Macrocarpones, novel metabolites from stromata of Hypoxylon macrocarpum, and new evidence on the chemotaxonomy of Hypoxylon species

Mühlbauer, Andrea; Triebel, Dagmar; Peršoh, Derek; Wollweber, H.; Seip, Stephan; Stadler, Marc

doi:10.1007/s11557-006-0021-z

Cited by 36 publications

(42 citation statements)

References 15 publications

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“…The occurrence of daldinins (1-3) in H. fuscum and the related H. fuscopurpureum (Mu¨hlbauer et al, 2002) provides additional proof that the genera Hypoxylon and Daldinia are closely linked chemotaxonomically, albeit daldinins E and F were so far not found in the latter genus. In contrast, mycelial cultures of these fungi consistently diverge in the production of dihydroisocoumarins by the former and naphthalene and chromone derivatives by the latter genus (Stadler et al, 2001a,c).…”

Section: Resultsmentioning

confidence: 90%

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Cyclic azaphilones daldinins E and F from the ascomycete fungus Hypoxylon fuscum (Xylariaceae)

et al. 2004

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Section: Resultsmentioning

confidence: 90%

“…As shown for Daldinia concentrica, the minor metabolites of these fungi also include highly oxidized binaphthalene derivatives and other aromatic components, as well as various types of small polyketides (Quang et al, 2002b). Studies by Mu¨hlbauer et al (2002) on Hypoxylon fuscum (Pers.:Fr.) Fr.…”

Section: Introductionmentioning

confidence: 99%

Cyclic azaphilones daldinins E and F from the ascomycete fungus Hypoxylon fuscum (Xylariaceae)

et al. 2004

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“…The equipment used for analytical and preparative HPLC has been described in detail [30]. Characteristic retention times (Rt) in these two different gradient systems, along with UV/visual and mass spectra in comparison with external and internal standards served for detection of the metabolites in crude extracts and intermediate products obtained during downstream processing and chromatography.…”

Section: Analytical Hplc Methodsmentioning

confidence: 99%

Novel Analgesic Triglycerides from Cultures of Agaricus macrosporus and Other Basidiomycetes as Selective Inhibitors of Neurolysin

et al. 2005

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The agaricoglycerides are a new class of fungal secondary metabolites that constitute esters of chlorinated 4-hydroxy benzoic acid and glycerol. They are produced in cultures of the edible mushroom, Agaricus macrosporus, and several other basidiomycetes of the genera Agaricus, Hypholoma, Psathyrella and Stropharia. The main active principle, agaricoglyceride A, showed strong activities against neurolysin, a protease involved in the regulation of dynorphin and neurotensin metabolism (IC 50 ϭ200 nM), and even exhibited moderate analgesic in vivo activities in an in vivo model. Agaricoglyceride monoacetates (IC 50 ϭ50 nM) showed even stronger in vitro activities. Several further co-metabolites with weaker or lacking bioactivities were also obtained and characterized. Among those were further agaricoglyceride derivatives, as well as further chlorinated phenol derivatives such as the new compound, agaricic ester. The characteristics of the producer organisms, the isolation of bioactive metabolites from cultures of A. macrosporus, their biological activities, and preliminary results on their occurrence in basidiomycetes, are described. Keywords agaricoglycerides, pain, fermentation, fungi, in vivo activity IntroductionNeurolysin (EC 3.4.24.16) is a zinc metalloprotease that inactivates particular biologically active peptides, such as neurotensin and dynorphin A, by specific cleavage [1]. Whereas the kappa-opioid receptor agonist dynorphin A is a well-known and obvious endogenous pain-relieving peptide, neurotensin has been reported to have analgesic properties when applied centrally in animal models [2]. Therefore, neurolysin inhibitors are likely to enhance the analgesic properties of neurotensin and/or dynorphin A by inhibiting cleavage and inactivation of these peptides. Accordingly, selective inhibitors of neurolysin are likely to emphasize the analgesic effects of the aforementioned peptides, which accumulate if their inactivation is prevented. Hence, neurolysin inhibitors appear useful alternatives to complement or substitute therapy with morphine and other opiates in the treatment of severe pain. However, only few specific inhibitors of this target have hitherto been found. Those Bioanalytical Chemistry, GKSS-Forschungszentrum Geesthacht GmbH, Max-Planck-Str. 1, D-21502 Geesthacht/Germany from microbial crude extracts was carried out, followed by identification of bioactive principles from the most promising hits by bioassay-guided fractionation.The current paper deals with the discovery of a new class of biologically active natural products from cultures of edible mushrooms and other basidiomycetes. Their production, isolation, and biological properties are described here, while their physicochemical parameters, structure elucidation, derivatization and total synthesis have been compiled in a patent application [7]. Further details on their structure elucidation will be reported concurrently. Results and DiscussionIsolation and Biological Activities of Agaricoglycerides (1ϳ4) and Their Co-metabolites...

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“…contains BNT and macrocarpones belonging to chemotype 1. 78 While H. fuscum (chemotype 2) shows some affinities to Daldinia childiae, as revealed from the presence of daldinal A and daldinins (40)(41)(42) besides BNT (43). Species of the fourth chemotype, including, e.g., H. fragiforme (Pers.…”

Section: Chemosystematics Of the Genus Hypoxylonmentioning

confidence: 99%

“…Later, these p-terphenyl compounds exhibited a strong antioxidant activity. [81][82][83] © From Japanese T. aurantiotincta, thelephantins A ¶H (76)(77)(78)(79)(80)(81)(82)(83), together with thelephorin A (84), 81 ganbajunin C (85), 79 ganbajunin E (86), 2-O-methylatrometin (87), 79 atromentin (88), and p-hydroxybenzoic acid, were isolated and characterized from its methanolic extract (Fig. 14).…”

Section: Antioxidative P-terphenyls From Thelephoraceae and Paxillacementioning

confidence: 99%

Inedible mushrooms: a good source of biologically active substances

2006

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ABSTRACT:In the course of our investigation on biologically active substances from inedible mushrooms in Japan, Germany, and Vietnam, we studied the chemical constituents of 22 species belonging to five families: Scutigeraceae, Polyporaceae, Xylariaceae, Thelephoraceae, and Paxillaceae. Various types of chemical substances were purified and characterized based on the modern spectroscopic methods and also on chemical reactions. These metabolites have shown a broad activity in many biological systems, such as antimicrobial, nematicidal, inhibition of NO production, antihuman immunodeficiency virus, tumor necrosis factor-α, and antioxidant activities. These isolated metabolites did not only show interesting activities, but also are employed as chemical markers supported for chemosystematics of these families. This review paper deals with the chemical constituents of 22 species, their biological activities, and also a discussion on chemosystematics.

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Macrocarpones, novel metabolites from stromata of Hypoxylon macrocarpum, and new evidence on the chemotaxonomy of Hypoxylon species

Cited by 36 publications

References 15 publications

Cyclic azaphilones daldinins E and F from the ascomycete fungus Hypoxylon fuscum (Xylariaceae)

Cyclic azaphilones daldinins E and F from the ascomycete fungus Hypoxylon fuscum (Xylariaceae)

Novel Analgesic Triglycerides from Cultures of Agaricus macrosporus and Other Basidiomycetes as Selective Inhibitors of Neurolysin

Inedible mushrooms: a good source of biologically active substances

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