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Messchendorp, L.; Gols, G.J.Z.; Loon, Joop J. A. van

doi:10.1023/a:1020999430889

Cited by 21 publications

(11 citation statements)

References 17 publications

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“…Post-ingestive effects against this insect have been reported for 3β-hydroxycinnamolide and 3β-acetoxydrimenin [64] and suggested for synthetic analogues (lactones) of polygodial (6) and warburganal (7) on Pieris brassicae and L. decemlineata larvae. [63] However, 6 did not affect orally injected S. littoralis. [62] Rhopalosiphum padi (% SI) [b] Myzus persicae (% SI) [b] …”

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 91%

“…[62] Family-and/or species-related differences in the drimane molecular target have been suggested. [63] Several structure-activity trends can be deduced from the antifeedant effect of the test compounds on R. Padi. In general, fluorination of the C-9 position decreased the activity of compounds with an 8(12)-exo-methylene double bond (13, 14 and 21 vs. 3, 4 and 22, respectively) and increased the activity of compounds with a carbonyl group at C-11 (11, 17 and 31 vs. 19, 9 and 51, respectively), especially for 9α-fluorodrimenin (17) and epoxide 31.…”

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

“…Similarly, previous results have shown the importance of the C-9 substituents on the antifeedant effects of drimanes. [62,63] Oral cannulation of S. littoralis L6 larvae showed that the non-fluorinated derivatives 19 and 51 were moderate post-ingestive antifeedants whereas the fluorinated derivative of 19 (i.e., 11) was toxic (pANCOVA2 Ͻ 0.05, see the Supporting Information). Post-ingestive effects against this insect have been reported for 3β-hydroxycinnamolide and 3β-acetoxydrimenin [64] and suggested for synthetic analogues (lactones) of polygodial (6) and warburganal (7) on Pieris brassicae and L. decemlineata larvae.…”

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

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Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

Abad¹,

Agulló²,

Cuñat³

et al. 2010

Eur J Org Chem

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The preparation of 9α‐fluoro analogues of both natural and unnatural drimane‐type sesquiterpenes is described. Their synthesis began with the initial preparation of methyl 8‐keto‐12‐nordriman‐11‐oate from β‐ionone and entailed the electrophilic fluorination of C‐9 for the stereoselective introduction of the fluorine atom. The drimane skeleton was completed from the intermediate 9α‐fluoro‐8‐keto‐12‐nordrimane system by means of different reactions at the C‐8 ketone carbonyl group, essentially Wittig methylenation, cyanohydrin formation or palladium‐catalysed carbonylation of the corresponding enol triflate. Further manipulation of the functionalization derived from these key reactions allowed the preparation, among others, of 9α‐fluorodrimanes, which are structurally and functionally related to albicanic acid, drimenin and olepupuane. Also described are the reactivities of some of the fluorine‐containing systems prepared and a comparative study of the antifeedant activities of a selection of 9α‐fluorodrimanes and the corresponding hydrogen analogues against several insect species with different feeding ecologies (Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi), which revealed a significant increase in the antifeedant activities of some of the fluorinated drimane analogues.

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Section: Evaluation Of Antifeedant Activitymentioning

confidence: 91%

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

Section: Evaluation Of Antifeedant Activitymentioning

confidence: 99%

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Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

Abad¹,

Agulló²,

Cuñat³

et al. 2010

Eur J Org Chem

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“…We therefore speculated that, as occurs with other closely related sesquiterpenoids, [13,14] these metabolites might act as chemical deterrents against insects and other parasites. Moreover, 3-hydroxydrimanes are considered to constitute a biochemical linkage between drimanes and rearranged drimanes, [15] and have proven to be useful building blocks for the synthesis of higher terpenoids of pharmacological interest.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of 3‐Hydroxydrimanes Mediated by Titanocene(III) – Evaluation of Their Antifeedant Activity

et al. 2005

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“…Nebularic acid A Drimanes comprise a class of sesquiterpenoid metabolites [1] that possess a broad spectrum of activities, including antifungal, [2] antibacterial, [3] antiviral, [4,5] cytotoxic, [6] antifeedant, [7] antiallergic, and antiinflammatory properties.[8]Drimane sesquiterpenoids have been isolated from higher plants such as Canella winterana, [9,10] Warburgia salutaris [11] and Drymus winteri, [12] as well as from fungi such as Aspergillus, [5] Panus, [13] and Lactarius species. [14] Here we report the isolation and structural elucidation of two nordrimane sequiterpenoid acids named nebularic acids, and two drimane sesquiterpenoid lactones from a culture of the basidiomycete Lepista nebularis.…”

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confidence: 99%

Nebularic Acids and Nebularilactones, Novel Drimane Sesquiterpenoids from the Fungus Lepista nebularis

2006

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Four (nor-)drimane sesquiterpenoids, nebularic acids A (1) and B (2) and nebularilactones A (3) and B (4), were isolated from a cultured Lepista nebularis strain by bioassay-guided chromatography, and their structures were elucidated by mass spectrometry and NMR spectroscopy. Nebularic acid A Drimanes comprise a class of sesquiterpenoid metabolites [1] that possess a broad spectrum of activities, including antifungal, [2] antibacterial, [3] antiviral, [4,5] cytotoxic, [6] antifeedant, [7] antiallergic, and antiinflammatory properties.[8]Drimane sesquiterpenoids have been isolated from higher plants such as Canella winterana, [9,10] Warburgia salutaris [11] and Drymus winteri, [12] as well as from fungi such as Aspergillus, [5] Panus, [13] and Lactarius species. [14] Here we report the isolation and structural elucidation of two nordrimane sequiterpenoid acids named nebularic acids, and two drimane sesquiterpenoid lactones from a culture of the basidiomycete Lepista nebularis.A strain of Lepista nebularis collected in Siberia appeared to produce antimicrobial metabolites, as revealed by an initial screening with crude extracts. The fungus was cultivated under the conditions of surface fermentation at 25°C in 500 mL Erlenmeyer flasks containing 100 mL medium composed of malt extract (20 g L -1 ), glucose (10 g L -1 ), yeast extract (1 g L -1 ) and (NH 4 ) 2 SO 4 (5 g L -1 ), at pH 6.0. After cultivation for 28 days at 25°C the mycelium cake from the culture medium (60 L) was harvested and extracted twice with ethyl acetate and methanol (each 10 L). The culture broth was thoroughly extracted with ethyl acetate and the combined extracts were dried and the solvents were evaporated. The residue (3.2 g) was subjected to column chromatography (silica gel 60, Merck, 0.063-0.1 mm, column 4 × 60 cm), with stepwise CHCl 3 and CHCl 3 /MeOH (9:1, 1:1, v/v) as eluents. Active components were isolated through bioassays (v.i. 1 H NMR spectrum of 1 showed 19 nonexchangeable protons including one olefinic proton at δ = 8.02 ppm and three methyl groups at δ = 0.88, δ = 0.92 and δ = 1.14 ppm. Analyses of 13 C, DEPT 135 and HMQC NMR spectra of 1 indicated the presence of two methine C-atoms (one of them sp 2 -hybridized) four methylene C-atoms, three methyl C-atoms and three quaternary C-atoms (one of them sp 2 -hybridized), a carboxy C atom (δ = 164.0 ppm) and a carbonyl C atom (δ = 204.3 ppm). The occurrence of the carboxy group and the carbonyl group was confirmed by the IR spectrum, which showed strong absorption bands at 1742 cm -1 and 1632 cm -1 . The 1 H-1 H COSY spectrum revealed the coupling systems H-1/H-2/H-3, and H-5/H-6. By HMBC all connectivities were fully assigned. The geminal arrangement of the methyl groups C-14 (δ = 20.9 ppm) and C-15 (δ = 32.6 ppm) was established by the correlation of H-14 (δ = 0.92 ppm) and H-15 (δ = 0.88 ppm) with C-4 (δ = 33.0 ppm), C-3 (δ = 40.7 ppm) and C-5 (δ = 49.4 ppm). Similarly, the correlation of H-13 (δ = 1.14 ppm) with C-10 (δ = 38.3 ppm), C-1 (δ = 36.8 ppm) and C-9 (δ = 175.4 ppm) sh...

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Cited by 21 publications

References 17 publications

Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

Preparation of 9α‐Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities

Total Synthesis of 3‐Hydroxydrimanes Mediated by Titanocene(III) – Evaluation of Their Antifeedant Activity

Nebularic Acids and Nebularilactones, Novel Drimane Sesquiterpenoids from the Fungus Lepista nebularis

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