Total Synthesis of the Cytotoxic 1,10‐seco‐Eudesmanolides Britannilactone and 1,6‐O,O‐Diacetylbritannilactone

Merten, Jörn; Wang, Yuzhou; Krause, Tilo; Kataeva, О. N.; Metz, Peter

doi:10.1002/chem.201002927

Cited by 15 publications

(6 citation statements)

References 27 publications

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“…2) and unambiguously veried the out-of-plane of 4-methyl and the 6a-orientation of the acetyl (OAc) group, which is in accord with data in the literature. 20 The synthesis of the target compounds 3a-l was carried out by esterication, followed by nucleophilic substitution. Using ABL as the starting material, the key analogue 1-O-acetyl-6-Ochloracetylbritannilactone (2) was rst synthesized through a standard esterication procedure.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1-O-acetylbritannilactone analogues from Inula britannica and in vitro evaluation of their anticancer potential

et al. 2014

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Section: Resultsmentioning

confidence: 99%

Synthesis of 1-O-acetylbritannilactone analogues from Inula britannica and in vitro evaluation of their anticancer potential

et al. 2014

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“…These sultone routes feature excellent control of the relative configurations of the stereogenic center located on the side-chains. Here it is relevant to note that very recently Metz and co-workers have also reported the total synthesis of two other cytotoxic 1,10- seco -eudesmanolides …”

Section: Synthetic Applications Of Sultonesmentioning

confidence: 94%

“…Here it is relevant to note that very recently Metz and co-workers have also reported the total synthesis of two other cytotoxic 1,10-seco-eudesmanolides. 103 Moreover, Metz and co-workers also demonstrated the application of the sultone route in the total synthesis of pamamycin-607 104 (33.1) by coupling the methyl ester (33.4) of the larger fragment 33.2 and the methyl ester 33.5 of smaller fragment 33.3. The methyl esters 33.4 and 33.5 were synthesized from the tricyclic sultones 33.6 and 33.7, respectively.…”

Section: Sultones In Natural Product Synthesismentioning

confidence: 99%

Recent Developments in the Synthesis and Application of Sultones

Mondal

2012

Chem. Rev.

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“…19 It has been reported that OODBL represses mast cell activation and displays several biological effects such as anti-cancer and anti-inflammatory activities. 20 , 21 OODBL induces an anti-tumor effect on leukemia cells by modulating MAPK pathway. 22 However, the effect of OODBL on OSCC progression is still unreported.…”

Section: Introductionmentioning

confidence: 99%

1, 6-O, O-Diacetylbritannilactone from Inula britannica Induces Anti-Tumor Effect on Oral Squamous Cell Carcinoma via miR-1247-3p/LXRα/ABCA1 Signaling

et al. 2020

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Introduction Oral squamous cell carcinoma (OSCC) is the most prevalent malignancy affecting the oral cavity and is associated with severe morbidity and high mortality. 1, 6-O, O-Diacetylbritannilactone (OODBL) isolated from the medicinal herb of Inula britannica has various biological activities such as anti-inflammation and anti-cancer. However, the effect of OODBL on OSCC progression remains unclear. Here, we were interested in the function of OODBL in the development of OSCC. Methods The effect of OODBL on OSCC progression was analyzed by MTT assays, colony formation assays, transwell assays, apoptosis analysis, cell cycle analysis, and in vivo tumorigenicity analysis. The mechanism investigation was performed by qPCR assays, Western blot analysis, and luciferase reporter gene assays. Results We found that OODBL inhibits the proliferation of OSCC cells in vitro. Moreover, the migration and invasion were attenuated by OODBL treatment in the OSCC cells. OODBL arrested cells at the G0/G1 phase and induced cell apoptosis. OODBL was able to up-regulate the expression of LXRα, ABCA1, and ABCG1 in the system. In addition, OODBL activated LXRα/ABCA1 signaling by targeting miR-1247-3p. Furthermore, the expression levels of cytochrome c in the cytoplasm, cleaved caspase-9, and cleaved caspase-3 were dose-dependently reduced by OODBL. Besides, OODBL increased the expression ratio of Bax to Bcl-2. Moreover, OODBL repressed tumor growth of OSCC cells in vivo. Discussion Thus, we conclude that OODBL inhibits OSCC progression by modulating miR-1247-3p/LXRα/ABCA1 signaling. Our finding provides new insights into the mechanism by which OODBL exerts potent anti-tumor activity against OSCC. OODBL may be a potential anti-tumor candidate, providing a novel clinical treatment strategy of OSCC.

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Total Synthesis of the Cytotoxic 1,10‐seco‐Eudesmanolides Britannilactone and 1,6‐O,O‐Diacetylbritannilactone

Cited by 15 publications

References 27 publications

Synthesis of 1-O-acetylbritannilactone analogues from Inula britannica and in vitro evaluation of their anticancer potential

Synthesis of 1-O-acetylbritannilactone analogues from Inula britannica and in vitro evaluation of their anticancer potential

Recent Developments in the Synthesis and Application of Sultones

<p>1, 6-O, O-Diacetylbritannilactone from Inula britannica Induces Anti-Tumor Effect on Oral Squamous Cell Carcinoma via miR-1247-3p/LXRα/ABCA1 Signaling</p>

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