New alkylated benzoquinones from mangrove plant Aegiceras corniculatum with anticancer activity

Abstract

Three new alkylated benzoquinones, 2-hydroxy-5-ethoxy-3-nonyl-1,4-benzoquinone (1), 5-O-butyl-embelin (2), and 2,5-dihydroxy-6-methyl-3-pentadecyl-1,4-benzoquinone (3), together with seven known analogues (4–10), were isolated from the stems and twigs of mangrove plant, Aegiceras corniculatum. Their structural elucidation was achieved by spectroscopic methods, chemical exchanging experiments, and semisynthesis method. The cytotoxic activities of all the isolated compounds were evaluated by MTT assay. Compounds 1, 2, 8, 9, and 10 possess varying degrees of selective cytotoxicity against HL-60, HepG2, BGC-823, and A2780 cell lines.

Keywords:

• Aegicerataceae
• alkylated benzoquinone
• Aegiceras corniculatum
• cytotoxic activity

Disclosure statement

No potential conflict of interest was reported by the authors.

Figure 1. New alkylated benzoquinones (1–3) and known analogues (4–6) from A. corniculatum.

Figure 2. Key HMBC correlations of 3 and 7 in pyridine solvent.

Figure 3. Possible mass fragmentations of compounds 3–6.

Figure 4. Chemical exchanging between alkylated benzoquinones.

Additional information

Funding

This work was financially supported by the Natural Science Foundation of China (NSFC, Nos. 21707082, 21575084 and 21475080).