Eugenunilones A–H: rearranged sesquiterpenoids from Eugenia uniflora

Abstract

Six rearranged sesquiterpenoid dimers and monomers with four kinds of new skeletons, meso-eugenunilone A (meso-1), (+)- and (-)-eugenunilones B-F [(+)-and (-)-2-6], along with two new biogenetically related members (+)- and...

A monocarbocyclic sesterterpenoid biosynthetic precursor of leucosceptroids from Leucosceptrum canum and its metabolic isomerization by a specialist insect

“…The methods and details for the 1 H/ 13 C NMR calculations, DP4+ probability analyses, and ECD computations are provided in the ESI† according to ref. 26–28.…”

Natural Sesquiterpenoids, Diterpenoids, Sesterterpenoids, and Triterpenoids with Intriguing Structures from 2017 to 2022

“…Four rearranged sesquiterpenoids eugenunilones C—F ( 20 — 23 ), possibly originated from the carbon skeleton of germacrane, have been isolated from the fruits of Eugenia uniflora , [ 46 ] an evergreen shrub native to South America. [ 47‐49 ] Structurally, eugenunilones C and D ( 20 and 21 ) possess new skeletons assembled on caged tricyclo[4.3.1.0 3,7 ]decane and bicyclo[3.2.1]octane scaffolds, respectively, while eugenunilones E and F ( 22 and 23 ) possess a rare tricyclo[4.4.0.0 2,10 ]decane ring system.…”

Natural Sesquiterpenoids, Diterpenoids, Sesterterpenoids, and Triterpenoids with Intriguing Structures from 2017 to 2022

“…[38] Another unusual germacrane derivative tomenphantadenine (19 ), with an adeninesubstituted unit, has been isolated from the whole plant of Elephantopus tomentosus L, and 19 showed potent antibacterial activity against the gram-positive Staphylococcusaureus . [39] Four rearranged sesquiterpenoids eugenunilones C-F (20 -23 ), possibly originated from the carbon skeleton of germacrane, have been isolated from the fruits of Eugenia uniflora , [40] an evergreen shrub native to South America. [41][42][43] Structurally, eugenunilones C and D (20 and 21 ) possess new skeletons assembled on caged tricyclo[4.3.1.0 3,7 ]decane and bicyclo[3.2.1]octane scaffolds, respectively, while eugenunilones E and F (22 and 23 ) possess a rare tricyclo[4.4.0.0 2,10 ]decane ring system.…”