Ajanolide A, a new germacranolide fromAjania fruticulosa

Адекенов, С. М.; Kulyjasov, A. T.; Ралдугин, В. А.; Bagryanskaya, I. Yu.; Gatilov, Yu. V.; Шакиров, М. М.

doi:10.1007/bf02495526

Cited by 8 publications

(3 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The coupling constants across the protons at positions H-5-H-7 (J 5,6 =11.0 Hz and J 6,7 was very small and not measurable) were equivalent to the literature values for heliangolides such as provincialin, heliangolidin, and ajanolide A. [21][22][23] Further relative stereochemistry of 2 was confirmed by NOESY experiment. The NOE correlations (Fig.…”

Section: Resultssupporting

confidence: 79%

“…The Z-configuration of the Δ 4 -double bond and the E-configuration of the Δ 1(10) -double bond were confirmed by NOE correlations between H-5 and H-15 and between H-6 and H-14, respectively. Therefore, compound 2 was identified as 3β-acetoxy-15-hydroxy-germacra-1(10)E,4Z-dien-6β,7α,11αH-12,6-olide (15-hydroxyajanolide A) 23) and named zawadskinolide B.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Sesquiterpenes and Other Constituents from Dendranthema zawadskii var. latilobum

Shin

Lee

Kim

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

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.

show abstract

Section: Resultssupporting

confidence: 79%

Section: Resultsmentioning

confidence: 99%

Sesquiterpenes and Other Constituents from Dendranthema zawadskii var. latilobum

Shin

Lee

Kim

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…The plant has been used to treat appendicitis, tuberculosis, and emphysema in Chinese folk medicine . The literatures have shown that the main secondary metabolism of the plant included sesquiterpenes, flavonoids, sesquiterpene lactone, and phenolics . In this paper, we investigated the insecticidal activities of the essential oil, and the compounds from A .…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents and Insecticidal Activities ofAjania fruticulosaEssential Oil

Liang

Guo

You

et al. 2016

Chemistry & Biodiversity

View full text Add to dashboard Cite

The insecticidal activity and chemical constituents of the essential oil from Ajania fruticulosa were investigated. Twelve constituents representing 91.0% of the essential oil were identified, and the main constituents were 1,8-cineole (41.40%), (+)-camphor (32.10%), and myrtenol (8.15%). The essential oil exhibited contact toxicity against Tribolium castaneum and Liposcelis bostrychophila adults with LD50 values of 105.67 μg/adult and 89.85 μg/cm(2) , respectively. The essential oil also showed fumigant toxicity against two species of insect with LC50 values of 11.52 and 0.65 mg/l, respectively. 1,8-Cineole exhibited excellent fumigant toxicity (LC50 = 5.47 mg/l) against T. castaneum. (+)-Camphor showed obvious fumigant toxicity (LC50 = 0.43 mg/l) against L. bostrychophila. Myrtenol showed contact toxicity (LD50 = 29.40 μg/cm(2) ) and fumigant toxicity (LC50 = 0.50 mg/l) against L. bostrychophila. 1,8-Cineole and (+)-camphor showed strong insecticidal activity to some important insects, and they are main constituents of A. fruticulosa essential oil. The two compounds may be related to insecticidal activity of A. fruticulosa essential oil against T. castaneum and L. bostrychophila.

show abstract