Angucyclines: Total syntheses, new structures, and biosynthetic studies of an emerging new class of antibiotics

Krohn, Karsten; Rohr, Jürgen

doi:10.1007/bfb0119236

Cited by 182 publications

(153 citation statements)

References 210 publications

(340 reference statements)

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“…To our knowledge, this is the first study reporting that angucyclinone antibiotics trigger activation of apoptotic pathways in tumor cells though many of this antibiotic group revealed antitumor activities (12)(13)(14)(15). The generation of ROS and disruption of mitochrondrial membrane potentials in CHM treatment lead to activation of intrinsic apoptotic pathway, consistent with the study that the action of angucycline antibiotic landomycin E induces KB-3-1 cells to apoptosis (16).…”

Section: Discussionsupporting

confidence: 84%

Induction of apoptosis by the angucyclinone antibiotic chemomicin in human tumor cells

He¹

2009

Oncol Rep

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Abstract. Chemomicin (CHM), an angucyclinone antibiotic extracted from the fermentation broth of Nocardia Mediterranei subsp. Kanglensis 1747-64, shows immunosuppressive activity. However, whether it can inhibit growth of tumor cells remains elusive. In the present study, we show that CHM potently inhibited the proliferations of eight various types of human tumor cell lines and non-cross resistant to multidrugresistant cells. In contrast to action of doxorubicin, the generation of reactive oxygen species was observed as early as 30 min after addition of CHM and its process did not involve iron. The apoptotic cells with chromatin condensation and Annexin V staining markedly increased after the human hepatoma HepG2 was exposed to 1, or 2 μg/ml CHM for 24 h. In the CHM-induced apoptosis, robust increment of p53 expression, activation of caspase-3, -7, -8, -9, cleavage of PARP and the phosphorylation of p38 and JNK, were detected by Western blot analysis. Further investigation revealed the disruption of mitochondrial membrane potential in the cells with CHM incubation for 4 h. Taken together, the results demonstrated that potent proliferation inhibitory effect of CHM on tumor cells is due to activation of the apoptotic pathway.

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Section: Discussionsupporting

confidence: 84%

Induction of apoptosis by the angucyclinone antibiotic chemomicin in human tumor cells

He¹

2009

Oncol Rep

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“…3Ј-OH, 4Ј-OH, 3-OH or 12b-OH [14,15]. Only the 4Ј-OH in the case of galtamycin B (11) and in the case of saquayamycin Z (14) both the 4Ј-OH and 3-OH are involved.…”

Section: Discussionmentioning

confidence: 99%

“…Looking for the molecular mass and formula of the compound by ESI-MS, the result was rather striking (C 73 H 102 O 29 , m/zϭ1465.63952 [MϩNa] ϩ ) and leads to the largest angucycline ever reported [14,15]. Thus we named the metabolite saquayamycin Z (14).…”

Section: Saquayamycin Zmentioning

confidence: 99%

Retymicin, Galtamycin B, Saquayamycin Z and Ribofuranosyllumichrome, Novel Secondary Metabolites from Micromonospora sp. Tü 6368

et al. 2005

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A detailed screening of the secondary metabolite pattern from Micromonospora sp. strain Tü 6368 resulted in the isolation of ten compounds belonging to five different structural families. The structures of the novel compounds 1-(a -ribofuranosyl)-lumichrome (3), retymicin (7), galtamycin B (11) and saquayamycin Z (14) were assigned by spectroscopic methods and chemical transformations. This strain fits our hypothesis that the metabolite analysis of biosynthetically talented strains leads readily to novel compounds.

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“…1,2 These natural products are isolated from the fermentation broth of Actinomycetes; they feature a benz [a]anthraquinone framework with varying degree of insaturation and oxygenation, and display a broad spectrum of biological activities including antitumor, antifungal and antiviral properties. 1,2 Their structural diversity has provided organic chemists with attractive targets for the development of various synthetic methodologies. Until now, most synthetic efforts have been directed toward angucyclines with an aromatic B ring.…”

Section: Introductionmentioning

confidence: 99%

Studies toward the synthesis of angularly-oxygenated angucyclines antibiotics

Lebrasseur¹,

Fan²,

Quideau

2004

Arkivoc

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The [bis(trifluoroacetoxy)]iodobenzene-mediated oxidative dearomatization of 2-alkoxyarenols, followed in situ by trapping of the resulting arenoxenium ions by soft external carbon-based nucleophiles, constitutes a rapid access to highly functionalized naphthoid cyclohexa-2,4-dienones. These synthons can serve as valuable intermediates in the construction of the angularly-oxygenated benz [a]anthraquinone ABCD tetracyclic ring system of aquayamycin-like angucyclinones. This methodology so far has led to the elaboration of five-membered ring analogues of the ABC tricyclic unit of these natural products.

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Angucyclines: Total syntheses, new structures, and biosynthetic studies of an emerging new class of antibiotics

Cited by 182 publications

References 210 publications

Induction of apoptosis by the angucyclinone antibiotic chemomicin in human tumor cells

Induction of apoptosis by the angucyclinone antibiotic chemomicin in human tumor cells

Retymicin, Galtamycin B, Saquayamycin Z and Ribofuranosyllumichrome, Novel Secondary Metabolites from Micromonospora sp. Tü 6368

Studies toward the synthesis of angularly-oxygenated angucyclines antibiotics

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