Photochemical isomers of tropolone alkaloids

Chommadov, B.; Yusupov, M. K.; Sadykov, A. S.

doi:10.1007/bf00607526

Cited by 5 publications

(8 citation statements)

References 48 publications

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“…All of these antitumor activities are related to ion chelation in the active site of ribonucleotide reductase. Colchicine and its structural analogues are of special interest as vascular targeting and apoptosisinducing agents, and its chemical synthesis as a great challenge and prominent target has been explored [7,51]. A series of O-alkylated tropolones and related -ketohydroxy compounds were synthesized with an expected ribonucleotide reductase inhibition and cytotoxicity against some cancer cell lines but no antitubulin activity [52].…”

Section: Chemical Synthesis and Modification Of Troponoidsmentioning

confidence: 99%

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Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Zhao

2007

CMC

107

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Tropone or tropolone and its derivatives (here together called troponoids) belong to a family of natural products with a seven-membered aromatic ring and various side groups. They are mainly synthesized by plants and fungi, and most troponoids play roles of antibacterial defenses in these organisms. With an increasingly severe situation of antibiotic resistant bacteria, as well as a requirement for antifungal medicines, troponoids have attracted extensive studies since they have powerful antibacterial and antifungal activity, particularly against antibiotic-resistant bacteria. In addition, many other biological activities such as antiviral, antitumor, antioxidant, anti-inflammatory, insecticidal, or enzyme inhibitor activities are associated with troponoids. After extensive studies in the 1960s-70s, interests in natural troponoids dedclined. However, chemical and biomedical studies on troponoids bloom again from the 1990s. To date great progress has been made with troponoid study in terms of identification of new natural troponoids, chemical synthesis and properties, biological activity, biosynthesis and metabolism. Particularly, bioassay-guided screening strategy and structure-activity relation-directed structure modification and drug design has resulted in the synthesis and discovery of many new derivatives. Many of them have great promise to be developed into new medicines for their potent and specific activities. This review presents the recent advances in troponoid studies and highlights multiple faceted biological activities of troponoids, as well as their relationships with chemical structures. Chemistry, biosynthesis, and production via biotechnology of troponoids are also briefly reviewed. Applications of troponoids in daily life, agriculture, medicine, and industry, and the related patents have been considered to further extend our understanding of the increasing impact of troponoids on humans.

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Section: Chemical Synthesis and Modification Of Troponoidsmentioning

confidence: 99%

“…3) have a long history [51]. Because of less selectivity but high toxicity and therefore limited clinical use, many studies still try to find modifications with a high therapeutic index [106].…”

Section: Tropone Alkaloidsmentioning

confidence: 99%

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Zhao

2007

CMC

107

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“…The UV/PDA spectrum of the compound showed two absorption maxima at 243 and 353 nm, similar to colchicine-type alkaloids. These data suggested that this compound was either (−)-2demethyl-(−)-colchicine or (−)-3-demethyl-(−)-colchicine (Chommadov et al, 1990). Both (−)-2-demethyl-(−)colchicine and (−)-3-demethyl-(−)-colchicine were isolated previously in our laboratory Alali et al, 2006a, d;Al-Mahmoud et al, 2006).…”

Section: Resultsmentioning

confidence: 70%

“…However, the UV/PDA spectrum of the compound showed two absorption maxima at 230 and 266 nm, indicating that this compound was a photoisomer of 2-demethyl-or 3-demethly-(−)-colchicine. These data suggested that this compound was either 2-demethylβ-lumicholchicine or 3-demethyl-β-lumicholchicine (Chommadov et al, 1990). As with peak 4 described above, this dereplication strategy quickly narrowed the structure to two possibilities.…”

Section: Resultsmentioning

confidence: 74%

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Colchicinoids from Colchicum crocifolium Boiss.: a case study in dereplication strategies for (–)‐Colchicine and related analogues using LC‐MS and LC‐PDA techniques

Alali

Gharaibeh

Ghawanmeh

et al. 2008

Phytochemical Analysis

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As a part of a project designed to investigate Colchicum species in Jordan, the chemical constituents of Colchicum crocifolium Boiss. (Colchicaceae) were investigated using LC-MS and LC-UV/Vis PDA. A decision tree for working with colchicinods has been developed by incorporating data from LC-UV/PDA and LC-MS. This dereplication strategy draws upon the UV/PDA spectra to classify compounds into one of four structural groups and combines this with retention time and mass spectra/molecular weight to identify the compounds. This strategy was applied on a small amount of extract (2 mg) of Colchicum crocifolium to dereplicate 10 known compounds from four different structural groups, namely (-)-demecolcine, 2-demethyl-(-)-colchicine or 3-demethyl-(-)-colchicine, N-deacetyl-(-)-colchicine, (-)-colchiciline, (-)-colchicine, beta-lumidemecolcine, 2-demethyl-beta-lumicolchicine or 3-demethyl-beta-lumicolchicine, N,N-dimethyl-N-deacetyl-beta-lumicornigerine, (-)-isoandrocymbine and (-)-autumnaline. Furthermore, a new compound was identi?ed as N,N-dimethyl-N-deacetyl-(-)-cornigerine. Three compounds, which had molecular ions at m/z 325, 340 and 374, could not be dereplicated into any obvious structural classes that have been isolated in our laboratories previously or reported in the literature.

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Identification of Odor Causing Compounds in a Commercial Dairy Farm

Lamichhane

Liang

et al. 2007

Water Air Soil Pollut: Focus

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Photochemical isomers of tropolone alkaloids

Cited by 5 publications

References 48 publications

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Colchicinoids from Colchicum crocifolium Boiss.: a case study in dereplication strategies for (–)‐Colchicine and related analogues using LC‐MS and LC‐PDA techniques

Identification of Odor Causing Compounds in a Commercial Dairy Farm

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