Phytochemistry

Volume 103, July 2014, Pages 171–177

Diarylheptanoids and phenylphenalenones from Musa itinerans fruits

• Fang Liu^{a, 1},
• Yu Zhang^{a, 1},
• Qian-Yun Sun^b,
• Fu-Mei Yang^b,
• Wei Gu^a,
• Jun Yang^a,
• Hong-Mei Niu^a,
• Yue-Hu Wang^{a, ,} ,
• Chun-Lin Long^{a, c, d, ,}

doi:10.1016/j.phytochem.2014.03.031

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Highlights

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Five phenylphenalenones and two diarylheptanoids were isolated from Musa itinerans.

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A putative biosynthetic pathway to the phenylphenalenone-related heterodimer is proposed.

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Two of the phenylphenalenones exhibited weak cytotoxic effects against a human lung adenocarcinoma cell line.

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Abstract

Two diarylheptanoids, musaitinerins A and B, one heterodimeric phenylphenalenone musaitinerone and four known phenylphenalenones, identified as 4-hydroxy-2-methoxy-9-phenyl-1H-phenalen-1-one, musanolone E, hydroxyanigorufone and irenolone were isolated from the fruits of Musa itinerans Cheesm. Their structures were elucidated using spectroscopic analyses. The antimicrobial activity of these compounds was evaluated against Escherichia coli, Staphylococcus aureus and Candida albicans; the cytotoxic activity of these compounds was also evaluated against human erythromyeloblastoid leukemia (K562) and human alveolar carcinoma epithelial (A549) cell lines, respectively. Musaitinerone and musanolone E exhibited weak effects against the A549 cell line, as compared with adriamycin. However, these two compounds did not exhibit any growth inhibition against K562 cells, S. aureus, E. coli or C. albicans. The other compounds were inactive against all of the tested cell lines and microorganisms, even at concentrations as high as 50 μM.

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Graphical abstract

Two diarylheptanoids, one dimeric phenylphenalenone and four known phenylphenalenones were isolated from Musa itinerans. Two of the phenylphenalenones exhibited weak effects against a human lung adenocarcinoma cell line.

InChIKeys

• UQMKPTIDKHEGFW-UHFFFAOYSA-N;
• WDYFQQLNUMDXBW-VPHBVFCQSA-N;
• VYTNNSDDSJDERW-QULCHTJLSA-N;
• WDYFQQLNUMDXBW-CJCPEHGCSA-N;
• HGNZXWVRMJVAIW-UHFFFAOYSA-N;
• HTELDEYOMOTOBI-UHFFFAOYSA-N;
• VTDWFCOFYNYWPA-UHFFFAOYSA-N;
• CFIUGIYVJPSAET-UHFFFAOYSA-N

Keywords

• Musaceae;
• Musa itinerans;
• Diarylheptanoids;
• Phenylphenalenones;
• Cytotoxicity

Corresponding authors. Address: Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People’s Republic of China. Tel.: +86 10 68930381; fax: +86 0871 65223318.

1

These authors contributed equally to this work.