Diaporthichalasin, a novel CYP3A4 inhibitor from an endophytic Diaporthe sp.

Pornpakakul, Surachai; Roengsumran, Sophon; Deechangvipart, Suchon; Petsom, Amorn; Muangsin, Nongnuch; Ngamrojnavanich, Nattaya; Sriubolmas, Nongluksna; Chaichit, Narongsak; Ohta, Tomihisa

doi:10.1016/j.tetlet.2006.11.102

Cited by 39 publications

(26 citation statements)

References 11 publications

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“…Specifcially, we deduced that the structure of phomopsichalasin is, in fact, identical to that of the more recently reported diaporthichalasin ( 7 ). ii To validate our analyses, we then showed that the proton and carbon NMR spectra of an authentic sample of diaporthichalasin recorded in methanol- d 4 were in excellent agreement with the NMR data reported for phomopsichalasin. i …”

Section: Resultssupporting

confidence: 67%

“…Bkk3) and structure determination of diaporthichalasin. ii Their thorough NMR analysis efforts led to the assignment of structure 7 (Scheme 1), which was confirmed by a single crystal x-ray structure determination, placing the assignment as 7 on secure ground. Interestingly, structure 7 shares the constitution of 1 , but differs in the relative configuration of several stereocenters.…”

Section: Resultsmentioning

confidence: 83%

“…Diaporthichalasin ( 7 ) was reported in 2007 and was deduced to have a structure diastereomeric with that of 1 . ii …”

mentioning

confidence: 99%

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Case Study of Empirical and Computational Chemical Shift Analyses: Reassignment of the Relative Configuration of Phomopsichalasin to That of Diaporthichalasin

2012

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Phomopsichalasin was isolated and assigned structure 1 over 15 years ago. Analysis of its proton NMR data led us to hypothesize that not all aspects of the relative configuration of this structure were correct. We have used both empirical and computational methods to propose an alternative structure. Diaporthichalasin was reported several years ago, and its structure was assigned as 7, a diastereomer of structure 1, and confirmed by a single crystal X-ray study. We have shown that diaporthichalasin and phomopsichalasin are identical; i.e., both have structure 7. Additional aspects of NMR interpretation that provide guidance for avoiding some of the pitfalls that can lead to incorrect structure assignments are discussed. These recommendations/reminders include i) the use of complementary solvents for acquiring NMR data that break accidental chemical shift degeneracy, ii) the importance of assigning coupling constants as extensively as possible, and iii) exercising caution when interpreting correlations in 2D spectra where overlapping resonances are involved.

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Section: Resultssupporting

confidence: 67%

Section: Resultsmentioning

confidence: 83%

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Case Study of Empirical and Computational Chemical Shift Analyses: Reassignment of the Relative Configuration of Phomopsichalasin to That of Diaporthichalasin

2012

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“…(+)-Fusarisetin A (1) possesses unique structural characteristics: 1) a fused pentacyclic ring system (A,B,C,D,E) which contains a trans decalin (A,B), a spiroskeleton (C,E), and a tetramic acid moiety fused with a tetrahydrofuran ring (D,E); and 2) 10 stereocenters, including two all-carbon quaternary centers (C1, C16). Structurally related natural products possessing tetramic acid rings include equisetin (3), [2] diaporthichalasin, [3] integramycin, [4] tirandamycin, [5] and others. [6] Recently, Li and co-workers reported the first synthesis of (À)-1 and revised its absolute configuration.…”

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confidence: 99%

Asymmetric Synthesis and Biosynthetic Implications of (+)‐Fusarisetin A

et al. 2012

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“…Diaporthe is one of the most abundant genera among the endophytic fungi isolated from Common Bean (Phaseolus vulgaris L.), corresponding to 11Á5% of the total isolates recorded by Gonzaga et al (2014). This fungal genus warrants further study for several reasons: (i) this genus does not possess any morphological markers that would allow characterization at the species level through classical taxonomy; (ii) species of this genus have been commonly found to be phytopathogens or endophytes on a wide variety of plant species (van Niekerk et al 2005;Udayanga et al 2012;Gomes et al 2013); and (iii) fungi from the genus Phomopsis have been reported to produce various compounds of biotechnological interest (Horn et al 1995;Wagenaar and Clardy 2001;Dai et al 2005;Silva et al 2005;Pornpakakul et al 2007;Rukachaisirikul et al 2008). Studies aiming to analyse and better characterize the genetic variability in this fungal genus are therefore of interest.…”

Section: Introductionmentioning

confidence: 99%