Monoterpene Hydroperoxides with Trypanocidal Activity from <i>Chenopodium ambrosioides</i>

Kiuchi, Fumiyuki; Itano, Yoshiaki; Uchiyama, Nahoko; Honda, Gisho; Tsubouchi, Akira; Nakajima‐Shimada, Junko; Aoki, Takashi

doi:10.1021/np010445g

Cited by 122 publications

(98 citation statements)

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“…Compounds (7, 9, 10, 16) and (18)(19)(20)(21)(22) detected during this study in the essential oils of leaves from 13 species medicinal plant belong to the genus Chenopodium. Other compounds have been isolated by diff erent authors.…”

Section: Resultsmentioning

confidence: 66%

“…Ascaridole has been documented with sedative and pain-relieving properties as well as antifungal eff ects 20 . Ascaridole was found to be a potent inhibitor in vitro development of Plasmodium falciparum 21 , Trypanosoma cruzi 22 , and Leishmania amazonensis 23 . Ascaridole also showed activity against diff erent tumor cell lines in vitro (CCRF-CEM, HL60, MDA-MB-231).…”

Section: Introductionmentioning

confidence: 99%

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Ascaridole and Related Peroxides From the Genus Chenopodium

Dembitsky¹,

Shkrob²,

Hanŭs³

2008

Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub

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Aim: Detection of monoterpenoid ascaridole and other terpenoids in the genus Chenopodium from the East Mediterranean.Method: Distribution of ascaridole in leaves of 13 species medicinal plant belonging to the genus Chenopodium was examined with the help of the GC-MS method.Results: cis-Ascaridole was found as a major peroxy monoterpenoid (up to 46.9 %) in the oil. Three minor isomers: cis-isoascaridole (1.1-6.4 %), trans-ascaridole (1-2 %), and trans-isoascaridole (1-2 %) were also detected. The biological activities and biosynthesis of ascaridole are further discussed. Conclusions:The results on Ascaridol and the major volatiles and semi-volatiles of wild species belonging to the genus Chenopodium provide important information on biologically active monoterpenoid compounds and volatile metabolites biosynthesized in wild medicinal plants growing in the East Mediterranean.

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Section: Resultsmentioning

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Ascaridole and Related Peroxides From the Genus Chenopodium

Dembitsky¹,

Shkrob²,

Hanŭs³

2008

Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub

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“…Trypanocidal Assay Trypanocidal assay was performed as described previously. 8) EtOH was used as a negative control. Ketoconazole and gentian violet were used as positive controls.…”

Section: Methodsmentioning

confidence: 99%

“…The activities were stronger than that of the anthelmintic monoterpene endoperoxide, ascaridole (MLCϭ23 mM) and were comparable to those of monoterpene hydroperoxides isolated from Chenopodium ambrosioides. 8) In the HeLa cell infection assay, compound 3 very strongly inhibited the infection of the trypomastigotes at 1 mg/ml (Table 1). Dehydrocostus lactone (1) also significantly inhibited the infection at 1 mg/ml, whereas zaluzanin D (2) did not inhibit the infection at the same concentration.…”

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confidence: 97%

Trypanocidal Terpenoids from Laurus nobilis L.

et al. 2002

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Trypanosoma cruzi, a parasitic protozoan of Zoomastigophoria, is the etiologic agent of Chagas' disease which is endemic in Central and South America.1) In our screening work on medicinal plants used in Asian counties for trypanocidal activity, extracts of the dried leaves of Laurus nobilis L. (Lauraceae) showed strong trypanocidal activity against epimastigotes of T. cruzi. Leaves of L. nobilis are used as a spice known as laurel or bay leaf. They are also used as a folk medicine for rheumatism and scabies.2) Although some biological activities such as inhibition of elevation of blood ethanol level in ethanol-loaded rat, 3) inhibition of nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages, 4) induction of glutathione Stransferase activity, 5) and nematocidal activity 6) were reported for the constituents of L. nobilis, nothing has been reported on anti-protozoan constituents of this plant. Here, we report the isolation and identification of trypanocidal constituents of L. nobilis. Results and DiscussionDried leaves of Laurus nobilis were successively extracted with hexane, CHCl 3 and MeOH, and each extract was tested for anti-trypanosomal effect by the HeLa cell infection assay.7) As the CHCl 3 and MeOH extracts inhibited infection and proliferation of T. cruzi, and the MeOH extract formed the major part of the extracts, the MeOH extract was further fractionated under the guidance of in vitro trypanocidal activity against epimastigotes of T. cruzi.8) The MeOH extract was suspended in aqueous MeOH and fractionated into hexane soluble, AcOEt soluble, and water soluble fractions. Since the AcOEt soluble fraction showed the strongest activity, it was fractionated by silica gel column chromatography to give three trypanocidal compounds (1-3). These compounds were also isolated from the CHCl 3 extracts.Compounds 1 and 2 were obtained as colorless needles from hexane, mp 58-60°C, and as a colorless oil, respectively. The 1 H-and 13 C-NMR spectra indicated that both compounds were guaiane-type sesquiterpene with three exocyclic methylene moieties. Based on comparisons of the spectral data with those reported, compounds 1 and 2 were identified with dehydrocostus lactone (1) 9) and zaluzanin D (2), 10) H-detected heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond connectivity (HMBC) spectra (Fig. 1) revealed the structure to be 1-hydroperoxy-pmenthan-2-en-8-ol acetate. Treatment of 3 with PPh 3 gave an acetoxy alcohol 4, which showed oxygen-bearing carbons at d C 67.0 (C-1) and d C 84.4 (C-8). This confirmed that 3 had a hydroperoxy and an acetoxy group at positions 1 and 8, respectively. Since nuclear Overhauser effect (NOE) experiments did not provide conclusive stereochemical information, the stereochemistry of 3 was determined by chemical correlations. Photo C-NMR spectra of 7 were identical with those of the diol 8, which was derived from 3 by alkaline hydrolysis followed by reduction with PPh 3 . 12)This result established that the relative stereochemi...

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“…The bicyclic monoterpene ascaridole and the phenylpropanoid safrole (Fig. 4) can be found in C. ambrosioides essential oil (Kiuchi et al, 2002;Tucker and Maciarello, 1998). This is an essential oil with anthelmintic activity that has been used to treat parasitosis and leishmaniasis (Monzote et al, 2009).…”

Section: Monoterpenes Phenylpropanoids and Prenylflavonoidsmentioning

confidence: 99%

Wild edible plants: Nutritional and toxicological characteristics, retrieval strategies and importance for today's society

Pinela

Ferreira

2017

Food and Chemical Toxicology

135

111

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A B S T R A C TWild edible plants (WEPs) are part of the cultural and genetic heritage of different regions of the world. In times of famine and scarcity, these sources of nutrients and health-promoting compounds have received high importance mainly in rural and suburban areas. Although currently underutilized, WEPs are still consumed traditionally by different communities and are gaining relevance in today's society. However, these foods lack recognition as significant contributors to the human diet in developed areas. This review describes the nutritional value of WEPs from the North-eastern region of Portugal and points out those containing potentially toxic compounds. Several retrieval strategies are presented with the aim of promoting the (re)use, production, commercialization and conservation of WEPs (wild harvested plants and crop wild relatives), and their importance for social, economic and agro-ecological development is highlighted.

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Monoterpene Hydroperoxides with Trypanocidal Activity from Chenopodium ambrosioides

Cited by 122 publications

References 13 publications

Ascaridole and Related Peroxides From the Genus Chenopodium

Ascaridole and Related Peroxides From the Genus Chenopodium

Trypanocidal Terpenoids from Laurus nobilis L.

Wild edible plants: Nutritional and toxicological characteristics, retrieval strategies and importance for today's society

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