Herboxidiene: a potent phytotoxic polyketide from Streptomyces sp. A7847

Isaac, Barbara G.; Ayer, Stephen W.; Elliott, Robert C.; Stonard, Richard J.

doi:10.1021/jo00052a042

Cited by 66 publications

(56 citation statements)

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“…Herboxidiene (compound 1, Fig. 1A) was isolated from Streptomyces chromofuscus A7847 (ATCC 49982) as a novel polyketide which selectively and effectively controls several annual weed species (10,16). Later, compound 1 was found to effectively reduce plasma cholesterol and possess stronger low-density lipoprotein receptor upregulation activity than tricholstatin A and TMC-49A, representing a new type of anticholesterol molecule (13).…”

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confidence: 99%

Identification of the Herboxidiene Biosynthetic Gene Cluster in Streptomyces chromofuscus ATCC 49982

Shao

Zeng

et al. 2012

Appl Environ Microbiol

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confidence: 99%

Identification of the Herboxidiene Biosynthetic Gene Cluster in Streptomyces chromofuscus ATCC 49982

Shao

Zeng

et al. 2012

Appl Environ Microbiol

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“…Herboxidiene, a microbial secondary metabolite, originally isolated from Streptomyces chromofuscus A7847, has been shown to possess several biological properties including herbicidal, anticholesterol, and antitumor activities (Isaac et al 1992;Koguchi et al 1997;Sakai et al 2002a, b). However, to the best of our knowledge, no evaluation of the antiangiogenic activity of herboxidiene has been reported to date.…”

Section: Discussionmentioning

confidence: 99%

Antiangiogenic activity of herboxidiene via downregulation of vascular endothelial growth factor receptor-2 and hypoxia-inducible factor-1α

et al. 2015

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Antiangiogenesis is now thought of as one of the most important approaches for anticancer therapy. In this study, we determined the antiangiogenic property of herboxidiene, a polyketide natural product. Herboxidiene effectively inhibited the proliferation of human umbilical vein endothelial cells (HUVECs) at concentrations not exhibiting cytotoxicity. Furthermore, the natural product significantly suppressed vascular endothelial growth factor-induced invasion and tube formation in HUVECs as well as neovascularization of the chorioallantoic membrane in developing chick embryos. We also identified an association between the antiangiogenic activity of herboxidiene and the downregulation of both the phosphorylation of VEGF receptor 2 (KDR/Flk-1) and the expression of hypoxia-inducible factor-1α at the transcriptional level. These results suggest that herboxidiene functions as a potential antiangiogenic agent and may be applicable for anticancer therapy by targeting tumor angiogenesis.

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“…It displayed potent and selective phytotoxicity against a myriad of broad leaf weeds over coplanted wheat. 151 In 2002, Yoshida isolated six structurally related compounds, among them GEX1A. 152, 153 GEX1A was identified as herboxidiene ( 50 ).…”

Section: Introductionmentioning

confidence: 99%

Achmatowicz reaction and its application in the syntheses of bioactive molecules

Ghosh

Brindisi

2016

RSC Adv.

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Substituted pyranones and tetrahydropyrans are structural subunits of many bioactive natural products. Considerable efforts are devoted toward the chemical synthesis of these natural products due to their therapeutic potential as well as low natural abundance. These embedded pyranones and tetrahydropyran structural motifs have been the subject of synthetic interest over the years. While there are methods available for the syntheses of these subunits, there are issues related to regio and stereochemical outcomes, as well as versatility and compatibility of reaction conditions and functional group tolerance. The Achmatowicz reaction, an oxidative ring enlargement of furyl alcohol, was developed in the 1970s. The reaction provides a unique entry to a variety of pyranone derivatives from functionalized furanyl alcohols. These pyranones provide convenient access to substituted tetrahydropyran derivatives. This review outlines general approaches to the synthesis of tetrahydropyrans, covering general mechanistic aspects of the Achmatowicz reaction or rearrangement with an overview of the reagents utilized for the Achmatowicz reaction. The review then focuses on the synthesis of functionalized tetrahydropyrans and pyranones and their applications in the synthesis of natural products and medicinal agents.

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Herboxidiene: a potent phytotoxic polyketide from Streptomyces sp. A7847

Cited by 66 publications

References 1 publication

Identification of the Herboxidiene Biosynthetic Gene Cluster in Streptomyces chromofuscus ATCC 49982

Identification of the Herboxidiene Biosynthetic Gene Cluster in Streptomyces chromofuscus ATCC 49982

Antiangiogenic activity of herboxidiene via downregulation of vascular endothelial growth factor receptor-2 and hypoxia-inducible factor-1α

Achmatowicz reaction and its application in the syntheses of bioactive molecules

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