Pilzpigmente, 41. Naphthochinon‐Farbstoffe aus den Schleimpilzen Trichia floriformis und Metatrichia vesparium (Myxomycetes)

Kopanski, L.; Li, Guang-Ren; Besl, Helmut; Steglich, Wölfgang

doi:10.1002/jlac.198219820913

Cited by 24 publications

(10 citation statements)

References 9 publications

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“…There was no possibility of inverse location of substituents on C-2 and C-3 on the basis of observation of the HMBC correlations ( 3 J) from H-8 to the C-1 carbonyl group and from H-11 to the C-4 carbonyl group. Thus, the structure of lindbladione was concluded to be 2,5,6,7-tetrahydroxy-3-(3-oxo-hex-1-enyl)- [1,4] Several pigments naphthoquinone derivatives in myxomycetes were previously reported, 4,5) and Steglich 1) said that lindbladione (1) was responsible for the color change from dark to red on treatment of the plasmodia of Lindbladia tubulina with mineral acid. However, no spectral data of 1 (except for UV data 6) ) could be found in the literature.…”

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confidence: 97%

Lindbladione and Related Naphthoquinone Pigments from a Myxomycete Lindbladia tubulina

et al. 2002

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The Myxomycetes (true slime molds) are an unusual group of primitive organisms that may be assigned to one of the lowest classes of eukaryotes. As their fruit bodies are very small and it is very difficult to collect much quantity of slime molds, chemical studies on the secondary metabolites of the myxomycetes to date have been limited. Early explorative studies carried out by Steglich 1) and Asakawa's 2)groups have demonstrated that myxomycetes have developed a rather unique secondary metabolism. During our studies on the search for natural products from myxomycetes, 3) we recently investigated a field-collected sample of fruit bodies of Lindbladia tubulina. Here we describe the isolation and structure elucidation of three naphtoquinone pigments, lindbladione (1), 7-methoxylindbladione (2), and 6,7-dimethoxylindbladione (3). The name and structure of lindbladione (1) were found in a symposium proceedings by Steglich's group, 1) but a SciFinder ® search found no description of experimental details or spectral data of compound 1 in the literature. This is the first report on full characterizations of compound 1 and isolation of two new compounds 2 and 3.The fruit bodies of Lindbladia tubulina, collected in Kochi Prefecture, Japan, were extracted with MeOH. The MeOH extract was partitioned between EtOAc and water, and the water-soluble fraction containing pigments was then subjected to chromatography on ODS and/or Sephadex LH-20, followed by further purification with HPLC on ODS to give three pigments (1-3).Lindbladione (1) was obtained as a dark brown solid, and shown to have the molecular formula C 16 H 14 O 7 by the high resolution (HR)-FAB-MS data (m/z 319.0816, [MϩH] ϩ , D Ϫ0.1 mmu). The UV spectrum of 1 showed absorption maxima at 265 and 367 nm, which were shifted to 271 and 379 nm, respectively, with the addition of alkali (NaOH), indicating the presence of phenol group(s). The 13 C-NMR spectrum of 1 (Table 1) H-1 H correlation spectroscopy (COSY) spectrum. Since eight out of ten unsaturation degrees were accounted for by 13 C-NMR data, 1 was inferred to have two rings. The presence of the npropyl group was further corroborated by the heteronuclear multiple bond connectivity (HMBC) correlations (from H 3 -16 to C-15 and C-14, from H 2 -15 to C-16 and C-14, and from H 2 -14 to C-16 and C-15), and this n-propyl group was shown to be attached to the carbonyl group resonating at d C 206.4 (C-13) by the HMBC correlations (from H 2 -14 to C-13 and from H 2 -15 to C-13). In the HMBC spectrum of 1, one olefinic proton at d H 8.07 (H-11) showed long-range connectivities with two carbonyl carbons at d C 206.4 (C-13) and 189.6 (C-4) and also with sp 2 carbons at d C 176.4 (C-2) and 122.5 (C-12), while another olefinic proton at d H 7. 45 (H-12) showed correlations with the carbonyl carbon at d C 206.4 (C-13) and the sp 2 carbon at d C 113.3 (C-3). From these observations, a 3-oxo-hex-1-enyl group was inferred to be at- * To whom correspondence should be addressed. Kochi 780-8039, Japan: and c The Kitasato Ins...

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confidence: 97%

Lindbladione and Related Naphthoquinone Pigments from a Myxomycete Lindbladia tubulina

et al. 2002

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“…Arcyriaflavin C (50) exhibited cell cycle inhibition effect at G1 and G2/M stage at 10 and 100 ng/ml, respectively (Nakatani et al, 2003). Arcyriaflavin C (50) also was found in Metatrichia vesparium (Kopanski et al, 1982). Staurosporinone (also known as K-252) (56) (Fig.…”

Section: Alkaloidsmentioning

confidence: 96%

“…The sporophores of Trichia species, Metatrichia floriformis, and M. vesparium produced trichione (77) and homotrichione (78) (Fig. 19) (Kopanski et al, 1982(Kopanski et al, , 1987. The lindbladione (79) and lindbladiapyrone (80) were isolated from plasmodia of Lindbladia tubulina after treatment with mineral acids (Steglich, 1989).…”

Section: Naphthoquinone Pigmentsmentioning

confidence: 99%

Secondary metabolites of slime molds (myxomycetes)

et al. 2005

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“…The main pigments of Arcyria denudata and A. nutans were found to be the bisindolylmaleimides arcyriarubins A, B, and C (6, 72, 73), and their derived indolopyrrolocarbazoles arcyriaflavins A, B, and C (74-76). 2,57 Arcyriaflavins B 75 and C 76 were also found in Metatrichia vesparium, 58 while a new derivative, arcyriaflavin D 77, was isolated from Dictydiaethalium plumbeum. 2 A large number of additional bisindoles were isolated from Arcyria denudata and A. nutans, including arcyroxepins 78 and 79, arcyriacyanin A 80, dihydroarcyriacyanin A 81, arcyroxocins 82 and 83, dihydroarcyroxocin A 84, arcyroxindole A 85, dihydroarcyriarubin B 86, and arcyriaverdin C 87.…”

Section: Slime Molds (Myxomycetes)mentioning

confidence: 99%

Indolocarbazole natural products: occurrence, biosynthesis, and biological activity

2006

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The indolocarbazole family of natural products, including the biosynthetically related bisindolylmaleimides, is reviewed (with 316 references cited). The isolation of indolocarbazoles from natural sources and the biosynthesis of this class of compounds are thoroughly reviewed, including recent developments in molecular genetics, enzymology and metabolic engineering. The biological activities and underlying modes of action displayed by natural and synthetic indolocarbazoles is also presented, with an emphasis on the development of analogs that have entered clinical trials for its future use against cancer or other diseases.

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Pilzpigmente, 41. Naphthochinon‐Farbstoffe aus den Schleimpilzen Trichia floriformis und Metatrichia vesparium (Myxomycetes)

Cited by 24 publications

References 9 publications

Lindbladione and Related Naphthoquinone Pigments from a Myxomycete <i>Lindbladia tubulina</i>

Lindbladione and Related Naphthoquinone Pigments from a Myxomycete <i>Lindbladia tubulina</i>

Secondary metabolites of slime molds (myxomycetes)

Indolocarbazole natural products: occurrence, biosynthesis, and biological activity

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