Sesterterpenes as Tubulin Tyrosine Ligase Inhibitors. First Insight of Structure−Activity Relationships and Discovery of New Lead

Piaz, Fabrizio Dal; Vassallo, Antonio; Lepore, Laura; Tosco, Alessandra; Bader, Ammar; Tommasi, Nunziatina De

doi:10.1021/jm801637f

Cited by 52 publications

(52 citation statements)

References 48 publications

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“…Ten Phlomis species are found in the flora of Jordan, which is considered one of most attractive countries in the Middle East due to its biodiversity (Dal Piaz et al, 2009; Malafronte et al, 2012). Among them, Phlomis kurdica Rech.f.…”

Section: Introductionmentioning

confidence: 99%

Phenylpropanoids and flavonoids from Phlomis kurdica as inhibitors of human lactate dehydrogenase

et al. 2015

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Two new flavonoids, jaceosidin 7-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (1) and hispidulin 7-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (2), and one new phenylpropanoid, 3,3′-dimethyl-lunariifolioside (3), along with 11 known compounds (4–14), were isolated from the aerial parts of Phlomis kurdica growing in Jordan. Structures of 1–3 were elucidated on the basis of spectroscopic data. These isolated compounds were assayed for their inhibitory activity against isoform 5 of human lactate dehydrogenase. Compound 4, luteolin 7-O-β-D-glucopyranoside, showed an IC50 value comparable to that of galloflavin, used as reference compound. Docking studies were carried out to hypothesize the interaction mode of compound 4 in the enzyme active site.

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Section: Introductionmentioning

confidence: 99%

Phenylpropanoids and flavonoids from Phlomis kurdica as inhibitors of human lactate dehydrogenase

et al. 2015

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“…Sal v ia is a very important genus comprising about 900 species in the plant family Lamiaceae [88]. They have high diversity in their secondary metabolites with numerous pharmacological effects.…”

Section: Introductionmentioning

confidence: 99%

“…Twenty-four tricyclic sesterterpenoids (Fig. 16, Table 1) were isolated from the aerial parts of Sal v ia dominica [88]. All of them contain a differentially functionalized decalin and furan-2-one rings joined with a substituted pentane side chain [88].…”

Section: Introductionmentioning

confidence: 99%

Sesterterpenoids with Anticancer Activity

Evidente¹,

Kornienko²,

Lefranc³

et al. 2015

CMC

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Terpenes have received a great deal of attention in the scientific literature due to complex, synthetically challenging structures and diverse biological activities associated with this class of natural products. Based on the number of C5 isoprene units they are generated from, terpenes are classified as hemi- (C5), mono- (C10), sesqui- (C15), di- (C20), sester- (C25), tri (C30), and tetraterpenes (C40). Among these, sesterterpenes and their derivatives known as sesterterpenoids, are ubiquitous secondary metabolites in fungi, marine organisms, and plants. Their structural diversity encompasses carbotricyclic ophiobolanes, polycyclic anthracenones, polycyclic furan-2-ones, polycyclic hydroquinones, among many other carbon skeletons. Furthermore, many of them possess promising biological activities including cytotoxicity and the associated potential as anticancer agents. This review discusses the natural sources that produce sesterterpenoids, provides sesterterpenoid names and their chemical structures, biological properties with the focus on anticancer activities and literature references associated with these metabolites. A critical summary of the potential of various sesterterpenoids as anticancer agents concludes the review.

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“…Twenty-four new sesterterpenes were isolated from the aerial parts of Salvia dominica. By means of chemical proteomics, the results showed that 18 out of the 24 sesterterpene lactones isolated from Salvia dominica interacted with tubulintyrosine ligase (TTL), an enzyme involved in the tyrosination cycle of the tubulin C-terminus, and inhibited TTL activity in cancer cells [81]. In 2009, Clerc and co-workers identified the 20S proteasome as a target of the natural product syringolin A (SylA), which exhibited significant anticancer activities ( Table 1) [82].…”

Section: Affinity Chromatographymentioning

confidence: 99%

Approaches to Target Profiling of Natural Products

Yue¹,

Shan²,

Yang³

et al. 2012

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Natural products have long been regarded as excellent sources for drug discovery given their structural diversity and wide variety of biological activities. Accordingly, the identification of the molecular targets of natural products is an important aspect of current drug discovery, as knowledge regarding a compound's molecular targets will greatly aid drug development and design. In this review, we will explore genomic, proteomic, and computational approaches to the elucidation of these mechanisms and the implications of these approaches for the target profiling of natural products. The recent applications of target profiling of natural products will also be reviewed.

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Sesterterpenes as Tubulin Tyrosine Ligase Inhibitors. First Insight of Structure−Activity Relationships and Discovery of New Lead

Cited by 52 publications

References 48 publications

Phenylpropanoids and flavonoids from Phlomis kurdica as inhibitors of human lactate dehydrogenase

Phenylpropanoids and flavonoids from Phlomis kurdica as inhibitors of human lactate dehydrogenase

Sesterterpenoids with Anticancer Activity

Approaches to Target Profiling of Natural Products

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