurations of the constituent fisetinidol moieties. The compounds comprised of the 3’,4’,7-trihydroxy-flavan-3,4-diols (21), epifisetinidol-4b-ol (22), epifisetinidol-4a-ol (23), the fisetinidol-4b-and 4a-ols (24&25) and the 3’,4’,5’,7- tetrahydroxyflavan-3-ol, robinetinidol (26) .

The seed contain13.5% moisture, 17.6% protein, 17.1% crude fat, 7.8% crude fibres, 41.4% starch and 2.6% ash. Analysis of the aril gave the following values: moisture 77.9;protein 0.7; fat,0.6; fibre1.2;carbohydrates19.9; and mineral matter, 0.7%; calcium,13.0mg.;phosphorus 54.0 mg. ;iron, 1.4mg.; thiamine, 222mcg; riboflavin, 59 mcg.; nicotinic acid, 0.36mg.; and ascorbic acid, 120 mg./100gm.The essential aminoacids found in the aril were: valine, 143 ; lysine 178; phenylalanine, 41; and tryptophan, 26 mg./100g. As calcium pectate, pectin occurs as 0.96% of the sugars (mostly glucose) analysis of the aril. The leaves contains 29.0% crude protein, crude fibre, 17.5%, ash 5.6 % as well as some trace amount of 1.14% Ca, 0.35% phosphorus are also present. Analysis of the fatty oil gave the following values: specific gravity, 0.9044; hD, 1.4546: saponification No., 185.3; iodine No., 80.7;acid value., 1.2; thiocyanogen value ., 56.0 and unsaponification matter, 0.6% etc ^26,27.

Pharmacological Studies

Abortifacient activity

The isoflavonoid isolated from root extract, tested on female rats, showed dose dependent estrogenic activity by increasing uteri weight from 15.5±0.25 mg in control to 34.2±068 mg in orally treated rats (1.25 mg/ kg/day for 4 days) ¹⁷

Anti inflammatory activity

The saponin (contain two genin acids, oleanolic acid (8) and echinocystic acid with xylose, arabinose and glucose as sugar moieties) obtained from fruits of P.dulce has been studied against the exduative and proliferative phase of inflammatory reaction in albino rats by using carrageenin inducd oedema and formaldehyde induced arthritis models.The ED₅₀ (mg/kg) of the saponin in this study was found to be 10.0 in comparison to hydrocortisone (9.8) which was used as the reference standard ^28.

Antivenom activity

Polyphenols from the aqueous extract of Pithecellobium dulce, was tested for their inhibitory activities against Naja kaouthia (NK) venom by invitro neutralization method. The extract could completely inhibit the lethality of the venom at 4 LD₅₀ concentration and the venom necrotizing activity at the minimum necrotizing dose while also inhibited up to 90% of the acetylcholinesterase activity of NK venom at much lower tannin concentration. The ED₅₀ of plant tannins in inhibiting NK venom activities varied according to condensed tannins and their content in the extracts. Molecular docking of the complexes between a- cobratoxin and either hydrolysable or condensed tannins at their lowest energetic conformations were proposed. The anti-venom activity of this plant polyphenols by selectively blocking the nicotinic acetylcholine receptor and non-selectively by precipitation of the venom proteins were suggested ^29.

Protease inhibitory activity

Delgado et al report ³⁰ for the first time the isolation and characterization of a protease inhibitor from the seeds of Pithecellobium dulce,. The purification of the P. dulce trypsin inhibitor (PDTI) was a direct process. After its extraction (pH 8.0) and precipitation (80% (NH₄)₂ SO₄), the pH was adjusted to 4.0, the supernatant was loaded onto a CM-Sepharose column, and a single peak of trypsin inhibitory activity was eluted (CM-TIA). The main component of CM- TIA was PDTI, a protein composed of two polypeptide chains joined by disulfide bridge(s), with a pI of 4.95 and a molecular weight determined by electrospray mass spectrometry of 19614 Da. The N-terminal sequence of PDTI has the highest similarity with the seed inhibitor of Acacia confusa. PDTI lacks chymotrypsin inhibitory activity. A low rate of cytotoxicity of CM- TIA toward RINm5F cells contrasted with a high rate of the active fraction G75-TIA (gel filtration chromatography; LC₅₀ of 0.04 mg/ml).

Spermicidal activity

In view of the importance of saponins as possible spermicidal agents, the saponins of P. dulce were also subjected to tests for spermicidal property by banergi et al.The sapogenin showed the activity in the dilution of 0.03% against human semen ^31.

Antimicrobial activity

The powder , methanolic and aqueous extracts of P. dulce seeds have proved fungistatic and possess fungicidal effects against plant pathogens ,Fusarium oxysporum, Botrytis cinerea,Penicillium digitatum and Rhizopus stolonifer. The ¹H NMR spectrum of active fractions in these extracts indicated the presence of two triacyl glycerols, glycerol 1,3-dilinoleoyl-2-decanoic, glycerol 1-linoleoyl-2- docosanoic-3- olein. Several triterpene saponins, pitheduloside A,B,E,F and I inhibited in vitro mycelial growth of Rhizopus stolonifer and colletotrichum gloeosporioides, respectively. The less-polar hexane extract and polar methanolic extract of this plant screened against various bacteria and fungi were also found to be active ^{32,33 &34}.

Antitubercular activity

The hexane, chloroform and alcoholic extracts of the leaves were studied for their antimycobacterial activity by BACTEC460TB- Radiospirometric system. The alcoholic extract at the concentration 20mg/ml showed highest activity when comparable with standard drugs like, streptomycin, isoniazid, rifampicin, ethambutol and pyrazinamide ^{35 &36}.

Conclusion

Though the existing chemical, pharmacological and clinical literature on the plant is impressive, the following topics remain open to future investigation: Characterization of the still unexplored constituents, isolation of the active principles and standardization of the extracts, pharmacological, pharmacognostical studies and mechanism of action. A programme is in operation for this plant at Central Drug Research Institute, Lucknow ³⁷ which aims at systematic pharmacological investigations , isolation of active constituents & chemical modification of natural products for the development of novel drugs in the areas of country’s high priority.

Acknowledgement

The authors are grateful to Director, NISCAIR, New Delhi for assistance in Literature collection. The authors are also thankful to Dr. S. Kavimani, Department of Pharmacology, Division of Pharmacy, Mother Therasa Institute of Health Sciences, Pondicherry and M. Jagadeesan, Head, Dept of Environmental and Herbal science, Tamil University, Thanjavur for their valuable suggestions and advice during the preparation of this manuscript.

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Table . 1 – Scientific classification of Manila tamarind

Table . 2 - Physical data of some constituents isolated from different parts of Manila Tamarind

* Structure not given.

Fig.1: Compounds Isolated from various parts of P.dulce

Compounds Isolated from various parts of P.dulce (Contd.)

About Author:

Mr.M.sugumaran, Asst professor , Adhiparasakthi college of Pharmacy, Melmaruvathur, TN obtained his post graduation, M.Pharm ( Pharmaceutical chemistry) in department of Pharmaceutical Sciences and Drug research , Punjabi University, Patiala through GATE examination. He was a recipient of Merit Scholarship under National Scholarship Scheme. He has 28 national and 2 international publication in reputed journals. He was appointed as a external Examiner and Question paper setter and paper evaluator for B.Pharm course by T.N Dr. M.G.R Medical University, and SRM University , Chennai . He was appointed as a Research Board of Advisor by American Biographical Institute , U S A in 2006. He was also a referee for Pharmacognosy magazine ( Phcog Mag) and Indian Journal Pharmaceutical Science in 2006 &2007. Until he guided 2 M.pharm students and acting as NSS Programme officer in the same institute since 2004.Currently he is doing his research work on Pithecellobium dulce benth under the guidance Dr.T.vetrichelvan., Principal , Adhiparasakthi College Of Pharmacy, Melmaruvathur in SASTRA University, Thanjavur, TN. He delivered oral/ poster presentation of his research work in various national/ international conferences He is a life member of IPGA, APTI, IHPA, ISP, IPS , Inpharm Association and Indian council of chemist.

T.Vetrichelvan
Adhiparasakthi College of Pharmacy, Melmaruvathur-603319 , Tamil Nadu