Antibiotika aus actinomyceten. zur chemischen konstitution des antibiotikums griseorhodin A

Eckardt, K.; Tresselt, D.; Ihn, W.

doi:10.1016/0040-4020(78)80022-2

Cited by 20 publications

(2 citation statements)

References 9 publications

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“…Purpuromycin , ( 1 , Figure ), a member of the rubromycin family of bisbenzannulated spiroketals, is a highly functionalized and oxygenated molecule. This group of natural products, (Figure ) also includes the rubromycins, − griseorhodins, − and heliquinomycin, − and has attracted considerable attention due to their structural complexity and significant biological profiles. For example, antibacterial 31-36 and antifungal 31-35 properties have been reported leading to clinical use. , In addition, their activities against reverse transcriptase, , DNA helicase, and human telomerase 39 indicate that this unique structural type has potential as anti-retroviral or anti-cancer agents.…”

Section: Introductionmentioning

confidence: 99%

A Concise Synthesis of the Naphthalene Portion of Purpuromycin

2008

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A concise synthesis of naphthalene compounds for incorporation into a synthetic sequence for the rubromycin family of natural products is presented. These highly substituted naphthalenes are generated in seven and nine steps, respectively, from 2,4,5-trimethoxybenzaldehyde. Three ring-forming methods were explored and the controlled oxygenation of different positions was investigated to yield differentially substituted/protected systems. Key steps to the final products include a Stobbe condensation to form the ring system and a novel series of regioselective oxidations to introduce the required oxygen functionality. These naphthalene products incorporate orthogonal protecting groups and are suitable for combination with a variety of coupling partners.

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Section: Introductionmentioning

confidence: 99%

A Concise Synthesis of the Naphthalene Portion of Purpuromycin

2008

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“…Based on the above, the structure of 1 was thus establised, on the basis of the analysis of 1D and 2D NMR spectroscopic experiments, as (2E,4Z,6E,8Z)-5,9-dimethyl-10-oxododeca-2,4,6,8-tetraenoic acid. Furthermore, the known compounds 2 and 3 were identified by comparison of their spectroscopic data with those in the literature as benzodipyran and 7-hydroxy-2-(2-hydroxypropyl)-5-methylchromone [6][7][8].…”

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confidence: 99%

A New Polyunsaturated Acid from the Marine-Derived Streptomyces violans (No. HTTA-F04129)

et al. 2014

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One new polyunsaturated acid (1), together with two known compounds, benzodipyran (2) and 7-hydroxy-2-(2-hydroxypropyl)-5-methylchromone (3) were isolated from the fermentation broth of the marine Streptomyces violans (strain HTTA-F04129). Their structures were elucidated on the basis of 1D and 2D NMR, HR-FAB-MS spectra, and IR spectra. Bioassay results showed that compound 1 possessed significant selective antitumor activity against A2780 cell line in vitro with IC 50 value 4.36 PM and antibacterial activity against E. coli with MIC value of 25 Pg/mL.

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Structural and Biosynthetic Investigations of the Rubromycins

et al. 2000

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The structure of the known secondary metabolite β‐rubromycin was corrected, based on spectroscopic and chemical investigations, from o‐quinone 1 to p‐quinone 6. By feeding [U‐13C3]malonic acid to the rubromycin‐producing strain, Streptomyces sp. A1, the polyketide origin of the skeleton was verified, but the identity of the starter unit and the folding mechanism of the polyketide chain are still unclear. From the culture broth of the strain A1, in addition to 6, the co‐metabolites γ‐rubromycin (3), δ‐rubromycin (4) and 3′‐hydroxy‐β‐rubromycin (7) were isolated. Their structures were determined or confirmed by detailed spectroscopic analysis. The rubromycins inhibit HIV‐1 reverse transcriptase (RT) and are cytostatically active against different tumor cell lines.

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Antibiotika aus actinomyceten. zur chemischen konstitution des antibiotikums griseorhodin A

Cited by 20 publications

References 9 publications

A Concise Synthesis of the Naphthalene Portion of Purpuromycin

A Concise Synthesis of the Naphthalene Portion of Purpuromycin

A New Polyunsaturated Acid from the Marine-Derived Streptomyces violans (No. HTTA-F04129)

Structural and Biosynthetic Investigations of the Rubromycins

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