Occurrence of a novel cis,cis,cis‐octadeca‐3,9,12‐trienoic (Z,Z,Z‐octadeca‐3,9,12‐trienoic) acid in Chrysanthemum (Tanacetum) zawadskii herb. (Compositae) seed oil

Tsevegsüren, N.; Fujimoto, Kenshiro; Christie, William W.; Endo, Yasushi

doi:10.1007/s11745-003-1498-6

Cited by 11 publications

(8 citation statements)

References 33 publications

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“…The spectrum of DMOX derivatives of Δ3,9,12‐18:3, as well as of Δ3‐18:1 and Δ3‐ trans ‐16:1, showed the base peak at m/z 152 (Lamberto and Ackman , Tsevegsuren et al. , Christie ). Possibly, the spectrum presented in Figure c corresponds to the real DMOX derivative of all ‐ cis ‐3,6,9,12,15‐octadecapentaenoic acid.…”

Section: Discussionmentioning

confidence: 99%

Isomerization of octadecapentaenoic acid (18:5n‐3) in algal lipid samples under derivatization for GC and GC‐MS analysis

Svetashev

Imbs

2014

Journal of Phycology

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During gas chromatography (GC) analysis of fatty acid (FA) composition of the dinoflagellate Gymnodinium kowalevskii, we found unex-pectedly low and irreproducible content of all-cis-3,6,9,12,15-octadecapentaenoic acid (18:5n-3), which is an important chemotaxonomic marker of several classes of microalgae. We compared chromatographic behavior of 18:5n-3 methyl ester and other GC derivatives obtained using different conventional methods of derivatization. The use of methods based on saponification or base-catalyzed transesterification resulted in a mixture of double-bond positional isomers of 18:5. On a SUPELCOWAX 10 column, the equivalent chain length (ECL) value for authentic 18:5n-3 methyl ester was 20.22, whereas the main component after base-catalyzed methylation had ECL 20.88. Attempts to prepare N-acyl pyrrolidides or 4,4-dimethyloxazoline (DMOX) derivatives of 18:5n-3 also gave inadequate results. These derivatives also showed a main peak corresponding to isomerized 18:5. Mass spectra for both DMOX and pyrrolidide derivatives of this compound showed the base peak at m/z 139, probably corresponding to 2,6,9,12,15-18:5 acid. Of all methods tested for methylation, only derivatization with 5% HCl or 1% sulphuric acid in methanol gave satisfactory results. Therefore, GC or GC-mass spectrometry analyses of algal lipids containing 18:5n-3 may be inaccurate when base-catalyzed methods of FA derivatization are applied. The best and simplest way to avoid incorrect GC results is to use standard acid-catalyzed methylation.

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Section: Discussionmentioning

confidence: 99%

Isomerization of octadecapentaenoic acid (18:5n‐3) in algal lipid samples under derivatization for GC and GC‐MS analysis

Svetashev

Imbs

2014

Journal of Phycology

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“…In conclusion, seven new compounds (1-7) and 13 known compounds (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were isolated from the aerial parts of D. zawadskii var. latilobum, and their structures were determined by spectroscopic analysis.…”

Section: Resultsmentioning

confidence: 95%

“…latilobum 2) and the previous report on its anti-inflammatory activity, 14) the isolated compounds (1-6, 8-18, 20) were evaluated for their inhibitory effects on NO release in LPSstimulated RAW 264.7 macrophage cells. As shown in Table 4, flavonoids such as apigenin (9), eriodictyol (10) and nepetin (12), as well as the sesquiterpene lactone, zawadskinolide F (6), showed moderate inhibitory activity against NO production with IC 50 values of 66.15, 132.55, 35.44, and 91.32 μM, respectively. The cytotoxic effects of these compounds were measured using the (4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay.…”

Section: Resultsmentioning

confidence: 99%

“…9) These isolates have a variety of biological functions such as antifungal, 3) cytotoxic, 10) antimicrobial 5) and antibiotic 4) effects, nitric oxide and cholesterol acyltransferase inhibition, 11) farnesyl protein transferase (FPTase) inhibition, 12) and quinone reductase modulation. 13) In addition, the 70% EtOH extract and its hexane-soluble fraction were reported to strongly inhibit inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) activity.…”

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confidence: 99%

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Sesquiterpenes and Other Constituents from Dendranthema zawadskii var. latilobum

Shin

Lee

Kim

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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Six new germacranolides, zawadskinolides A-F (1-6), and a new eudesmane glucoside, chrysantiloboside (7) were isolated from the aerial parts of Dendranthema zawadskii var. latilobum, along with thirteen known constituents. Their structures were elucidated by means of spectroscopic evidence. Bioassay showed that flavonoids such as apigenin (9) farnesyl protein transferase (FPTase) inhibition, 12) and quinone reductase modulation.13) In addition, the 70% EtOH extract and its hexane-soluble fraction were reported to strongly inhibit inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) activity.14) In the course of our studies on the constituents of the MeOH extract of the aerial parts of D. zawadskii var. latilobum, six new sesquiterpene lactones, zawadskinolides A-F (1-6), and a new eudesmane glucoside, chrysantiloboside (7), together with thirteen known compounds were isolated. Since NO and prostaglandin E 2 are considered the major inflammatory mediators and in keeping with the traditional medical applications of this herb 2) and the previous report on its anti-inflammatory activity, 14) the isolates were evaluated for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. In this paper, we report the isolation, structural elucidation and biological evaluation of these compounds. Results and DiscussionDried aerial parts of D. zawadskii var. latilobum were extracted with MeOH and then fractionated with hexane, CH 2 Cl 2 , EtOAc, n-BuOH and water. By combined chromatographic separations of these extracts, seven new and thirteen known compounds were isolated. Their structures were elucidated using physicochemical and spectroscopic methods.

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“…Interestingly, the seed oil of A. scaber contains unusual trans-Δ3-enoic acids namely tΔ3-16:1; tΔ3, cΔ9-18:2 and tΔ3, cΔ9, 12-18:3 while the seed oil of Chrysanthemum zawadskii Herb. contains cΔ3, cΔ9, 12-18:3 2,3 .…”

Section: Introductionmentioning

confidence: 99%

Effects of Aster scaber Seed Oil Containing trans-Δ3 Fatty Acids on Lipid Profiles of Hamsters and Rats

et al. 2015

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Occurrence of a novel cis,cis,cis‐octadeca‐3,9,12‐trienoic (Z,Z,Z‐octadeca‐3,9,12‐trienoic) acid in Chrysanthemum (Tanacetum) zawadskii herb. (Compositae) seed oil

Cited by 11 publications

References 33 publications

Isomerization of octadecapentaenoic acid (18:5n‐3) in algal lipid samples under derivatization for GC and GC‐MS analysis

Isomerization of octadecapentaenoic acid (18:5n‐3) in algal lipid samples under derivatization for GC and GC‐MS analysis

Sesquiterpenes and Other Constituents from Dendranthema zawadskii var. latilobum

Effects of <i>Aster scaber</i> Seed Oil Containing <i>trans</i>-Δ3 Fatty Acids on Lipid Profiles of Hamsters and Rats

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