Chapter 3 Aconitum Alkaloids

Amiya, Takashi; Bando, Hideo

doi:10.1016/s0099-9598(08)60228-x

Cited by 13 publications

(25 citation statements)

References 127 publications

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“…A large number of diterpenoid alkaloids have been isolated from various species of Aconitum and Delphinium (Ranunculaceae) [1, 2]. The pharmacological properties of C 19 -norditerpenoid alkaloids, including aconitine, mesaconitine, hypaconitine and jesaconitine, have been studied extensively and reviewed [1, 2]. Aconitine and mesaconitine are representative toxins that exhibit activity both centrally and peripherally, with predominant effects on the cardiovascular and respiratory systems, by preventing the normal closing of sodium channels [3, 4].…”

Section: Introductionmentioning

confidence: 99%

Structure–activity relationships and the cytotoxic effects of novel diterpenoid alkaloid derivatives against A549 human lung carcinoma cells

et al. 2010

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The cytotoxicity of three alkaloids from the roots of Aconitum yesoense var. macroyesoense as well as 36 semi-synthetic C20-diterpenoid atisine-type alkaloid derivatives against A549 human lung carcinoma cells was examined. Ten acylated alkaloid derivatives, pseudokobusine 11-veratroate (9), 11-anisoate (12), 6,11-dianisoate (14), 11-p-nitrobenzoate (18), 11,15-di-p-nitrobenzoate (22), 11-cinnamate (25) and 11-m-trifluoromethylbenzoate (27), and kobusine 11-p-trifluoromethylbenzoate (35), 11-m-trifluoromethylbenzoate (36) and 11,15-di-p-nitrobenzoate (39), exhibited cytotoxic activity, and 11,15-dianisoylpseudokobusine (16) was found to be the most potent cytotoxic agent. Their IC50 values against A549 cells ranged from 1.72 to 5.44 μM. In the occurrence of cytotoxic effects of atisine-type alkaloids, replacement by an acyl group at both C-11 and C-15 resulted in the enhancement of activity of the parent alkaloids compared to that from having hydroxy groups at this position, and the presence of a hydroxy group at the C-6 position was required for the cytotoxic effects. These acylated alkaloid derivatives inhibit cell growth through G1 arrest.

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Section: Introductionmentioning

confidence: 99%

Structure–activity relationships and the cytotoxic effects of novel diterpenoid alkaloid derivatives against A549 human lung carcinoma cells

et al. 2010

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“…Aconitum species are a particularly rich source of biologically active diterpenoid and norditerpenoid alkaloids (Amiya and Bando, 1988), with many alkaloids reported from this genus (Wang and Liang, 2002). Aconitum alkaloids exhibit a range of effects in the central nervous system (Ameri, 1998;Fu et al, 2006), and one such alkaloid, songorine, has been shown to enhance excitatory synaptic transmission in the rat hippocampus mediated by non-competitive inhibition at GABA A receptors (Zhao et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

Antiplasmodial activity of atisinium chloride from the Bhutanese medicinal plant, Aconitum orochryseum

Wangchuk

Bremner

Samten

et al. 2010

Journal of Ethnopharmacology

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“…1,2 Aconitum plants are used in “bushi”, an herbal traditional Chinese medicine prescribed to treat hypometabolism, dysuria, cardiac weakness, chills, neuralgia, gout, and certain rheumatic diseases. 3–5 Among the C 19 -diterpenoid alkaloids, aconitine ( 1 ), jesaconitine ( 3 ), mesaconitine ( 8 ), and hypaconitine ( 9 ) exhibit particularly high toxicity, while the C 20 -diterpenoid alkaloids lucidusculine ( 37 ), kobusine ( 51 ), pseudokobusine ( 71 ), and atisine are much less toxic. However, despite the extreme toxicities of some C 19 -diterpenoid alkaloids, only two studies appeared in the literature in 2005 and 2006.…”

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confidence: 99%

Evaluation of Aconitum diterpenoid alkaloids as antiproliferative agents

Wada

Ohkoshi

Zhao

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Little information has been reported on the antitumor effects of the diterpenoid alkaloid constituents of Aconitum plants, used in the herbal drug “bushi”. This study was aimed at determining the antitumor activities of Aconitum C19-and C20-diterpenoid alkaloids and synthetic derivatives against lung (A549), prostate (DU145), nasopharyngeal (KB), and vincristine-resistant nasopharyngeal (KB-VIN) cancer cell lines. Newly synthesized C20-diterpenoid alkaloid derivatives showed substantial suppressive effects against all human tumor cell lines tested. In contrast, natural and derivatized C19-diterpenoid alkaloids showed only a slight or no effect. Most of the active compounds were hetisine-type C20-diterpenoid alkaloids, specifically kobusine and pseudokobusine analogs with two different substitution patterns, C-11 and C-11,15. Notably, several C20-diterpenoid alkaloids were more potent against multidrug-resistant KB subline KB-VIN cells. Pseudokobusine 11-3′-trifluoromethylbenzoate (94) is a possible promising new lead meriting additional evaluation against multidrug-resistant tumors.

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Chapter 3 Aconitum Alkaloids

Cited by 13 publications

References 127 publications

Structure–activity relationships and the cytotoxic effects of novel diterpenoid alkaloid derivatives against A549 human lung carcinoma cells

Structure–activity relationships and the cytotoxic effects of novel diterpenoid alkaloid derivatives against A549 human lung carcinoma cells

Antiplasmodial activity of atisinium chloride from the Bhutanese medicinal plant, Aconitum orochryseum

Evaluation of Aconitum diterpenoid alkaloids as antiproliferative agents

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