Conformation and Configuration of Humulene Di- and Triepoxides Generated from Four Possible Conformations of Humulene 9,10-Epoxide

Hayano, Kiyoharu; Mochizuki, Katsura

doi:10.3987/com-00-8851

Cited by 2 publications

(7 citation statements)

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“…These data in combination with the RDBE value of four indicated an 11‐membered carbon ring with two epoxides and was therefore determined to be a humulene diepoxide. This was further confirmed by 1 H and 13 C NMR comparison to that previously reported for humulene diepoxide C‐I ( rac ‐ 8 ) …”

Section: Resultsmentioning

confidence: 99%

“…Further confidence in this structure was garnered through 1 H and 13 C NMR comparison to that previously reported for humulene diepoxide C‐II ( rac ‐ 9 ) …”

Section: Resultsmentioning

confidence: 99%

“…Results from these assays did not show significant activity across the majority of species, with the exception of C. auris (see the Supporting Information, Table S1 andF igure S6). In particular, good activity was observed forb oth( +)-8 (MIC 50 = 8.53 mm) 13 CNMR assignment for (+)-humulene diepoxiolC -II (11).…”

Section: Biological Activityo F(+ +)-Humulene Diepoxide C-i and C-iimentioning

confidence: 98%

“…[7a] Surprisingly, however, the relative stereochemistry of the humulene diepoxides C-E remained unknown for a considerable period of time. [10] Subsequently, Hayano and Mochizuki [11] demonstrated that pure diastereoisomers of humulene diepoxides D ( 5) and E (6) could be obtained from humulene-9,10-epoxide (7) on treatment with meta-chloroperoxybenzoic acid (mCPBA), which further revealed that humulene diepoxide C was produced as two racemic diastereoisomers, that is, racemic C-I (rac-8) and racemic C-II (rac-9) (Scheme 1). However, since this time there have been no attempts to assign relative stereochemistry to the humulene diepoxide C diastereomers found in hops essential oil.…”

Section: Introductionmentioning

confidence: 99%

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Humulene Diepoxides from the Australian Arid Zone Herb Dysphania: Assignment of Aged Hops Constituents

Tan

Agnew‐Francis

Hofmann

et al. 2020

Chemistry A European J

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Dysphania is an abundant genus of plants,m any of which are endemict ot he Australianc ontinent, occurring primarily in arid and temperate zones. Despite their prevalence, very few investigationsi nto the phytochemistry of native Dysphania have been undertaken. Described herein, is the isolation and elucidation of two enantiomeric diastereomers of humulene diepoxide Cf rom D. kalpari and D. rhadinostachya,o fw hich unassigned diastereomerso fh umulene diepoxide Ch ave been previously reported as components in beer brewedf rom aged hops. In addition, two (+)-humu-lene diepoxiols (humulene diepoxiol C-I and C-II) were isolated from D. rhadinostachya. Analysis of Chinook hopso il confirmedt he presence of both humulene diepoxide C-I and C-II as trace components, and in turn enabled GC-MSp eak assignment to the relative stereochemistry.A nticancera ssays did not reveal any significant activityf or the (+)-humulene diepoxides. Antifungal assayss howed good activity against ad rug-resistant strain of C. auris,w ith MIC 50 values of 8.53 and 4.91 mm obtainedf or (+)-humulene diepoxide C-I and C-II, respectively.Scheme1.Biosynthesis of the humulene (1)skeleton starting from farnesyl diphosphate (2), including oxidation of 1 to the diepoxides A-E shown with relative stereochemistry.[a] Y.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

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Section: Resultsmentioning

confidence: 99%

“…Further confidence in this structure was garnered through 1 H and 13 C NMR comparison to that previously reported for humulene diepoxide C‐II ( rac ‐ 9 ) …”

Section: Resultsmentioning

confidence: 99%

Section: Biological Activityo F(+ +)-Humulene Diepoxide C-i and C-iimentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Humulene Diepoxides from the Australian Arid Zone Herb Dysphania: Assignment of Aged Hops Constituents

Tan

Agnew‐Francis

Hofmann

et al. 2020

Chemistry A European J

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show abstract

“…177 The conformation and configuration of humulene di-and tri-epoxides, which were obtained from four possible conformations of humulene 9,10-epoxide, have been studied. 178 Novel and stereoselective routes for the preparation of oxa-triquinanes and oxa-sterpuranes have been reported. 179 Total syntheses of racemic coriolin 180-182 and 1-desoxyhypnophilin 183 have been described.…”

Section: Himachalane Longifolane and Longipinanementioning

confidence: 99%

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Conformation and Configuration of Humulene Di- and Triepoxides Generated from Four Possible Conformations of Humulene 9,10-Epoxide

Cited by 2 publications

References 4 publications

Humulene Diepoxides from the Australian Arid Zone Herb Dysphania: Assignment of Aged Hops Constituents

Humulene Diepoxides from the Australian Arid Zone Herb Dysphania: Assignment of Aged Hops Constituents

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