Clerodane diterpenes from Baccharis sagittalis : insect antifeedant activity

Cifuente, Diego Alberto; Borkowski, Eduardo Jorge; Sosa, Marta E.; Gianello, José C.; Giordano, Óscar S.; Tonn, Carlos E.

doi:10.1016/s0031-9422(02)00437-5

Cited by 50 publications

(40 citation statements)

References 20 publications

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“…The most active isomer was the C-12R (26) (PFI = 25.5) while C-12S diastereomer (27) did not show any activity. This behavior would find explanation in the different diagrams of electrostatic potential from SAR studies based on theoretical calculus (Cifuente et al 2002).…”

Section: Neo-clerodane-diterpenesmentioning

confidence: 92%

“…Taking into account the grain production of Argentina it is an interesting insect model to use in antifeedant activity studies toward clerodane diterpenes. In this order a considerable number of this kind of compounds (23-49) has been isolated in our laboratory from plants of the Asteraceae and Labiatae families Luco et al 1994;Gallardo Varas et al 1996;Ceñ al et al 1997;Enriz et al 2000;Simirgiotis et al 2000;Cifuente et al 2002;Gonzá lez Coloma et al 2005;Juan et al 2006). From this set of diterpenes, compounds 50-55 were prepared by chemical transformations.…”

Section: Neo-clerodane-diterpenesmentioning

confidence: 99%

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Plant secondary metabolites from Argentinean semiarid lands: bioactivity against insects

Sosa

Tonn

2007

Phytochem Rev

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Section: Neo-clerodane-diterpenesmentioning

confidence: 92%

Section: Neo-clerodane-diterpenesmentioning

confidence: 99%

Plant secondary metabolites from Argentinean semiarid lands: bioactivity against insects

Sosa

Tonn

2007

Phytochem Rev

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“…The α-substituted butenolide ring moiety was assigned to be attached at C-12 by the HMBC correlations of H-14 with C-12, and H-12 with C-13. Comparison of the NMR data of compound 1 with those of marrubiagenine [12] and 1α,7α-dihydroxyneocleroda-3,13-dien-16,15 : 18,19-diolide [13] showed the existence of an extra glucose at C-17 in compound 1. The additional β-D-glucopyranosyl moiety linked at C-17 was further supported by the long-range HMBC correlation between H-1′ (δ H 4.22) and C-17 (δ C 72.7).…”

mentioning

confidence: 94%

New Clerodane Diterpenes from Tinospora sagittata var. yunnanensis

Jiang

Jiao

et al. 2014

Planta Med

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Four new clerodane diterpenes, namely sagittatayunnanosides A-D (1-4), were isolated from the roots of Tinospora sagittata var. yunnanensis, together with two known compounds, tinospinoside C (5) and tinospinoside E (6). The structures of the four new compounds were well elucidated by extensive analyses of the MS, IR, and 1D and 2D NMR data. The cytotoxic and antifouling activities of compounds 1-6 were evaluated.

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“…The herb is also used in the treatment of carbuncles, lung abscesses, breast lumps, and goiter. Additionally, DB was reported to display a range of pharmacological properties, including antitumor (Grynberg et al 1999), antifeedant (Cifuente et al 2002), anti-inflammatory (Demetzos et al 2001), and antisalmonellal activities (Teponno et al 2006). DB and related remedies are used for the treatment of thyroid gland diseases and a variety of tumors (Tang 1995;Rasikari et al 2005).…”

Section: Introductionmentioning

confidence: 99%

Metabolic activation of furan moiety makes Diosbulbin B hepatotoxic

Lin

Gao

et al. 2015

Arch Toxicol

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Diosbulbin B (DIOB), a furanoid, is a major constituent of herbal medicine Dioscorea bulbifera L. Exposure to DIOB caused liver injury in humans and experimental animals. The mechanisms of DIOB-induced hepatotoxicities remain unknown. The present study demonstrated that DIOB induced hepatotoxicities in a time- and dose-dependent manner in mice. H&E stained histopathologic image showed the occurrence of necrosis in the liver obtained from the mice treated with DIOB at dose of 200 mg/kg. Pretreatment with KTC protected the animals from hepatotoxicities and hepatic GSH depletion induced by DIOB, increased area under the concentration-time curve of blood DIOB, decreased urinary excretion of GSH conjugates derived from DIOB, and increased urinary excretion of parent drug. Pretreatment with BSO exacerbated DIOB-induced hepatotoxicities. In order to define the role of furan moiety in DIOB-induced liver toxicities, we replaced the furan of DIOB with a tetrahydrofuran group by chemical hydrogenation of the furan ring of DIOB. No liver injury was observed in the animals given the same doses of tetrahydro-DIOB. The furan moiety was essential for DIOB-induced hepatotoxicities. The results implicate the cis-enedial reactive metabolite of DIOB was responsible for the observed toxicities. The observed modest depletion of hepatic GSH in DIOB-treated animals suggests the actions of one or more reactive metabolites, and the hepatic injury observed could be due at least in part to reactions of these metabolites with crucial biomolecules. Cytochrome P450 3A enzymes are implicated in DIOB-induced hepatotoxicities by catalyzing the formation of the reactive metabolite of DIOB.

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Clerodane diterpenes from Baccharis sagittalis : insect antifeedant activity

Cited by 50 publications

References 20 publications

Plant secondary metabolites from Argentinean semiarid lands: bioactivity against insects

Plant secondary metabolites from Argentinean semiarid lands: bioactivity against insects

New Clerodane Diterpenes from Tinospora sagittata var. yunnanensis

Metabolic activation of furan moiety makes Diosbulbin B hepatotoxic

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