A Novel Bioactive .DELTA. lactone FD-211 Taxonomy, Isolation and Characterization.

Nozawa, Osamu; Okazaki, Tetsuji; Sakai, Noriyoshi; Komurasaki, Toshi; Hanada, Kazunori; Morimoto, Shigeo; Chen, Zeng-Xiang; He, Bi-Mei; Mizoue, Kazutoshi

doi:10.7164/antibiotics.48.113

Cited by 23 publications

(19 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 4 had molecular formula C 12 H 18 O 4 , which was confirmed by high-resolution electron-impact mass spectrometry. An analysis of PMR and 13 C NMR spectra, 1 H-1 H COSY, HSQC, and HMBC spectra for 4 (Table 4) and a comparison of them with the data for 3 indicated that 4 had the same spiro [4,5]decene skeleton. The differences in chemical shifts of protons in the (S)-and (R)-MTPA esters (4a and 4b) proved the absolute configuration of C-10 as S. The 1D NOE-correlations of HC-10 in 4b with protons of the C-8 methyl and with HC-6D confirmed that these protons and H 3 C-1ccc were axial and that C-8 had the R-configuration in 4.…”

mentioning

confidence: 96%

“…2). Thus, 3 was (5S,8R,10S)-8,10-dihydroxy-2,2,8-trimethyl-1-oxaspiro [4,5]dec-3-en-7-one. Compound 4 had molecular formula C 12 H 18 O 4 , which was confirmed by high-resolution electron-impact mass spectrometry.…”

mentioning

confidence: 98%

“…In continuation of the search for producers of biologically active compounds among marine isolates of microscopic fungi, we determined that the fungus Myceliophthora lutea Costantin [4], which was isolated from marine sediments of Sakhalin Bay (Sea of Okhotsk), synthesizes compounds with antibacterial and cytotoxic activities. Little is known about secondary metabolites from fungi of the genus Myceliophthora although these fungi are often encountered and can be isolated from various substrates [5][6][7][8]. Herein we present data on the isolation and identification of known acremine A (2) [9] and previously unknown compounds called by us isoacremine D (1) and spiroacremines A (3) and B (4).…”

mentioning

confidence: 99%

“…It was shown that isoacremine D exhibited antimicrobial activity against Staphylococcus aureus at a concentration of 200 Pg/mL and cytotoxic activity against embryos of the sea urchin Strongylocentrotus nudus. It was found that 1-4 exhibited cytotoxic activity against sea urchin sperm cells.Keywords: acremines, marine isolate of the fungus Myceliophthora lutea, NMR data, 1-oxaspiro [4,5]decenes.Facultative and obligate marine microscopic fungi are sources of biologically active secondary metabolites [1][2][3]. In continuation of the search for producers of biologically active compounds among marine isolates of microscopic fungi, we determined that the fungus Myceliophthora lutea Costantin [4], which was isolated from marine sediments of Sakhalin Bay (Sea of Okhotsk), synthesizes compounds with antibacterial and cytotoxic activities.…”

mentioning

confidence: 99%

“…Keywords: acremines, marine isolate of the fungus Myceliophthora lutea, NMR data, 1-oxaspiro [4,5]decenes.…”

mentioning

confidence: 99%

See 4 more Smart Citations

Biologically active metabolites from the marine isolate of the fungus Myceliophthora lutea

et al. 2011

View full text Add to dashboard Cite

The new compound isoacremine D (1) and acremine A (2) that was previously unknown for marine organisms were isolated from the marine isolate of the fungus Myceliophthora lutea. It was found that acremine A in CHCl 3 was converted through the action of light into spirocompounds called by us spiroacremines A (3) and B (4). The structures of the compounds were elucidated based on NMR spectroscopic and high-resolution mass spectrometric data. The absolute stereochemistry of the spiroacremines was determined by Mosher's method. It was shown that isoacremine D exhibited antimicrobial activity against Staphylococcus aureus at a concentration of 200 Pg/mL and cytotoxic activity against embryos of the sea urchin Strongylocentrotus nudus. It was found that 1-4 exhibited cytotoxic activity against sea urchin sperm cells.Keywords: acremines, marine isolate of the fungus Myceliophthora lutea, NMR data, 1-oxaspiro [4,5]decenes.Facultative and obligate marine microscopic fungi are sources of biologically active secondary metabolites [1][2][3]. In continuation of the search for producers of biologically active compounds among marine isolates of microscopic fungi, we determined that the fungus Myceliophthora lutea Costantin [4], which was isolated from marine sediments of Sakhalin Bay (Sea of Okhotsk), synthesizes compounds with antibacterial and cytotoxic activities. Little is known about secondary metabolites from fungi of the genus Myceliophthora although these fungi are often encountered and can be isolated from various substrates [5][6][7][8]. Herein we present data on the isolation and identification of known acremine A (2) [9] and previously unknown compounds called by us isoacremine D (1) and spiroacremines A (3) and B (4). The last two compounds are apparently artifacts of the isolation process.The fungus was cultivated on solid medium for 21 d at 22°C in order to produce the metabolites. The dried EtOAc extract of the biomass produced a CHCl 3 extract, separation of which over silica gel and Sephadex LH-20 afforded pure 1 and 2 ( Fig. 1) in addition to 3 and 4, which were not present in the starting total EtOAc extract according to TLC (Fig. 2).The empirical formula of 1 was determined as C 12 H 14 O 3 on the basis of the high-resolution mass spectrum and NMR spectra. The PMR spectrum of 1 contained three 3H-singlets in the range 1.55-2.27 ppm, indicative of three tertiary methyls in its structure. The DEPT and HSQC spectra of 1 confirmed the presence of three methyls (G C 17.6, 31.0, 31.0 ppm) and also indicated that three methine groups were present (G C 101.2, 106.5, 113.4). The remaining six C atoms were classified as quaternary (G C 165.9, 153.0, 150.8, 128.6, 123.1, 69.7). Figure 1 shows the key HMBC-correlations of 1.

show abstract

mentioning

confidence: 96%

mentioning

confidence: 98%

mentioning

confidence: 99%

mentioning

confidence: 99%

“…Keywords: acremines, marine isolate of the fungus Myceliophthora lutea, NMR data, 1-oxaspiro [4,5]decenes.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Biologically active metabolites from the marine isolate of the fungus Myceliophthora lutea

et al. 2011

View full text Add to dashboard Cite

show abstract

Synthesis of Bioactive Side‐Chain Analogues of TAN‐2483B

Somarathne

McCone

Brackovic

et al. 2019

Chemistry An Asian Journal

View full text Add to dashboard Cite

The fungal metabolite TAN‐2483B has a 2,6‐trans‐relationship across the pyran ring of its furo[3,4‐b]pyran‐5‐one core, which has thwarted previous attempts at its synthesis. We have now developed a chiral pool approach to this core and prepared side‐chain analogues of TAN‐2483B. The synthesis relies on ring expansion of a reactive furan ring‐fused dibromocyclopropane and alkynylation of the resulting pyran. The furan ring is constructed by palladium‐catalysed carbonylative lactonisation. Various side‐chains are appended through Wittig‐type chemistry. The prepared analogues showed micromolar activity towards cancer cell lines HL‐60, 1A9 and MCF‐7 and certain human disease‐relevant kinases, including Bruton's tyrosine kinase (Btk).

show abstract

α‐Pyrones and Pyranes from the Plant Pathogenic Fungus Pestalotiopsis scirpina

Li¹,

Wu²,

Ding³

et al. 2012

Eur J Org Chem

View full text Add to dashboard Cite

Three new α‐pyrones, scirpyrones A–C (1–3), and four new pyranes, scirpyranes A–D (4–7), were isolated from solid cultures of the plant pathogen Pestalotiopsis scirpina. Their structures were elucidated primarily by NMR experiments. The absolute configurations of C‐7 and C‐2′ in 1, C‐7 in 2, and C‐6 and C‐7 in 3 were deduced on the basis of circular dichroism (CD) data, whereas those of the secondary alcohols in 4–7 were determined by a modification of Mosher's method. Compound 1 is the first described 6‐(5‐oxotetrahydrofuran‐2‐yl)‐2H‐pyran‐2‐one. Compounds 4–6 showed significant cytotoxicity towards MCF‐7 cells.

show abstract

A Novel Bioactive .DELTA. lactone FD-211 Taxonomy, Isolation and Characterization.

Cited by 23 publications

References 10 publications

Biologically active metabolites from the marine isolate of the fungus Myceliophthora lutea

Biologically active metabolites from the marine isolate of the fungus Myceliophthora lutea

Synthesis of Bioactive Side‐Chain Analogues of TAN‐2483B

α‐Pyrones and Pyranes from the Plant Pathogenic Fungus Pestalotiopsis scirpina

Contact Info

Product

Resources

About