The structure of fukinone, a constituent of Petasites japonicus maxim

Naya, Keizo; Takagi, Ichiro; Kawaguchi, Y.; Asada, Y.; Hirose, Yoshio; Shinoda, Naoko

doi:10.1016/s0040-4020(01)96317-3

Cited by 62 publications

(19 citation statements)

References 14 publications

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“…From the extract of Sample 1, two eremophilanes, i.e., fukinone (1) [34] and dehydrofukinone (2) [35], were isolated in 16 and 0.4% yields, respectively, together with ethyl ferulate (12; 1.5%). From the extract of Sample 1, two eremophilanes, i.e., fukinone (1) [34] and dehydrofukinone (2) [35], were isolated in 16 and 0.4% yields, respectively, together with ethyl ferulate (12; 1.5%).…”

mentioning

confidence: 99%

Chemical and Genetic Study of Ligularia duciformis and Related Species in Sichuan and Yunnan Provinces of China

Nagano

Hanai

Yamada

et al. 2012

Chemistry & Biodiversity

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The chemical constituents of the root extracts and the evolutionarily neutral DNA base sequences were studied for 28 samples of Ligularia duciformis, L. kongkalingensis, and L. nelumbifolia collected in Sichuan and Yunnan Provinces of China. The samples could be classified into four chemotypes (1-4). Sesquiterpenoids having eremophilane and oplopane skeletons were isolated from two (Chemotype 1) and three (Chemotype 2) samples, respectively. Two new oplopane derivatives were isolated and their structures were determined. In 18 samples, phenylpropenoids were the major components (Chemotype 3). In five samples, neither phenylpropenoids nor sesquiterpenoids were found (Chemotype 4). Despite this large chemical variety, no correlation was found between the chemotype and the morphological criteria of species identification. The analysis of the evolutionarily neutral DNA regions also indicated that the samples were not separated into distinct clades and that introgression was extensive.

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mentioning

confidence: 99%

Chemical and Genetic Study of Ligularia duciformis and Related Species in Sichuan and Yunnan Provinces of China

Nagano

Hanai

Yamada

et al. 2012

Chemistry & Biodiversity

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“…2), a sesquiterpene ketone first isolated in 1968 from P. japonicus Maxim. (17). It has been proposed that fukinone is likely to be oxidized to fukinone epoxide and to subsequently undergo Favorskii skeletal rearrangement.…”

Section: Biosynthesis Of Bakkenolide Amentioning

confidence: 99%

Actualities in the phytochemical research on selected terpenes

2019

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A short review of our recent research on the essential oil phytochemical composition of Petasites albus (L.) Gaertn. and Petasites hybridus (L.) G. Gaertn., B. Mey. & Scherb. (Asteraceae) as well as on the oils of Globularia cordifolia L., Globularia meridionalis (Podp.) O. Schwarz and Globularia punctata Lapeyr. (Plantaginaceae) is presented. All essential oils contained a variety of oxygenated sesquiterpenes among their major constituents, including a bakkane type sesquiterpene fukinanolid (bakkenolide A). The paper is focused on: i) a short overview of the abundance of major terpenes in the essential oils of Petasites and Globularia species from Croatia; ii) possible biosynthetic pathways of major identified sesquiterpenes; and iii) biological activities (literature data) of major sesquiterpenes from Petasites and Globularia species.

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“…The known compounds were furanoeremophilane (7) (Ishii et al, 1966), furanoeremophilan-6β-ol (8 = ligularol) (Ishii et al, 1965), 6β-isobutyroyloxyfuranoeremophilane 9 et al, 1974), 6β-isobutyroyloxyfuranoeremophilan-10β-ol (16) (Jennings et al, 1976), 6β-angeloyloxyfuranoeremophilan-9-one (17) (Bohlmann et al, 1986) (Naya et al, 1968), 7αH-eremophil-11-en-8-one (24) (Bohlmann et al 1986), bakkenolide A (25) (Abe et al, 1968), (2R,3S)-5-acetyl-6-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-3-yl (Z)-2-methylbut-2-enoate (26) (Bohlmann et al, 1977) (Bohlmann et al, 1977), 5,6dimethoxy-2-(prop-1-en-2-yl)benzofuran (28) (Murae et al, 1968), and 5-acetyl-6-hydroxy-2-(prop-1-en-2-yl)benzofuran (29 = euparin) (Kamthong and Robertson, 1939) (Fig. 7).…”

Section: Chemical Analysis-isolation Of Root Chemicalsmentioning

confidence: 99%

Chemical constituents of hybrids of Ligularia cyathiceps and L. lamarum/L. subspicata collected in China: Structures of subspicatins M, N, O1, and O2, and related compounds

et al. 2017

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Three natural hybrids and an introgressed individual of Ligularia were evaluated based on a combination of morphology, root chemicals, and nucleotide sequences of evolutionally neutral regions to understand the chemical outcomes of hybridization and introgression. Six previously undescribed eremophilane sesquiterpenes were isolated from hybrids between L. cyathiceps and L. lamarum/L. subspicata, and benzofurans were isolated from L. subspicata for the first time. Their structures were elucidated based on spectroscopic analyses. Some compounds produced by hybrids have not been detected in either parental species, indicating that the metabolic profile was altered by hybridization and introgression.

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The structure of fukinone, a constituent of Petasites japonicus maxim

Cited by 62 publications

References 14 publications

Chemical and Genetic Study of Ligularia duciformis and Related Species in Sichuan and Yunnan Provinces of China

Chemical and Genetic Study of Ligularia duciformis and Related Species in Sichuan and Yunnan Provinces of China

Actualities in the phytochemical research on selected terpenes

Chemical constituents of hybrids of Ligularia cyathiceps and L. lamarum/L. subspicata collected in China: Structures of subspicatins M, N, O1, and O2, and related compounds

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