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A Zearalenone Derivative from the Liquid Culture of the Lichen, Baeomyces Placophyllus

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A Zearalenone Derivative from the Liquid Culture of the Lichen, Baeomyces Placophyllus J. Hattori Bot. Lab. No. 92: 285- 289 (Aug. 2002) A ZEARALENONE DERIVATIVE FROM THE LIQUID CULTURE OF THE LICHEN, BAEOMYCES PLACOPHYLLUS 2 3 YOSHlKAZU YAMAMOTO*l, YASUHIRO KINOSHITA , KAORU KINOSHITA , 3 3 KIYOTAKA KOYAMA AND KUNIO TAKAHASHI ABSTRACT. A zearalenone derivative, 6-( 4,5-dihydroxy-1 0-methyl-6-oxo-7-undecenyl)-resorcylic acid lactone, was isolated from the liquid culture of a thallus-derived mycobiont and a thallus of Baeomyces placophyllus. The structure including the stereochemistry was established by spectro­ scopic studies. KEy WORDS: Baeomyces placophyllus; lichen; mycobiont liquid culture; zearalenone derivative; 6-( 4,5-dihydroxy-l 0-methyl-6-oxo-7 -undecenyl) resorcylic acid lactone. INTRODUCTION Lichens produce many characteristic phenols, such as depsides, depsidones, dibenzo­ furans, pulvinates, chromones and quinones (Culberson 1969). However, 20% of about 100 lichen-derived cultures produced the same metabolites as those of their natural thalli, 20% had extraordinary products that were not synthesized in their natural thalli, and 60% did not have produced as detected by high performance chromatography (Yoshimura et a1. 1994). Mycobiont cultures without the algal partner often synthesize novel and extraordi­ nary constituents, e.g., Cladonia cristatella (cristazarins, Yamamoto et a1. 1996), Evernia esorediosa (dibenzofurans, Miyagawa et a1. 1993), Graphis scripta var. pulverulenta (graphislactones, Tanahashi et a1. 1997), Graphis scripta (graphenone, Miyagawa et a1. 1994), Graphis desquamescens (graphisquinone, Miyagawa et a1. 1994), Stereocaulon japonicum (dibenzofurans, Miyagawa et a1. 1997), Usnea diffracta (decarboxystenosporic acid and anthraquinones, Yamamoto et a1. 1998) and Usnea orientalis (dibenzofurans, Kon et a1. 1997). In the course of our search for new bioactive compounds from cultures and natural thalli of lichens, we cultured the mycobiont of Baeomyces placophyllus separated from its tissue culture and found it produced known compounds. We report herein the iso­ lation and identification of the compounds in this mycobiont and natural thallus of the lichen. EXPERIMENTAL General IH and l3C NMR spectra were recorded on a JEOL GSX-400 spectrometer in DMSO- I Department of Biological Production Science, Faculty of Bioresource Sciences, Akita Prefec­ tural University, 241-7, Kaidobata-nishi, Shimoshinjo-nakano, Akita 010--0195, Japan. 2 Innovative Technology Laboratory, Nippon Paint Co., Ltd., 4-1-15, Minamishinagawa, Shina­ gawa, Tokyo 140-8675, Japan. 3 Meiji Pharmaceutical University, Noshio, Kiyose, Tokyo 204-8588, Japan. * Author to whom correspondence should be addressed. 286 J. Hattori Bot. Lab. No. 92 200 2 d6, CDC13 and CD2Ci2 with TMS as an internal standard. Analytical HPLC was carried out with a photodiode array detector at 28°C under the following conditions: column, 150 mmX4.6 mm packed with Shiseido Capsel Pack C18 AG-120; solvent system, MeOH­ H20-H3P04 (75: 25: 0.9) at a flow rate of 1 ml min- I. Plant material and culture Baeomyces placophyllus (Lam.) Ach. thallus (id no. E803-06) was collected on Au­ gust, 1985 in Hokkaido, Japan. After collection, marginal segments of the thallus were im­ mediately used for tissue culture induction. The mycobiont was separated from its tissue culture (strain no. BAPL-O I) and then was cultured in Lilly-Barnett liquid-medium (90 ml) containing glucose 2% w/v in 300 ml Erlenmeyer flasks on a rotatory shaker at 130 rpm at 15°C in the dark for 3 weeks. Isolation and identification ofmetabolites After 3 weeks the culture broth of the B. placophyllus mycobiont was passed through a 150 pm nylon mesh to remove liquid-medium. Harvested mycelia were freeze-dried for 24 hr and treated with chloroform overnight. The chloroform solution was evaporated to yield the extract (1 .3 g), which had a main component with a Rt of 2.77 min and Am.x of 210, 262 and 302 nm by HPLC analysis with a photodiodearray detector. Its Rt and UV spectra were different from ordinary lichen metabolites such as depsidones and depsides. The extract was dissolved and chromatographed to afford 1 as needles, mp 183-186°C (un­ corr.) recrystallyzed from CHCI3- MeOH-acetone. Then, a natural thallus (dry weight 48.0 g) was extracted with CHCI3; the CHCl3 extract (533 mg) was subjected to column chromatography on Si gel (CHCI3-MeOH) and purified by HPLC over Si gel (Nuc\eosil 50-5, 1 X25 cm), eluted with CHCI3- MeOH, resulting in the isolation of the same com­ pound 1 (2.3 mg). Compound 1: colorless needles, mp 183-186°C (uncorr.) (from CHCI3-MeOH-ace­ tone). ElMS mlz (reI. int.%): 364 (M+, 37), 346 (l0), 251 (24), 221(97), 192 (lOO), 176 (97). HREIMS mlz: 364.1520 (calcd. 364.1522, CI9H2407)' IR vm•x (KBr) cm- I: 3460, 1740,1690,1650,1630 (sh), 1570, 1460, 1350, 1320,1300, 1260,1220,1160,1040. UV (CHCI3) Am.x (log t:) nm: 238 (3 .94), 265 (4.15), 304 (3.79). IH NMR (DMSO-d6): 8 1.09 (lH, m, 10-CH2), 1.33 (s, 3H, 17-CH3), 1.34 (lH, m, IO-CH2), 1.38 (m, lH, ll-CH2), 1.58 (m, lH, ll-CH2), 2.42 (m, lH, 12-CH2), 2.62 (m, lH, 4-CH2), 2.66 (m, IH, 12-CH2), 3.07 (m, IH, 4-CH2)' 3.74 (s, IH, OCH3), 3.74 (m, IH, 9-CH), 4.72 (d, IH, J=6.4Hz, 9-0H), 4.89 (d, IH, J=4.2 Hz, 8-0H), 4.32 (dd, lH, J=4.2, 3.1 Hz, 8-CH), 5.30 (m, IH, 3-CH), 6.25 (m, lH, 5-CH), 6.29 (d, IH,J=2.3Hz, 13-CH), 6.31 (d, lH,J=2.3Hz, 15-CH), 6.51 The relative stereochemistry of 1. Y. Y AMAMOTO ET AL.: A zearaleone derivative from Baeomyces placophyllus 287 (d, J= 11.9 Hz, 6-CH), 11.23 (s, lH, 16-0H). l3c NMR (DMSO-d6) 8: 19.9 (17-CH), 26.8 (11-CH2), 30.9 (10-CH2), 34.3 (l2-CH2), 35.7 (4-CH2), 55.1 (-OCH), 71.1 (9-CH), 72.3 (3-CH), 81.3 (8-CH), 98.7 (15-CH), 106.9 (B-CH), 108.2 (l6a-C), 127.2 (6-CH), 143.0 (5-CH), 145.1 (12a-C), 161.8 (16-C), 162.5 (14-C), 169.7 (I-C), 201.6 (7-C). Acetonide la: Acetone dimethyl acetal (0.4 ml, 3.25 .umo1) and a solution of p-tolue­ nesulfonic acid monohydrate in acetone (1.14 mg/0.8 ml acetone, 6.0.umol) was added to 1 (6.4 mg, 18.umol) at O°e. The mixture was stirred at room temperature for 17 h. Saturated NaHCO) was added, and the mixture was extracted with CHCl) for three times. The com­ bined organic layers were washed with saturated NaCi, dried over Na2S04, and evaporated to give acetonide (la, 5.1 mg) with a 71.6% yield. IH NMR (CDCI): 8 1.37 (s, 3H, ace­ tonide di-CH), 1.42 (s, 3H, 17-CH), 1.63 (s, lH, acetonide di-CH), 1.78 (m, lH), 2.33 (dt, lH, J=4.7, 11.7 Hz), 3.22 (dt, IH, J=4.7, 11.7 Hz), 3.79 (s, lH, OCH), 4.32 (m, lH, 9-CH), 4.69 (d, J=6.6 Hz, 8-CH), 5.54 (m, lH, 3-CH), 6.14 (dt, J=4.7, 11.5 Hz, 5-CH), 6.25 (d, IH, J=2.7 Hz, 13-CH), 6.34 (d, IH, J=2.7 Hz, 15-CH), 6.39 (br.d, J= 11.5 Hz, 6- CH), 11.97 (s. 16-0H). RESULTS AND DISCUSSION Baeomyces placophyllus (Lam.) Ach., a member of the Lecanorales, has a whitish­ green thin thallus with small marginal lobes with pinkish pseudopodetia; it grows abun­ dantly on soil in polar regions and high mountains of the Northern Hemisphere (McCune & Goward 1995). The first tissue culture from its thallus, collected in Japan in 1985, by the Yamamoto method and separated the mycobiont from its tissue culture. This mycobiont was cultured in Lilly-Barnett liquid-medium (Lilly & Barnett 1951). Harvested and dried mycelia were extracted with chloroform and the extract was chromatographed to provide a main constituent. We isolated the zearalenone derivative, identified the structure by com­ paring NMR data, and established the stereochemistry of the compounds from the ace­ tonide prepared. Moreover, we found this compound to be present in the natural thallus of lichen. Although this zearalenone derivative (1) was the main metabolite of the culture of B. placophyllus, it was a minor metabolite of the lichen thallus. This is the first isolation of a zearalenone derivative from a lichen. Zearalenone derivatives have been isolated from the fungi, especially Fusarium spp. and are known to be fungal hormones and toxins for ani­ mals (Turner & AldridgeI983). They have been proved to be biosynthesized via a polyke­ tide pathway by labeling experiments. Two 4' ,5' -dihydroxyzearalenones were reported in fungi, an unidentified fungus (Ellestad et al. 1978) and Drechslera portulacae (Sugawara et al. 1992). Derivative 1 had a molecular formula CI9H2407 as determined by HREIMS and con­ firmed by l3C NMR and DEPT analysis. The IR spectrum of 1 exhibited hydroxyl l (3460 cm-I) and carbonyl (1740 and 1690cm- ) absorptions. The IH, l3C and 2D NMR data suggested the structure of 1 was 6-(4,5-dihydroxy-lO-methyl-6-oxo-7-undecenyl)-re­ sorcylic acid lactone (CA Index name: (5Z)-3,4,9,10,11 ,12-hexahydro-8,9,16-trihydroxy- 14-methoxy-3-methyl-l H-2-benzoxy-acyclotetradecin-l, 7(8H)-dione). Recently, this com­ pound, namely L-783,277, was reported as a new resorcinolic acid lactone from a Phoma sp. as a specific inhibitor of MEK (Map kinase) (Zhao et al.
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