Unified Total Synthesis, Stereostructural Elucidation, and Biological Evaluation of Sarcophytonolides

Takamura, Hiroyoshi; Kikuchi, Toru; Iwamoto, Kohei; Nakao, Eiji; Harada, Naoki; Otsu, Taichi; Endo, Noriko; Fukuda, Yuji; Ohno, Osamu; Suenaga, Kiyotake; Guo, Yue; Kadota, Isao

doi:10.1021/acs.joc.8b01634

Cited by 21 publications

(18 citation statements)

References 95 publications

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“…Several cembranoids embodying a lactone moiety with different structural features such as α-methylene-γ-lactone, α,β-unsaturated-γ-lactone, ,, and α,β-unsaturated-ε-lactone , and even biscembranoids biogenerated from Diels–Alder addition involving α,β-unsaturated-γ-lactone , were discovered from soft corals collected in the South China Sea by using this method. Attracted by their complex and unique structures, medicinal chemists showed great attention to them. ,, …”

Section: Resultsmentioning

confidence: 99%

“…Intriguingly, a wide range of structurally diverse derivatives of cembranoids have been discovered to date, including skeletal variants, , norcembranoids, , and biscembranoids. , Those secondary metabolites deserve an intensive investigation for their significant biological activities ranging from antibacterial and cytotoxicity to NF-κB inhibitory properties. Their fascinating structures and potent bioactivities make them attractive for total synthesis …”

Section: Introductionmentioning

confidence: 99%

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Rare Cembranoids from Chinese Soft Coral Sarcophyton ehrenbergi: Structural and Stereochemical Studies

Zhang

et al. 2019

J. Org. Chem.

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A detailed chemical research of soft coral Sarcophyton ehrenbergi from the South China Sea yielded five new cembranoids 1–5 featuring an α,β-unsaturated-γ-lactone moiety rarely at C-6 to C-19, along with one known related diterpene 6. The structures and absolute configurations of 1–5 were established in the light of extensive spectroscopic data analysis, chemical reaction, X-ray diffraction analysis, TDDFT/ECD (time-dependent density functional theory/electronic circular dichroism) calculations, and biosynthesis path. This study led to the stereostructural revision of 6, which was misassigned by erroneously applying the empirical ECD helicity rule, indicating a challenging and risky work to determine the structure of this type of marine cembranoids. In the TNF-α inhibitory biotest, compound 2 exhibited a potent inhibitory activity (IC50 = 8.5 μM), which was analogous to the positive control dexamethasone (IC50 = 8.7 μM).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Rare Cembranoids from Chinese Soft Coral Sarcophyton ehrenbergi: Structural and Stereochemical Studies

Zhang

et al. 2019

J. Org. Chem.

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“…[ 19 ] So, it is not surprising that several erroneous structures are continually being detected and revised. [ 17,20‐22 ] Hence, there has been a growing interest in re‐examining and determining the absolute configuration of the known compounds. Herein, the absolute stereochemistry of known compounds 6 , 11 and 12 were established, for the first time, by using Mosher's method or X‐ray diffraction analysis, respectively.…”

Section: Resultsmentioning

confidence: 99%

Polyoxygenated Cembranoids from Soft Coral Lobophytum Crassum and Their Anti‐tumoral Activities

et al. 2021

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Main observation and conclusion Four new cembranoids, 6‐oxo‐cembrene‐A (1), lobocrassins G—H (2—3), and 14‐epi‐lobophytolide B (4), along with eight known related compounds (5—12), were isolated from the South China Sea soft coral Lobophytum crassum. Their structures were established by extensive spectroscopic analysis and by comparison of the spectral data with those reported in the literatures. The absolute stereochemistry of 14‐epi‐lobophytolide B (4) was established by time‐dependent density functional theory electronic circular dichroism (TDDFT‐ECD) calculations, whereas that of three known metabolites (6, 11 and 12) was also determined, for the first time, by using modified Mosher's method and/or X‐ray diffraction analyses. In bioassay, the cembranoids 6, 7 and 12 showed significant anti‐tumoral activity against A549, HT‐29, SNU‐398 and Capan‐1 tumor cell lines with IC50 values ranging from 1.5 to 7.4 μmol/L. A preliminary structure‐activity relationship was also discussed.

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“…Takamura and co‐workers presented the stereoselective total synthesis of sarcophytonolide F 131 and sarcophytonolide G 132 (Scheme 3), [179] these are cembranolide diterpene with 14‐membered macrocycle fused with butenolide unit, extracted from the soft corals of genus Sarcophyton . Sarcophytonolides F and G possess numerous biological activities such as antibacterial, antiviral, antifouling, cytotoxic, ichthyotoxic, and protein tyrosine phosphatase 1B inhibitory activities.…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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Unified Total Synthesis, Stereostructural Elucidation, and Biological Evaluation of Sarcophytonolides

Cited by 21 publications

References 95 publications

Rare Cembranoids from Chinese Soft Coral Sarcophyton ehrenbergi: Structural and Stereochemical Studies

Rare Cembranoids from Chinese Soft Coral Sarcophyton ehrenbergi: Structural and Stereochemical Studies

Polyoxygenated Cembranoids from Soft Coral Lobophytum Crassum and Their Anti‐tumoral Activities

Metathesis Reactions in Natural Product Fragments and Total Syntheses

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