Reaction of guaianolide achillin with chlorine in methanol

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

doi:10.1007/bf02495170

Cited by 3 publications

(2 citation statements)

References 17 publications

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“…Furthermore, its (1 R ,1 R ,3 S ,4 S ,5 S ,6S,7 S ,9 R ,10 R ) absolute configuration was also defined by the calculated ECD data (Figure S2, Supporting Information). Therefore, the structure 7 was deduced for chrysanthemulide G. To date, more than 60 chlorine-containing guaianolide sesquiterpenoids have been isolated from the Asteraceae species, − and no chlorine-containing solvents were used during the process of extraction and isolation. Therefore, it is believed that compound 7 is a naturally occurring substance.…”

Section: Resultsmentioning

confidence: 99%

Highly Oxidized Guaianolide Sesquiterpenoids with Potential Anti-inflammatory Activity from Chrysanthemum indicum

Xue

Chen

et al. 2018

J. Nat. Prod.

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Ten new highly oxidized monomeric (1-8) and dimeric guaianolides (9 and 10), along with two known guaianolide derivatives (11 and 12), were isolated from the aerial parts of Chrysanthemum indicum using a bioassay-guided fractionation procedure. The new compounds were characterized by the basic analysis of the spectroscopic data obtained, and the absolute configurations were determined by both empirical approaches and ECD calculations. Inhibitory effects of 1-12 on nitric oxide production were investigated in lipopolysaccaride (LPS)-mediated RAW 264.7 cells, and most of them (1-8 and 11) displayed IC values in the range 1.4-9.7 μM. Moreover, a mechanistic study revealed that the potential anti-inflammatory activity of compound 1 appears to be mediated via suppression of an LPS-induced NF-κB pathway and down-regulation of MAPK activation.

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Section: Resultsmentioning

confidence: 99%

Highly Oxidized Guaianolide Sesquiterpenoids with Potential Anti-inflammatory Activity from Chrysanthemum indicum

Xue

Chen

et al. 2018

J. Nat. Prod.

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“…We've carried out the reaction of dienes with chlorine gas using available guaianolides of achillin, grossmisin and leucomisin to obtain new chlorine derivatives [45][46][47][48].…”

Section: Synthesis Of Chlorine-containing Sesquiterpene Lactonesmentioning

confidence: 99%

Heteroatom-Containing Natural Sesquiterpene Lactones and Methods for their Obtaining

Адекенов¹,

Атажанова²

2013

Eur Chem Tech J

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This review shows the data about isolated heteroatom-containing sesquiterpene lactones from various genera of Asteraceae family, natural occurence, isolation methods and their biological activity. Chlorinecontaining sesquiterpene lactones were isolated from genera of Artemisia L., Achillea L., Acroptilon Cass, Centaurea L., Chartolepis Cass, Eupatorium L., Jurinea Cass, Rhaponticum Adams, Saussurea DC. The greatest quantity of chlorine-containing sesquiterpene lactones were isolated from Centaurea genus. 25 new sesquiterpene lactones with chlorine atom in molecule were isolated and characterized. The sesquiterpene lactones, which in their structure contained a sulphur atom as a component of various alkoxyl-, thiohydroxygroups and acid residues, were isolated from genera of Eupatorium L., Petasites Mill, Helenium L., Acritopappus R.M. King and H. Rob., Arctium L., Saussurea DC. Nitrogen atom in the structure of natural sesquiterpene lactones is present in the form of amino groups as a part of ester groups as well as amino acids as Michael adducts. Nitrogen-containing sesquiterpene lactones were isolated from Acanthospermum Schrank, Saussurea DC. Isolated heteroatom-containing sesquiterpene lactones possess bactericidal, antifungal, cytotoxic, antiviral, virucidal, antiulcer and others activities. Another method for obtaining heteroatom-containing sesquiterpene lactones is a directed synthesis of chlorine-, fluorine-, bromine-, sulphur- and nitrogen-containing sesquiterpene lactones. On the basis of sesquiterpene lactone artemisinin known as an effective antimalarial preparation, we synthesized over 200 derivatives, among which fluorine-, chlorine-, bromine-, nitrogen-, sulphur- and azide-containing derivatives of artemisinin were obtained.

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ChemInform Abstract: Reaction of Guaianolide Achillin with Chlorine in Methanol.

Alebastrov¹,

Ралдугин²,

Шакиров³

et al. 2001

ChemInform

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Reaction of Guaianolide Achillin with Chlorine in Methanol. -The reaction of sesquiterpene lactone achillin (I) with chlorine in methanol affords four chlorinated and methoxylated products (III)-(VI). (V) is an intermediate in the formation of both dichlorides (III) and (IV). -(ALEBASTROV, O. V.; RALDUGIN, V. A.; SHAKIROV, M. M.; BAGRYANSKAYA, I. YU.; GATILOV, YU. V.; KULYJASOV, A. T.; ADEKENOV, S. M.; TOLSTIKOV, G. A.; Russ.

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Reaction of guaianolide achillin with chlorine in methanol

Cited by 3 publications

References 17 publications

Highly Oxidized Guaianolide Sesquiterpenoids with Potential Anti-inflammatory Activity from Chrysanthemum indicum

Highly Oxidized Guaianolide Sesquiterpenoids with Potential Anti-inflammatory Activity from Chrysanthemum indicum

Heteroatom-Containing Natural Sesquiterpene Lactones and Methods for their Obtaining

ChemInform Abstract: Reaction of Guaianolide Achillin with Chlorine in Methanol.

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