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Bode, Helge B.; Walker, Martina; Zeeck, Axel

doi:10.1002/1099-0690(200009)2000:18<3185::aid-ejoc3185>3.0.co;2-3

Cited by 59 publications

(52 citation statements)

References 11 publications

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“…HMBC correlations to these carbon signals from H-6 and H-7 further confirmed the positioning of these two functional groups. This new compound, given the trivial name palmarumycin CP 17 ( 3 ), has the same overall molecular arrangement as observed in CJ-12,37211 and cladospirone B12 with variations occurring only in the nature of the substituents at C-2 and C-4.…”

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confidence: 71%

Antileishmanial Constituents of the Panamanian Endophytic Fungus Edenia sp.

et al. 2008

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Bioassay-directed fractionation of extracts from the fermentation broth and mycelium of the fungus Edenia sp. led to the isolation of five antileishmanial compounds, preussomerin EG1 (1), palmarumycin CP 2 (2), palmarumycin CP 17 (3), palmarumycin CP 18 (4), and CJ-12,371 (5). Compounds 3 and 4 are new natural products, and this is only the second report of compound 1. The structures of compounds 1−5 were established by spectroscopic analyses (HRMS and NMR). All metabolites caused significant inhibition of the growth of Leishmania donovani in the amastigote form, with IC 50 values of 0.12, 3.93, 1.34, 0.62 and 8.40 μM, respectively. Compounds 1−5 were inactive when tested against Plasmodium falciparum or Trypanasoma cruzi at a concentration of 10 μg/mL, indicating that they have selective activity against Leishmania parasites. Compounds 1−5 showed weak cytotoxicity to Vero cells (IC 50 of 9, 162, 174, 152 and 150 μM, respectively), however, the therapeutic window of these compounds is quite significant with 75, 41, 130, 245 and 18 times (respectively) more anti-leishmanial activity than cytotoxicity.Leishmaniasis is a major tropical disease which largely affects populations those of the developing world. According to the World Health Organization (WHO), leishmaniasis can be classified into four main forms: visceral leishmaniasis (the most dangerous because it can be mortal), cutaneous leishmaniasis (the most common form, which causes a variety of skin lesions), mucocutaneous leishmaniasis (which begins with skin ulcers that can spread, causing tissue destruction, mainly of the nose and mouth), and diffuse cutaneous leishmaniasis (produces chronic skin lesions which are very difficult to cure). 1 Current treatment against leishmaniasis is based on toxic chemotherapeutic compounds, such as sodium stibogluconate and meglumine antimonate, that have several serious side effects which themselves can be fatal to patients. 1,2 Moreover, these agents are expensive and therapies are required for relatively long durations, two characteristics which combine to exclude many patients from having access to any treatment. 1,2 While approximately 600,000 infections are officially reported each year, *Author to whom correspondence should be addressed. (Table 1), interpreted from multiplicity-edited HSQC data as 10 quaternary, two methylene, and eight methine carbons. This spectrum also had resonances for a cyclic ketone (δ C 202.0, C-4) and a naphthalene ring system [δ C 146.3 (C-1'); 110.5 (C-2'); 127.6 (C-3'); 121.9 (C-4'); 134.1 (C-4a'); 121.9 (C-5'); 127.6 (C-6'); 110.5 (C-7'); 146.3 (C-8'); 113.5 (C-8a')]. HMBC correlations supported these assignments as did data comparisons with known compounds 2 and 5. The chemical shift of the two-carbon resonance at δ C 146.3 was consistent with the placement of a dioxin bridge to C-1' and C-8' of the naphthalene core. Finally, the chemical shifts of the signals at δ C 157.2 and 147.6 were consistent with the positioning of phenolic hydroxy groups at C-5 and C-8. HMBC correlati...

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confidence: 71%

Antileishmanial Constituents of the Panamanian Endophytic Fungus Edenia sp.

et al. 2008

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“…F‐24′707, the strain was described as the producer of the antifungal spirobisnaphthalene compound cladospirone bisepoxide ( 37 ) 52–54. A combination of different media and cultivation vessels resulted in the isolation of eight new spirobisnaphthalenes (cladospirones B–I ( 39 – 46 )) and six known members of this class of compounds (palmarumycins C 2 ( 47 ), C 3 ( 48 ), and C 12 ( 49 ), diepoxins σ ( 38 ), η ( 50 ), and δ ( 51 )) in yields of up to 2.6 g L −1 (Scheme ) 55. For this strain the major breakthrough was a solid‐phase cultivation in P flasks with wet oat grains as a single substrate, probably due to the more natural living conditions compared to standard liquid cultures.…”

Section: Fungimentioning

confidence: 94%

Big Effects from Small Changes: Possible Ways to Explore Nature's Chemical Diversity

et al. 2002

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“…BA-10763, to produce new secondary metabolites when grown in different culture media provides additional support for the notion that manipulation of culture conditions of endosymbiotic fungi is a promising approach for the expression of certain silent biosynthetic pathways. 6,9–11 Interestingly, all the isolable compounds encountered were of heptaketide origin and biogenetically related to each other, 21 with differences only in hydroxylation, O -methylation, and substitution of a nitrogen atom for an oxygen atom in the O -heterocyclic ring. In addition, the yield of herbarin ( 8 ) was found to be significantly higher when this fungus was cultured in potato dextrose agar (PDA) (8.3% of extract weight) compared with potato dextrose broth (PDB) (1.7% of extract weight).…”

Section: Resultsmentioning

confidence: 98%

Maximizing Chemical Diversity of Fungal Metabolites: Biogenetically Related Heptaketides of the Endolichenic Fungus Corynespora sp.

et al. 2010

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In an attempt to explore the biosynthetic potential of the endolichenic fungus, Corynespora sp. BA-10763, its metabolite profiles under several culture conditions were investigated. When cultured in potato dextrose agar, it produced three new heptaketides, 9-O-methylscytalol A (1), 7-desmethylherbarin (2), and 8-hydroxyherbarin (3) together with biogenetically related metabolites, scytalol A (4), 8-O-methylfusarubin (5), scorpinone (6), and 8-O-methylbostrycoidin (7) that are new to this organism, and herbarin (8) a metabolite previously encountered in this fungal strain. The use of malt extract agar as the culture medium led to the isolation of 6, 8, 1-hydroxydehydroherbarin (9), and 1-methoxydehydroherbarin (10), that was found to be an artifact formed during the extraction of the culture medium with methanol. The structures of all new compounds were determined by interpretation of their spectroscopic data and chemical interconversions.

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Cited by 59 publications

References 11 publications

Antileishmanial Constituents of the Panamanian Endophytic Fungus Edenia sp.

Antileishmanial Constituents of the Panamanian Endophytic Fungus Edenia sp.

Big Effects from Small Changes: Possible Ways to Explore Nature's Chemical Diversity

Maximizing Chemical Diversity of Fungal Metabolites: Biogenetically Related Heptaketides of the Endolichenic Fungus Corynespora sp.

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