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Alresly, Z.; Lindequist, U.; Lalk, M.; Porzel, A.; Arnold, N.; Wessjohann, L. A.; Bioactive Triterpenes from the Fungus Piptoporus betulinus Rec. Nat. Prod. 10, 103-108, (2016)
Phytochemical investigation of the ethyl acetate extract of the fruiting bodies from the basidiomycete Piptoporus betulinus led to the isolation of a new bioactive lanostane triterpene identified as 3 b -acetoxy-16-hydroxy-24-oxo-5α-lanosta-8- ene-21-oic acid (1). In addition, ten known triterpenes, polyporenic acid A (5), polyporenic acid C (4), three derivatives of polyporenic acid A (8, 10, 11), betulinic acid (3), betulin (2), ergosterol peroxide (6), 9,11-dehydroergosterol peroxide (7), and fomefficinic acid (9), were also isolated from the fungus. All isolated compounds were tested for antimicrobial activity against some Gram-positive and Gram-negative bacteria as well as against a fungal strain. The new triterpene and some of the other compounds showed antimicrobial activity against Gram-positive bacteria.
Tanemossu Fobofou, S. A.; Franke, K.; Sanna, G.; Porzel, A.; Bullita, E.; La Colla, P.; Wessjohann, L. A.; Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum Bioorg. Med. Chem. 23, 6327-6334, (2015) DOI: 10.1016/j.bmc.2015.08.028
From the ethno-medicinally used leaves of Hypericum roeperianum we isolated a new tricyclic acylphloroglucinol (1), a new tetracyclic acylphloroglucinol (2), and a new prenylated bicyclic acylphloroglucinol (3) together with four known prenylated (4–7) and three known tetracyclic acylphloroglucinol derivatives (8–10). Structure elucidation was based on UV, IR, [α]D25, 1D- and 2D-NMR experiments. Furthermore, empetrifranzinans A (8) and C (9) were synthesized regioselectively in only two steps. The isolated compounds were evaluated for their cytotoxicity against PC-3 and HT-29 cancer cell lines as well as antibacterial and anthelmintic activities. They were also tested in cell-based assays for cytotoxicity against MT-4 cells and for anti-HIV activity in infected MT-4 cells. Significant anthelmintic activity against Caenorhabditis elegans was exhibited by compound 7 (3-geranyl-1-(2′-methylbutanoyl)-phloroglucinol), which might provide a new lead.
Pando, O.; Stark, S.; Denkert, A.; Porzel, A.; Preusentanz, R.; Wessjohann, L. A.; The Multiple Multicomponent Approach to Natural Product Mimics: Tubugis, N-Substituted Anticancer Peptides with Picomolar Activity J. Am. Chem. Soc. 133, 7692-7695, (2011) DOI: 10.1021/ja2022027
The synthesis of a new generation of highly cytotoxic tubulysin analogues (i.e., tubugis) is described. In the key step, the rare, unstable, and synthetically difficult to introduce tertiary amide–N,O-acetal moiety required for high potency in natural tubulysins is replaced by a dipeptoid element formed in an Ugi four-component reaction. Two of the four components required are themselves produced by other multicomponent reactions (MCRs). Thus, the tubugis represent the first examples of the synthesis of natural-product-inspired compounds using three intertwined isonitrile MCRs.
Ramos Leal, I. C.; Netto dos Santos, K. R.; Itabaiana Júnior, I.; Ceva Antunes, O. A.; Porzel, A.; Wessjohann, L.; Machado Kuster, R.; Ceanothane and Lupane Type Triterpenes from Zizyphus joazeiro – An Anti-Staphylococcal Evaluation Planta Med. 76, 47-52, (2010) DOI: 10.1055/s-0029-1185947
The present paper describes the phytochemical and anti-staphylococcal activity investigation of the dichloromethane extract of the Brazilian plant Zizyphus joazeiro Mart. The purification steps were guided by bioassays against 17 bacterial strains of clinical sources, including methicillin-resistant (MRSA) and ‐sensitive (MSSA) Staphylococcus aureus as well as MRSA (ATCC 33591) and MSSA (ATCC 29213) reference strains. One of the more active fractions is comprised of three lupane-type triterpenes, the methylbetulinate (1) as well as the known betulinic (2) and alphitolic (3) acids and, for the first time in the Z. joazeiro, two ceanothane type triterpenes, the methylceanothate (4) and the epigouanic acid A (5). These substances were assayed against one clinical (PVL+) and the reference strains of S. aureus as well as the ATTC 12228 strain of S. epidermidis, in concentrations that varied from 128 to 0.125 µg/mL in order to establish the minimum inhibitory concentration (MIC) of the drugs. The minimum bactericide concentration (MBC) was also evaluated to distinguish the bactericidal from bacteriostatic activity of the crude fractions and single compounds. Compounds 3 and 4 possess the highest antibacterial activity. They inhibit all bacteria tested at 32 µg/mL and 16 µg/mL, respectively, while the other compounds showed no activity at 128 µg/mL. In contrast to single compounds, the triterpenoid fraction showed bactericidal activity at 256 µg/mL. Structural elucidations are based on 1D and 2D NMR spectroscopy as well as HR‐FT‐ICR‐MS experiments.
Geissler, T.; Brandt, W.; Porzel, A.; Schlenzig, D.; Kehlen, A.; Wessjohann, L.; Arnold, N.; Acetylcholinesterase inhibitors from the toadstool Cortinarius infractus Bioorg. Med. Chem. 18, 2173-2177, (2010) DOI: 10.1016/j.bmc.2010.01.074
Inhibition of acetylcholinesterase (AChE) and therefore prevention of acetylcholine degradation is one of the most accepted therapy opportunities for Alzheimer´s disease (AD), today. Due to lack of selectivity of AChE inhibitor drugs on the market, AD-patients suffer from side effects like nausea or vomiting. In the present study the isolation of two alkaloids, infractopicrin (1) and 10-hydroxy-infractopicrin (2), from Cortinarius infractus Berk. (Cortinariaceae) is presented. Both compounds show AChE-inhibiting activity and possess a higher selectivity than galanthamine. Docking studies show that lacking π–π-interactions in butyrylcholinesterase (BChE) are responsible for selectivity. Studies on other AD pathology related targets show an inhibitory effect of both compounds on self-aggregation of Aβ-peptides but not on AChE induced Aβ-peptide aggregation. Low cytotoxicity as well as calculated pharmacokinetic data suggest that the natural products could be useful candidates for further drug development.
Teichert, A.; Lübken, T.; Schmidt, J.; Porzel, A.; Arnold, N.; Wessjohann, L.; Unusual Bioactive 4-Oxo-2-alkenoic Fatty Acids from Hygrophorus eburneus Z. Naturforsch. B 60, 25-32, (2005) DOI: 10.1515/znb-2005-0105
From fruit bodies of the basidiomycete Hygrophorus eburneus (Bull.: Fr.) Fr. (Tricholomataceae) eight fatty acids (C16, C18) with γ -oxocrotonate partial structure could be isolated. Initial tests demonstrate their bactericidal and fungicidal activity. The structures of (2E,9E)-4-oxooctadeca- 2,9,17-trienoic acid (1), (2E,11Z)-4-oxooctadeca-2,11,17-trienoic acid (2), (E)-4-oxohexadeca-2,15- dienoic acid (3), (E)-4-oxooctadeca-2,17-dienoic acid (4), (2E,9E)-4-oxooctadeca-2,9-dienoic acid (5), (2E,11Z)-4-oxooctadeca-2,11-dienoic acid (6), (E)-4-oxohexadec-2-enoic acid (7), and (E)-4- oxooctadec-2-enoic acid (8) were elucidated on the basis of their spectroscopic data.
Lübken, T.; Schmidt, J.; Porzel, A.; Arnold, N.; Wessjohann, L.; Hygrophorones A–G: fungicidal cyclopentenones from Hygrophorus species (Basidiomycetes) Phytochemistry 65, 1061-1071, (2004) DOI: 10.1016/j.phytochem.2004.01.023
Twenty new 5-(hydroxyalkyl)-2-cyclopentenone derivatives (hygrophorones) could be isolated from Hygrophorus latitabundus, H. olivaceoalbus, H. persoonii, and H. pustulatus. Their fungicidal activity was exemplarily tested. The hygrophorones have structural similarities to the antibiotic pentenomycin. Chemically, hygrophorones are 2-cyclopentenones with hydroxy or acetoxy substituents at C-4 and/or C-5. An odd-numbered 1′ oxidized alkyl chain (C11, C13, C15, or C17) is attached at C-5. In addition, from H. persoonii the new γ-butyrolactone derivative [5-(E)-2-hydroxytetradexylidene-5H-furan-2-one] could be isolated. Some hygrophorones are responsible for the color reaction of the stipes of these fungi upon treatment with potassium hydroxide solution. Structural elucidations are based on 1D (1H, 13C) and 2D (COSY, NOESY, HSQC, HMBC) NMR spectroscopic analyses as well as HR-FT-ICR-MS investigations.A series of new cyclopentenone derivatives and butyrolactones with antifungical activity could be isolated from fruit bodies of the basidiomyceteous genus Hygrophorus. Structural elucidations are based on 1D and 2D NMR spectroscopic analyses as well as HR-FT-ICR-MS investigations.
