Cantharidin derivatives from the medicinal insect Mylabris phalerata

Thirteen new cantharidin derivatives including six cantharimide-amino acid adducts (1–6), five cantharimide dimers (7–11) and two cantharimide-aromatic compound hybrids (12–13) were isolated from Mylabris phalerata Pallas. Compounds 1–5 represent the first natural products combined through cantharim...

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Bibliographic Details
Published inTetrahedron Vol. 73; no. 40; pp. 5932 - 5939
Main Authors Deng, Yuan-Yuan, Zhang, Wei, Li, Ni-Ping, Lei, Xue-Ping, Gong, Xue-Ying, Zhang, Dong-Mei, Wang, Lei, Ye, Wen-Cai
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.10.2017
Elsevier
Subjects
Cantharidin derivatives
Chemical constituent
Chemistry
Chemistry, Organic
Mylabris phalerata
Physical Sciences
Science & Technology
Cantharidin derivatives
NAHMNIGDAZVEDN-MSKXDSNOSA-N
Chemical constituent
Mylabris phalerata
CELLS
APOPTOSIS
NORCANTHARIDIN
CHINESE BLISTER BEETLE
CANCER
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Summary:Thirteen new cantharidin derivatives including six cantharimide-amino acid adducts (1–6), five cantharimide dimers (7–11) and two cantharimide-aromatic compound hybrids (12–13) were isolated from Mylabris phalerata Pallas. Compounds 1–5 represent the first natural products combined through cantharimide and neutral amino acids. Compounds 7–11 are the first cantharimide dimers consisting of two different cantharimide cores. Their structures with absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray diffraction, and semi-synthesis. Compound 6 showed weak cytotoxicity against HepG2, A549 and MDA-MB-231 cells with IC50 values of 15.70 ± 3.06, 20.67 ± 4.05 and 23.79 ± 4.54 μM, respectively. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.08.034