p-Menthene-type monoterpene peroxy dimers from Pilea aquarum subsp. brevicornuta

[Display omitted] •An unusual class of dimeric monoterpene peroxides have been identified from Pilea Lindl.•The chemical structures and absolute configurations of all isolates were determined by multiple methods.•Probable biogenetic pathways for 1–3 were proposed. Chemical investigation on Pilea aqu...

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Published inTetrahedron letters Vol. 85; pp. 153463 - 153468
Main Authors Yang, Guoxun, Zhou, Pengjun, Li, Yongjun, Ding, Jie, Hu, Jinfeng
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.11.2021
Elsevier
Subjects
Chemistry
Chemistry, Organic
Cytotoxicity
Dimeric Peroxide
Monoterpene
Physical Sciences
Pilea aquarum subsp. brevicornuta
Pileadimenthenol
Science & Technology
Monoterpene
Cytotoxicity
Pileadimenthenol
Pilea aquarum subsp. brevicornuta
Dimeric Peroxide
Pilea aquarum subsp
brevicornuta
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Summary:[Display omitted] •An unusual class of dimeric monoterpene peroxides have been identified from Pilea Lindl.•The chemical structures and absolute configurations of all isolates were determined by multiple methods.•Probable biogenetic pathways for 1–3 were proposed. Chemical investigation on Pilea aquarum subsp. brevicornuta led to the identification of three previously unknown dimeric p-menthene-type monoterpene peroxides, pileadimenthenols A-C (1–3). Their chemical structures and absolute configurations were determined by extensive spectroscopic analyses, X-ray crystal diffraction and ECD calculations. Plausible biogenesis of 1–3 was also proposed. Among the isolates, 2 showed weak cytotoxic activity against HCT-116.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.153463