New sesquiterpene lactones from Inula species

Bohlmann, Ferdinand; Mahanta, Pradip K.; Jakupovic, Jasmin; Rastogi, R. C.; Natu, Arvind A.

doi:10.1016/s0031-9422(00)94308-5

Cited by 213 publications

(97 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Column eluate was collected in 24-mL test tubes and, based on TLC similarities, recombined into 5 fractions [A, 1-74, 23 mg; B, 75-83, 32 mg; C, 84-96, 1.176 g; D, 97-108, 223 mg; E, 109-150, 48 mg]. Further purification of the bioactive fraction C was accomplished using repeated VLC procedures on silica gel, as described previously, 14,15 to yield pure compounds 1, 4, and 6. Identification was accomplished by comparison of spectroscopic data with that reported in the literature.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Bioassay-guided isolation of anti-algal constituents from Inula helenium and Limonium myrianthum

Cantrell¹,

Mamonov²,

Ryabushkina³

et al. 2006

Arkivoc

View full text Add to dashboard Cite

Over 70 crude plant extracts, primarily from Kazakhstan, were screened against the freshwater phytoplanktons Oscillatoria perornata and Selenastrum capricornutum. Extracts from Limonium myrianthum and Inula helenium both demonstrated selective inhibition against the odorproducing cyanobacterium O. perornata compared to activity against the green alga S. capricornutum. Bioassay-guided fractionation of the L. myrianthum dichloromethane extract resulted in the identification of nepodin, torachrysone, chrysophanol, and physcion. Nepodin demonstrated the desired selective inhibition with lowest-complete-inhibition concentration values of 100 µg/mL and >100 µg/mL towards O. perornata and S. capricornutum, respectively. Similarly, chrysophanol also demonstrated the desired selective inhibition with lowest-completeinhibition concentration values of 10 µg/mL and >100 µg/mL, respectively. Bioassay-guided fractionation of the I. helenium hexane extract resulted in the isolation of alantolactone, isoalantolactone, and 11αH,13-dihydroisoalantolactone. Activities of these three isolated constituents as well as those of synthetic isomers are reported.

show abstract

Section: Resultsmentioning

confidence: 99%

“…Identification was accomplished by comparison of spectroscopic data with that reported in the literature. 14,15 Derivatization of I. helenium compounds. Compounds 1 and 4 were converted to their respective mono-epoxide isomers 5α-epoxyalantolactone (2) and 4(15)α-epoxyisoalantolactone (5) using previously described methods.…”

Section: Resultsmentioning

confidence: 99%

Bioassay-guided isolation of anti-algal constituents from Inula helenium and Limonium myrianthum

Cantrell¹,

Mamonov²,

Ryabushkina³

et al. 2006

Arkivoc

View full text Add to dashboard Cite

show abstract

“…In some Inula, Doronicum and Pulicaria species, thymyl derivatives rather than sesquiterpenoids are the major root constituents. [20][21][22][23] A review by Talavera-Aleman and collaborators 24 estimated that only 10% of known functionalized thymyl derivatives have been employed in biological testing, showing vast array of diverse activities, such as antimicrobial 4,5,22,[25][26][27] (several papers reporting inhibitory activity against plants' pathogenic fungi 22,26 ), antioxidant, 28 antinociceptive, 29 anti-parasitic (antileishmanial), 30,31 antiprotozoal, 32 insecticidal 33 and piscicidal 34 activity. The usefulness of thymyl derivatives as transdermal drug delivery enhancers has also been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Lazarević

Kolarević

Stojanović

et al. 2017

ACSi

View full text Add to dashboard Cite

Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.

show abstract

“…Alantolactone and isoalantolactone, first isolated from Inula helenium [1], are the main active constituents in Radix Inulae, commonly used in a folk medicine called Tu-Mu-Xiang in China [2]. Current literature shows that alantolactone and isoalantolactone possess various antimicrobial [3], antiinflammatory [4], and antitumor activities [5][6][7][8][9][10] both in vivo and in vitro.…”

Section: Introductionmentioning

confidence: 99%

Metabolism Analysis of Alantolactone and Isoalantolactone in Rats by Oral Administration

Wang

Peng

et al. 2018

Journal of Chemistry

View full text Add to dashboard Cite

Alantolactone and isoalantolactone are the major active ingredients of Inulae Radix. Their metabolism in vivo and in vitro was investigated by UPLC-Q-TOF-MS for the first time. As a result, nine metabolites in vivo including cysteine conjugates, oxidates, dehydrogenates, and hydrates were detected in rat bile after oral administration. The metabolites produced in vitro by incubation with rat liver microsomes were found to be substantially identical to those detected in vivo. However, no metabolites were detected in the samples of plasma, feces, and urine or in the incubates of gastric juice, intestinal juice, and intestinal bacteria. These results reveal that the liver is the main metabolic organ for alantolactone and isoalantolactone, and the first pass effect of the liver appears to be the reason for the low oral bioavailability of the two lactones.

show abstract

New sesquiterpene lactones from Inula species

Cited by 213 publications

References 22 publications

Bioassay-guided isolation of anti-algal constituents from Inula helenium and Limonium myrianthum

Bioassay-guided isolation of anti-algal constituents from Inula helenium and Limonium myrianthum

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Metabolism Analysis of Alantolactone and Isoalantolactone in Rats by Oral Administration

Contact Info

Product

Resources

About