Stemospironine, a new insecticidal alkaloid of Stemona japonica Miq. isolation, structural determination and activity.

Sakata, Kanzo; Aoki, Katsuyuki; Chang, Ching-Fung; Sakurai, Akira; Tamura, Saburo; Murakoshi, S.

doi:10.1271/bbb1961.42.457

Cited by 82 publications

(49 citation statements)

References 3 publications

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“…However, in-depth toxicological studies would be required to prove that the extracts have no adverse effects on mammals. Stemofoline was already reported to be highly toxic against silkworm larvae, Bombyx mori, but proved to be completely inactive against larvae of the cabbage armyworm Mamestra brassicae, even at concentrations as high as 100 ppm (7). In light of these results, Stemona species might also provide selective agricultural pesticides without harmful side effects toward nontarget organisms.…”

Section: Resultsmentioning

confidence: 96%

Feeding Deterrence and Contact Toxicity of Stemona AlkaloidsA Source of Potent Natural Insecticides

Brem

Seger

Pacher

et al. 2002

J. Agric. Food Chem.

131

173

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On the basis of chronic feeding bioassays with neonate larvae of Spodoptera littoralis reared on an artificial diet, the methanolic leaf and root extracts from Stemona collinsae displayed very high insect toxicity compared to those of two Aglaia species, a commercial Pyrethrum extract, and azadirachtin, whereas S. tuberosa extracts demonstrated low activity in roots and no activity in leaves. Beyond that, in leaf disk choice tests against fifth instar larvae, S. collinsae showed strong antifeedant activity, whereas S. tuberosa was characterized by remarkable repellency. The anti-insect properties of both species were based on pyrrolo[1,2-a]azepine alkaloids, from which didehydrostemofoline (asparagamine A) was the major compound of the roots of S. collinsae, exhibiting the highest toxicity in feeding assays. Saturation and hydroxylation of the side chain in the co-occurring stemofoline and 2'-hydroxystemofoline, respectively, led to an increasing loss of activity. Contact toxicity tests with stemofoline and didehydrostemofoline exhibited even higher activities than those of Pyrethrum extract. Tuberostemonine was the dominating alkaloid in the roots of S. tuberosa, showing outstanding repellency but no toxic effects.

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Section: Resultsmentioning

confidence: 96%

Feeding Deterrence and Contact Toxicity of Stemona AlkaloidsA Source of Potent Natural Insecticides

Brem

Seger

Pacher

et al. 2002

J. Agric. Food Chem.

131

173

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“…Extracts from Stemona and Croomia have been used for centuries in Chinese and Japanese traditional medicines for the treatment of respiratory diseases and against enteric helminths and ectoparasites on humans and cattle (Xu et al 1982;Sakata et al 1978) and as insecticides (Xu, 2000;Brem et al 2002;Kaltenegger et al 2003).…”

Section: Alkaloids From Stemonaceaementioning

confidence: 99%

Plant Natural Products as a Source for Developing Environmentally Acceptable Insecticides

Isman

Akhtar

2007

Insecticides Design Using Advanced Technologies

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“…Moreover, different ways to prepare structurally diverse analogues of active compounds were elaborated to find an efficient synthetic route (Frankowski et al 2008(Frankowski et al , 2011. In continuation of previous investigations on insecticidal activities (Sakata et al 1978;Jiwajinda et al 2001;Brem et al 2002;Kaltenegger et al 2003) follow-up studies focused on the mode of action by using biochemical and electrophysiological approaches (Tang et al 2008). With regard to the acetylcholinesterase inhibiting properties of Stemona alkaloids, bioassays with naturally-occurring as well as synthetically prepared derivatives informed about structure-activity relationships (Wang et al 2007a;Baird et al 2009;Chaiyong et al 2010;Sastraruji et al 2010Sastraruji et al , 2012Ramli et al 2013Ramli et al , 2014Lai et al 2013).…”

Section: Introductionmentioning

confidence: 99%

Structural classification and biological activities of Stemona alkaloids

Greger

2019

Phytochem Rev

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Stemona alkaloids represent a unique class of natural products exclusively known from the three genera Stemona, Stichoneuron, and Croomia of the monocotyledonous family Stemonaceae. Structurally they are characterized by a central pyrroloazepine core usually linked with two butyrolactone rings. The great diversity, comprising 215 derivatives, is created by the formation of additional CC linkages and oxygen bridges together with ring cleavages and eliminations of the lactone rings. Based on biosynthetic considerations they can be grouped into three structural types represented by the croomine, stichoneurine, and protostemonine skeleton. Due to the formation of characteristic terminal lactone rings and the central pyrrolidine ring pandanamine and pandamarilactonine, isolated from Stichoneuron calcicola, were suggested to represent biogenetic precursors. The taxonomically complex S. tuberosa group can be clearly segregated by the formation of stichoneurines, while the other Stemona species are characterized by protostemonine derivatives. Croomine derivatives are more widespread found in both groups and in the genus Croomia. Of chemotaxonomic significance are the different transformations of protostemonine into stemofolines with a cage-type structure or into pyridoazepines characterized by a six-membered piperidine ring. Stimulated by the great interest in the antitussive activity of Stemona alkaloids, differences in transport mechanisms and potencies via different administrative routes were investigated. Follow-up studies on the significant insecticidal activities focused on the mode of action by using biochemical and electrophysiological approaches. Screening for acetylcholinesterase inhibitory properties revealed a much higher potency for stemofoline derivatives compared to pyridoazepines, but showed also significant activity for isomers of stenine with a stichoneurine skeleton. Evaluating synergistic growth inhibitory effects with cancer chemotherapeutic agents stemofoline exhibited the most potent effect in the reversal of permeability glycoprotein-mediated multidrug resistance. The anti-inflammatory activity of some derivatives was identified as an inhibition of the expression of inflammatory mediators. Comparing the diverse bioactivities of Stemona alkaloids stemofoline-type derivatives are the most versatile compounds representing promising lead structures for further development as commercial agents in agriculture and medicine.

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Stemospironine, a new insecticidal alkaloid of Stemona japonica Miq. isolation, structural determination and activity.

Cited by 82 publications

References 3 publications

Feeding Deterrence and Contact Toxicity of Stemona AlkaloidsA Source of Potent Natural Insecticides

Feeding Deterrence and Contact Toxicity of Stemona AlkaloidsA Source of Potent Natural Insecticides

Plant Natural Products as a Source for Developing Environmentally Acceptable Insecticides

Structural classification and biological activities of Stemona alkaloids

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