The Insecticidal Activity of Some Norditerpene Dilactones

Singh, Pritam; Russell, Graeme B.; Hayashi, Yûji; Gallagher, Rex T.; Fredericksen, Susan

doi:10.1111/j.1570-7458.1979.tb02861.x

Cited by 29 publications

(11 citation statements)

References 19 publications

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“…One of the two angular methyl groups in NB is subjected to a pronounced shielding due to the y-effect of the hydroxyl group at C-1 (this is also the case in other type A, dilactones 1, 8 and 10). Thus, the methyl resonance at 618.7 in 3 is assigned to C-20, leaving the methyl carbon signal at 624.0 to C-18.…”

Section: Type a Dilactonesmentioning

confidence: 94%

Carbon‐13 NMR studies of the biologically active nor‐diterpenoid dilactones from Podocarpus plants

et al. 1980

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Carbon-13 NMR signals of the biologically active norditerpenoid dilactones from Podocarpus plants were fully assigned by using selective 'H decoupling, coupling constants ('J,,), spin-lattice relaxation times ( T1) and correlation of the spectra of more than thirty dilactone congeners. The spectra of five nagilactones, B, C, D, E and F, which constitute representative members of three major structural types of the dilactones: (A) 8 : 14, 9 : 11-dienolide (or-pyrone) type, (B) 701: 8or-epoxy-9: 11-enolide type, and (C) 7 : 8,9: 11-dienolide type, were extensively analysed. Some characteristic steric interactions for the substituents on the ring system can be demonstrated from the spectral properties.

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Section: Type a Dilactonesmentioning

confidence: 94%

Carbon‐13 NMR studies of the biologically active nor‐diterpenoid dilactones from Podocarpus plants

et al. 1980

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“…colorless needles (CHCl 3 /hexane); mp 194–195 °C (lit 191–193 °C);32 [α]26 D -272.1 ( c 0.53, CHCl 3 :CH 3 OH 9:1) (lit. −332.7);32 UV (CH 3 OH) λ max (log ε) 260 (4.21); CD (CH 3 OH) [θ] 296 -5.1.…”

Section: Methodsmentioning

confidence: 99%

Biologically Active Tetranorditerpenoids from the Fungus Sclerotinia homoeocarpa Causal Agent of Dollar Spot in Turfgrass

Herath

Carvalho

et al. 2009

J. Nat. Prod.

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Nine new tetranorditerpenoid dilactones (2-10), together with two previously reported norditerpenoids dilactones (1, 11), and two known putative biosynthetic intermediates oidiolactone-E (12) and 13 were isolated from an ethyl acetate extract of a culture medium of Sclerotinia homoeocarpa. Structures and absolute configuration of these compounds were determined by spectroscopic methods and confirmed by X-ray crystallographic analysis of representative compounds. Compounds were evaluated for herbicidal, antiplasmodial and cytotoxic activities. Compounds 1, 2, 6, 7, 11 were more active as growth inhibitors in a duckweed bioassay (I 50 values of 0.39 -0.95 µM) than more than half of 26 commercial herbicides previously evaluated using the same bioassay. Some of these compounds exhibited strong antiplasmodial activities as well, but they also had cytotoxic activity thus precluding them as potential antimalarial agents.Malaria continues to be a major cause of morbidity and mortality in many parts of the tropics and subtropics. Every year about 500 million people become ill with malaria and over a million people, most of them young children, die of this disease. 1 Wide-spread resistance to first-line antimalarial drugs has hampered the effective control of this disease. Many efforts are underway to develop new classes of antimalarials to counter this trend. 2 One of these involves searching for compounds to inhibit unique metabolic pathways in the apicoplast. 2,3 Plasmodium parasites, which cause malaria in humans, contain an organelle called the apicoplast. 4 The apicoplast is very similar to plastids (chloroplasts are one of several plastid forms) of plants and is believed to have been acquired by the engulfment of an ancestral alga and retention of the algal plastid. The apicoplast is essential for the survival of parasites, and it contains many plant-like metabolic pathways such as essential amino acid, heme, and type *To whom correspondence should be addressed. Tel.: 1-662-915-1019. Fax: 1-662-915-1006. dhammika@olemiss.edu . NIH Public AccessAuthor Manuscript J Nat Prod. Author manuscript; available in PMC 2010 December 1. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author ManuscriptII fatty acid biosynthesis not present in the vertebrate hosts of malaria parasites. 4 Several studies have been initiated to evaluate antimalarial activity of herbicides and natural phytotoxins which are known to inhibit metabolic pathways of the plastid in plants. 5 -7 A number of plant pathogenic fungi are known to release phytotoxins that disrupt biological processes in plants. [8][9][10] Some of these have also been shown to inhibit metabolic pathways in the plastid; 11 thus, plant pathogens could be a potential source of antimalarial compounds.As part of a program to search for antimalarial compounds from natural sources, we initiated a project to screen phytopathogenic fungi for antimalarial activity. Sclerotinia homoeocarpa is the causal agent of "dollar spot," the most prevalent disease of turfgrass in...

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“…With the scattered occurrence of the different podolactone-type inhibitors (Sasse et al 1981) the question arises as to their biological role. Cartwright et ai (1977) and Kato et al (1977) have identified momilactone B as a phytoalexin as well as a plant-growth inhibitor and Ito and Kodama (1976) and Singh et al (1979) suggested that podolactones protect against predation by insects. Brown and Sanchez L. (1974) have also suggested that they are possible allelopathic agents though this seems unlikely (Sasse et al 1981) even though they can delay germination.…”

Section: Floweringmentioning

confidence: 99%

Some physiological effects of podolactone‐type inhibitors

Sasse

Wardrop

Rowan

et al. 1982

Physiologia Plantarum

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Podolactone‐type inhibitors, including harringtonolide and lycoricidinol, affect several bioassays at 1 to 10 μM. Although these compounds were less active than abscisic acid in inhibiting growth of coleoptiles of wheat embryos, podolactone A significantly decreased the number of mature spikelets of Lolium temulentum at a lower concentration than abscisic acid. Lycoricidinol was more active than podolactone E, the most active of the podolactones, in three bioassays. Inhibition of growth induced by gibberellic acid or zeatin with podolactone‐type compounds was not competitive. Harringtonolide was a strong inhibitor of growth at higher concentrations but did not affect auxin transport, while podolactone E and lycoricidinol inhibited it. Lycoricidinol, podolactone E and harringtonolide did not retard senescence of leaf‐discs. The promotive effects of gibberellic acid in the barley endosperm bioassay were counteracted by podolactone A.

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The Insecticidal Activity of Some Norditerpene Dilactones

Cited by 29 publications

References 19 publications

Carbon‐13 NMR studies of the biologically active nor‐diterpenoid dilactones from Podocarpus plants

Carbon‐13 NMR studies of the biologically active nor‐diterpenoid dilactones from Podocarpus plants

Biologically Active Tetranorditerpenoids from the Fungus Sclerotinia homoeocarpa Causal Agent of Dollar Spot in Turfgrass

Some physiological effects of podolactone‐type inhibitors

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