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Isolation and Identification of Indole-3-Ethanol (Tryptophol) from Cucumber Seedlings

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Isolation and Identification of Indole-3-Ethanol (Tryptophol) from Cucumber Seedlings Plaint Physiol. (1967) 42, 520-524 Isolation and Identification of Indole.3-Ethanol (Tryptophol) from Cucumber Seedlings1'2 David L. Rayle3 and William K. Purves Department of Biological Sciences, University of California, Santa Barbara, California 93106 Received January 30, 1967. Summinary. Crulde ether extracts of green shoots of Culciumiis sativtus L. promoted the elongation of cucumber hypocotyl segments. Puirification of the extract was accomplished by DEAE cellulose, silicic acid, and magnesium silicate chromatography followed by gel filtration and preparative thin layer chromatography. Idelntification of the growth promoter as indole-3-ethanol was achieved bynmass spectrometry, thin layer and gas chromatography, ain( ultraviolet andl visil)le spectroscopy, as wvell as ly physiological characteristics. The cenitral role of indolic compounIds as plant ctiltnlre meldia containing trvptophan or tryptamine grnowth reguilators is well established. However, (2). Perlex and( Stowe observed lEt production few growth-promoting indolic compotin(ds have been from tryptophan by 1acilli s cerciis and( by Taphrina isolated in puire form from plaint tissute. The most deforimans (15, 16). \Wightman has reported some extenisively sttidied is indole-3-acetic acid (TAA), evideince for the occuirrence of lEt iII toIllato seed- which has been isolate(d in crystalline form from lings after the applicatioii of tryptophaii or indole- sev-eral sources (5, 10, 20). Toines et al. have iso- 3-lactic acid throtigh the cut stenms (23). In this lated pure indoleacetonitrile from immattire cabbage system it wvas postulatedl that iindolelactic acid was heads (8). Indoleacetaldehy-lde has been i(lentified decarboxvlated to lF,t which was theni oxidized to in plant tissue by Larsen (11). E-idence for the JAA. Libbert aind Brunin have presente(d chroma- occurrence of other growth-promotinig in(Iolic com- tographic (lata showing that lEt -was formed when poutndls, stich as indolepyrulvic acid (18), indole- the TAA-formiing enizyme of peas was inccubated acetamide (1), the ethyl ester of IAA (19), and( for 12 hours in a tryptophani soltutioni (14). others, is based primarily on chromatographic This paper offers evi(lence for the natural behavior of cruide extracts in 1 or 2 solvents. occurrence of lEt in cuctumber shoots. Our method While chromatographic data are valuable, they arc for the purificationi of lEt should l)e applicable to niot concltisive, especially when uise(d as the sole other ineutral inidolic compotuinds. A method is criteria with imptire preparationis. dlescribedl for the bioassay of TEt tusilng the cuctumber The nattural occulrrenice of iiidole-3-ethanol hypocotyl. (IEt) in higher plants has not previously been lemonstrated. Ev-idence lbase(l on paper chroma- Materials and Methods tographic methods and color tests in(licated that 4cetobacterx- ylinm. can pro(ltice JEt. It was pro- RoaSsa(lV. See(Is of Ctcmniis satiZIus L. cv. posed that JEt and( TIAA might arise from indole- Natioinal Pickling (WV. Atlee Btirpee Seed Co.) ace-taldehyde in this organism by a dismtitatiol were soaked for 2 hotirs an(l sown in vermiculite reaction (12). Kaper andl V-el(dstra, tising chroma- (Terralite, Zonolite Co.) moistenied with tap water. tographic techiniques, have (lemioiistrate(l JEt as a Seedlinlgs w-ere grow-n tundler constaint illtumination prodtuct of physiological origini from AgrobacteriumIi (640 ft-c) for 5 to 6 days in a growth chamber at tumefactens (9). Bailey and Gordon reported the 26 to 217°. Segmeints wvere cuit so that the apical tentative identification of lEt in Diplodia llCiS 2.5 cm of the hypocotyl w-as iincludedl as well as the still qutiiescent epicotyl. The cotyle(lonis were remove(l in all cases. The segments were distrib.- tited in lots of ; inito Sten(ler dishes containing ' This work Avas supported by National Scieince Founil- 5 ml of the test medliumni. D)ishes -were returine(d dation grants GB-3248 and GB-4922. conistarnt 2 This material was included in a doctoral tlhesis sul)- to the grow-th chamber and( kept tindler itted by D. L. Rayle to the Graduate Division of the iullumination throulghouit the incubation periodl. Utniversity of California, Santa Barbara. After 4 to 6 houirs the segimienits were measured to 3 National Defense Education Act predoctoral fellow. the nearest 0.5 mm. Hypocotyl segmtents of Cucur- Presenit address: MSU/AEC Planit Research Laboratory, Zuicchili were Michigani State University, East Lansing, Michigan bit(a pcpo L. cv. For(lhook Improved 48823. uised in a similar mianner. 520 RAYLE AND PURVES-IXNOLE-3-ETHANOL IN CUCUAMBER SEEDLINGS 521 Extractiont and Puirification. Seeds of C. saitivus were sown as described above and grown in the light (640 ft-c). After 7 to 8 days the shoots were harvested, weighed, and extracted with ethyl ether -10 (approximately 2 liters per kg fr wt tisstue) for 2 to 3 hoturs at room temperature. After de- 8 cantation of the first extract, the tisstue was ground 0 in a meat grinder and extracted twice more with I fresh ethyl ether. The combined ether fractions 0 were separated from the cellular water and evap- E Z E 0 orated to dryness. The gummy green residue was z z 0 0 resuspended in double distilled water (250 ml per I.- 4 kg fr wt tissue) and filtered throtugh a 4 cm pad 0 z I0 of DEAE-cellulose. This operation ridded the ex- 0 tract of pigments. DEAE-cellulose has the further w advantage of binding IAA. The growth-promoting filtrate was extracted 5 times with equal volumes of ethyl ether. The combined ether fractions were 1 5 9 13 17 21 25 29 33 37 41 evaporated aind the water fractionl discarded. Sev- TUBE NUMBER eral 5 to 15 kg batches of tissue were extracted, FIG. 1. Elution of cucumber factor from Sephadex processed as described above, and stored at 40 until LH-20 by methanol. 10-ml Fractions collected. Selected a total of 93 kg of tissue had been extracted. At fractions assayed for biological activity (4 hr incubation) this time, the residutes from each batch were com- and for absorption at 280 nm. bined to yield 3.21 g of a yellow oil. The combined residues were dissolved in a minimal amotunt of was clamped between 2 Eastman Chromagram petroleum ether (b.p. 30 to 600): ethyl ether (3:1, chamber plates and developed with 100 % CHCl3. v/v) and placed oni a silicic acid column (2.9 X 25 The chromatogram was divided into several zones cm). The coltumn was eluted in a stepwise fashion and the silica gel scraped off and eluted with using increasing concentrations of ethyl ether in anhydrous ethyl ether. An aliquot of the RF 0.15 petroleum ether according to Nlethod A of Hirsch to 0.3 eluate was active in the bioassay. The active and Ahrens (7). The growth promoting fractions eluate was evaporated under nitrogen yielding 2.7 from this step as well as all subsequent steps were mg of material. Final purification was achieved determined by removing aliquiots of the various by rechromatography on Sephadex LH-20 as de- fractions, evaporating the solvent, anid dissolving scribed above. The active fractions were combined the residue in 5 ml of water which was then bio- and evaporated under nitrogen leaving 2.5 mg of assayed. Activity was observed in the 100 % ethyl ether fractions. The active fractionis from the I silicic acid coltumni were combined aind evaporated 100 130 (b) to dryness. The residue (117 mg) was suispende(d A a : in mini-mal amount of CCI CHC13 (3:1, v/v) M+ and placed on a 2.0 X 20 cm magnesitum silicate 30 _ 161 (a) M-1 (Bio-Rad) column packed in CCl4. The Z column was eluted in a stepwise pattern tusing in- .20 _- 4 a creasing conceintrations (0, 10, 20, 30, 40 and 50 %, z 143 v/v) of CHCI, in CC14. At each step, 100 ml of 0 10 4 116 (C) solvent was tused. Finally, the coluimn was eluted 0 l l III I !1 with 250 ml of 100 % CH,CI3. The 100 % OHCI3 II fractions contained the growth-active substance. 4 DO - 130 Further purification was obtained by evaporating -JJl (b) the active fractions to dryness and dissolving the B residue (33 mg) in a minimal amoulnt of absolute z I0- 161 methanol. The methanol solution was placed on a (a) Sephadex LH-20 coluimn (2.5 X /7 cm) and eluted 2 with methanol. Ten-ml fractioins were collected using an automatic fraction collector. Selected fractions were assayed for biological activity and I[I I, ~~~~~~~~~~~~~~116(c) for absorption at 280 nm (fig 1). The active fractions were evaporated in a rotary flash evap- 40 60 80 100 120 140 160 orator leaving 3.5 mg of residue which was dis- m/e solved in and an ethyl ether streaked oni Eastman FIG. 2. Mass spectra. A) Cucumber factor. B) Chromagram sheet (Type K 301 R2). The sheet Indole-3-ethanol. 522 PLANT PHYSIOLOGY a light yellow gum. The progress of the purifica- This fragmentation pattern is characteri-tic of tion was followed by removing an aliqtuot of the simple indoles and can be readily visualized if one active material after each step in the purification assumes that the first electron to be remove(l orig- procedure and spot-chromatographing the residue inates from the indole nitrogen. This characteristic on silica gel in several solvents. Organic com- was of value in the structulral identification of pounds were detected by exposing the dry chroma- 5-methoxyindole-3-acetic acid isolatedl from boviine togram to iodine vapor. pineal glands (13). A secondary fragmelntatioin The purity of the final preparation was checked pathway of cuicumber factor appears to be the loss by thin layer chromatography in 5 solvents of of water from the molecular ion resuilting in thle widely differing polarity: ethyl ether hexane peak at m/e 143.
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