8-Methoxygriseorhodin C, a new member of griseorhodin antibiotic.

Yang, Jianxin; Fan, Shaoxia; Pei, Hongsheng; Zhu, Bo; Xu, Wensi; Naganawa, Hiroshi; Hamada, Masa; Takeuchi, Tomio

doi:10.7164/antibiotics.44.1277

Cited by 17 publications

(14 citation statements)

References 6 publications

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“…The IR spectrum indicated the presence of hydroxyl (3357 cm −1 ) and carbonyl (1693 cm −1 ) functional groups. The UV spectrum showed absorption maxima at 307, 352, 368 and 506 nm similar to those of the rubromycin class of antibiotics [29,30,31,32,33,34,35]. …”

Section: Resultsmentioning

confidence: 99%

“…In the 13 C NMR spectrum, all of the 25 carbons assignable to γ-rubromycin core were detected. Comparison with the MS data showed that five carbon atoms were lacking [31,56,57]. The 1 H- 1 H COSY spectrum established only one H-3/H-4 spin system.…”

Section: Resultsmentioning

confidence: 99%

“…These compounds possess a naphthoquinone ring and an isocoumarin ring connected through a 5,6-spiroketal system. The rubromycins α ( 3 ), β ( 4 ), γ ( 5 ) [29,30], δ and 3′-hydroxy-β-rubromycin [31]; the griseorhodins A ( 6 ), C ( 7 ) and G [32]; the DK-7814s A ( 8 ), B and C [33]; purpuromycin ( 9 ) [34] and heliquinomycin ( 10 ) [35] are compounds that are structurally related to the rubromycin family (Figure 1). Rubromycins show inhibitory activity against human telomerase and the reverse transcriptase of human immunodeficiency virus-1 [36].…”

Section: Introductionmentioning

confidence: 99%

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Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.

et al. 2014

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Hyaluromycin (1), a new member of the rubromycin family of antibiotics, was isolated from the culture extract of a marine-derived Streptomyces sp. as a HAase inhibitor on the basis of HAase activity screening. The structure of 1 was elucidated through the interpretation of NMR data for the compound and its 3″-O-methyl derivative in combination with an incorporation experiment with [1,2-13C2]acetate. The compound’s absolute configuration was determined by the comparison of its circular dichroism (CD) spectrum with those of other rubromycins. Hyaluromycin (1) consists of a γ-rubromycin core structure possessing a 2-amino-3-hydroxycyclopent-2-enone (C5N) unit as an amide substituent of the carboxyl function; both structural units have been reported only from actinomycetes. Hyaluromycin (1) displayed approximately 25-fold more potent hyaluronidase inhibitory activity against hyaluronidase than did glycyrrhizin, a known inhibitor of plant origin.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.

et al. 2014

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Section: Introductionmentioning

confidence: 99%

“…5,6,8,9 Notably, 8-methoxygriseorhodin C (4) exhibits potent activity against strains of MRSA (methicillin resistant Staphylococcus aureus, MIC¼0.78 mg/ mL). 6 These natural products also exhibit cytotoxic activity against KB-nasopharynx cells and HLE (human leukocyte elastase). 5,9 In addition to their potent antimicrobial and cytotoxic properties, griseorhodins A (1) (IC 50 12.2 mM) and C (2) (IC 50 5.87 mM) also inhibit human telomerase.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of the carbon skeleton of the griseorhodins

2015

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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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8-Methoxygriseorhodin C, a new member of griseorhodin antibiotic.

Cited by 17 publications

References 6 publications

Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.

Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.

Synthesis of the carbon skeleton of the griseorhodins

Structural and Biosynthetic Investigations of the Rubromycins

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