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Novel Analgesic Triglycerides from Cultures of Agaricus Macrosporus

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Novel Analgesic Triglycerides from Cultures of Agaricus Macrosporus J. Antibiot. 58(12): 775–786, 2005 THE JOURNAL OF ORIGINAL ARTICLE [_ ANTIBIOTICSJ Novel Analgesic Triglycerides from Cultures of Agaricus macrosporus and Other Basidiomycetes as Selective Inhibitors of Neurolysin Marc Stadler, Veronika Hellwig†, Anke Mayer-Bartschmid, Dirk Denzer, Burkhard Wiese, Nils Burkhardt Received: July 4, 2005 / Accepted: November 22, 2005 © Japan Antibiotics Research Association Abstract The agaricoglycerides are a new class of fungal secondary metabolites that constitute esters of Introduction chlorinated 4-hydroxy benzoic acid and glycerol. They are produced in cultures of the edible mushroom, Agaricus Neurolysin (EC 3.4.24.16) is a zinc metalloprotease that macrosporus, and several other basidiomycetes of the inactivates particular biologically active peptides, such as genera Agaricus, Hypholoma, Psathyrella and Stropharia. neurotensin and dynorphin A, by specific cleavage [1]. The main active principle, agaricoglyceride A, showed Whereas the kappa-opioid receptor agonist dynorphin A is strong activities against neurolysin, a protease involved in a well-known and obvious endogenous pain-relieving the regulation of dynorphin and neurotensin metabolism peptide, neurotensin has been reported to have analgesic ϭ (IC50 200 nM), and even exhibited moderate analgesic in properties when applied centrally in animal models [2]. vivo activities in an in vivo model. Agaricoglyceride Therefore, neurolysin inhibitors are likely to enhance the ϭ monoacetates (IC50 50 nM) showed even stronger in vitro analgesic properties of neurotensin and/or dynorphin A by activities. Several further co-metabolites with weaker or inhibiting cleavage and inactivation of these peptides. lacking bioactivities were also obtained and characterized. Accordingly, selective inhibitors of neurolysin are likely to Among those were further agaricoglyceride derivatives, as emphasize the analgesic effects of the aforementioned well as further chlorinated phenol derivatives such as the peptides, which accumulate if their inactivation is new compound, agaricic ester. The characteristics of the prevented. Hence, neurolysin inhibitors appear useful producer organisms, the isolation of bioactive metabolites alternatives to complement or substitute therapy with from cultures of A. macrosporus, their biological activities, morphine and other opiates in the treatment of severe pain. and preliminary results on their occurrence in However, only few specific inhibitors of this target have basidiomycetes, are described. hitherto been found. Those mostly constituted peptides [3ϳ5], and otherwise there are few examples for non- Keywords agaricoglycerides, pain, fermentation, fungi, peptidic inhibitors of this enzyme, such as particular in vivo activity hydroxamates [6]. Therefore, a high throughput screening (HTS) for novel selective non-peptidic neurolysin inhibitors M. Stadler (Corresponding author),V. Hellwig, A. Mayer- B. Wiese: Bayer CropScience AG, RD-R-Discovery Chemistry, Bartschmid, D. Denzer, N. Burkhardt: Bayer Health Care, Monheim, Germany. Pharma Division, Research Center Wuppertal, Bldg. 0452, † Present address: Institute for Coastal Research, Marine P. O.B. 10 17 09, D-42096 Wuppertal, Germany. Bioanalytical Chemistry, GKSS-Forschungszentrum Geesthacht E-mail: [email protected] GmbH, Max-Planck-Str. 1, D-21502 Geesthacht/Germany 776 OH HO~ oJ:,o & OH c1 I _,;;;, o~o I _,;;;, c1 Cl~ ~ Cl 0 0 0 0 1: (R = Cl); 2: (R = H) 3: (R = H); 4: (R = Acetyl) OH ol O Cl -;:;--- Cl o I c1 I _,;;;, o~ o I _,;;;, c1 + c1 I _,;;;, o~ o I _,;;;, c1 0 0 0 0 1a 1b -0~ 0poH Cl Cl Cl Cl Cl Cl 0-------- 0-......_ 0 5 6 7 Fig. 1 Chemical structures of metabolites isolated from Agaricus macrosporus. 1: Agaricoglyceride A; 2: Agaricoglyceride B; 1a/b: Monoacetyl-agaricoglycerides A (isolated as inseparable mixture); 3: Agaricoglyceride C; 4: Agaricoglyceride D; 5: DCMB; 6: 3,5-Dichloro-4-anisic acid; 7: Agaricic ester. from microbial crude extracts was carried out, followed by Results and Discussion identification of bioactive principles from the most promising hits by bioassay-guided fractionation. Isolation and Biological Activities of Agaricoglycerides The current paper deals with the discovery of a new class (1ϳ4) and Their Co-metabolites (5ϳ7) of biologically active natural products from cultures of Agaricoglyceride A (1) was identified as the main active edible mushrooms and other basidiomycetes. Their principle of the crude extract of A. macrosporus and later production, isolation, and biological properties are produced in gram scale as described in the Experimental described here, while their physicochemical parameters, for intensified biological evaluation, including a structure elucidation, derivatization and total synthesis have derivatization and in vivo studies. Chromatographic been compiled in a patent application [7]. Further details separation by preparative HPLC (Fig. 2) yielded several on their structure elucidation will be reported concurrently. further congeners (structures see Fig. 1), of which only the mixture of monoacetyl agaricoglycerides (1a/b) was more active than the parent compound (Table 1). Since the monoacetyl derivatives of compound 1 were detected in methanolic crude extracts prepared from growing cultures, they constitute original natural products rather than 777 Mycelial extract (56 g) Flash chromatography C1B water:ACN 50% ACN 80% ACN Intermediate product 1 a Intermediate product 1b 17 g 32 g HPLC (MZ Kromasil CB) HPLC (MZ Kromasif CB) 0. 1% TFA:ACN gradient 0.1% TFA:ACN gradient /System BJ /System BJ DCMB (5) Agaricic ester (7) Intermediate product 2 Intermediate product 4 280 mg 19 mg 3.2g 87mg 3,5-Dichloroanisic acid (6) HPLC Merck UchrospherC1B HPLC Waters Symmetry 240 mg 0. 1% TFA:ACN gradient 0.1% TFA:ACN 1:1 (System A) (SystemD) Agaricoglyceride A (1) M onoacetyl-agarico­ Agaricoglyceride D (4) 1.5 g glycerides (1a/1b) 7 mg 5mg Intermediate product 3 332mg HPLC Waters Symmetry 0.1% TFA:ACN gradient /SystemC) Agaricoglyceride C (3) Agaricoglyceride B (2) 8 mg 1.7 mg Agaricoglyceride A (1) 82 mg Fig. 2 Scheme illustrating the isolation of secondary metabolites from the mycelial crude extract of Agaricus macrosporus (200 liters scale; Q6/2 medium) isolation artifacts. Their biological activities were Table 1 Biological activities of compounds 1ϳ7 against confirmed for the mixture 1a/b , which were later on also neurolysin and ACE prepared using the synthetic scheme depicted in Fig. 3. IC [mM] IC [mM] Synthetic agaricoglyceride A (1) was also obtained via this Compound 50 50 route and showed identical biological activities to that of against neurolysin against ACE the natural product [7]. 1 0.2 Ͼ10 Agaricoglyceride B (2) still showed activities in the 1a,b 0.05 Ͼ10 micromolar range. However, despite differing in only one 2 1 Ͼ10 chlorine substitution from the main component, its activity 3 Ͼ10 Ͼ10 was significantly lower than that of agaricoglyceride A (1). 4 Ͼ10 Ͼ10 Agaricoglycerides C and D (3, 4), as well as the known co- 5 Ͼ10 Ͼ10 metabolites (5 and 6) and the novel agaricic ester (7) were 6 Ͼ10 Ͼ10 found devoid of activity against neurolysin up to 10 mM. 7 Ͼ10 Ͼ10 In vivo Activity As demonstrated in Fig. 4, agaricoglyceride A monoacetate in about the same concentration range, and morphine (1b) showed significant in vivo activity in the cold plate caused a similar effect, albeit already at a dosage of model at 10 mg/kg. Agaricoglyceride A (1) was also active 3 mg/kg. The results suggest a great analgesic potential for 778 R1 R2 OH 5 eq R1COCI OJ__O Lindlar catalyst OJ-.:0 HO~OH R1nO~OnR1 R2nO~OnR2 NEt / H / THF-MeOH, 3 0 0 2 0 0 DCM, rt, 4d rt, 1d 2 eq R1COCI, NEt3 j / DCM, rt, 4d R3 R3 OH 5 eq R3COCI O.J.-:0 Lindlar catalyst O.J.-:0 R1nO~OnR1 R17(0~0nR1 R27(0~0nR2 0 0 NEt3 / H2/ THF-MeOH, DCM, rt, 4d 0 0 rt, 1d 0 0 Cl Cl Cl 60Bn OOH _ 60Ac R1 = R = R3- I ob ,,- Cl 2 ,,- Cl ,,- Cl Fig. 3 General scheme for synthetic preparation of agaricoglycerides. For detailed descriptions, see Ref. 7. Decreasing Temperature Cold-Plate in Rats Effects of Agaricoglyceride monoacetate 30 minutes after application 12 T 10 ' ::;; w U) .. 9.4 i 8 .o - T E 8.0 :, * 6 .a.- ti!., I Q. .,E 5.4 • Mean Terrperature ,_ 4. a. - - 2 .0->--- .....__ * Krusltal- Wallisand Dunnett Test p< 0. 05 o.0 n =12 NaCl+ 4% DMSO, 10% 1 rrg/l<g i.p. 3rrg/l<g i. p. 10rrg/ l<g i.p. Ethanol, 20% Sol utol i .p. n=11 n=12 n=11 n=11 Fig. 4 In vivo analgesic activities of agaricoglyceride A monoacetate (1a/b). agaricoglycerides, albeit their biological activities remain to adrenergic, glutamate, gamma aminobutyric acid and other be optimized and these in vivo effects confirmed in other receptors was noted up to concentrations of 10 mM. animal models. Interestingly, the agaricoglycerides were Furthermore, the pure agaricoglycerides neither showed devoid of activity in a large number of biochemical and cytotoxic nor modulatory effects in various reporter cell cellular assays, emphasizing their selectivity towards assays that were conducted concurrently up to neurolysin. Enzyme classes that were not inhibited by concentrations of 10 mM. agaricoglycerides included, e.g., trypsin, chymotrypsin, phosphodiesterases 1ϳ6, caspases 1ϳ7, cathepsins BϳD, HPLC Analyses during Fermentation and Optimization several protein phosphatases, serine/threonin and thyrosine of Culture Media kinases, and matrix metalloproteases. No modulation of The agaricoglycerides were detected in various 779 Table 2 Producers of agaricoglycerides, origin, taxonomy, and (in brackets) maximal production rates for agaricoglyceride A in Q6/2 medium at 300 hours of fermentation. Aside from strains DSM 14593 and DSM 14594, which were subjected to preparative work, all other producers were identified by analytical HPLC of their crude extracts only Species Strain Origin/collector/isolator [production rates] Agaricus arvensis Schaeff.:Fr. MUCL 35030 leg. C. Decock, 1992, from Warcoing (Belgium)** [2.4 mg/liter] A. bisporus (Lange) Imbach* DSM 14900 leg. H. Müller, September 1991, from spores of cultivated mushrooms, Wuppertal (Germany) [4.9 mg/liter] A.
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