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The Journal of Organic Chemistry 1959 Volume 24 No.6

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The Journal of Organic Chemistry 1959 Volume 24 No.6 THE JOURNAL OF Organic Chemistry Volume 24, Number 6 . Js±Y 14, 1959 _________________________________________________ Ju-Y>e [C ontribution f r o m t h e I n s t it u t e o f P a p e r C h e m is t r y ] Studies on the Barks of the Family Salicaceae. I. Tremuloidin, a New Glucoside from the Bark of Populus tremuloides1 IRWIN A. PEARL a n d STEPHEN F. DARLING Received December 19, 1.9i>S A new glucoside has been isolated from the bark of Populus tremuloides. This glucoside, which we have named tremuloidin, is a monobenzoate of salicin and an isomer of populin. Tremuloidin was completely methylated to tetramethyltremuloidin which, in turn, was debenzoylated to a tetramethylsalicin yielding 3,4,6-tri-O-methyl-D-glucopyranoside on acid hydrolysis. Thus, tremuloidin was identified as 2-benzoylsalicin. Tremuloidin was oxidized with dilute nitric acid to 2-benzoylhelicin. All products and intermediates were characterized by means of infrared absorption spectra. In 1830 the glucoside salicin was discovered in the color with concentrated sulfuric acid, properties now bark of Salix helix by Leroux,2 and in the same year known to be exhibited by similarly related and con­ Braconnot3 isolated salicin from the bark of the stituted substances. Dobbin and White6 improved European quaking aspen, Populus tremula, along Schiff’s benzoylation technique for preparing syn­ with a new substance which he named “populin.” thetic populin from salicin and noted that their Although the structural formulas for these com­ synthetic compound had the same melting point pounds remained unknown for a long time, Piria4 5 (180°) as a purified natural material. The uncer­ demonstrated that salicin could be hydrolyzed with tainty of absolute identity was continued by Dobbin dilute acid or enzymatically to yield salicyl alcohol and White who wrote: “The purified natural prod­ and glucose and that the phenolic hydroxyl in salicyl uct behaved in every other respect exactly as our alcohol was involved in the glucosidic linkage because synthetic sample did.” In 1906, Irvine and Rose7 salicin could be oxidized to helicin, the glucoside of completely methylated salicin and hydrolyzed the salicylaldehyde. Piria even showed the relationship resulting pentamethylsalicin to 2,3,4,6-tetramethyl- between salicin and populin by demonstrating that glucose. This finding together with the fact that sal­ populin yielded salicin and benzoic acid when sap­ icin is hydrolyzed by emulsin proves salicin to be onified with barium hydroxide solution. Somewhat o-hydroxymethylphenyl-0-/3-D-glucopyranoside (I). later Schiff6 showed that the benzoyl group in pop­ Many years later Richtmyer and Yeakel8 methyl­ ulin must be attached to the glucose and not the ated synthetic populin with methyl iodide and silver salicyl alcohol moiety because populin could be oxi­ oxide. The resulting tetramethylpopulin was deben­ dized to benzoylhelicin, a compound he prepared by zoylated to a tetramethylsalicin, which on hydroly­ benzoylating helicin. In addition, Schiff benzoylated sis with hydrochloric acid yielded 2,3,4-tri-O- salicin by several methods and obtained a synthetic methyl-D-glueosei Thus, the structure of synthetic populin which he compared with a sample of natural populin was proved to be 6-benzoylsalicin (II), and populin from Piria’s laboratory. Identity was estab­ the intermediate tetramethylpopulin and tetra­ lished by such properties as taste, solubility, and methylsalicin had the structures III and IV, re- (1) Presented before the Division of Cellulose Chemistry at the 135th meeting of the American Chemical Society, 16) L. Dobbin and A. I). White, Pharm. ./., [4] 19, 233 Boston, Mass., April 5-10, 1959. (1904). (2) Leroux, Ann. Chim. Phys., [2] 43, 440 (1830). (7) J. C. Irvine and It. E. Rose, J. Chern. Soc., 89, 814 (3) H. Braconnot, Ann. Chim. Phys., [2] 44, 296 (1830). (1906). (4) R. Piria, Ann., 56, 35 (1845); 96, 375 (1855). (8) N. K. Richtmyer and E. H. Yeakel, J. Am. Chem. (5) H. Schiff, Ann., 154, 1 (1870). Soc., 56, 2495 (1934). 731 7 3 2 PEARL AND DARLING VOL. 2 4 spectively. Richtmyer and Yeakel reported for syn­ less needles melting at 201-202°. The yield thetic populin [a]D — 2.0° (c = 5 in pyridine). It is amounted to 0.37% based on the original oven- interesting to note that as early as 1852 Biot and dried P. tremuloides bark. Further concentration of Pasteur9 recorded for natural populin f a ] D — the filtrate yielded crystals of saliein melting at 193— 20.75° (c = 1 in absolute ethanol), while much later 194° and very different from the first crystals in Bridel10 reported fa]D — 24.73° (in 60% acetone). water solubility and taste. However, none of the investigators of synthetic Recrystallization of the 201-202° melting ma­ populin ever compared rotations of synthetic and terial from water and then from methanol raised the1 natural populins. melting point to 207-208°. The specific rotation in During the past century the presence of saliein pyridine [«]d + 17.1° (c = 3.1) increased slightly and populin has been reported in the barks of a on standing 72 hr. to + 19.5°. The rotation in number of species of P o p u lu s , n but unfortunately, 80% acetone [cx]d ■ 12.3° (c = 1.5) remained un­ the presence of these glucosides was usually demon­ changed on standing. Hydrolysis with alkali at room strated by some indirect physical, chemical, or bio­ temperature yielded benzoic acid and saliein, and chemical procedure such as increase in glucose con­ analysis of the pure compound and of its acetate in­ centration upon hydrolysis, oxidation, and deter­ dicated it to be a monobenzoate of saliein. Thus, the mination of salicylic acid, or calculation of enzymo- new compound, which we have named “tremu- lytic indices. Some of these procedures would give loidin,” is an isomer of synthetic populin. valid results when applied to solutions of glucose and In order to obviate the remote possibility that only the two pure glucosides, but results obtained natural populin and synthetic populin are not iden­ on aqueous extracts of P o p u lu s barks might be very tical and that the populin isolated by investigators misleading when interpreted in the light of our pres­ more than one hundred years ago without recording ent knowledge of possible components of P o p u lu s the melting point might actually be identical with bark extracts. our tremuloidin, the work of the early investigators was repeated. Natural populin was isolated from the* H bark of P . trem ula according to Braconnot3 and from the leaves of P . alba according to Herberger.12 The isolated populin was compared with synthetic populin8 by means of optical activity, mixed melting point, and infrared absorption spectra, and the two were found to be identical.Therefore, “tremuloidin” was a new monobenzoate of saliein with benzoyl substitution at some position other than the 6-posi- tion on the glucose, which is the known benzoyl I. R, = 1 {‘ — R3 — 11; = R., = H substitution of populin.8 II. R. = R; = R3 = R5 = H; R4 = C6H5CO Controlled periodate oxidation13 of tremuloidin III. Ri — Ri = R3 = Ro = CH3; R4 = CeHsCO IV. Ri = R2 = R3 = R& = CH3; R4 = H developed no acidity and consumed one mole of V. Ri R2 — R 3 = R4 = H; Rs = C6H5CO periodate, indicating a compound containing only VI. Ri = CsHsCO; R2 = R 3 = R 4 — R5 = H two adjacent hydroxyl groups. Of the possible mon­ VII. R, = R 3 = R4 — R5 = H; R, = C6H:,CO VIII. R, = R- = R4 = Rä = H ; R3 = CeHsCO obenzoates of saliein other than 6-glucose substitu­ IX. Ri = H: Ro = R3 = R4 = R5 = CH, tion (V-VIII) only VI and VIII with substitution XII. R i = C jR C O ; Ro = R., = R4 = Ro = CH3CO XIII. R, = C6H5CO; R2 = R3 = R4 = Rä = CHs at positions 2 and 4, respectively, would satisfy X. R. = Ro = Rs = H; R4 = CeHoCO these criteria. The anomalous dextrorotation of the XI. R, = C6H5CO; R2 = Ro = R4 = H tetraacetate of tremuloidin, [«]d + 33.9° (c = In the course of our investigations on P o p u lu s 2.5 in chloroform); suggested the structure VI be­ tremuloides, American quaking aspen, some fresh cause the data of Pigman14 indicated that acetates bark obtained in late May was extracted with 95% of several glucosides substituted in the 2-glucose po­ ethanol, and the ethanol extract was concentrated sition demonstrated this anomalous dextrorotation. to approximately 25% solids. The fresh concen­ For determining the exact location of benzoyl sub­ trated extract was evaporated to dryness and ex­ stitution in tremuloidin, the general procedure of tracted with water at 25°. The extract was purified Richtmyer and Yeakel8 was employed. by treating with basic lead acetate, filtering, and re­ Tremuloidin was methylated completely with moving the lead with hydrogen sulfide. Upon partial methyl iodide and silver oxide to yield tetramethyl- concentration, the clear filtrate deposited color­ tremuloidin as a sirup which failed to crystallize, (9) J. B. Biot and L. Pasteur, Compt. rend., 34, 600 (1852). (12) J. K Herberger, Buchners Report Pharm., 51, 266 (10) M. Bridel, J. Pharm. Chim., [7j 20, 14 (1919,). (1835). (11) For a complete bibliography see W. Thies and C. (13) J. It. Dyer in D. Gliek, Methods of Biochemical VVehmer, in G. Klein, Handbuch der Pflanzenanalyze, Bd. Analysis, Vol. 3, pp. 123, Interscience, New York, 1946. Ill, 2 Teil, 845, Vienna, 1932. See also A. Kuhn and G. (14) W. W. Pigman, J. Research Natl. Bur. Standards. 33, Schäfer, Pharm. Zfj., 82, 949 (1937). 129,144(1944). j u n e 1959 s t u d ie s o n S a l i c a c e a e 733 but whose purity was demonstrated by paper chro­ FREQUENCY.
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