Abstract
Dibohemamines A-C (5-7), three new dimeric bohemamine analogues dimerized through a methylene group, were isolated from a marine-derived Streptomyces spinoverrucosus. The structures determined by spectroscopic analysis were confirmed through the semi-synthetic derivatization of monomeric bohemamines and formaldehyde. These reactions, which could occur under mild conditions, together with the detection of formaldehyde in the culture, revealed that this dimerization is a non-enzymatic process. In addition to the unique dimerization of the dibohemamines, dibohemamines B and C were found to have nm cytotoxicity against the non-small cell-lung cancer cell line A549. In view of the potent cytotoxicity of compounds 6 and 7, a small library of bohemamine analogues was generated for biological evaluation by utilizing a series of aryl and alkyl aldehydes.
Original language | English (US) |
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Pages (from-to) | 3491-3495 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 22 |
Issue number | 10 |
DOIs | |
State | Published - Mar 1 2016 |
Keywords
- bohemamine
- cancer
- cytotoxicity
- marine-derived streptomyces
- non-enzymatic biosynthesis
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry