Antileishmanial and antifungal activities of xanthanolides isolated from Xanthium macrocarpum

Lavault, M.; Landreau, Anne; Larcher, Gérald; Bouchara, Jean‐Philippe; Pagniez, Fabrice; Pape, Patrice Le; Richomme, Pascal

doi:10.1016/j.fitote.2005.03.019

Cited by 63 publications

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“…Representative examples of the cis-fused xanthanolides are the sundiversifolide (4), [7][8][9][10]11) the diversifolide (5) 10,12) and the 8-epi-xanthatin (9) 11,13,14) ; xanthatin (7) 11,15) and 11α,13-dihydroxanthatin (8) belong to the trans series. 11,16) They are known for their wide variety of interesting allelopathic, 17) cytotoxic, 18) anti-leishmanial, 19) and anti-MRSA activity. 5) As part of our ongoing program directed towards the synthesis of xanthanolides, we have established an efficient access to both cis-and trans-xanthanolides starting from the bicyclic lactone 2 with a cis ring juncture, which can be prepared from the Evans aldol adduct 1 as the common key intermediate in an optically pure form, and have achieved the total synthesis of four xanthanolides, 4, 5, 6 and 7.…”

Section: Multidrug-resistant Pathogens Such As Methicillin-resistantmentioning

confidence: 99%

“…Representative examples of the cis-fused xanthanolides are the sundiversifolide (4), 7-10,11) the diversifolide (5) 10,12) and the 8-epi-xanthatin (9) 11,13,14) ; xanthatin (7) 11,15) and 11α,13-dihydroxanthatin (8) belong to the trans series. 11,16) They are known for their wide variety of interesting allelopathic, 17) cytotoxic, 18) anti-leishmanial, 19) and anti-MRSA activity.…”

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Enantioselective Synthesis of 8-<i>epi</i>-Xanthatin and Biological Evaluation of Xanthanolides and Their Derivatives

et al. 2012

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An enantioselective synthesis of 8-epi-xanthatin (9) has been accomplished starting from the bicyclic lactone 3, which has been used for the synthesis of other xanthanolides, sundiversifolide (4) and diversifolide (5), through a synthetic route without the use of a selenium species. Additionally we have evaluated antimicrobial activities of five natural xanthanolides and their derivatives. Although the synthetic xanthanolides did not show any activity against methicillin-resistant Staphylococcus aureus (MRSA), some of the synthetic intermediates did exhibit moderate antimicrobial activities.Key words xanthanolide; enantioselective synthesis; antimicrobial activity; methicillin-resistant Staphylococcus aureus Multidrug-resistant pathogens such as methicillin-resistant Staphylococcus aureus (MRSA) continue to pose clinical challenges. 1,2) Recently the emergence of community-acquired MRSA has compounded the problem 3,4) and focused increased attention on efforts to develop new anti-MRSA drugs.In 1997, Sato et al. 5) reported that xanthatin (7), a member of the xanthanolides, 6) a sesquiterpene family possessing the characteristic oxabicyclo[5.3.0] decene core as its common basic carbon framework, exhibited potent anti-MRSA activity with an MIC value of 7.8 µg/mL. Xanthanolide sesquiterpenes were isolated from Helianthus annuus L. or Xanthium sp. and divided into two groups according to the configuration of their cis-and trans-ring junctions. Representative examples of the cis-fused xanthanolides are the sundiversifolide (4), 7-10,11) the diversifolide (5) 10,12) and the 8-epi-xanthatin (9) 11,13,14) ; xanthatin (7) 11,15) and 11α,13-dihydroxanthatin (8) belong to the trans series. 11,16) They are known for their wide variety of interesting allelopathic, 17) cytotoxic, 18) anti-leishmanial, 19) and anti-MRSA activity.5) As part of our ongoing program directed towards the synthesis of xanthanolides, we have established an efficient access to both cis-and trans-xanthanolides starting from the bicyclic lactone 2 with a cis ring juncture, which can be prepared from the Evans aldol adduct 1 as the common key intermediate in an optically pure form, and have achieved the total synthesis of four xanthanolides, 4, 5, 6 and 7. In this report we describe an enantioselective synthesis of 8-epi-xanthatin (9) starting from 3, which is the intermediate for 4 and 5, and the biological evaluation of the compound library including the five xanthanolides and their derivatives (Chart 1).8-epi-Xanthatin (9), commonly isolated from the extracts of the aerial parts of various species in the genus Xanthium, has also been obtained upon elimination of acetic acid from xanthumin (8-epi-2-acetoxy-3-hydroxanthatin). It has been shown Note * To whom correspondence should be addressed. e-mail: shishido@ph.tokushima-u.ac.jp 12) total synthesis of 1. In our previous synthesis of xanthatin (7), 15) which possesses a similar basic carbon framework and functionalities except for the stereochemistry on the ring junction, we employed two types of syn...

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Section: Multidrug-resistant Pathogens Such As Methicillin-resistantmentioning

confidence: 99%

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confidence: 99%

Enantioselective Synthesis of 8-<i>epi</i>-Xanthatin and Biological Evaluation of Xanthanolides and Their Derivatives

et al. 2012

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“…Riªng c¸c c©y ch©n voi mÒm, nóc ¸o chïm tô t¸n Ýt ®−îc sö dông. [1,2,[4][5][6][7][8][9][10][11][12].…”

Section: §èI T−îngunclassified

Bio-activities of the methanol extracts from some species belonging to the family Asteraceae in Lam Dong province

Duc¹,

Phan²,

Thuan³

et al. 2012

V J Bio

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“…Some studies concern the in vitro evaluations of purified compounds. Xanthinin, a xanthanolide from Xanthium macrocarpum harbouring an a-methylene-g-butyrolactone moiety, coumarin from Cadophyllum brasiliense, clerosterol from Cassia fistula and Jangambin from Ocotea duckei exhibited significant biological activities at promastigote or amastigote stages [75][76][77][78]. A new taxoid from Taxus baccata, 10-deacethylbaccatin III, was reported to be highly active (IC 50 : 70 nM) against the intracellular amastigote stage.…”

Section: Plant Products Against Leishmaniamentioning

confidence: 99%

Development of new antileishmanial drugs – current knowledge and future prospects

Pape

2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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Leishmaniasis is a protozoan vector borne disease prevalent throughout the world and present in at least 88 countries. The parasite is transmitted by infected phlebotomine sandfly bites. While conventional therapies i.e. pentavalent antimonials, amphotericin B and pentamidine continue to play a major role, it is evident that new drugs or strategies must circumvent the limitations, such as a long-term parenteral administration, toxicity, the high cost in endemic countries and the emergence of resistance, that prevail. One of the most promising drugs is miltefosine, a new oral, approved alkylphospholipid for visceral leishmaniasis with only slight adverse effects. Although we have now this recent and encouraging advance, there is still a need to develop safe, efficient and affordable new treatments for the different clinical forms that exist. This review summarises conventional therapy and the current efforts in the discovery of drugs to treat leishmaniasis with the emphasis on drug combinations to enhance efficiency and prevent the emergence of resistance, the investigation of natural products with the objective of offering new bioactive chemical structures and the development of novel antileishmanial targets.

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Antileishmanial and antifungal activities of xanthanolides isolated from Xanthium macrocarpum

Cited by 63 publications

References 13 publications

Enantioselective Synthesis of 8-<i>epi</i>-Xanthatin and Biological Evaluation of Xanthanolides and Their Derivatives

Enantioselective Synthesis of 8-<i>epi</i>-Xanthatin and Biological Evaluation of Xanthanolides and Their Derivatives

Bio-activities of the methanol extracts from some species belonging to the family Asteraceae in Lam Dong province

Development of new antileishmanial drugs – current knowledge and future prospects

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