2021
DOI: 10.1021/acs.orglett.1c03812
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Euphohyrisnoids A and B, Two Highly Rearranged Lathyrane Diterpenoids from Euphorbia lathyris

Abstract: cetane and tricyclo[8.4.1.0 3,7 ]pentadecane skeleton, respectively, were isolated from the seeds of Euphorbia lathyris. Their structures were determined by detailed spectroscopic analysis and were further confirmed by single-crystal X-ray diffraction. 1 significantly inhibited adipogenesis in 3T3-L1 adipocytes by retarding cell differentiation at the early stage.

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Cited by 19 publications
(10 citation statements)
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“…Euphohyrisnoids A ( 984 ) and B ( 985 ), two novel diterpenoids with unprecedented skeletons, might be biosynthetically derived from [4 + 2] cycloaddition and ene-cyclization of lathyranes, respectively. 206 Euphopia F ( 986 ), a 5/7/7 tricyclic diterpenoid, was hypothesized to be a cyclopropane-opening and a C-5–C-11 cyclization product of lathyrane diterpenoid. 202 Eupholathone ( 987 ) and euphornin E ( 988 ) from E. lathyris are two tetracyclic diterpenoids, featuring a 5/7/7/4-fused ring system.…”
Section: Isolated Diterpenoidsmentioning
confidence: 99%
“…Euphohyrisnoids A ( 984 ) and B ( 985 ), two novel diterpenoids with unprecedented skeletons, might be biosynthetically derived from [4 + 2] cycloaddition and ene-cyclization of lathyranes, respectively. 206 Euphopia F ( 986 ), a 5/7/7 tricyclic diterpenoid, was hypothesized to be a cyclopropane-opening and a C-5–C-11 cyclization product of lathyrane diterpenoid. 202 Eupholathone ( 987 ) and euphornin E ( 988 ) from E. lathyris are two tetracyclic diterpenoids, featuring a 5/7/7/4-fused ring system.…”
Section: Isolated Diterpenoidsmentioning
confidence: 99%
“…Previous investigation of this species revealed diterpenoids as the main components, some of which displayed significant phytotoxic and anti-inflammatory activities . In our continuous search for biologically important diterpenoids from Euphorbia plants, euphylonoids A ( 1 ) and B ( 2 ), two highly modified jatrophane diterpenoids, as well as their biogenetically related precursor euphylonoid C ( 3 ) (Figure ), were isolated from whole plants of E. hylonoma . Herein, we report the structural elucidation, putative biosynthetic pathways, and lipid-lowering efficacy of 1–3 .…”
mentioning
confidence: 95%
“…1,2 Their intriguing structures and broad bioactivities have been reported. 3,4 Among them, 6/6/6 tricyclic diterpenoids with a gem-dimethyl unit in one ring, such as abietane, cassane, pimarane, cleistanthane, and podocarpane diterpenoids, are several important subclasses. Their structural changes were mainly reflected in ring-opening or carbon reduction (Figure 1), such as 3,4-seco-cleistanthane.…”
Section: ■ Introductionmentioning
confidence: 99%