Cyclohexylethanoids and related glucosides from Millingtonia hortensis

Hase, Takeshi; Kawamoto, Yuka; Ohtani, Kazuhiro; Kasai, Ryoji; Yamasaki, Kazuo; Picheansoonthon, Chayan

doi:10.1016/0031-9422(94)00939-q

Cited by 49 publications

(39 citation statements)

References 13 publications

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“…Compounds b1-b3 ( Figure 1) were identified as cornoside, decaffeoylverbascoside and icariside B 5 (Jensen et al, 1973;Aasen et al, 1974;Endo & Hikino, 1984;Miyase et al, 1988;Kuwajima et al, 1993;Hase et al, 1995;Kanchanapoom et al, 2002). Compounds d1 and d2 ( Figure 1) were identified as lupeol and rengyolone (Endo & Hikino, 1984;Nishino, et al, 1988;Bianco et al, 1993;Hase et al, 1995;Tian et al, 1997;Gauthier et al, 2006;Ahiahonu & Goodenowe, 2007;Siddiqui et al, 2007).…”

Section: Phytochemical Studymentioning

confidence: 99%

Chemical and biological investigation of someClerodendrumspecies cultivated in Egypt

Wahba¹,

AbouZid²,

Sleem³

et al. 2010

Pharmaceutical Biology

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Section: Phytochemical Studymentioning

confidence: 99%

Chemical and biological investigation of someClerodendrumspecies cultivated in Egypt

Wahba¹,

AbouZid²,

Sleem³

et al. 2010

Pharmaceutical Biology

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“…The 1 H NMR spectrum showed two doublets at 6.97 (J=10.2 Hz, 2H) and 6.21 (J=10.2 Hz, 2H), which could be assigned, respectively, to H-2′/H-6′ and H-3′/H-5′ of a quinoid derivative (Hase et al 1995). Additionally, this spectrum 1 2 123´4´56F ig.…”

Section: Chemical Characterization Of Jacaranonementioning

confidence: 93%

Anti-malarial, anti-trypanosomal, and anti-leishmanial activities of jacaranone isolated from Pentacalia desiderabilis (Vell.) Cuatrec. (Asteraceae)

et al. 2011

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Leishmaniasis, Chagas disease, and malaria affect the poorest population around the world, with an elevated mortality and morbidity. In addition, the therapeutic alternatives are usually toxic or ineffective drugs especially those against the trypanosomatids. In the course of selection of new anti-protozoal compounds from Brazilian flora, the CH(2)C(l2) phase from MeOH extract obtained from the leaves of Pentacalia desiderabilis (Vell.) Cuatrec. (Asteraceae) showed in vitro anti-leishmanial, anti-malarial, and anti-trypanosomal activities. The chromatographic fractionation of the CH(2)Cl(2) phase led to the isolation of the bioactive compound, which was characterized as jacaranone [methyl (1-hydroxy-4-oxo-2,5-cyclohexandienyl)acetate], by spectroscopic methods. This compound showed activity against promastigotes of Leishmania (L.) chagasi, Leishmania (V.) braziliensis, and Leishmania (L.). amazonensis showing an IC(50) of 17.22, 12.93, and 11.86 μg/mL, respectively. Jacaranone was also tested in vitro against the Trypanosoma cruzi trypomastigotes and Plasmodium falciparum chloroquine-resistant parasites (K1 strain) showing an IC(50) of 13 and 7.82 μg/mL, respectively, and was 3.5-fold more effective than benznidazole in anti-Trypanosoma cruzi assay. However, despite of the potential against promatigotes forms, this compound was not effective against amastigotes of L. (L.) chagasi and T. cruzi. The cytotoxicity study using Kidney Rhesus monkey cells, demonstrated that jacaranone showed selectivity against P. falciparum (21.75 μg/mL) and a selectivity index of 3. The obtained results suggested that jacaranone, as other similar secondary metabolites or synthetic analogs, might be useful tolls for drug design for in vivo studies against protozoan diseases.

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“…15 It was also isolated, as a halleridone from the African medicinal plant Halleria lucida (Scrophulariaceae), 16 and as a cytotoxic constituent from Cornus controversa (Cornaceae). 17 It has since been isolated from the flowers of the Thai medicinal plant, Millingtonia hortensis (Bignoniaceae), 18 but has not previously been isolated from Nyctanthes. It has been suggested that rengyolone (halleridone) could arise biogenetically from a p-hydroxyphenylethanol precursor.…”

Section: Resultsmentioning

confidence: 99%

“…It has been suggested that rengyolone (halleridone) could arise biogenetically from a p-hydroxyphenylethanol precursor. [18][19][20] Compound 2 2 2 2 2 was obtained as a colorless solid and its molecular formula was determined to be C 28 H 34 O 13 by HRFABMS and 13 C-NMR data ( ) and enol-ether system (1635 cm -1 ).…”

Section: Resultsmentioning

confidence: 99%