2007
DOI: 10.3390/12081606
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Antibacterial Thymol Derivatives Isolated from Centipeda minima

Abstract: Abstract:Two new monoterpenoids, 8,10-dihydroxy-9(2)-methylbutyryloxythymol (1) and 10-hydroxy-8,9-dioxyisopropylidene-thymol (2), together with five known thymol derivatives: 8,9,10-trihydroxythymol (3), thymol-β-glucopyranoside (4), 9-hydroxythymol (5), 8,10-dihydroxy-9-isobutyryloxythymol (6), and 8-hydroxy-9,10-diisobutyryloxythymol (7), were isolated from Centipeda minima. Their structures were identified by means of spectroscopic analyses. Interestingly, compound 2 is not an extraction artifact according… Show more

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Cited by 59 publications
(39 citation statements)
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“…Interestingly, this genus has been used as substitutes for oregano, which also contains thymol as commented before (Tucker & DeBaggio, ). Alternatively, the species Centipeda minima (Asteraceae), commonly used in Chinese folk medicine, is rich in derivatives of thymol (Liang et al, ). Therefore, all the essential oils of these species can be used as natural sources of thymol and standardized for further uses.…”
Section: Resultsmentioning
confidence: 99%
“…Interestingly, this genus has been used as substitutes for oregano, which also contains thymol as commented before (Tucker & DeBaggio, ). Alternatively, the species Centipeda minima (Asteraceae), commonly used in Chinese folk medicine, is rich in derivatives of thymol (Liang et al, ). Therefore, all the essential oils of these species can be used as natural sources of thymol and standardized for further uses.…”
Section: Resultsmentioning
confidence: 99%
“…In some Inula, Doronicum and Pulicaria species, thymyl derivatives rather than sesquiterpenoids are the major root constituents. [20][21][22][23] A review by Talavera-Aleman and collaborators 24 estimated that only 10% of known functionalized thymyl derivatives have been employed in biological testing, showing vast array of diverse activities, such as antimicrobial 4,5,22,[25][26][27] (several papers reporting inhibitory activity against plants' pathogenic fungi 22,26 ), antioxidant, 28 antinociceptive, 29 anti-parasitic (antileishmanial), 30,31 antiprotozoal, 32 insecticidal 33 and piscicidal 34 activity. The usefulness of thymyl derivatives as transdermal drug delivery enhancers has also been reported.…”
Section: Introductionmentioning
confidence: 99%
“…[20] The silanes 4 were additionally functionalized to form chiral five-membered silyl rings (6) without loss of enantioselectivity using iridium-catalyzed intramolecular dehydrogenation. [21] We determined the absolute configuration of hydrosilylation products by X-ray analysis of the compounds 6 b and 6 v. [22] The phenol derivatives with chiral motifs at the ortho-position are also core structures and useful precursors [23] for bioactive natural products, [24] and 7 b was obtained in 86 % yield by oxidative hydrolysis [20] of the cyclic silane 6 b. Chiral 3-substituted 2,3dihydrobenzofurans [25] are precursors for the anticancer active (À)-thespesone [26] or single-stranded abiotic metallofoldamers. [27] (S)-(+)-3-Methyl dihydrobenzofuran (8 b) was obtained through an intramolecular Mitsunobu reaction [20] of 7 b in 62 % yield (the product was highly volatile).…”
mentioning
confidence: 99%