Eudesmanolides from Dimerostemma brasilianum

Bohlmann, Ferdinand; Singh, Pahup; Jakupovic, Jasmin; King, Robert M.; Robinson, Harold

doi:10.1016/0031-9422(82)80139-8

Cited by 22 publications

(26 citation statements)

References 5 publications

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“…In this study, we also report a known germacrolide (1) and a known germacranolide (3) that appear for the first time in this genus along with a known eudesmanolide (2). Interestingly, in a previous study of D. brasilianum, fourteen eudesmanolides and no germacranolides were reported (Bohlmann et al, 1982).…”

Section: Resultsmentioning

confidence: 97%

Sesquiterpene Lactones from Dimerostemma Species (Asteraceae) and in vitro Potential Anti-Inflammatory Activities

Stefani

Schorr

Tureta

et al. 2006

Zeitschrift Für Naturforschung C

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Two Brazilian species of Dimerostemma (Asteraceae) were chemically investigated. Two known sesquiterpene lactones (STLs), a germacrolide and an eudesmanolide, were isolated from D. episcopale while D. brasilianum afforded the new germacranolide 1 ,5 ,10α-trihydroxy-8α-angeloyloxy-germacra-3,11(13)-dien-6α,12-olide in addition to a known one. Structure identification based on NMR and MS analyses. 1 ,10α,4α,5 -Diepoxy-8α-angeloyloxycostunolide isolated from D. brasilianum was studied for its anti-inflammatory activity. This STL completely inhibited DNA binding of the transcription factor NF-κB at a concentration of 5 μm and 10 μm in Jurkat T and Raw 264.7 cells, respectively. Elastase release from human neutrophils was reduced to 50% at a concentrations of 23 μm after stimulation with PAF and of 27 μm after stimulation with fMLP without showing cytotoxic effects. Additionally, elastase was also directly inhibited.

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Section: Resultsmentioning

confidence: 97%

Sesquiterpene Lactones from Dimerostemma Species (Asteraceae) and in vitro Potential Anti-Inflammatory Activities

Stefani

Schorr

Tureta

et al. 2006

Zeitschrift Für Naturforschung C

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“…[17,19Ϫ21] The spectra obtained with compound 8 are very similar to those of compound 7, with one exception. On the basis of spectra previously described for chromomoric acid F [18] and our compound 7 we assume that the correct structure is as shown in Figure 1. The mass spectrum of 8 shows M ϩ peaks at m/z ϭ 400 and 402 (1:0.98) (C 19 H 29 BrO 4 ).…”

Section: Resultsmentioning

confidence: 98%

“…They are similar to chromomoric acids B and F, isolated from Chromolaena morii and C. chasleae. [17,18] Chromomoric acid B methyl ester has also been found in other species such as Schistostepnium, [19] Montanoa, [20] and [a] 309 modified Mosher method. The compounds gave positive results in a brine shrimp toxicity assay, a sea urchin eggs test (Paracentrotus lividus), and a crown gall tumor on potato disks test (Agrobacterium tumefaciens).…”

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confidence: 99%

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

Řezanka

Dembitsky

2002

Eur J Org Chem

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Eight new brominated oxylipins 1−8, including two glycosides, were isolated from the Red Sea invertebrates Dendrophyllia sp., Dendronephthya sp. (red variety), Dendronephthya sp. (yellow variety), and Tubipora musica. Their structures were elucidated mainly on the basis of NMR spectroscopic data. The relative and absolute configurations were determined by analysis of NOESY and CD data and by the IntroductionThe ongoing investigation of the chemical constituents of soft corals of the Anthozoa class has resulted in the isolation of a number of different active metabolites.[1] Among them, halogenated compounds Ϫ predominantly steroids, [2] diterpenes, [3] alkaloids, [4] and prostanoids [5] Ϫ have received much attention because of their strong antiinflammatory and antitumor activities. The chemistry of prostaglandins has now entered a new stage, thanks to newly discovered, predominantly halogenated, compounds. The first paper describing the isolation of prostaglandins from a Caribbean gorgonian coral [6] was published more than 30 years ago; 16 years later, halogen-substituted prostaglandins were isolated for the first time from an octocoral. [5] Marine prostanoids, predominantly halogenated, are distributed among a number of different marine sources and include, for example, chloro-punaglandins [7Ϫ10] from octocorals living in the Pacific ocean, chloro-epoxy prostanoids from Clavularia viridis, [11] punaglandins from Hawaiian octocorals, [5] and also substituted chloro-, bromo-, and iodovulones [12Ϫ16] from corals.Further metabolites with different but similar structures Ϫ including a cyclopentenone ring Ϫ were found in Dendrophyllia sp. They are similar to chromomoric acids B and F, isolated from Chromolaena morii and C. chasleae. [17,18] Chromomoric acid B methyl ester has also been found in other species such as Schistostepnium, [19] Montanoa, [20] and [a] 309 modified Mosher method. The compounds gave positive results in a brine shrimp toxicity assay, a sea urchin eggs test (Paracentrotus lividus), and a crown gall tumor on potato disks test (Agrobacterium tumefaciens).

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“…[352,353] The (À)enantiomer of 138 was later isolated from several other plants. [177,349,[354][355][356][357][358][359][360][361][362][363][364][365][366][367] Full 1 H-and 13 C-NMRd ata in CDCl 3 and C 6 D 6 have been reported. [367,368]…”

Section: Compounds From J3mentioning

confidence: 98%

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

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This review summarises known sesquiterpenes whose biosyntheses proceed through the intermediate germacrene A. First, the occurrencea nd biosynthesis of germacrene Ai nN ature and its peculiar chemistry will be highlighted , followed by ad iscussion of 6-6 and 5-7 bicyclic compounds and their more complex derivatives. For each compound the absolutec onfiguration, if it is known,a nd the reasoning for its assignment is presented. 2. Germacrene A 2.1. Occurrence in Nature (À)-Germacrene A(1,S cheme 2) was first isolated in 1970 from the gorgonian Eunicea mammosa. [7] Its absolute configuration was established as (S)-(À)-1 through its Cope rearrangement to (+ +)-b-elemene (2)f or which the configurational assignment was performed by chemical correlation of (À)-elemol(3)t o (À)-2. [8, 9] Compound (À)-1 is also believed to occur in the soft coral Lobophytum, [10] andi st he alarm pheromone of the aphid Terioaphis maculata. [11, 12] In the course of this work it was noticed that the optical rotation([ a] D 25 = À26.8, c 1.0, CCl 4)w as significantly highert han initially reported ([a] D 25 = À3.2, c 14.4, CCl 4), [7] which is explainableb yapartial rearrangement of purified (À)-1 to (+ +)-2,o ra lternatively, 1 isolated from E. mammosa was not enantiomerically pure. However,the opticalrotation of (+ +)-2 ([a] D 25 =+15.1, neat) reported in this initial study [7] matches the reported value for (À)-2 ([a] D 25 = À15.8, c 0.50, CHCl 3)o btainedb yC ope rearrangement of (+ +)-1, [13] thus disfa-Scheme1.Te rpene cyclisation modes for FPP. Scheme2.Structure of 1 and its absolute configurationbyc hemicalcorrelation.

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Eudesmanolides from Dimerostemma brasilianum

Cited by 22 publications

References 5 publications

Sesquiterpene Lactones from Dimerostemma Species (Asteraceae) and in vitro Potential Anti-Inflammatory Activities

Sesquiterpene Lactones from Dimerostemma Species (Asteraceae) and in vitro Potential Anti-Inflammatory Activities

Brominated Oxylipins and Oxylipin Glycosides from Red Sea Corals

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

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