Absolute Structures of Monoterpenoids with a δ-Lactone-Containing Skeleton from <i>Ligularia hodgsonii</i>

Chen, Jianjun; Li, Wenxian; Gao, Kun; Jin, Xiaojie; Yao, Xiaojun

doi:10.1021/np200693z

Cited by 17 publications

(11 citation statements)

References 15 publications

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“…Monoterpenoid lactone liguhodgcin was isolated from Ligularia hodgsonii and was used in traditional Chinese medicine in the treatment of flu, coughs, ulcers and tuberculosis. In addition, this compound proved to be moderately active against the cell lines HL-60 (leukemia), SMMC-7721 (hepatoma) and HeLa (cervical carcinoma) [20].…”

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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“…It has also been proven that the aqueous and/or ethanolic extracts of many CHMs, including those from Ligularia species, possess a good capacity to scavenge free radicals, and show antioxidant and even hepatoprotective effects in vivo [13][14][15][16]. The phytochemical studies and clinical uses of L. hodgsonii suggested that the therapeutic effects of this herb might be based on such an extract and/or components with antioxidant properties [1][2][3][4][5][6][7][8].…”

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confidence: 99%

“…Ligularia hodgsonii Hook., family Asteraceae, is a medicinal plant whose roots and rhizomes are used as a herbal medicine (named Chuan Zi Wan in Chinese) in the south-western region of China and as a substitute for Asteris Radix et Rhizoma (Zi Wan in Chinese) for the treatment of cough, excessive phlegm, hepatitis and inflammation [1][2][3]. Previous studies indicated that L. hodgsonii contained essential oils [4], polysaccharides [5], terpenoids [6,7], phenolic acids, flavonoids [8], and pyrrolizidine alkaloids (PAs) [9]. Naturally-derived essential oils, polysaccharides and polyphenolic compounds are common functional ingredients in Chinese herbal medicines (CHMs) with various biological properties such as antimicrobial, antioxidant, anti-inflammatory and hepatoprotective activities [5,[10][11][12].…”

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confidence: 99%

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Chemical Composition of the Essential Oil of Ligularia hodgsonii and Free Radical Scavenging Activity of the Oil and Crude Extracts

Zhou

Tang

Song

2014

Natural Product Communications

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The chemical composition of the essential oil from roots and rhizomes of Ligularia hodgsonii was analyzed by gas chromatography (GC) and GC-mass spectrometry (MS). Forty-seven components were identified, representing 77.0% of the total oil. The main constituents were l-(+)-ascorbic acid 2,6dihexadecanoate (15.7%), selina-6-en-4-ol (8.4%) and 9,10-dimethyl-1,2,3,4,5,6,7,8-octahydroanthracene (6.6%). The free radical scavenging activities of the essential oil, aqueous extract, ethanolic extract, and crude polysaccharides of L. hodgsonii, as well as some of their major components, were investigated using DPPH and ABTS assays. The essential oil displayed a lower capacity to quench free radicals than the extracts; the ethanolic and aqueous extracts showed considerably higher antioxidant potential that deserves further study.

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“…16 The structure and absolute configuration of liguhodgcin A 19, from Ligularia hodgsonii, have been established by X-ray analysis. 17 The authors propose a biosynthetic route to liguhodgcin A 19 from L-threonine via senecic acid.…”

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Hill

Sutherland

2012

Nat. Prod. Rep.

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Absolute Structures of Monoterpenoids with a δ-Lactone-Containing Skeleton from Ligularia hodgsonii

Cited by 17 publications

References 15 publications

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

Biotransformation of Lactones with Methylcyclohexane Ring and Their Biological Activity

Chemical Composition of the Essential Oil of Ligularia hodgsonii and Free Radical Scavenging Activity of the Oil and Crude Extracts

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