Metabolites from the Marine-Derived Fungus Chromocleista sp. Isolated from a Deep-Water Sediment Sample Collected in the Gulf of Mexico

Park, Young Chul; Gunasekera, Sarath P.; Lopez, Jose V.; McCarthy, Peter J.; Wright, Amy E.

doi:10.1021/np058113p

Cited by 82 publications

(72 citation statements)

References 23 publications

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“…15) However, PAs and their derivative compounds normally show weak cytotoxicity against various cancer cell lines. 16,6) In accordance with our present work, the cytotoxicity of the isolated PAs is also weak against cancer cell lines such as A549, PC-3, and MCF-7. However, their ability to potentially inhibit NO production suggests that the PA class may serve a beneficial role in other pharmacological applications.…”

Section: Resultssupporting

confidence: 91%

Anti-inflammatory Activity of Pyrrolizidine Alkaloids from the Leaves of Madhuca pasquieri (Dubard)

Hoang

Tran

Lee

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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A novel pyrrolizidine alkaloids, madhumidine A (1), and two known alkaloids, lindelofidine benzoic acid ester (2) and minalobine B (3) were isolated from the leaves of Madhuca pasquieri (Dubard) H. J. LAM. The chemical structures of these alkaloids were established mainly by NMR techniques and mass spectrometry. Their anti-inflammatory activity was evaluated against lipopolysaccharide-induced nitric oxide production in macrophage RAW264.7 cell. In addition, the cytotoxic activity of all isolated compounds was tested against a panel of cancer cell lines.

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Section: Resultssupporting

confidence: 91%

Anti-inflammatory Activity of Pyrrolizidine Alkaloids from the Leaves of Madhuca pasquieri (Dubard)

Hoang

Tran

Lee

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…[14][15] A number of these are marine natural products or their derivatives. 16 Divergent access to 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones appeared achievable in one-pot from 3,5-dimethyl-1H-pyrrole-2-carbaldehyde 5 and the many commercially available substituted phenylacetic acids. We had previously shown that the K + salt of 5 (generated using KH in THF) is smoothly N-acylated by methyl chloroformate, Employing the method with a systematic series of mono-substituted phenylacetic acid derivatives carrying F, Cl, Br, Me, OCH 3 and NO 2 groups at each of the 2ʹ-, 3ʹ -and 4ʹ -positions similarly provided analogues 7-24 (Scheme 1).…”

Section: Synthesis and Preliminarymentioning

confidence: 99%

Synthesis and preliminary evaluation of 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones as angiogenesis inhibitors

Kirk

Bezos

Willis

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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. (2016). Synthesis and preliminary evaluation of 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones as angiogenesis inhibitors. Bioorganic and Medicinal Chemistry Letters, 26 (7), 1813-1816. Synthesis and preliminary evaluation of 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones as angiogenesis inhibitors Abstract Sunitinib (Sutent®) is a receptor tyrosine kinase (RTK) and angiogenesis inhibitor approved for the treatment of renal cell carcinomas, gastrointestinal stromal tumours and pancreatic neuroendocrine tumours. A key structural motif retained throughout medicinal chemistry efforts during sunitinib's development was the indoline-2-one group. In the search for new anti-angiogenic scaffolds, we previously reported that nonindoline-2-one-based derivatives of semaxanib (SU5416, a structurally simpler sunitinib predecessor that underwent Phase III trials) are active as angiogenesis inhibitors, indicating that the group is not essential for activity. This Letter describes the synthesis and structure-activity relationships of another class of nonindoline-2-one angiogenesis inhibitors related to sunitinib/semaxanib; the 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones. A focussed library of 19 analogues was prepared using a simple novel process, wherein commercially available substituted arylacetic acids activated with an amide coupling reagent (HBTU) were reacted with the potassium salt of 3,5-dimethyl-1H-pyrrole-2-carbaldehyde in one-pot. Screening of the library using a cell-based endothelial tube formation assay identified 6 compounds with anti-angiogenesis activity. Two of the compounds were advanced to the more physiologically relevant rat aortic ring assay, where they showed similar inhibitory effects to semaxanib at 10 μg/mL, confirming that 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones represent a new class of angiogenesis inhibitors. Disciplines Medicine and Health Sciences Publication DetailsKirk, N. S., Bezos, A., Willis, A. C., Sudta, P., Suksamrarn, S., Parish, C. R., Ranson, M. & Kelso, M. J. (2016). Synthesis and preliminary evaluation of 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones as angiogenesis inhibitors.

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“…This was supported by the HMBC spectrum ( Figure S2), which showed correlations between 6-OH with C-5, C-6 and C-7. However, the absolute configuration at C-6 was not determined by Marfey's method because the hydroxyproline residue decomposed under acidic conditions (Park et al 2006;Li et al 2011). Thus, the structure of 1 was elucidated as cyclo-(2-hydroxy-Pro-Gly).…”

Section: Resultsmentioning

confidence: 99%

A new minor diketopiperazine from the sponge-derived fungus Simplicillium sp. YZ-11

Yan

Fang

et al. 2015

Natural Product Research

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Metabolites from the Marine-Derived Fungus Chromocleista sp. Isolated from a Deep-Water Sediment Sample Collected in the Gulf of Mexico

Cited by 82 publications

References 23 publications

Anti-inflammatory Activity of Pyrrolizidine Alkaloids from the Leaves of <i>Madhuca pasquieri</i> (Dubard)

Anti-inflammatory Activity of Pyrrolizidine Alkaloids from the Leaves of <i>Madhuca pasquieri</i> (Dubard)

Synthesis and preliminary evaluation of 5,7-dimethyl-2-aryl-3H-pyrrolizin-3-ones as angiogenesis inhibitors

A new minor diketopiperazine from the sponge-derived fungus Simplicillium sp. YZ-11

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