Sesquiterpene lactones from the roots of Lindera strychnifolia

Liu, Qing; Ahn, Jong Hoon; Kim, Seon Beom; Lee, Chul; Hwang, Bang Yeon; Lee, Mi Kyeong

doi:10.1016/j.phytochem.2012.11.004

Cited by 33 publications

(22 citation statements)

References 26 publications

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“…They are found in every ecosystem because they are the products of the secondary metabolism of microorganisms [1], insects [2], plants [3] and even marine organisms [4]. Lactones have a wide spectrum of biological activity and are quite a large group of compounds with bactericidal [5,6], fungicidal [7,8] or cytotoxic activities [9,10]. Tetrenoline, a lactone with the polyene bond system, is primarily bactericidal, particularly against Gram-positive bacteria [11].…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

et al. 2016

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Abstract:The aim of the study was to obtain biological active compounds during biotransformation. Three bicyclic halolactones with methylcyclohexane ring (2-chloro-4-methyl-9-oxabicyclononan-8-one, 2-bromo-4-methyl-9-oxabicyclo[4.3.0]nona--8-one and 2-iodo-4-methyl-9-oxabicyclo[4.3.0]nonan-8-one) obtained from the corresponding γ,δ-unsaturated acid were subjected to a screening biotransformation using 22 fungal strains. Two of these strains (Cunninghamella japonica AM472 and Fusarium culmorum AM10) were able to transform halolactones into 2-hydroxy-4-methyl-9-oxabicyclo[4.3.0]nonan-8-one by hydrolytic dehalogenation with good yield. The biotransformation product was structurally different from its synthetically prepared analog.All halolactones and hydroxylactones were tested for their biological activity. The chlorolactone inhibited growth of Staphylococcus aureus (max ∆OD = 0), Escherichia coli (max ∆OD = 0.3) and Candida albicans (max ∆OD = 0) strains. Bromolactone caused inhibition of growth of Staphylococcus aureus (max ∆OD = 0) and Fusarium linii (max ∆OD = 0) strains. Iodolactone limited growth of Staphylococcus aureus (max ∆OD = 0), Escherichia coli (max ∆OD = 0.25), Candida albicans (max ∆OD = 0.45) and Pseudomonas fluorescens (max ∆OD = 0.42) strains. Hydroxylactone caused inhibition of growth of Staphylococcus aureus (max ∆OD = 0.36) and Pseudomonas fluorescens (max ∆OD = 0.39) strains only. The test performed on aphids Myzus persicae (Sulz.) showed that chloro-and bromolactone exhibited deterrent activity after 24 h (ID = 0.5 and 0.4, respectively), while hydroxylactone was a weak attractant (ID = −0.3).

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Section: Introductionmentioning

confidence: 99%

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

et al. 2016

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“…The relative stereochemistry of 7 was determined by NOESY, which showed correlations between H-5 and H-6, Me-14. The CD data substantiated the absolute configuration at the 8-position to be R. 9,13,14 On the basis of the obtained data, compound 7 was determined as (1R, 3S, 5R, 6R, 8R, 10S)-6-methoxy-8-hydroxy-1,3-cycloeudesma-4(15),7(11)-dien-12,8-olide and was named linderolide T.…”

Section: Introductionmentioning

confidence: 65%

“…8 We previously isolated nineteen sesquiterpenes from the roots of Lindera strychifolia and reported the cytotoxicity against HSC-T6 hepatic stellate cells. 9 In a continuation of our research, L. strychnifolia inhibited lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW264.7 macrophage cells. Further extensive chromatographic separation of L. strychnifolia afforded additional sixteen compounds (1-16) (Fig.…”

Section: Introductionmentioning

confidence: 86%

“…2B and Supplementary data). 9,13,14 In conclusion, compounds 1 and 2 were elucidated as (1R, 3S (Table 1). In the 13 C NMR spectrum of 3, a ketal signal was observed at d C 103.0 (C-8) instead of hydroxymethine at d C 78.0 of 1 ( Table 2).…”

Section: Introductionmentioning

confidence: 91%

“…The absolution configuration at the 8-position was expected to be R from the negative Cotton effect at 226 nm in the CD spectrum. 9,13,14 On the basis of the obtained data, compound 6 was determined as (1R, 3S, 4S, 5S, 8R, 10R)-4-hydroxy-6-oxo-1,3-cycloeudesma-7(11)-en-12,8-olide and named linderolide S. Compound 7 19 was isolated as an amorphous powder and its molecular formula was determined to be C 16 (Tables 1 and 2), suggested that 15-CH 3 and hydroxyl groups of 4 were replaced by exo-methylene group in 7, which was supported by the HMBC correlation between C-4 (d C 149.6) and H-5 (d H 3.51). The presence of additional methoxyl group was easily deduced from the signals at d H 3.45 and d C 57.3 in HSQC spectrum.…”

Section: Introductionmentioning

confidence: 99%

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