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ALLELOCHEMICALS ISOLATED from TISSUES of the INVASIVE WEED GARLIC MUSTARD (Alliaria Petiolata) I

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ALLELOCHEMICALS ISOLATED from TISSUES of the INVASIVE WEED GARLIC MUSTARD (Alliaria Petiolata) I Joumal of Chemical Ecology. HII. 25. No. II. 1999 ALLELOCHEMICALS ISOLATED FROM TISSUES OF THE INVASIVE WEED GARLIC MUSTARD (Alliaria petiolata) I STEVEN F. VAUGHN* and MARK A. BERHOW Bio(lc/ive Agents Research USDA. ARS. Nll/ional Cemer jiJl' Agricultural Utilization Research 1815 N. University 51.. Peoria. Illinois 61604 <Received February 8. 1999: accepted June 23. 1999) Abstract-Garlic mustard (Alliaria {'etiolala) is a naturalized Eurasian species that has invaded woodlands and degraded habitats in the eastern United States and Canada. Several phytotoxic hydrolysis products of glucosinolates. principally allyl isothiocyanate (AITC) and benzyl isothiocyanate (BzITC). were isolated from dichloromethane extracts of garlic mustard tissues. AITC and BzITC were much more phytotoxic to wheat (Triticulll aestil'lllll) than their respective parent glucosinolates sinigrin and glucotropaeolin. However. garden cress (Le{'idium sativlIIn) growth was inhibited to a greater degree by glucotropaeolin than BzITC. possibly due to conversion to BzITC by endogenous myrosinase. Sinigrin and glucotropaeolin were not detected in leaf/stem tissues harvested at the initiation of flowering. but were present in leaves and stems harvested in the autumn. Sinigrin levels in roots were similar for both sampling dates. but autumn-harvested roots contained glucotropaeolin at levels over three times higher than spring-harvested roots. The dominance of garlic mustard in forest ecosystems may be attributable in part to release of these phytotoxins. especially from root tissues. Key Words-Garlic mustard. AIlia ria {'etiolala. Brassicaceae. glucosinolates. allelopathy. phytotoxins. allyl isothiocyanate. benzyl isothiocyanate. sinigrin. glucotropaeolin. "To whom correspondence should be addressed. I Names are necessary to report factually on available data; however. the USDA neither guarantees nor warrants the standard of the product. and the use of the name by USDA implies no approval of the product to the exclusion of others that may also be suitable. 2495 0098-0331/99/1100-2495516.00/0 1999 Plenum Publishing Corporation 2496 VAUGHN AND BERHOW INTRODUCTION Garlic mustard [Alliaria petiolata (Bieb) Cavara & Grande (Brassicaceae)] is an herbaceous biennial that has invaded, and now dominates, much of the hardwood forest understory in the eastern and midwestern United States and southeastern Canada (Cavers et a!., 1979; Nuzzo, 1991, 1993, 1998). It is displacing native flora, and it is unlikely that its elimination from heavily infested areas is possible (Anderson et a!., 1996). Populations of native understory plants have been found to decline in areas with a heavy infestation of garlic mustard, which can be as high as 20,000 seedlings/m2 (Trimbur, 1973; Yost et a!., 1991). Groundcover by native ephemerals declined as cover by garlic mustard increased (Nuzzo, 1998). Recent studies have shown that garlic mustard may also pose a threat to organ­ isms other than higher plants, as Porter (1994) reported that adults of the endan­ gered West Virginia white butterfly [Pief·is virginiana (w. H. Edwards»), which normally feed on several Dentaria spp. (Brassicaceae), preferentially laid their eggs on garlic mustard plants. This occurs even though the plant appears to be moderately toxic to the developing larvae (Haribal and Renwick, 1998). Glucosinolates and/or their degradation products appear to be primarily responsible for the pesticidal activity of species in the Brassicaceae (syn. Cru­ ciferae) (Brown et a!., 1991; Grossman, 1993; Brown and Morra, 1995; Mayton et a!., 1996; Mancini et a!., 1997; Vaughn and Boydston, 1997). Glucosinolates are a class of glucose- and sulfur-containing organic anions whose biologically active degradation products are produced when plant cells are ruptured and the glucosino­ lates, which are present in vacuoles, are hydrolyzed by the enzyme myrosinase ((3­ thioglucosidase glucohydrolase; EC 3.2.3.1) (VanEtten and Tookey, 1983). These metabolites include substituted isothiocyanates, nitriles, thiocyanates, and oxazo­ lidinethiones, which vary depending on the side-chain substitution, cell pH, and cell iron concentration (Cole, 1976; Daxenbichler and VanEtten, 1977; Fenwick et a!., 1983; Uda et aI., 1986; Chew, 1988). Some ofthese degradation products have been found to be potent phytotoxins (Wolf et a!., 1984; Oleszek, 1987; Bialy et a!., 1990; Yamane et a!., 1992a,b; Brinker and Spencer, 1993; Brown and Morra, 1995; Vaughn et a!., 1996; Vaughn and Boydston, 1997; Vaughn and Berhow, 1998). The leaves and seeds of garlic mustard have been previously shown to contain a high percentage ofglucosinolates (up to 3% offresh weight in seeds), with the predomi­ nant glucosinolate being allyl glucosinolate (sinigrin) (Nielsen et aI., 1979; Larsen et a!., 1983; Daxenbichler et a!., 1991). It is presently unclear whether the dominance of garlic mustard in forest groundlayers is due to competition, allelopathy, or both (Randall, 1996), although a recent report by McCarthy and Hanson (1998) discounted allelopathy as a pri­ mary mechanism. To further elucidate if allelopathy plays a role in garlic mustard dominance, we present results from a bioassay-guided isolation and identifica­ tion of phytotoxins from garlic mustard plants. GARLIC MUSTARD ALLELOCHEMICALS 2497 METHODS AND MATERIALS Spectroscopy. Gas chromatography-mass spectrometry (GC-MS) was per­ formed on a Hewlett-Packard (HP) 6890 GC system attached to a HP 5972A Mass Selective Detector. Columns used were fused silica HP-5MS capillaries (0.25-JLm film thickness, 30 m x 0.25 mm ID). The GC operating parame­ ters were as follows: splitless injection mode; temperature programmed from 40: to 315 D C at SOC/min with a 2-min initial and a lO-min final temperature hold; He carrier gas flow rate at 1.1 mljmin, with the injector temperature set at 250 D C. Spectra were compared with known standards or by computer with the Wiley/NBS Mass Spectral Registry (McLafferty and Stauffer, 1989). Extract Preparation. Garlic mustard tissues (100 g samples) were sequen­ tially extracted using a Soxhlet apparatus with hexane, CH2Cb, and MeOH, and concentrated by rotoevaporation at low (20:C for hexane and CH2Ch extracts, 50°C for MeOH extracts) water bath temperatures, preventing possible loss of volatile extraction products. A water extract was obtained by soaking the solvent­ extracted tissues in 250 ml of distilled water overnight in a refrigerator at 2°C, after which the marc was washed with two additional 250-ml aliquots, and the extracts lyophilized. Compounds in the crude CH2Ch extract, subsequently found to be active in the bioassays, were separated on a lipophilic Sephadex LH­ 20 (Supelco, Inc., Bellefonte, Pennsylvania) column into three separate fractions using 100% CHCl}; 50% CHCh/50% MeOH; and 100% MeOH as solvents. Seedling Radicle Elongation Bioassay. Wheat (Triticum aestivufll L., Car­ dinal) and cress (Lepidium sativum L. Curly Cress, Brassicaceae) seeds were used in routine bioassays of extracts. Wheat and cress seeds were surface steril­ ized with 0.5% (wIv) commercial chlorine bleach for 15 min, rinsed with sterile distilled water (SDW) twice and subsequently soaked with additional SDW for 2 hr. Seeds were wrapped in sterile paper towels saturated with water and incu­ bated overnight in darkness at 25'C. All crude extracts were assayed by adding extracts to autoclaved water agar in 9.0-cm plastic Petri dishes at the concen­ tration of 1 mg extract/ml agar after the agar had cooled to - 40°C. Column fractions from crude extracts were assayed at concentrations of 0.1 and 0.5 mg extract/ml agar. After the agar had solidified and all solvent had evaporated from the agar, six germinated seedlings of each bioassay species per plate were placed on the agar in the Petri dishes. Dishes were incubated in darkness at 25:C on 45: slants for 24-48 hr, then evaluated for inhibition of radicle growth. Allyl isothiocyanate (AITC), benzyl isothiocyanate (BzITC), and sinigrin standards were obtained from a commercial source (Sigma, St. Louis, Missouri). The glucotropaeolin standard used in bioassays was extracted and purified to greater than 98% from cress seeds by the method of Thies (1988). Solutions of the isothiocyanates (dissolved in acetone) and intact glucosinolates (dissolved in water) were added to cooling water agar to give final concentrations of 0, 2498 VAUGHN AND BERHOW 6 10-3, 10-4 , 10-5 , and 10- M (controls contained acetone only). Plates were sealed with Parafilm (American National Can, Neenah, Wisconsin) to prevent volatilization of the isothiocyanates. Radicle lengths (five plates of six seedlings each of wheat and cress) were measured after 48 hr of incubation, and Iso values (the amount of each compound required to reduce radicle elongation by 50%) were estimated from the intercept of 50% of the control with a best fit line of the data using nonlinear regression analysis (SlideWrite Plus, Advanced Graphics Software, Inc., Carlsbad, California). Glucosinolate Analysis. Glucosinolate concentrations were determined from leaf/stem and root tissues of garlic mustard plants that were harvested on May 7, 1998 (at initiation of flowering), and on October 30, 1998, from plants growing in a oak-hickory (Quercus-Carya) forest in Peoria, Illinois. The ana­ lytical method employed was a modification of a high-performance liquid chro­ matography (HPLC) method developed by Betz and Fox (1994). In brief, 5 g of freeze-dried plant material was added to 200 ml boiling 70% (vIv) MeOH with stirring for 15 min, and then cooled and filtered through Whatman No.2 filter paper. The marc was washed twice with 50 ml aliquots of 70% MeOH. The resulting extract was concentrated to 5-10 ml by rotoevaporation and was diluted to 25 ml to form a working solution. Glucosinolates were purified from the extracts through the use of disposable solid-phase extraction (SPE) columns (Sep-Pak tC 18 , Waters Corp., Milford, Massachusetts). Each column was pre­ conditioned with 5 ml 100% MeOH, followed by 5 ml 0.005 M tetrabutylam­ monium hydrogen sulfate (THS; Sigma). Five milliliters of the working solution was added to the column, and the column was subsequently washed with 5 ml of 0.005 M THS to remove unwanted compounds.
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