Eremophilane sesquiterpenes from Eremophila mitchelli

Massy-Westropp, RA; Reynolds, GD

doi:10.1071/ch9660303

Cited by 19 publications

(12 citation statements)

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“…[14] The presence of unusual terpenoid metabolites with a ketone group became evident as early as 1932 with the isolation of eremophilone ketone and its oxygenated derivatives from the wood oil of E. mitchellii. [17,28,69] Subsequently, it was suggested that the skeleton, of what now has become known as the eremophilane type, arises by methyl migration in precursors possessing the isoprenoid skeleton and configuration of the normal and biosynthetically regular eudesmanes. [14] The presence of eudesmol has been established and three derivatives accumulate in E. scoparia.…”

Section: Cyclic Sesquiterpenesmentioning

confidence: 99%

“…eremophilone (42) and eudesmane sesquiterpenes are dominant in only three species: E. mitchellii, E. scoparia and E. rotundifolia. [17,28,65,69,70] Two aromatic sesquiterpenes, (1R, 4R)-calamenene (60) and (1R, 4R)-7-hydroxy-calamenene (61) characterize the essential oils of E. drummondii and E. virens. [73,74] The unusual keto alcohol (+)-oplopanone (62) was isolated from E. miniata.…”

Section: Cyclic Sesquiterpenesmentioning

confidence: 99%

“…[61] The chemical analysis of the resins from leaves and terminal branches of E. virgata and E. interstans revealed a complex mixture of oxygenated sesquiterpenes. [75,76] Separation of these secondary metabolites led to the identification of five new cadinene sesquiterpenes (65)(66)(67)(68)(69). Another group of sesquiterpenes represented in Eremophila belong to the zizaene series with the tricyclo[6.2.1.0.…”

Section: Cyclic Sesquiterpenesmentioning

confidence: 99%

“…8,9-Dihydro-freelingyne (28) E. freelingii [63] Freelingnite (29) E. freelingii [64] Eremoacetal (30) E. rotundifolia [59] Dendrolasin (31) R = H E. rotundifolia [66] 4-Hydroxydendrolasin (32) R = OH E. rotundifolia [66] Dihydrophymaspermones (E-and Z-) (33) E. rotundifolia [59] Abdel Nasser Singab et al [67] 4-Hydroxydihydromyodesmone (35) E. alternifolia E. latrobei E. scoparia [67] 1-((5S)-2-(Furan-3-yl)-2-hydroxy-5methylcyclopentyl)-3-methylbut-2en-1-one (36) E. alternifolia E. latrobei E. scoparia [67] 4-Hydroxy-4-methyl-1-(2,3,4,5tetrahydro-5-methyl[2,3′-bifuran]-5-yl) pentan-2-one (37) E. duttonii [45] (R)-5-((R,E)-4-Hydroxy-2-methyl-5-(5-oxo-2,5-dihydrofuran-3-yl)pent-2enyl)-3-methylfuran-2(5H)-one (38) R = OH E. homoplastica [68] (R,E)-4-Methyl-5-((R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)-1-(5-oxo-2,5dihydrofuran-3-yl)pent-3-en-2-yl acetate (39) R = OAc E. homoplastica [68] (R,E)-3-Methyl-5-(2-methyl-5-(5-oxo-2,5dihydrofuran-3-yl)pent-2-enyl)furan-2(5H)-one (40) R = H E. homoplastica [68] (S,E)-2,6-Dimethyl-9-(5-oxo-2,5-dihydrofuran-3-yl)nona-2,6-dien-4-yl acetate (41) E. forrestii [68] Abdel Nasser Singab et al Eremophila: ethnobotany, biology & chemistry [17,28,69] (2R,3R,4aR,5S)-2-Hydroxy-3-isopropyl-4a,5-dimethyl-3,4,4a,5,6,7hexahydronaphthalen-1(2H)-one (43) R1 = a-OH; R2 = CH3 E. mitchellii [28,69,79] (R)-2-((2S,8S,8aR)-8,8a-Dimethyl-4oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)propanal (44) R1 = H; R2 = CHO E. rotundifolia [80] 9-Hydroxy-7(11),9-eremophiladien-8-one (45) R = OH E. mitchellii [28,69,79] (4aR,5S)-4a,5-Dimethyl-3-(propan-2ylidene)-4,4a,5,6,7,8hexahydronaphthalen-2(3H)-one (46) R = H E. mitchellii [28,69,79] (4aR,5S)-4a,5-Dimethyl-3-(prop-1-en-2-yl)-3,4,4a,5,6,7-hexahydronaphthalen-1(2H)-one (47) R1 = H; R2 = CH3 E. mitchellii [17] 2-((8S,8aR)-8,8a-Dimethyl-4-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)acrylaldehyde (48) R1 = H; R2 = CHO E. mitchellii <...>…”

Section: Serrulatanesmentioning

confidence: 99%

“…The only sterol definitively identified so far is the ubiquitous phytosterol, b-sitosterol (163) in E. mitchellii and E. georgei. [14,69] Triterpenes also rarely occur and only three have been isolated, such as ursolic (164) and oleanolic acid (165) from E. caerulea and 3-epi-oleanolic acid (166) from E. platycalyx (Table 7). [14,54] Fatty acids E. oppositifolia contains a branched threefold unsaturated fatty acid (167) accompanied by smaller amounts of stearic (168), oleic and palmitic acid (169) and esters of n-hexanoic (170), n-heptanoic (171), and n-octanoic acid (172).…”

Section: Sterols and Triterpenesmentioning

confidence: 99%

See 4 more Smart Citations

The genus Eremophila (Scrophulariaceae): an ethnobotanical, biological and phytochemical review

Singab

Youssef

Ashour

2013

Journal of Pharmacy and Pharmacology

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Objectives Eremophila (Scrophulariaceae) is an endemic Australian genus with 214 species, which is commonly known as Fuchsia bush, Emu bush or Poverty bush. Plants of this genus played an important role for the Australian Aborigines who used them widely for medicinal and ceremonial purposes. Many studies have been carried out on many species of this genus and have generated immense data about the chemical composition and corresponding biological activity of extracts and isolated secondary metabolites. Key findings Thorough phytochemical investigations of different Eremophila species have resulted in the isolation of more than 200 secondary metabolites of different classes with diterpenes as major constituents. Biological studies and traditional clinical practice demonstrated that Eremophila and its bioactive compounds possess various pharmacological properties. Plants were employed especially as a cardiotonic drug and also as potent anti-inflammatory, antimicrobial and antiviral agents. Summary Further investigations are required to explore other Eremophila species, to evaluate the different biological activities of either their extracts or the isolated compounds and the possible underlying modes of action.

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