Bisabololoxide derivatives from Artemisia persica, and determination of their absolute configurations by ECD

Moradi-Afrapoli, Fahimeh; Ebrahimi, Samad Nejad; Smieško, Martin; Raith, Melanie; Zimmermann, Stefanie; Nadjafi, Farsad; Brun, Reto; Hamburger, Matthias

doi:10.1016/j.phytochem.2012.08.017

Cited by 12 publications

(5 citation statements)

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“…8) with improved pharmacological properties [17]. Another line of research has been focussed on new antiprotozoal compounds against tropical parasites, and a structurally diverse series of active compounds were identified [12,[29][30][31][32][33][34][35][36][37][38][39][40]. One of the promising compounds in this project was cynaropicrine which was identified as the antitrypanosomal constituent of an extract of Centaurea salmantica (l " Fig.…”

Section: Selected Applicationsmentioning

confidence: 96%

Combined Use of Extract Libraries and HPLC-Based Activity Profiling for Lead Discovery: Potential, Challenges, and Practical Considerations

Potterat

Hamburger

2014

Planta Med

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Introduction !The unique contribution of natural products to drug discovery is undisputed. Approximately 35 % of the new chemical entities approved as drugs over the past 30 years are directly derived from natural products [1]. However, despite this impressive track record, we have witnessed over the past two decades in the pharmaceutical industry a steady decline of interest for natural products. Various factors have contributed to this apparently paradoxical situation. Emerging technologies may have appeared at one time more promising and "easy" than natural products, which are often perceived as "old-fashioned" at the top management level. However, there have also been more objective reasons for this decline. With the advent of high throughput screening (HTS) in the 1990s, natural product research struggled to find its place in the new drug discovery environment. The classical approach relying on several iterative steps of bioactivity-guided fractionation could not keep pace with the fast turnaround and the tight deadline of HTS-based screening programs [2]. At the same time, the technological advances in HTS, in particular with respect to automation and data management, and significant developments in chromatography and spectroscopy have opened entirely new possibilities for the investigation of natural product extracts. In a time where most major pharmaceutical companies have discontinued their natural product screening activities, these new opportunities have been recognized by biotech companies, and by an increasing number of academic research groups. Switching to a database format for extract handling enables efficient library management and smooth data transfer to screening facilities. The use of new strategies combining, in a more or less seamless manner, HPLC microfractionation with spectroscopic and bioactivity data enables prioritization of hits and identification of bioactive constituents at an early stage [2]. In this context, we set up a tailored technology platform for library-based lead discovery. Its core features are an extract library in 96-well format combined with a customized database, automated liquid handling, HPLC-based tracking of bioactivity, on-line (DAD and ESI-and APCI-MS, including HR-MS) and off-line (microprobe NMR) spectroscopy for structure elucidation. We describe here the different components of this platform and discuss the potential of our workflow Abstract ! A 96-well format plant extract library and a tailored technology platform have been set up for the discovery of new natural product lead compounds. The considerable advantages of the library approach are discussed. Key considerations such as sample generation, logistics, and data management are addressed. The potential of a HPLC-based profiling approach combining offline bioassays with in-line and off-line spectroscopy (including HR-ESIMS and microprobe NMR) for tracking bioactivity is demonstrated with a selection of examples encompassing different types of bioassay formats. The information generated by this approac...

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Section: Selected Applicationsmentioning

confidence: 96%

Combined Use of Extract Libraries and HPLC-Based Activity Profiling for Lead Discovery: Potential, Challenges, and Practical Considerations

Potterat

Hamburger

2014

Planta Med

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“…Greve 等 [37] (68). Moradi-Afrapoli 等 [42] 对菊科植物 Artemisia persica 的地上部分进行提取分离, 最后从中分离鉴定 4 个新的双酰氧基倍半萜二酯(69～ 72), 药理学研究显示所有化合物对多药耐药恶性疟原虫株 K1 均表现出一定的抑制活性. Cubukcu 等 [43] 从菊科植物 Artemisia abrotanum L 的地上部分分离得到 1 个新的倍半萜 1(S * )-Hydroxy-α-bisabololoxide A acetate (73), 并发现该化合物有一定的抑制多药耐药恶性疟原虫株 K1 的活性.…”

Section: Asteraceaeunclassified

“…). Topcu 等 [44] 从松节藻科植物 Laurencia obtusa 中分离得到 1 个溴化倍半萜 (8R * )-8-Bromo-10-epi-β-snyderol (74), 该化合物可抑制耐氯喹恶性疟原虫株 W2 和氯喹敏感疟原虫株 D6 的活性. König 等 [45] 测定了从松节藻科植物 Laurencia implicata 中分离鉴定的 3 个倍半萜( 75 1996 [40] Zingiberene-3,6-β-endoperoxide (67) Asteraceae Senecio selloi/Eupatorium rufescens 42.31 (FCH5) 1996 [40] Yingzhaosu A (68) Annonaceae Artabotrys uncinatus 0.12 (K1) 2005 [41] 69 Asteraceae Artemisia persica 2.8±0.4 (K1) 2013 [42] 70 Asteraceae Artemisia persica 14.9±1.7 (K1) 2013 [42] 71 Asteraceae Artemisia persica 20.1±0.7 (K1) 2013 [42] 72 Asteraceae Artemisia persica 19.1±2.2 (K1) 2013 [42] 1(S * )-Hydroxy-α-bisabololoxide A acetate (73) Asteraceae Artemisia abrotanum 17.17 (K1) 1990 [43] 图 4 植物来源单环金合欢烷型倍半萜类化合物的化学结构 Figure 4 Chemical structures of monocyclofarnesane-type sesquiterpenoids from plants 现出一定的抑制作用. 78).…”

Section: Asteraceaeunclassified

Research Progress on Antimalarial Natural Sesquiterpenoids from Plants from 1972 to 2022

Wu,

Xiao,

Shen

et al. 2023

Chinese Journal of Organic Chemistry

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“…Outros estudos da atividade antimalárica de terpenos demostram que esses metabólitos são promissores para tal atividade. Sequiterpenos bisabolanos p-mentânicos isolados das partes aéreas da Artemisia persica se mostraram ativas quando testadas in vitro frente a uma cepa resistente (K1) de Plasmodium falciparum, mostraram excelente atividade antiplasmódica com CI50 de 2,8 µg/mL (Moradi-Afrapoli et al, 2013). Vale ressaltar que, uma potente droga antimalárica é o arteether, derivada da artemisinina, um sequiterpeno lactona isolado da Artemisia annua (Klayman, 1985, Van Agtmael et al, 1999Graul, 2001).…”

Section: Atividade Antimaláricaunclassified

Potencial antileishmania, antimalárico e antitrypanossoma de espécies de Casearia: Uma revisão integrativa

Oliveira

Silva

Cardoso

et al. 2021

RSD

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O tratamento de doenças parasitárias tem como um de seus maiores desafios a resistência desenvolvida pelos parasitos contra os medicamentos disponíveis. Portanto, a busca por alternativas terapêuticas é urgente. Este estudo realizou uma revisão integrativa da literatura que avaliou o potencial antileishmania, antimalárico e antitrypanossoma de plantas do gênero Casearia. A busca dos artigos científicos foi realizada no Portal de Periódicos da CAPES (PPC), Biblioteca Virtual em Saúde (BVS), PUBMED e SCIELO, utilizando-se os seguintes descritores: Casearia e antileishmania; Casearia e antimalárico; e Casearia e antitrypanossoma. Um total de 122 publicações foram coletadas para triagem, destes, 11 foram incluídos na revisão integrativa. Na atividade antileishmania, a Casearia sylvestris se destacou, com extrato hexano da madeira e casca do caule e o extrato etanólico da casca da raiz apresentando atividade contra diferentes espécies de Leishmania (CI50<100 µg/mL), porém com elevada toxicidade (CC50<100 µg/mL). Dentre as substâncias isoladas, o flavonoide Tricina se mostrou ativo contra Leishmania e não citotóxico. Quanto a atividade antimalárica, 11 extratos de 3 espécies, C. elliptica, C. coriaceae e C. sylvestris mostraram-se ativos (CI50<100 µg/mL), no entanto, apresentaram toxicidade. Na atividade antitrypanossoma, as casearinas isoladas das folhas de C. sylvestris, apresentaram grande potencial contra a forma tripomastigota de T. cruzi (CI50<3,0 µg/mL), porém, apresentaram elevada toxicidade. As espécies de Casearia são, portanto, promissoras quanto à sua atividade antiparasitária, mas sua toxicidade é um problema. No entanto, os flavonoides da espécie apresentam bom índice de seletividade e, alterações moleculares e/ou formulações adequadas podem reduzir a toxicidade dos outros componentes.

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Bisabololoxide derivatives from Artemisia persica, and determination of their absolute configurations by ECD

Cited by 12 publications

References 24 publications

Combined Use of Extract Libraries and HPLC-Based Activity Profiling for Lead Discovery: Potential, Challenges, and Practical Considerations

Combined Use of Extract Libraries and HPLC-Based Activity Profiling for Lead Discovery: Potential, Challenges, and Practical Considerations

Research Progress on Antimalarial Natural Sesquiterpenoids from Plants from 1972 to 2022

Potencial antileishmania, antimalárico e antitrypanossoma de espécies de Casearia: Uma revisão integrativa

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