Components of the Lauraceae family—I

Takeda, Ken’ichi; Sakurawi, K.; Ishii, Hiroshi

doi:10.1016/s0040-4020(01)93822-0

Cited by 110 publications

(58 citation statements)

References 7 publications

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“…1) data established the structure of 1 as majorenolide [23] [24]. 1 H-NMR Spectrum of 1 was similar to that of litsenolide A 2 (4) [25] in the part of (E)-6-dodec-10-enyl a,b'-unsaturated keto moiety. Thus, four olefinic H-atoms were assigned the signals at d 6.75 (tt, J ¼ 7.6, 3.2, HÀC (6) (3), HÀC(4), and CH 2 (5), respectively, and was also revealed by the COSY plot.…”

mentioning

confidence: 60%

“…2) experiments, the structure of majorynolide was identified as 2 [23] [24], which corresponds to (2E)-2-(dodec-11-ynylidene)-4,5-dihydro-4-(hydroxymethyl)furan-2(3H)-one. Compounds 4 -7, 10, and 11 have the same b-hydroxy-g-methylene a,b'-unsaturated-g-lactone structure as that of litsenolide A 1 [25]. The absolute configuration at C(3) was determined to be (S), based on the correlations between the [a] D value and the known configuration at C(3) for a series of 2-alkylidene-3-hydroxy-4-methylbutanolide derivatives [7] [33].…”

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confidence: 98%

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Antimycobacterial Butanolides from the Root of Lindera akoensis

Chang

Cheng

Peng

et al. 2008

Chemistry & Biodiversity

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Three racemic butanolides, majorenolide (1), majorynolide (2), and majoranolide (3), with 18 known compounds, including ten butanolides, i.e., litsenolide A(2) (4), litsenolide B(2) (5), litsenolide C(1) (6), litsenolide C(2) (7), hamabiwalactone A (8), hamabiwalactone B (9), litseakolide A (10), litseakolide B (11), isoobtusilactone (12), and obtusilactone (13); one lignan, i.e., (+/-)-syringaresinol (14), two flavans, i.e., (+)-catechin (15), and (-)-epicatechin (16), one coumarin, i.e., scopoletin (17), and four steroids, i.e., a mixture of beta-sitosterol (18) and stigmasterol (19), and a mixture of beta-sitosteryl-3-O-beta-D-glucoside (20) and stigmasteryl-3-O-beta-D-glucoside (21) were isolated from the root of Lindera akoensis. The structures of the isolates were elucidated by in-depth spectroscopic analysis. Compounds 1-3 were previously assigned a delta-lactone structure, which was then revised to a gamma-lactone structure, based on 1D-NMR data. The cigar-HMBC technique was used to confirm the accuracy of the gamma-lactone structure, and the zero [alpha] (20)_D value of compounds 1-3 suggested that they were considerably racemized. Nine butanolides 1-3, 4-8, and 10 showed antimycobacterial activities against M. tuberculosis H(37)Rv, with MIC values of 15-50 microg/ml.

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confidence: 60%

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confidence: 98%

Antimycobacterial Butanolides from the Root of Lindera akoensis

Chang

Cheng

Peng

et al. 2008

Chemistry & Biodiversity

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“…All reactions were routinely carried out under an inert atmosphere of dried nitrogen. 1 To a solution of 4 (140 mg, 0.426 mmol) in dry toluene (5 ml) at room temperature, N 2 was purged for 15 min. Then, azobisisobutyronitrile (7 mg, 0.0426 mmol) and tri-n-butyltin hydride (0.34 ml, 1.278 mmol) were added at room temperature.…”

Section: Methodsmentioning

confidence: 99%

The first asymmetric synthesis of marliolide from readily accessible carbohydrate as chiral template

Mailar

Choi

2016

Carbohydrate Research

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“…There are several other natural products with 2-alkyl or alkylidene-3-hydroxy or acyl-4-methyl butyrolactone moiety possessing interesting biological properties. Some of the examples include blastmycinone (2), (À)-NFX-2 (3), (À)-NFX-4 (4) [4], lipid metabolites 5 and 6 [5] and (À)-litsenolides B 1 (7), B 2 (8), C 1 (9), C 2 (10) [6] (Fig. 3).…”

Section: Introductionmentioning

confidence: 99%