The carbon-13 nuclear magnetic resonance spectra of the antibiotic polyacetylenic nitrile, diatretyne 2 (7-cyanohept-trans-2-ene-4,6-diynoic acid), and related compounds

Hearn, Milton T. W.; Turner, John L.

doi:10.1039/p29760001027

Cited by 21 publications

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“…Compound 6 was identified as (2 E )-decene-4,6,8-triyn-1-ol (dehydromatricarianol), which is a common polyacetylene metabolite produced by basidiomycete fungi [8]. The J value for the coupling between H-2 and H-3 was 16.0 Hz, confirming that the double bond had the E -configuration.…”

Section: Resultsmentioning

confidence: 99%

Isolation and Structural Elucidation of Chondrosterins F–H from the Marine Fungus Chondrostereum sp.

Chen

Xie

et al. 2013

Marine Drugs

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The marine fungus Chondrostereum sp. was collected from a soft coral of the species Sarcophyton tortuosum from the South China Sea. Three new compounds, chondrosterins F–H (1, 4 and 5), together with three known compounds, incarnal (2), arthrosporone (3), and (2E)-decene-4,6,8-triyn-1-ol (6), were isolated. Their structures were elucidated primarily based on NMR and MS data. Incarnal (2) exhibited potent cytotoxic activity against various cancer cell lines.

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Section: Resultsmentioning

confidence: 99%

Isolation and Structural Elucidation of Chondrosterins F–H from the Marine Fungus Chondrostereum sp.

Chen

Xie

et al. 2013

Marine Drugs

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“…Additionally, methyne hydrogen at 5.14 ppm showed correlations with methylene carbon at 24.5 ppm, which is attached to the lactone ring, as evidenced in the 1 H NMR spectrum. Furthermore, 1 H- 13 C long-range correlation of methylene hydrogens H-1' with carbons C-2', C-3', C-4' and C-5', as well as those of the methyl hydrogens H-8' with carbons C-7', C-6', C-5' and C-4', enabled us to identify the polyacetylene system and the unequivocal 13 C NMR chemical shift assignments of carbons C-2' to C-7' ( Table 1). The low 13 C NMR chemical shift at 4.5 ppm observed for methyl group C-8' is due to high shielding effect of the triple bonds.…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, 1 H- 13 C long-range correlation of methylene hydrogens H-1' with carbons C-2', C-3', C-4' and C-5', as well as those of the methyl hydrogens H-8' with carbons C-7', C-6', C-5' and C-4', enabled us to identify the polyacetylene system and the unequivocal 13 C NMR chemical shift assignments of carbons C-2' to C-7' ( Table 1). The low 13 C NMR chemical shift at 4.5 ppm observed for methyl group C-8' is due to high shielding effect of the triple bonds. Therefore, polyacetylene 1 is named as 5-octa-2,4,6-triynyl-furan-2(5H)-one, which was compared with previously published polyine signals.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, polyacetylene 1 is named as 5-octa-2,4,6-triynyl-furan-2(5H)-one, which was compared with previously published polyine signals. [13][14][15][16] More than 750 naturally occurring polyacetylene derivatives belong predominantly to the family Asteraceae, subtribe Heliantheae. They are also present in several other plant families (Apiaceae, Araliaceae), as well as certain basidiomycete fungi.…”

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A new polyacetylene from Vernonia scorpioides (Lam.) Pers. (Asteraceae) and its in vitro antitumoral activity

Buskuhl¹,

Freitas²,

Monachè³

et al. 2009

J. Braz. Chem. Soc.

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A fração diclorometano obtida pelo particionamento do extrato hidroalcoólico obtido das folhas e flores de Vernonia scorpioides (Asteraceae) resultou no isolamento e caracterização de um novo poliacetileno, 5-octa-2,4,6-triinil-furan-2(5H)-ona. A determinação estrutural foi baseada em dados de espectrometria de Ressonância Magnética Nuclear mono e bidimensionais, de Massas e de Infravermelho. Foi investigado o potencial antitumoral e genotóxico do novo poliacetileno e os resultados encontrados sugerem genotoxicidade e citotoxicidade, onde a morte celular ocorreu via apoptose, envolvendo um mecanismo dependente de caspase.The dichloromethane fraction obtained from hydroalcoholic crude extract of leaves and flowers of Vernonia scorpioides (Asteraceae) was investigated, resulting in the isolation and structure elucidation of a new polyacetylene namely 5-octa-2,4,6-triynyl-furan-2(5H)-one. The structure of the isolated compound was determined based on IR, NMR (1D and 2D) and MS spectrometric data. The antitumor potential, including cytotoxicity to tumor cells and genotoxicity, was investigated. The results suggest that apoptotic cell death may have occurred, at least in part, via a caspasedependent mechanism.Keywords: polyacetylene, Vernonia scorpioides, cytotoxicity, genotoxicity, Asteraceae IntroductionThe widespread genus Vernonia (Asteraceae) is characterized by the fact that it produces highly oxygenated sesquiterpene lactones, such as glaucolides and hirsutinolides, some of which are allenic lactones. Many other compounds have also been isolated, such as thiophenes and dithio compounds.1,2 Among the species of Vernonia, cytotoxicity has been described for isolated sesquiterpene lactones from V. cinerea, 3 V. lasiopus, 4 and V. amygdalina. 5 Besides sesquiterpene lactones, polar compounds from water-soluble extracts of Vernonia have also been found to have cytotoxic and imunomodulatory activities such as those from the edible leaves of V. amygdalina 6 and from the roots of V. kotschyana 7 and V. anthelmintica. 8The species Vernonia scorpioides (Lam.) Pers., which is very common in Brazil, is popularly known as "Piracá", "Enxuga" or "Erva-de-São-Simão" and usually grows in poor deforested neotropical soils.9 Alcoholic extract from the fresh leaves is widely used in topical applications, to treat a variety of skin disorders, including chronic wounds, such as ulcers of the lower limbs. In previous studies, chloroform and hexane crude extracts of V. scorpioides leaves have shown fungicide activity, 10 moderate bactericide activity and mild wound healing effects.11 In addition, in mice treated with dichloromethane extract of the leaves, the Ehrlich tumor disappeared completely.12 Therefore, as part of our ongoing search for bioactive compounds of V. scorpioides, a new polyacetylene isolated from the dichloromethane fraction is described, and its antitumor potential, as well as in vitro cytotoxicity to tumor cells and cell death via genotoxicity, are evaluated. Results and DiscussionThe crude ethanol extract of V. s...

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“…Fractions 3, 5 and 7 were further chromatographed on Sephadex LH-20 CC (CHCl 3 –MeOH, 1:1) and purified by preparative HPLC (Pre-HPLC, MeCN–H 2 O) to give three new compounds 1 – 3 and known ones. The known compounds were determined to be ( E )-2-decen-4,6,8-triyn-1-ol ( 4 ) [ 18 ] and 4,6,8-decatriyn-1-ol ( 5 ) [ 19 ].…”

Section: Resultsmentioning

confidence: 99%

A Viscidane Diterpene and Polyacetylenes from Cultures of Hypsizygus marmoreus

Zhang

Dong

et al. 2015

Nat. Prod. Bioprospect.

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Investigation on the cultures of Hypsizygus marmoreus resulted in the isolation of a new viscidane diterpene, 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol (1) and two new polyacetylenes, (E)-10-(1,1-dimethyl-2-propenyloxy)-2-decene-4,6,8-triyn-1-ol (2) and 10-(1,1-dimethyl-2-propenyloxy)deca-4,6,8-triyn-1-ol (3), together with two known polyacetylenes, (E)-2-decen-4,6,8-triyn-1-ol (4) and 4,6,8-decatriyn-1-ol (5). Their structures were elucidated on the basis of extensive spectroscopic studies. Compound 1 is the first finding of viscidane diterpene in mushrooms. Compounds 1, 3 and 5 were tested for cytotoxicity against human tumor cell lines HL-60, SMMC-7721, A-549, MCF-7 and SW-480. None of the compounds showed cytotoxic activity (IC50 > 40 µM).Graphical AbstractElectronic supplementary materialThe online version of this article (doi:10.1007/s13659-015-0058-2) contains supplementary material, which is available to authorized users.

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The carbon-13 nuclear magnetic resonance spectra of the antibiotic polyacetylenic nitrile, diatretyne 2 (7-cyanohept-trans-2-ene-4,6-diynoic acid), and related compounds

Cited by 21 publications

References 0 publications

Isolation and Structural Elucidation of Chondrosterins F–H from the Marine Fungus Chondrostereum sp.

Isolation and Structural Elucidation of Chondrosterins F–H from the Marine Fungus Chondrostereum sp.

A new polyacetylene from Vernonia scorpioides (Lam.) Pers. (Asteraceae) and its in vitro antitumoral activity

A Viscidane Diterpene and Polyacetylenes from Cultures of Hypsizygus marmoreus

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