Synthesis and structure–activity relationships of cassiarin A as potential antimalarials with vasorelaxant activity

Morita, Hiroshi; Tomizawa, Yuichiro; Deguchi, Jun; Ishikawa, Tokio; Arai, Hiroko; Zaima, Kazumasa; Hosoya, Tsuyoshi; Hirasawa, Yusuke; Matsumoto, Takayuki; Kamata, Katsuo; Ekasari, Wiwied; Widyawaruyanti, Aty; Wahyuni, Tutik Sri; Zaini, Noor Cholies; Honda, Toshio

doi:10.1016/j.bmc.2009.10.013

Cited by 36 publications

(10 citation statements)

References 28 publications

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“…This result was similar to β ‐hexosaminidase inhibitory activity against RBL‐2H3 cells . Recently, new antimalarial natural products, the chromone alkaloid cassiarins, were discovered from Cassia siamea , and the biological activity was dependent on the size of the substitution by SAR analysis . Kaur et al .…”

Section: Resultssupporting

confidence: 70%

“…[19] Recently, new antimalarial natural products, the chromone alkaloid cassiarins, were discovered from Cassia siamea, and the biological activity was dependent on the size of the substitution by SAR analysis. [20] Kaur et al [21] reported that the antimalarial activity of 8-quinolinamine, primaquine analogues were drastically changed by amino acids added any amino group to the side chain of the primaquine in his paper, for example the introduction of lysine/ornithine increased, but of histidine/cysteine disappeared this biological activity.…”

Section: Resultsmentioning

confidence: 99%

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Antimalarial and Antileishmanial Activities of Phytophenolics and Their Synthetic Analogues

Morimoto

Cantrell

Khan

et al. 2017

Chemistry & Biodiversity

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Thirty-seven phytophenolics and their synthetic analogues were evaluated for activity against two protozoal pathogens, Leishmania donovani and Plasmodium falciparum (D6 and W2 clones), respectively. 4,6-Dimethoxyaurone demonstrated the highest activity with IC values of 13.2 and 16.9 μm against L. donovani and P. falciparum (W2 clone), respectively, without undesired cytotoxicity against VERO cells. The moiety having two benzene rings was critical to maintain the antiprotozoal activities based on the observation that both coumaranones and chromones were inactive while other test compounds, including coumarans and aurones, remained active. There was no correlation between antiprotozoal activities and previously evaluated insect antifeedant activity against common cutworms (Spodoptera litura). Flavonoids, including aurones, pterocarpans, and lignan like dihydrobenzofurans, structural analogues of coumarans, are abundant in fruits and vegetables, so these phytophenolics may act as natural antiprotozoal agents in humans.

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Section: Resultssupporting

confidence: 70%

Section: Resultsmentioning

confidence: 99%

Antimalarial and Antileishmanial Activities of Phytophenolics and Their Synthetic Analogues

Morimoto

Cantrell

Khan

et al. 2017

Chemistry & Biodiversity

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“…Cassiarin J (260) inhibited moderate P. falciparum 3D7 (IC 50 value of 0.3 µM), and 258, 259, and 261 (IC 50 values of >50, >50, 1.4 µM, respectively) were found to be less active than 260. 91) Cassiarins A (256) is a promising antimalarial drug: it showed powerful effectiveness against P. falciparum (IC 50 3D7 value of 0.023) and exhibited a high selectivity index (>4348) toward human cell cytotoxicity (IC 50 MCF7 value of >100). 92) It is also powerful against P. berghei mouse malaria, with an ED 50 value of 0.17 mg/kg.…”

Section: Cassia Siameamentioning

confidence: 99%

Chemical Constituents and Bioactivities of Several Indonesian Plants Typically Used in Jamu

Widyowati

Agil

2018

Chem. Pharm. Bull.

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This article reviews the chemical constituents and bioactivities of several Indonesian plants typically used in Jamu prescriptions in Indonesia. Jamu is Indonesia traditional medicine: it consists of either a single ingredient or a mixture of several medicinal plants. One plant family always used in Jamu is Zingiberaceae (ginger), such as Curcuma domestica/C. longa, C. xanthorrhizae, C. heyneana, C. zedoaria, C. aeruginosa, Zingiber aromaticum, Alpinia galanga. We also report other commonly used plant families such as Justicia gendarussa and Cassia siamea, whose activities have been extensively explored by our department.

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“…albopictus. Singh and Prakash, [40] reported that larvicidal activity was observed against A. stephensi when six different concentration were used (5,10,20,30,40 and 50 mg/l). Similarly in the present study six different concentration were used (1000 ppm, 2000 ppm, 3000 ppm, 4000 ppm and 5000 ppm) against Ae.…”

Section: Discussionmentioning

confidence: 99%

“…stephensi, Piper longum and Piper nigrum [15,16], Cassia fistula [17], Coriandrum sativum [18] against Ae. aegypti, P. nigrum against Culex quinquefasciatus [19], Cassia siamea against Plasmodium berghei [20], Cassia auriculata against An. stephensi and Culex quinquefasciatus [21], Lantana camera against Ae.…”

Section: Introductionmentioning

confidence: 99%

Pupal Emergence Inhibition Activity of Acalypha Indica Leaf Extract Against Dengue Vector, Aedes Albopictus Mosquito

Ashwini¹,

Taju²,

Thirunavukkarasu

et al. 2017

Int J Pharm Pharm Sci

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Objective: To investigate the larvicidal activities of six varying extracts of Acalypha indica (A. indica) leaves from family Euphorbiaceae against the dengue mosquito vector, Aedesalbopictus (Ae. albopictus) in laboratory. Methods:Leaves from the study plants were separated, air dried in room temperature, grounded and extracted with different solvents (petroleum ether, chloroform, ethyl acetate, n-butanol, ethanol and aqueous) by solvent apparatus and aqueous extract by maceration method. The extra solvents were evaporated to obtain crude extracts by using rotary evaporator. The crude extracts of six different solvents were dissolved in dimethyl sulphoxide (DMSO) to prepare test dosages of 1000, 2000, 3000, 4000 and 5000 ppm. Third instar larvae of Ae. albopictus were exposed to 1000, 2000, 3000, 4000 and 5000 ppm concentrations of petroleum ether, chloroform, ethyl acetate, n-butanol, ethanol and aqueous extracts of A. indica and compared with control to determine the larvicidal effects. Larval bioassays were carriedout according to World Health Organisation (WHO) procedures. The rate of larval mortality was recorded after 24h and 48 h of time exposure. Three duplicate trials were made for each tested dosage. IC50 and IC90 values were calculated by using probit analysis.Results: Based on probit analysis result the 24h and 48h LC50 and LC90 of petroleum ether extract of A. indica against Ae. albopictus was found to be 2805.43 ppm and 2376.11 ppm, 3825.14 ppm and 3327.8 ppm, respectively. An LC50 and LC90 value of chloroform extracts of A. indicaa gainst third instar larvae was found to be 2276.5 ppm and 4015.8 ppm (24h), 2213.36 ppm and 3430.43 ppm (48h), respectively. An LC50 value of 4472.17 ppm and 2469.61 ppm, and LC90 value of 4215.84 ppm was obtained on ethylacetate extract treatment against Ae. albopictus for 24h and 48h exposure, respectively. The 24h and 48 h LC50 and LC90 values of n-butanol extracts of A. indica was found to be 2777.88 ppm and 3628.19 ppm, 2225.61 ppm and 2518.86 ppm, respectively. In the present study, the larvicidal bioassays demonstrated that the n-butanolextract was most effective with 100% mortality against larvae of Ae. albopictus at 3000, 4000 and 5000 ppm compared to other extracts. All other extracts (petroleum ether, chloroform and ethyl acetate) of A. indica at high concentration (4000 ppm and 5000 ppm) manifested a significant (P<0.01 and 0.05) knock down effect of 100% moratality after 24h and 48h exposure. While the third instar lavae of Ae. albopictus were found to be most susceptabile and produced no mortality to ethanol and aqueous extract at varying parts per million. Conclusion:A. indica leaf extract was tested for the first time against dengue vector Ae. albopictus and the results revealed that A. indica can be used to control dengue vector. Further this extract needs to be evaluated under field conditions for proper exploitation of Ae. albopictus mosquito larvae. Thus, the present study provided a first report on A. indica as a prompting mosquito larvicid...

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Synthesis and structure–activity relationships of cassiarin A as potential antimalarials with vasorelaxant activity

Cited by 36 publications

References 28 publications

Antimalarial and Antileishmanial Activities of Phytophenolics and Their Synthetic Analogues

Antimalarial and Antileishmanial Activities of Phytophenolics and Their Synthetic Analogues

Chemical Constituents and Bioactivities of Several Indonesian Plants Typically Used in Jamu

Pupal Emergence Inhibition Activity of Acalypha Indica Leaf Extract Against Dengue Vector, Aedes Albopictus Mosquito

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