The literature on karanja is evaluated critically.   As with any other material, there is still a vast

area of research remaining uncovered but the present

information does point out areas where seeds andoil available in a large amount in the country can

 be utilized. To mention some of the uses, the use of karanjin as a nitrification inhibitor and karanja oil as a synergist-cum-solvent for chlorinated msecti­  cides might consume considerable amounts of these materials. Similarly, karanja cake meal can be

processed and used as a cheap cattle feed. The

oil is already finding considerable use in soap making.Besides, it is a potential source of fatty acid

Mukerjee, S K

Parmar, B S

Sahrawat, K L

ICRISAT Open Access Repository

Pongamia glabra: Constituents & Uses* B. S. PARMAR, K. L. SAHRAWAT & S. K. MUKERJEE Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi 110012 PONGAMIA GLABRA Vent. (Leguminosae, Papilionaceae), a medium sized glabrous tree, popularly known as karanja, is an important shade tree of India. Considered to be a native of Western Ghats, it is capable of growing under a wide range of agroc1imatic conditions and is a common sight around coastal areas, river banks, tidal forests and roadsides. The isolates from the various parts of this tree have been used as a folk remedy since ancient times. The bark and roots are hot, acrid, bitter anthelmintic and alexi­phannic and find application in CLlring diseases of eye, vagina and skin. They also form a useful remedy for tumours, piles, wounds, ulcers, itching troubles, urinary discharges and a number of other diseases. Seeds find use as external application in skin diseases1 and the juice of leaves is prescribed in flatulence, dyspepsia, diarrhoea, cough, leprosy and gonorrhoea2, in addition to the traditional use of leaves as a preservative for books and stored grains. The wood of this tree can also be used as timber, but it is susceptible to attack by insect pests and is not durable. These uses have generated a lot of scientific interest and karanja is, at present, one of the most exten­sively chemically investigated plants. A large num­ber of biogenetic ally related compounds have been isolated and characterized and the industrial uses of some of them established. The present review gives a brief account of the chemistry and uses of these chemical constituents. Karanjin, the principal furanofl.avonoid _ consti­tuent (approximately 1·25%, oil basis) of the plant, was the first crystalline compound reported as early as 1925 (ref. 3). It was isolated from the seed oil4 and roots5 and its structure, constitution and synthesis were thoroughly investigated6-S by several groups of workers. It was followed by the discovery of pongamol9, another minor compo­nent (0'85%, oil basis), whose structure remained elusive for a long time. It was finally established10 to be a novel diketone, by both degradative and synthetic methodsll. With the advent of new physical methods for the structural elucidation of natural products, the other minor chemical constituents of the oil as well as of various other parts of the tree began to be discovered in early 60's. The structures of the various important products isolated so far are shown in Chart 1, while Table 1 lists the sources and the common and generic names of the com­pounds. It is obvious from Chart 1 that the various furano and chromeno derivatives of P. glabra possess angular orientation of the furan or the chromene ring. Further, most of these are derivatives of ·Contribution No. 113 from the Division of Agricultural Chemicals, IARI, New Delhi 110012. 608 resorcinol in so far as ring A is concerned. The methoxylated derivatives as observed in the chro­meno chalkones, viz. glabrachromene I and II, and pongachalkone, have been discovered only recently. HO 1 OH o n. R = OeH3 m, R:: H V, RI=H; R2=OCH3 VI, RI=OCH3i R2=H AI R2 '"' , ..... o o IV o OCH3 OC� VU. RI=OCH3; Aa=H VlU, RI:: R2:: OCH3 lX, RI=R2:::;H wc�' /, ...... o X, R I, R2 :::; - 0 - CHZ - 0-Xl, RI=RZ=H Xil RI 0 xm R:: OCH3 XlV R=H o 0 XVI XVll CHART 1 PARMAR et al.: PONGAMIA GLABRA: CONSTITUENTS & USES TABLE 1 - CONSTITUENTS OF Pongamia glabra SI No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 Common name Kaempferol Kanugin Desmethoxykanugin Tetra-o-methyl fisetin Karanjin Kanjone Pongapin 3'-Methoxy-pongapin Pongaglabrone Pongachromene Karanja chromene (-}I-solonchocarpin Glabrachromene-I Glabrachromene-II Pongachalkone Pongamol Glabrin y-Sitosterol �-Sitosterol Chemical name FLAVONoIDS 3,5,7,4'-Tetrahydroxyfiavone (I) 3,7,5'-Trimethoxy-3',4' -methylenedioxyfiavone (II) 3,7-Dimethoxy-3',4'- methylenedioxyflavone (III) 3,7,3',4'-tetramethoxyflavone (IV) FURANO FLAVONOIDS 3-Methoxyfurano-(2",3": 7,8)-fiavone (V) 6-Methoxyfurano-(2",3": 7,8)-fiavone (VI) 3-Methoxy-3',4'-methylenedioxyfurano-(2",3" : 7,8)-fiavone (VII) 3,5'-Dimethoxy-3',4'-methylenedioxyfurano­(2",3": 7,8)-fiavone (VIII) 3',4'-Methylenedioxy furano-(2",3": 7,8)-fla­vone (IX) CHROMENOFLAVONES Source Flowers Root, stem Root, stem, seed Stem Seeds do do Leaves Seed 3-Methoxy-3' -4' -methylenedioxy-2",2" -dime- Stem thy1chromeno-(6"S': 7,8)-fiavone (X) 3-Methoxy-2",2" -dimethy1chromeno-(6",5": 7,8)- Seeds flavone (XI) 2",2"-Dimethy1chromeno-(6",S" : 7,8)-ftavanone do (XII) CHROMENOCHALKONES 2' -H ydroxy-6' -methoxy-3, 4-methylenedioxy-2", Leaves 2" -dimethy1chromeno-(5" ,6" : 3 ',4')-chalkone (XIII) 2' -Hydroxy-3,4-methylenedioxy-2",2" -dimethyl- do chromeno-(5",6": 3',4')-chalkone (XIV) 2'-Hydroxy-6'-methoxy-2",2"-dimethylchro- Heartwood meno-(5",6": 3',4')-chalkone (XV) FURANO-DIKETONE 4-Methoxy-5-(<»-benzoyl acetyl)-coumarone (XVI) MISCELLANEOUS Seeds 4,5-Dihydroxy-N-methyl pipecolic acid (XVII) do Flowers Wood Reference 12, 13 14 15 16 3-8 17 18 19 20 21 22 23 24 25 26 9 27, 28 12 29 The biogenetic relation between the chromene ring and the furan ring in flavonoids is well known30• in white oil was more effective than that of the oil dissolved in acetone32• Karanjin, however, does not possess any contact insecticidal activity against the red flour beetle, Tribolium castaneum Herbst.32. Isolation and identificc.tion of the various consti­tuents of P. glabra led to attempts to find out their remunerative outlets. Some of the results avail­able on the various aspects of its biological spectrum are enunciated here. As a Source of Pesticidal and Allied Chemicals Biocidal activity - Karanja and its isolates have been tested for their piscidal, insecticidal, nemati­cidal, bactericidal and antitubercular activity by several workers. Rangaswami and Seshadri31 were the first to report the piscidal activity. Against the cockroach (Periplaneta americana Linn.) both the oil and karanjin have been found active32,33 and against the housefly (Musca domestica Linn.), the dorsal application of the oil dissolved Singh34. reported the biological activity of some of the components of karanja seed cake against the mustard aphid (LiP aphis erysimi Kalt.). His results (Table 2) indicated that although the alcohol extract as well as some of the purer furanoflavonoids possessed aphicidal activity, karanjin seems to be primarily responsible for it and could be used for this purpose, with advantage. The nematicidal activity of the water extract of karanja cake has been investigated against second stage larvae of root-knot nematode, Meloidogyne incognita and it has been found inferior to neem and mahua cakes35. Karanja cake has been reported to be more effective at low levels of nematization36, 609 j. SCIENT. IND. RES., VOL. 35, OCTOBER 1976 TABLE 2 - ACTIVITIES OF VARIOUS ISOLATES FROM KARANJA AGAINST Lipaplzis erysimi KALT. Test fraction Cold ethanol extract of deoiled cake Hot ethanol extract of deoiled cake Cold ethanol extract of defatted seeds Hot ethanol extract of defatted seeds Karanjin (crude) Karanjin (pure) Pongaglabrone Pongamol LCso % 0·06 0·07 0·07 0·06 0·07 0·06 0·10 0·16 but Singh37 observed that in larger dose, the cake completely controlled the root-knot of tomato. The antibacterial activity of karanja oil seems to be governed by the test technique38; the cup-plate method39 indicates the oil to be active against both gram-positive and gram-negative organisms. Os­mani and Naidu32; however, failed to observe any antibacterial activity against Bacillus chinens1·s of both oil and karanjin. Similarly, the soap pre­pared from the oil has been found to be devoid of any antibacterial activity4o. Ramaswamy and Sirsi41a reported that karanjin possesses arititu ber­cular activity at 10-5 dilution. Synergistic activity - Karanja oil has been reported to synergize endrin against houseflies41b• Parmar et al.'2,43 investigated this property of the oil with pyrethrins as well as chlorinated insecticides. It was found that the oil synergized the knock-down capability of pyrethrins against the housefly, M. domestica Linn. With chlorinated insecticides, this oil synergized the action of lindane, endrin, hepta­chlor and thiodan, but antagonized BHe and toxaphene against Tribolium castaneum Herbst. Aldrin and dieldrin were antagonized at lower levels, and at higher levels, this antagonism was masked. Parmar44 also studied mixtures of karanja oil and piperonyl butoxide as pyrethrum synergists against M. domestic a Linn. and found that the use of the mixture was more economical than that of piperonyl butoxide when u5ed alone. Parmar and Gulati33 compared the synergistic potential of karanjin with piperonyl but oxide and found it to be a significantly inferior pyrethrum synergist a.gainst M. domestica Linn. and Periplaneta americana Linn. Attri et al.45 observed that both karanja oil and karanjin antagonized pyrethrins against Tribolium castaneum, but pongapin (a methylenedioxy analogue of karanjin) was mildly synergistic. As a Source of Slow Release Plant Nutrients Non-edible oilseed cakes, in general, and karanja and neem (Azadirachta indica), in particular, have since long been used in Indian agriculture as sources of slow release nutrients. Various aspects relating to the manurial value of these cakes under different conditions have been investigated46-49• The chemi­cal compositions of different oil cakes have been reported by Prakash et al.50• The results of these workers coupled with the earlier observations re­corded with these oil cakes led to the hypothesis 610 that the non-fatty minor constituents of the oilseeds may be responsible for their slow release charac­teristics. This aspect has been investigated in detail recently. Singh34, while investigating the ability of various karanja extractives in influencing the efficiency of ammoniacal fertilizers, observed that the addi­tion of crude extractives to ammonium sulphate caused accumulation of ammonia in incubated soils. He also observed stabilization of soil structure by the addition of these extractives. Sahrawat et at.51 compared the extractives from bark, leaves and seeds of karanja and found the seed extract to be most active in inhibiting nitrification. Bark extract and leaves ranked next in order. The major furanoflavonoid from seeds, viz. karanjin, was therefore investigated extensively52. It gives a matching performance to N-serve, a well-estab­lished nitrification inhibitor, in both laboratory inCubations and greenhouse experiments with rice crop. As a Source of Non-edible Industrial Oil India has a potential to produce over one lakh tonnes of karanja seed and 30,000 tonnes of oil; of this hardly one-fourth is presently utilized53. Seed is mainly valued for the oil which can be put to a number of industrial (leather dressing, soap making, lubrication, illumination, etc.) and medicinal uses1,2. The IS: 3492 specifications54 for pongam oil are summarized in Table 3. Karanj a oil resembles groundnut oil in composition and its fatty acid composition is; palmitic, 3'7-7·9; stearic, 2·4-8'9; arachidic, 2'2-4·7; behenic, 4'2-5'3; lignoceric, 1·1-3·5; oleic, 44·5-71·3; linolenic, 10'8-18·3; and eicosenoic, 9·5-12·4%2. The presence of furanoflavonoids caused difficulties in the industrial use (soap making) of this oil. Recently, techniques have been evolved for the removal of these toxic constituents and at present purified karanj oil is extensively used in the manufacture of cheaper quality soap. As a Source of Cheap Cattle Feed Singh34 assessed the protein quality of processed seed and cake meals and reported the presence of 16 amino acids, including the 10 essential amino acids (Table 4). Feeding trials on albino rats conducted by the same author established the acceptability of this material to the test animals. TABLE 3 - SPECIFICATIONS FOR PONGAM OIL Characteristics Moisture and insoluble impurities Colour (Lovibond scale, Y + 5 R) d300 n40 D Acid val. Sap. val. Iodine val. (\vij's) Unsaponifiable matter Titre Filtered sample kept at 300 for 24 hr Requirement :;}0·25 % :;}40 0·925-0·940 1·4734-1·4790 :;}20 185-195 80-90 :;}3·0% :;}31° No turbidity PARMAR et al : PONGAMIA GLABRA: CONSTITUENTS & USES TABLE 4 - AMINO ACID COMPOSITION OF PROCESSED KARANJA SEED AND CAKE MEAL [Values m parentheses mdicate amino aC Id (g) per 100 g protem or per 16 g of llltrogen] Ammo aC Id Leucme Ly sme MethIonine Arginme ValIne Tryptophan HlstIdme Isoleucme Threonine Phenyl alamne AspartIc aCi d Serine Glutamic acid Glycme Alanine Tyrosine Summary Amino aCId (%) III Seed meal 2·70 (8'99) 2 65 (8'82) 2·02 (6'73) 1·90 (6'33) 1'85 (6'17) 1 67 (5 57) 1-52 (5 06) 1 03 (3'43) 0 98 (3 27) 0 70 (2 33) 2·75 (9'16) 1 72 (5'73) 4 45 (14 80) 1'50 (5'00) 1 40 (4 70) 1·75 (5'83) Cake meal 2 85 (9 49) 2·81 (9 36) 2 05 (6 83) 1 87 (6 23) 1·14 (3'78) - -1·74 (5 79) 1'50 (5 00) 1'00(3 33) 0 76 (2 53) 3·18 (10'59) 2·05 (6 83) 4 62 (15'38) 1 66 (5 53) 1 22 (4'06) 1 82 (6 06) The literature on karanja is evaluated critically. As with any other material, there is still a vast area of research remaining uncovered but the present information does point out areas where seeds and oil available in a large amount in the country can be utilized. To mention some of the uses, the use of karanjin as a nitrification inhibitor and karanja oil as a synergist-cum-solvent for chlorinated msecti­cides might consume considerable amounts of these materials. Similarly, karanja cake meal can be processed and used as a cheap cattle feed. The oil is already finding considerable use in soap making. Besides, it is a potential source of fatty acids. References 1. KIRTIKAR, K R & BASU, B. D , Indtan medtetnal plants, I, 830 (Prabasl Press, Allahabad), 1918. 2. The Wealth oj Indta Raw matenals, Vol 8 (CouncIl of Scientific & Industnal Research, New Delhi), 1969, 206 3. LIMAYE, D. B ,  Abstracts oj proceedtngs oj Indtan Sctence Congress 1925, 118; 1926, 151. 4. BEAL, G D & KATTI, M C T, J. Am. pharm. Ass, 14 (1926), 1086; Chem. Zentr, II (1926), 596 5. MANJUNATH, B L ,  SEETHARAMIAH, A. & SIDDAPA, S ,  Chern Ber , 72 (1939), 93, 97. 6. SESHADRI, T. R. & VENKAT'l.RASWARLU, V ,Proc Indtan A cad. Set , 13A (1941), 414; 17A (1943), 16 7. ANEJA, R. MUKERJEE, S. K. & SESHADRI, T R, Tetra­hedron, 2 (1958), 203. 8 RAIZADA, K S ,  SARIN, P. S. & SESHADRI, T R, ]. SCtent. tnd. Res , 19B (1960), 76 9. RANGASWAMI, S & SESHADRI, T. R., Curro Set , 9 (1940), 179. 10. NARAYANSWAMI, S., RANGASWAMI, S. & SESHADRI, T R, J. chern Soc, (1954), 1871 11. MUKERJEE, S. K. & SESHADRI, T. R,] chem. Soc , (1955), 2048. 12. MURTI, P. B R & SESHADRI, T R, Proc Indtan Acad Set., 20A (1944), 279 13. PANKAJAMANI, K. S, Ph D. theSIS, DelhI Umverslty, 1953, 35. 14. RANGASWAMI, S, RAO, J V. & SESHADRI, T. R, Proc Indtan Acad Set, 16A (1942), 319. 15. MITTAL, O. P. & SESHADRI, T R,] chern Soc , (1956), 2176. 16. MUKERJEE. S. K ,  SAR.KAR, S C & SESHADRI, T R, Indtan ]. Chem. 7 (1969), 1275. 17 ANEJA, R. KHANNA, R N & SESHADRI, T. R,] chern. Soc , (1963), 163 18. ANEJA, R ,  MUKERJEE. S K. & SESHADRI, T. R, Tetra­hedron, 2 (1958), 203. 19 SHARMA, (MIS S) P ,  A study oj new flavonotd components of the leaves of Pongamta glabra, Ph D. theSIS, Delhi UmversIty, 1975 20 KHANNA, R N. & SESHADRI, T. R. , Tetrahedron, 19 (1963), 219 21. MUKERJEE, S K, SARKAR, S C & SESHADRI, T. R, Tetrahedron, 25 (1969). 1063 22. NAIKSATAM, P. G & BRINGI, N V, Ind�an ]. Chem, 11 (1973), 1188 23 NAIKSATAM, P G. & BRINGI, N V., Indtan] Chem, 11 (1973). 209 24 MAHEY, S , SHARMA, P ,  MUKERJEE, S. K & SESHADRI, T R ,  Ind�an] Chem , 10 (1972), 585. 25. SHARMA, P, MUKERJEE, S. K & S ESHADRI, T R ,  Indtan ] Chem , II (1973), 985 26 SUBRAMANYAM, K, MADHASUDHANA RAO, J & JAGA­NADHA RAO, K V ,  Curr Set , 42 (1973), 129. 27. RAO, N. V S & RAO, J V ,  Proe Indtan A cad Set, 14A (1941), 123 28 SAMPTHA KUMAR, P. S, MURTl, V V. S. & SESHADRI, T R, Tetrahedron Lett , (1971), 4451. 29 SARKAR, S C, MU:ECERJEE, S. K & SESHADRI T R Tetrahedron, 25 (1969), 1063 " 30. ANEJA, R, MUKERJEE, S. K. & SESHADRI, T. R, Tetra­hedron, 4 (1958), 256 31. RANGASW AMY, S & SESHADRI, T. R., Indian J. Pharm, 3 (1941), 3 32 OSMANI, Z H & NAIDU, M B ,  SCt Cult, 22 (1956), 235 33 PARMAR, B S & GULATI, K C ,  Indtan J. Ent., 31 (1969), 239 34 SINGH, U V ,  Studus on better ut�lIzattOn oj non-edtble o�lseed cakes - ka1anJ (Pongamta glabra) seed cake, Ph D theSIS, postgraduate School, IARI, New DelhI, 1966 35 MISHRA, S D & PRASAD, S K ,  Indtan J. Ent , 35 (1973) 104 ' 36 MISHRA, S D & PRASAD, S K ,  Indtan J. Nematol , (in press), personal commumcatlOn 37 SINGH, R S, Plant ProteettOn BuUettn (FAG), 13 (1965), 35 38 BHAT, S G, KANE, J G & SREENIVASAN, A, Indtan Gtlseeds ] , 1 (1957), 298 39 PATEL, R P. & TRIVEDI, B. M ,  Indzan J. med Res. 50 (1962), 218 40 JAMBOT:ECAR, D. K ,  KANE, J G & KHORANA, M. L., Indtan] Ph arm , 24 (1962), 154 4la. RAMASWAMY, A S. & SIRS I, M, Indtan ]. Pharm , 22 (1960), 34. 41b Annual report (1966-67), ReglOnal Research Laboratory, Hy derabad, CSIR, New Delhi, 33 (22 8) 42 PARM'l.R, B S, Investtgattons relattng to synergtsts for tnsecttctdes (pyrethrtns), Ph D. theSIS, Postgraduate School, IARI, New Delhi, 1969. 43 PARMAR, B S, ATTRI, B S ,  SINGH, R P & MUKERJEE, S K ,  Pesttctdes, 9 (1975), 29 44. PARMAR, B S. Pyr Post, 12 (1974), 121. 45 ATTRI, B S ,  GUPTA, S. C, MUKERJEE, S. K ,  PARMAR, B S & SINGH, R P ,  Pyr Post, 12 (1973), 87 46 YASHWANT, I, WED, D & PANSE, V. G., J. agrte. Set , 3 (1933). 820 47. PAL, C. B & RAKSHIT, S C, Proe nat. Inst Sez (Indta) 33 (1937). 213. ' 48 KHAN, A J, Set. Club (Indta), 5 (1952). 235. 49. NAIK, B N, BADHE, N N & BALLAL, D K, The Poona Agncultural College Magaz!ne, 51 (1961), 27. SO. PARKASH, 0, SHARMA, T. R & KHAN, A, J. Proc. Instn Chem , Indta, 25 (1953), 31. 51 SAHRAWAT, K L, PARMAR, B S & MUKERJEE, S. K., Indtan ]. agnc Set., 44 (1974), III press 52. SAHRAWAT, K. L & MUKER]EE, S. K, Plant and Sotl, (1977) (accepted for publIcatlOn) 53. Drrectorate of Non-ed ible oIls and soap Illdustry, Non­edtble atls and soap tndustry, Review 1953-1973 2 1974. ' , 54. IS 3492 (IndIan Standards InstItutlOn New Delhi ) 1965. " 611 

Pongamia glabra: constituents & uses

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Pongamia glabra: constituents & uses

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