Benzyl Benzoate Glycoside and 3-Deoxy-<scp>d</scp>-manno-2-octulosonic Acid Derivatives from <i>Solidago decurrens</i>

Shiraiwa, Ken; Yuan, Shunzong; Fujiyama, Ayako; Matsuo, Yosuke; Tanaka, Takashi; Jiang, Zhi‐Hong; Kouno, Isao

doi:10.1021/np2007582

Cited by 10 publications

(9 citation statements)

References 6 publications

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“…After decurrensides A–E ( 5–9 ) were isolated from the Chinese herb Solidago decurrens , 30 the proposed structure 8a was synthesized; however, the NMR spectroscopic data did not match the natural product. 31 This discrepancy led to the revelation that the depicted structures 5a–9a did not match the compound names.…”

Section: Structural Revision Based On Computational Prediction Of Nmentioning

confidence: 99%

Recent trends in the structural revision of natural products

et al. 2018

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Covering: 2012 to 2017 This article reviews recent reports on the structural revision of natural products. Through a critical assessment of the original and revised published structures, the article addresses why each structure was targeted for revision, discusses the techniques and key discrepancies that led to the proposal of the revised structure, and offers measures that may have been taken during the original structure determination to prevent error. With the revised structures in hand, weaknesses of original proposals are assessed, providing a better understanding on the logic behind structure determination.

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Section: Structural Revision Based On Computational Prediction Of Nmentioning

confidence: 99%

Recent trends in the structural revision of natural products

et al. 2018

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“…Acetylated derivatives 2 and 3 are potent and uncompetitive inhibitors of F1 ATPase and have been implicated as potential anticancer therapeutics. 8,9 Despite the occurrence of the DBO moiety in other microbial and plant natural products (Scheme S1), such as decurrenside A from the goldenrod plant, 10 the antibiotic sorangicin A from myxobacteria 11 and a marine toxin palytoxin from zoanthids, 12 the enzymatic basis for the formation of this moiety has not been elucidated to date.…”

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confidence: 99%

Efficient Biosynthesis of Fungal Polyketides Containing the Dioxabicyclo-octane Ring System

et al. 2015

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Aurovertins are fungal polyketides that exhibit potent inhibition of ATP synthase. Aurovertins contain a 2,6-dioxabicyclo[3.2.1]-octane ring that is proposed to be derived from a polyene precursor through regioselective oxidations and epoxide openings. In this study, we identified only four enzymes are required to produce aurovertin E 4. The core polyketide synthase produces a polyene α-pyrone 10. Following pyrone O-methylation by a methyltransferase, a flavin-dependent monooxygenase (FMO) and an epoxide hydrolase can iteratively transform the terminal triene portion of the precursor into the dioxabicyclo[3.2.1]-octane scaffold. We demonstrate that a tetrahydrofuranyl polyene 12 is the first stable intermediate in the transformation, which can undergo epoxidation and anti-Baldwin 6-endo-tet ring opening to yield the cyclic ether product. Our results further demonstrate the highly concise and efficient ways in which fungal biosynthetic pathways can generate complex natural product scaffolds.

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“…Decurrenside A-D were isolated from the methanolic extracts of the plant Solidago decurrens by Kuono and co-workers 80 in 2012. The molecular structure 160 was assigned to decurrenside D by 1D and 2D NMR spectra analyses and by comparison with spectroscopic data of known compounds (Figure 31).…”

Section: Decurrensidesmentioning

confidence: 99%

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

Della‐Felice¹,

Pilli²,

Sarotti³

2018

J. Braz. Chem. Soc.

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Quantum chemical calculations of nuclear magnetic resonance (NMR) shifts and coupling constants have been extensively employed in recent years mainly to facilitate structural elucidation of organic molecules. When the results of such calculations are used to determine the most likely structure of a natural product in advance, guiding the subsequent synthetic work, the term "computer-guided synthesis" could be coined. This review article describes the most relevant examples from recent literature, highlighting the scope and limitations of this merged computational/experimental approach as well.

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Benzyl Benzoate Glycoside and 3-Deoxy-d-manno-2-octulosonic Acid Derivatives from Solidago decurrens

Cited by 10 publications

References 6 publications

Recent trends in the structural revision of natural products

Recent trends in the structural revision of natural products

Efficient Biosynthesis of Fungal Polyketides Containing the Dioxabicyclo-octane Ring System

Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives

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