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Antiseptics and Anthelminthics

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Antiseptics and Anthelminthics ANTISEPTICS AND ANTHELMINTHICS. Part III. Pharmacology of Certain l~lavones with ~pecial Reference to their Anthelminthic Action. BY HARBHAJAN SINGH MAHAL, ~VLSC., PH.D., A.I.C. (From the Pharmacological Laboratory, Haffkine It~stitute, and the Royal Instlh,,tc of Science, Bombay.) Received February 26, 1937. (Commurricated by Dr. K. Venkataraman, Ph.D., D.SC., F.I.C.) THE study of the chemistry of the flavones, the great group of naturally occurring colouring matters, was originated by Piccard 1 who isolated a yellow pigment, chrysin, from the leaf buds of the poplar (Populus pyra- midalis Salisb., P. nigra Linn., P. monilifera Ait.), which contained chrysin to the extent of 0.5 per cent. On the basis of degradative and synthetic experiments Kostanecki 2 assigned to ehrysi n the constitution of a 2-phenyl-5:7-dihydroxybenzo-7-pyrone (I). 2-Phenyl benzo-F-pyrone or flavone, the parent member of the series, has been found in nature as the meal or farina which occurs on the leaves, stalks and seed capsules of many varieties of Primula, e.g., P. pulverulenta, P. Japonica (Muller 8) ; its synthe- sis had already been accomplished by Feuerstein and Kostanecki. 4 Since 1873 numerous derivatives of flavone, having different numbers of hydroxyls or methoxyls or both in different positions of the molecule and in the form of glykosides, have been ~solated from the roots, stems, barks, fruits, flowers and leaves of various medicinal and other plants; to cite a few baiealein (II) from the roots of Scutellaria baicalensis Georgi, quercetagetin (III) from the fowers of Tagetes patula, tricin (IV) from 'Khapli' wheat and rhamnetin (V) from the husks of Persian berries. Due to the wide O O O OH C_? F\ HO CO HO CO HO CO (1) (ii) (I~i) 1 Piccard, Ber., i873, 6, 884; 1874, 7, 888; 1877, 10, 176. Kostanecki, Ibid., 1893, 26, 2901. a M~uUer,J. Chem. Soc., 1915, 107, 875. 4 Feuerstein and Kostanecki, Bet., 1898, 31, 1757. 186 Antiseptics and .4 nlhelminthics~[II 187 o OMe O OH vx/ ivx/ IG\/- HO CO HO CO (IV) iv) occurrence of the flavones in nature several methods for their synthesis have been developed by various workers, the more important being by Kostanecki and others, 5 Robinson and his pupils, 6 Baker, v Mahal and Venkataraman, s Algar and Flynn 9 and Mahal, Rai and Venkataraman. 1~ Although so much is known about the chemistry of the flavone group and in spite of their wide occurrence in medicinal plants, e.g., apigenin (VI) and genkwanin (vii) in the Chinese drug ' Yuen-hua ' (Nakao and Tsengn), which is reputed to have diuretic and anthelminthic properties and amar- belin in the seeds of Cuscuta reflexa Roxb. (AgarwaW) also reputed to have anthelminthic properties, very little has been mentioned in literature about the pharmacology of this extensive series of natural and synthetic colouring matters. Koike TM appears to have been the first to study the pharmacology of the flavones; he observed that they showed diuresis in normal rabbits and the diuretic action of the polyhydroxyflavones increased with increas- ing number of hydroxyls. Fukuda, 14 a little later, also confirmed the previous observation of Koike and found further that flavonols and their glykosides are cardiac stimulants, vaso constrictors, and increased the blood pressure. Ratnagiriswaran, Sehra and Venkataraman 1~ isolated a flavone, caly- copterin, from the leaves of Calycopteris floribunda reputed to have laxative and anthelminthic properties (Nadkarni18). On the experimental results of Dr. K. Venkatachalam, Research Officer, Medical College, Madras, who found that calycopteri n is toxic to round worms (Ascaris lumbricoides) suspended in a mixture of bile with aqueous sodium carbonate approximat- ing to the composition of the intestinal fluid in which the worms reside, they 5 Kostanecki and others, Ibid., 1898, 31, 1757; 1899, 32, 2448; 1904, 37, 3167. 6 Robinson and his pupils, J. Chem. Soc, 1918, 113, 859; 1924, 125, 2193. Baker, Ibid., 1933, 143, 1381. s Mahal and Venkataraman, Ibid., 1934, 145, 1767. 9 Algar alad Flynn, Proc. Royal Irish Acad., 1934, Ser. B, 42, separate issue. 10 Mahal, Rai and Venk,ataraman, J. Chem. Sot., 1935, 147, 866. ix Nakao and Tseng, J. Pharm. ?5oc. lapan, 1932, No. 602, 343 ; 1933, No. 608, 905. 12 Agarwal, J. Ind. Chem. Soc., 1936, 13,531. 18 I(oike, Folia Pharmacol. Japon., 1931, 12, No. 1, 89, Breviaria, 6. 1, Fukuda,'Arch. Exptl. Path. Pharmakol., 1932, 164, 685. t~ Ratnagiriswaran, Sehra and Venkataraman, Biochem. f., 1934, 28, 1964. 16 Nadkarni, Indian Materia Medica, p. 238. 188 Harbhajan Singh Mahal suggested that calycopterin is the anthelminthic constituent of the leaves of Calycopteris floribunda. The present author and Venkataraman ~7 having further shown that calycopterin is 6 : 4'-dihydroxy-3 : 5 : 7 : 8-tetramethoxy flavone (VIII), the study of the pharmacology, particularly the anthelmin- thic properties, of flavones has been undertaken. o o =oo/N/\ /--\oH I / g\_/ k,\$\j N/N/ HO CO HO CO (VI) (Wn) MeO O 0 ~oo/\/\ /--\o~ Ho/\/N_/--\ ~o//\/\/ Io=oNJ I\/\/ I I-\__/ MeO CO CO (vni) (Ix) O O .oN\J-\ .oFy; o \J \/re, C O C--Me (x) (xi) The flavones that have been studied in tlm present work are (a) chrysin (I) and genkwanin (VII) which are both phloroglucinol derivatives and are therefore of special interest as it is well known that filix derivatives, e.g., male fern, kamala and kausso, which have long been used as specific anthel- minthics are phloroglucinol derivatives; (b)7-hydroxyflavone (IX) and 6-hexyl-7-hydroxyflavone (X), derivatives respectively of resorcinol and hexylresorcinol, which are known antiseptics. Along with the study of the pharmacology of benzo-y-pyrones or flavones, .i-methylumbelliferone (XI), a member of the closely related group of benzo-a-pyrones or coumarins, has. also been examined. The anthelminthic action of the compounds has been studied in vitro by (A) directly immersing round-worms (Ascaris lumbricoides), tape-worms (To~nia serrata) and leeches (Hirudo medicinalis) in different concentrations of the solution of the substances, (B) by the use of Dale and Laidlaw's apparatus. TM The results obtained in the experiments (A) and (B) show that the compounds do not have any anthelminthic properties; calycopterin itself has also been tried again and has likewise given negative results. iv Mahal and Venkataraman, Curr. Sci., 1935, 4, 311. as Dale and Laidlaw, J. Pharm. Exper. Therap., 1912, 4, 75. ~4nlise#tics and ,4nt/~e[minl~ics--[#[ 189 Although these tests in vitro cannot be taken as a conclusive proof that the substances have no anthelminthic action, yet it is a fair indication against their being good anthelminthics. Owing to the very high cost of produc- tion of these compounds in sufficient ~luantities their tests in vivo have not been tried. Other physiological actions of these compounds have also been studied and it has been observed that they inhibit the movements of the isolated rabbit's gut and uterus in concentrations of about 1-140,000 (Plate XlII, Figs. 5, 6 and 7) ; cause depression in the blood pressure, increase the move- ments of respiration and cause contraction in the uterus of dogs in doses varying from 20-40 rag. per kg. weight of the body of the animals (Plates XlV and XV, Figs. 8, 9, 10, 1] and 12) and in concentrations varying from 1-100,000-500,000 inhibit the beats of an isolated frog's heart (Plate XVI, Figs. 13, 14 and 15). The antiseptic properties of chrysin, genkwanin and 4-methyl-umbelli- ferone have been studied on the growth of B. coli and it has been observed that chrysin and ~enkwanin have no effect on the growth of the bacilli, but 4-methylumbelliferone, however, inhibits the growth of the bacilli in 1-1,000 concentration while in concentration 1-10,000 only a slight inhibi- tion has been observed. Germicidal properties of the compounds have been tested by the Rideal Walker's phenol coefficient test and all the compounds are found to have phenol coefficients less than one. Experimental. Anthelminthic action of 7-hydroxyflavone (IX), 6-hexyl-7-hydroxyflavone (X), chmsin (I), genkwanin (VII), calycopterin (VIII) and 4-methylumbelli- ferone (XI)--Method (A).--The compounds being insoluble in water, they were dissolved in minimum amounts of cold N/10 aqueous caustic soda and the stock solutions so obtained were further diluted to the required concen- .trations by adding the requisite amounts of water, saline or Locke's solution depending upon whether the compounds were to be tried in water, saline or Locke's solution. 6-Hexyl-7-hydroxyflavone being insoluble even in caustic soda solution was used in the form of an emulsion in gum tragacanth. 10 c.c. of each solution of different concentrations was placed in different watch glasses and 2-5 segments of tape-worms previotlsly washed with saline were placed in each. Their activity was constantly watched and when they had completely stopped showing any physical movements they were removed from the watch glasses, washed with saline and put into fresh Locke's solution to see if they could recover their original activity, Leeches and round-worms, for the tests, were dipped into the solution in test-tubes, 190 Harbhajan Singh Mahal plugged loosely with cotton, so that they could not come out of the solution. The results so obtained in a series of experiments with different compounds were as follows :- TABLE I. 7-Hydroxvflavone, 7-hydroxy-6-hexylflavone, chrysin, genkwanin, calycopterin and 4-methylumbelliferone. Conc. ,. 1-1,000 1-5,000 1-10,000 1-50,000 1-100,000 Control in listilled water Leeches .
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