The Chemistry of Eremophila Spp. XXV. New Cembrene Derivatives From E. dempsteri, E. platycalyx and E. fraseri

Ghisalberti, EL; Jefferies, PR; Mori, Trevor A.

doi:10.1071/ch9861703

Cited by 14 publications

(17 citation statements)

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“…Monoterpenes are not widely represented in the genus Eremophila; only a restricted number of Eremophiia species has been analysed by GLC-MS. [21] A few monoterpenes have been identified: geranyl acetate (1) is the major component in E. abietin, 1,8-cineole (2) in E. scoparia and E. dalyana, (+)-verbenone (3) in E. dempsteri, and (+)-fenchone (4) in E. caerulea. [14,[52][53][54] E. alternifolia yielded 4% essential oil mainly composed of fenchone (4) and limonene (8). a-Pinene (9) predominated the essential oils from E. duttoni, E. freelingii and E. longifolia, which were produced in small amounts (<1%).…”

Section: Monoterpenes and Iridoidsmentioning

confidence: 99%

“…Catalpol (11) E. maculata [56] Abdel Nasser Singab et al Eremophila: ethnobotany, biology & chemistry [55] Isomenthone (13) E. longifolia [55] Menthone (14) E. longifolia [55] a-Terpineol (15) E. longifolia [55] Piperitone (16) O E. longifolia [55] 4-Carene (17) E. longifolia [55] Abdel Nasser Singab et al Eremophila: ethnobotany, biology & chemistry biologically active cembrene metabolites. [14,52,54,86] These carry the same absolute configuration at C-1 and all retain the double bond at C-12 with differences in the levels of oxidation on methyl groups at C4 and C8. The observation that both the acyclic and cembrene diterpenes from Eremophila contain cis double bonds indicate that they derive from a common biosynthetic intermediate.…”

Section: Cembrenesmentioning

confidence: 99%

“…(2E,6Z)-2-((3Z,7E)-9-Acetoxy-4,8-dimethylnona-3,7-dienyl)-6-methylocta-2,6-dienedioic acid (77) R1 = H; R2 = OAc E. glutinosa [84] (1Z,5E,9Z,13E)-2,10-Dimethylpentadeca-1,5,9,13-tetraene-1,6,14-tricarboxylic acid (78) R1 = CH3; R2 = COOH; R3 = CH3 E. exilifolia [83] (1Z,5E,9Z,13Z)-2,10-Dimethylpentadeca-1,5,9,13-tetraene-1,6,14-tricarboxylic acid (79) R1 = COOH; R2 = CH3; R3 = CH3 E. exilifolia [83] (1Z,5E,9E,13E)-10-Formyl-2methylpentadeca-1,5,9,13-tetraene-1,6,14-tricarboxylic acid (80) R1 = CH3; R2 = COOH; R3 = CHO E. glutinosa [83] (1Z,5E,9E,13E)-2-Methylpentadeca-1,5,9,13tetraene-1,6,10,14-tetracarboxylic acid (81) R1 = CH3; R2 = COOH; R3 = COOH E. glutinosa [83] (1E,5Z,9E,13E)-2,6-Dimethylpentadeca-1,5,9,13-tetraene-1,10,14-tricarboxylic acid (82) E. glutinosa [83] Abdel Nasser Singab et al Eremophila: ethnobotany, biology & chemistry [83] (S,2E,6E,10Z)-6-Formyl-2,10,14trimethylhexadeca-2,6,10-trienedioic acid (84) R = CHO E. glutinosa [83] Epoxycembranediol (85) E. georgei [85] ( [52] Abdel Nasser Singab et al Eremophila: ethnobotany, biology & chemistry [54] (1R,8R,12R,13R,Z)-12-(Hydroxymethyl)-4,15,15-trimethyl-14-oxabicyclo[11.2.1] hexadec-4-ene-8-carbaldehyde (90) R1 = CH2OH; R2 = CHO E. platycalyx [54] 19-Acetoxy-3,15-epoxycembr-11-en-19-oic acid (91) R1 = CH2OAc; R2 = COOH E. gilesii [14] ( E. granitica [52] ((1S,5R,12S,Z)-12-(2-Hydroxypropan-2-yl)-9-methylcyclotetradec-8-ene-1,5-diyl)dimethanol (93) E. clarkei [86] 2-((1R,3Z,11Z)-8-(Hydroxymethyl)-4,12dimethylcyclotetradeca-3,11dienyl)propan-2-ol (94) E. dempsteri [54] Abdel Nasser Singab et al Eremophila: ethnobotany, biology & chemistry E. dempsteri [54] 2-((3,4,5,6,8aHexahydro-4,7-dimethyl-2H-1benzopyran-2-yl)-methylene)-6 methyl-5-heptenoic acid (96) E. foliosissima E. gilesii [87] [88]…”

Section: Decipianesmentioning

confidence: 99%

“…[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). [108,109] In most cases superficial analysis of the fats and fatty acids isolated from the resin has failed to reveal other than the usual fatty acids (Table 8).…”

Section: Sterols and Triterpenesmentioning

confidence: 99%

“…[81] Other lignans include phillyrin (190) from E. racemosa, a new dihydroxylignan from E. dalyana, (+)epieudesmin (193) and (+)-methylxanthoxylol (194) from E. calorhabdos. [53,74,91] Ursolic acid (164) E. caerulea [14] Oleanolic acid (165) R = b-OH E. caerulea [14] 3-Epi-oleanolic acid (166) R = a-OH E. platycalyx [54] Abdel Nasser Singab et al…”

Section: Phenolic Compoundsmentioning

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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