Highly substituted chromanols from cultures of

Achenbach, Hans; Mühlenfeld, Andreas; B, Weber; Brillinger, G. U.

doi:10.1016/s0040-4039(00)85680-4

Cited by 10 publications

(9 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Analysis of the 1 H, 13 C NMR, COSY, HSQC, HMBC, NOESY ( Table 2 , Supplementary Materials, Figures S41–S46 ) and (+)-HRESIMS data of 3 , revealed that it has the same planar structure as that of one of the highly substituted chromanols, isolated from cultures of Aspergillus duricaulis [ 17 ]. However, there were no details of the 1 H and 13 C NMR data of the isolated compounds.…”

Section: Resultsmentioning

confidence: 99%

“…Chromatographic fractionation and further purification of the ethyl acetate extract of N. fennelliae KUFA 0811, yielded a previously undescribed 2,3-dihydro-4 H -chromen-4-one dimer which we have named paecilin E ( 1 ), in addition to the previously described dehydromevalonic acid lactone [ 6 ], byssochlamic acid [ 7 ], β-sitostenone [ 8 ], ergosta-4,6,8 (14), 22-tetraen-3-one [ 9 ], cyathisterone [ 10 ], dankasterone A ( 2 ) [ 11 ], chevalone B [ 12 ], helvolic acid [ 5 ], aszonalenin [ 13 ], secalonic acid A [ 14 ] and fellutanine A [ 13 ]. The ethyl acetate extract of N. tsunodae KUFC 9213 furnished, besides sartorypyrone B and helvolic acid which were previous isolated in our first study [ 5 ], byssochlamic acid [ 7 ], hopan-3β,22-diol ( 5 ) [ 15 ], chevalone C [ 16 ], a chromanol derivative ( 3 ) [ 17 , 18 ], (3β,5α,22 E )-3,5-dihydroxyergosta-7,22-dien-6-one ( 4 ) [ 19 ], the alkaloid harmane ( 7 ) [ 20 ], and lumichrome ( 6 ) [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A New Dihydrochromone Dimer and Other Secondary Metabolites from Cultures of the Marine Sponge-Associated Fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213

et al. 2017

View full text Add to dashboard Cite

A previously unreported dihydrochromone dimer, paecilin E (1), was isolated, together with eleven known compounds: β-sitostenone, ergosta-4,6,8 (14), 22-tetraen-3-one, cyathisterone, byssochlamic acid, dehydromevalonic acid lactone, chevalone B, aszonalenin, dankasterone A (2), helvolic acid, secalonic acid A and fellutanine A, from the culture filtrate extract of the marine sponge-associated fungus Neosartorya fennelliae KUFA 0811. Nine previously reported metabolites, including a chromanol derivative (3), (3β, 5α, 22E), 3,5-dihydroxyergosta-7,22-dien-6-one (4), byssochlamic acid, hopan-3β,22-diol, chevalone C, sartorypyrone B, helvolic acid, lumichrome and the alkaloid harmane were isolated from the culture of the marine-sponge associated fungus Neosartorya tsunodae KUFC 9213. Paecilin E (1), dankasterone A (2), a chromanol derivative (3), (3β, 5α, 22E)-3,5-dihydroxyergosta-7,22-dien-6-one (4), hopan-3β,22-diol (5), lumichrome (6), and harmane (7) were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. While paecilin E (1) was active against S. aureus ATCC 29213 and E. faecalis ATCC 29212, dankastetrone A (2) was only effective against E. faecalis ATCC 29212 and the multidrug-resistant VRE E. faecalis A5/102. Both compounds neither inhibit biofilm mass production in any of the strains at the concentrations tested nor exhibit synergistic association with antibiotics.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A New Dihydrochromone Dimer and Other Secondary Metabolites from Cultures of the Marine Sponge-Associated Fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213

et al. 2017

View full text Add to dashboard Cite

show abstract

“…At higher temperatures the signals at 6 165.7 and 12 1.9 were either very broad or non-observable (16). In the fully coupled spectrum of 3 the expected 'J and coupling constants were observed for C-5 (6 139.3), C-3 (6 97.4), 7-OMe (6 62.6), and 6-Me (6 15.7).…”

mentioning

confidence: 90%

“…However, since only one set of NMR signals was observed (even at -55"C), the lactone 3 must be by far the most predominant structure. A literature search for structurally related compounds revealed, among others, the natural product 4-fomyl-3,5-dihydroxy-7-methoxy-6-methyll(3H)-isobenzofuranone (8), an antibacterial metabolite of Aspergillus duricaulis (16). Considering the structural similarities between metabolites 3 and 8, it was expected that approximate chemical shifts for the 1 3 c NMR of 3 could be calculated from those of 8 using empirical parameters for substituted benzene rings (17).…”

mentioning

confidence: 99%

“…Taking into consideration all of these data the structure of 4-(hydroxymethy1)-7-methoxy-6-methyl-1 (3H)-isobenzofuranone and the trivial name of convolvulol were proposed for 5. The "C NMR chemical shifts of the literature compound 5-hydroxy-4-(hydroxymethyl)-7-methoxy-6-methyl-l(3H)-isobenzofuranone (10) (16) were used in order to calculate "theoretical" chemical shifts for 5. All of the calculated shifts were within 2 ppm of the experimental values ( Table 4).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Phytotoxic metabolites of Phomopsisconvolvulus, a host-specific pathogen of field bindweed

Tsantrizos¹,

Ogilvie²,

Watson³

1992

Can. J. Chem.

View full text Add to dashboard Cite

. Can. J. Chem. 70, 2276Chem. 70, (1992. Phornopsis corzvolvulus is a host-specific pathogen which causes leaf spots and anthracnose lesions in the important perennial weed Corzvolvulus arvensis (field bindweed). Investigation of the n~etabolites produced by the fungus led to the isolation of the known fungal metabolites ergosterol (1) and ergosterol peroxide (2), in addition to four novel phytotoxins: the phthalides convolvulanic acid A (3), convolvulanic acid B (4), convolvulol (5), and the a-pyrone convolvulopyrone (6). The latter compounds were assigned the structures of 4-carboxy-3-hydroxy-7-methoxy-6-methyll(3H)-isobenzofuranone (3), 4-carboxy-7-methoxy-6-methyl-1(3H)-isobenzofuranone (4), 4-(hydroxymethy1)-7-methoxy-6-methyl-l(3H)-isobenzofuranone (5), and 3-[4-methoxy-3-methyl-a-pyron-6-yl]-2-methyl-2-butenoic acid (6) [Traduit par la r6dactionl

show abstract

Stoffwechselprodukte von Mikroorganismen, 35. Mitt. Asperdurin, ein neues antimykotisches Phthalid aus Aspergillus duricaulis

Mühlenfeld

Achenbach

1988

Archiv der Pharmazie

View full text Add to dashboard Cite

Aus Fermentationsextrakten von Aspergillus duricaulis wurde das neue Phthalid Asperdurin (4) isoliert und in seiner Struktur aufgeklart, 4 zeigt ausgepragte antifungische Wirksamkeit. Metabolites of Microorganisms, XXXV'): Asperdurin, a Novel Antimycotic Phthalide from ApergiZZus dru&auZisFrom fermentation extracts of Aspergillus duricaulis the novel phthalide asperdurin (4) was isolated and its structure elucidated. 4 exhibits significant antifungal activity.Kulturen von Aspergillus duricaulis (Tu 679) zeichnen sich durch signifikante antibakterielle Wirkung aus, als deren Trager Cyclopaldsaure (1)2,3) und ihr 5-0-Prenylether (2)49 5 ) erkannt wurden.

show abstract

Highly substituted chromanols from cultures of

Cited by 10 publications

References 3 publications

A New Dihydrochromone Dimer and Other Secondary Metabolites from Cultures of the Marine Sponge-Associated Fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213

A New Dihydrochromone Dimer and Other Secondary Metabolites from Cultures of the Marine Sponge-Associated Fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213

Phytotoxic metabolites of Phomopsisconvolvulus, a host-specific pathogen of field bindweed

Stoffwechselprodukte von Mikroorganismen, 35. Mitt. Asperdurin, ein neues antimykotisches Phthalid aus Aspergillus duricaulis

Contact Info

Product

Resources

About