Neo-clerodane insect antifeedants from Scutellaria alpina subsp. javalambrensis

Muñoz, Dulce M.; Torre, Marı́a C. de la; Rodrı́guez, Benjamı́n; Simmonds, Monique S. J.; Blaney, W. M.

doi:10.1016/s0031-9422(96)00608-5

Cited by 39 publications

(24 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…201,329 From a chemotaxonomic point of view, compound 879 is the first 8β,13 S -epoxy- neo -clerodan-15,16-olide derivative found in European Scutellaria species, although these structural features are shown by several neo -clerodanes isolated from Asian Scutellaria species. 330 …”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

View full text Add to dashboard Cite

The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

show abstract

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

View full text Add to dashboard Cite

show abstract

“…Approximately 150 neo-clerodanes have been isolated (Merritt and Ley 1992 ;Ortego et al 1995 ), and among these, eriocephalin and teucvin were quite effective along with ajugarins isolated from Ajuga remota (Kubo et al 1982(Kubo et al , 1983Pickett et al 1987 ). Jodrellin-B, also reported from Scutellaria woronowii , was the most active compound in this series, and scutalpin-C from Scutellaria alpina javalambrensis was very active against S. littoralis (Munoz et al 1997 ). It has been shown that saturation of the dihydrofuran ring and addition of the tigloyl ester function at C-1 results in decreased activity (Anderson et al 1989 ;Cole et al 1990 ).…”

Section: Clerodane Diterpenesmentioning

confidence: 62%

Phytochemical Pesticides

Walia¹,

Saha²,

Rana³

2014

Advances in Plant Biopesticides

View full text Add to dashboard Cite

Many phytochemical pesticides exhibiting broad spectrum of activity against pests and diseases have long been considered as attractive alternative to synthetic chemical pesticides as they are biodegradable, target specifi c, and pose no or less hazard to the environment or to human health. Although a large number of studies suggest that plant-based materials do affect arthropod pests, vectors, and other pathogens, yet only a handful of botanicals are currently used in agriculture, and there are few prospects for commercial development of new botanical products. Several factors appear to limit the success of botanicals, most notably regulatory barriers and the availability of competing products of microbial origin that are cost-effective and relatively safe compared with their predecessors. In the context of agricultural pest management, botanical pesticides are best suited for use in organic food production and can play a much greater role in the production and post-harvest protection of food and food products in developing countries. There is thus a need to organize natural sources, develop quality control, adopt standardization strategies, and modify regulatory mechanisms.

show abstract

“…The 1 H and 13 C NMR spectroscopic data were similar to those of 1 except for the chemical shifts ascribable to H-6, H 2 -18, C-4 and C-18. In contrast, the chemical shifts of H 2 -18 [d H 2.41 (d, J = 4.3 Hz), 3.28 (dd, J = 1.9, 4.3 Hz)], C-4 (d C 64.8) and C-18 (d C 50.8) were well correlated with those of neo-clerodanes with an oxyrane moiety at C-4 (Bozov et al, 1993;de la Torre et al, 1995;Malakov and Papanov, 1996;Muñoz et al, 1997;Esquivel et al, 2001;Raccuglia et al, 2010). These data implied that 6 had a 4,18;8b,13-diepoxy-neo-clerodane-15,16-olide structure.…”

Section: Resultsmentioning

confidence: 96%

“…More than 100 neo-clerodanes have been isolated from this genus, and have been classified into 8b-hydroxy-neo-clerod-13-en-15,16-olides (Cole et al, 1990;Miyaichi et al, 1994;de la Torre et al, 1997;Hussein et al, 1996;Malakov and Papanov, 1996;Kizu et al, 1997;Rodríguez et al, 1997;Esquivel et al, 2001;Nguyen et al, 2009;Shang et al, 2010;Raccuglia et al, 2010;Wang et al, 2012), 8b,13-epoxy-neo-clerodane-15,16-olides (Bozov et al, 1993;Malakov and Papanov, 1996;Kizu et al, 1997;Esquivel et al, 2001;Nguyen et al, 2009;Shang et al, 2010;Raccuglia et al, 2010;Lee and Shim, 2011;Wang et al, 2012) and 11,16;15,16-diepoxy-neo-clerodanes (Cole et al, 1990;de la Torre et al, 1995de la Torre et al, , 1997Rodríguez et al, 1997;Ohno et al, 1996Ohno et al, , 1997Kizu et al, 1998;Bruno et al, 2000;Wang et al, 2012), respectively. These neo-clerodanes have attracted interest of researchers for their biological activities, which include anti-feedant (Cole et al, 1990;Muñoz et al, 1997;Raccuglia et al, 2010), anti-oxidant (Nguyen et al, 2009) and anti-cancer activities (Wang et al, 2012).…”

Section: Introductionmentioning

confidence: 99%