Carboxymethyl flavonoids and a chromone with antimicrobial activity from Selaginella moellendorffii Hieron.

Abstract:

:Five new carboxymethyl flavonoids named 5-carboxymethyl-3', 4', 7-trihydroxyflavone (1), (2S)- 5-carboxymethyl-3', 4', 7-trihydroxyflavonone (2a), (2R)-5-carboxymethyl-3', 4', 7-trihydroxyflavonone (2b), (2S)-5-carboxymethyl-4', 7-dihydroxyflavonone (3), 5- carbomethoxymethyl-4', 7-dihydroxyflavone (4), and a new chromone named 5-carboxymethyl-7-hydroxychromone (5), together with two known compounds 5-carboxymethyl-4'-hydroxyflavone-7-O-β-d-glucopyranoside (6), 5-carboxymethyl-4', 7-dihydroxyflavone (7) were isolated from Selaginella moellendorffii Hieron. Their structures including absolute configuration were elucidated by extensive spectroscopic methods and experimental electronic circular dichroism (ECD) spectra. What's worth mentioning is that a carboxymethyl substituent appeared at the C-5 position of all isolated compounds, only recently discovered in genus Selaginella. Compounds 2a and 2b were identified as a pair of chiral isomers; compound 5 was discovered as the first chromone comprising a carboxymethyl side chain. Furthermore, all compounds were evaluated for their antibacterial activities against various Gram-positives and Gram-negatives, and compared to the reference drugs amoxicillin and norfloxacin. As a result, compounds 3 and 4 exhibited as potent antimicrobial agents with a broad spectrum, and compound 5 appeared as the most promising one to combat Gram-positives.

journal_name

Fitoterapia

journal_title

Fitoterapia

authors

Zou Z,Xu P,Wu C,Zhu W,Zhu G,He X,Zhang G,Hu J,Liu S,Zeng W,Xu K,Tan G

doi

10.1016/j.fitote.2016.04.022

subject

Has Abstract

pub_date

2016-06-01 00:00:00

pages

124-9

eissn

0367-326X

issn

1873-6971

pii

S0367-326X(16)30096-X

journal_volume

111

pub_type

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