Larvicidal activity of para-Benzoquinones

Sousa, Damião Pergentino de; Vieira, Ygor W.; Uliana, Marciana P.; Melo, Manuela A; Brocksom, Timothy J.; Cavalcanti, Sócrates C.H.

doi:10.1007/s00436-010-1942-7

Cited by 16 publications

(12 citation statements)

References 20 publications

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“…Plants and marine organisms have been shown to produce a number of cytotoxic quinones and hydroquinones, including avarone, bolinaquinone, juglone, and lapachol 39,40 . Lapachol, isolated from Tabebuia avellanedae, and structurally related derivatives have shown modest larvicidal activity against mosquitoes 41,42 . Further modifications of 1 were implemented to prepare a derivative potentially exhibiting mosquito toxicity without antifeedant activity.…”

Section: Derivatization Of Cinnamodialmentioning

confidence: 99%

Semi-synthetic Cinnamodial Analogues: Structural Insights into the Insecticidal and Antifeedant Activities of Drimane Sesquiterpenes Against the Mosquito Aedes aegypti

Manwill

Kalsi

et al. 2019

Preprint

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The Aedes aegypti mosquito serves as a major vector for viral diseases, such as dengue, chikungunya, and Zika, which are spreading across the globe and threatening public health. In addition to increased vector transmission, the prevalence of insecticideresistant mosquitoes is also on the rise, thus solidifying the need for new, safe and effective insecticides to control mosquito populations. We recently discovered that cinnamodial, a unique drimane sesquiterpene dialdehyde of the Malagasy medicinal plant Cinnamosma fragrans, exhibited significant larval and adult toxicity to Ae. aegypti and was more efficacious than DEET -the gold standard for insect repellents -at repelling adult female Ae. aegypti from blood feeding. In this study several semisynthetic analogues of cinnamodial were prepared to probe the structure-activity relationship (SAR) for larvicidal, adulticidal and antifeedant activity against Ae. aegypti. Initial efforts were focused on modification of the dialdehyde functionality to produce more stable active analogues and to understand the importance of the 1,4-dialdehyde and the α,ßunsaturated carbonyl in the observed bioactivity of cinnamodial against mosquitoes. This study represents the first investigation into the SAR of cinnamodial as an insecticide and repellent against the medically important Ae. aegypti mosquito. Scheme 1. Derivatization of 1 into structural analogues. Reagents and conditions: (a) NaClO 2 , NaH 2 PO 4 •H 2 O, H 2 O 2 , MeCN, H 2 O, r.t., 24 h; (b) TMS-CHN 2 , MeOH:Et 2 O, 0 o C, 30 min;( c) H 2 N-NH 2 , CH 2 Cl 2 :EtOH, 2 h; (d) MeOH, r.t.; (e) HOCH 2 CH 2 OH, p-TsOH, benzene, reflux, 24 h. Scheme 2. Synthesis of lactols 8 and 9, and formation of 10 from lactol 9. Reagents and conditions: (a) 1 eq. MeMgBr, THF, 78 o C, 2 h; (b) CDCl 3 , 22 d. Scheme 3. Synthesis of 1,4-dione 13. Reagents and conditions: (a) 5 eq. MeMgBr, THF, 78 o C, 2 h; (b) 3.3 eq. PCC, DCM, 0 o C → r.t., 2h. Scheme 4. Reaction mechanism of the reaction of 1 with L-cysteine methyl ester via a cationic azomethine (A) to form the pyrrolidine (16).

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Section: Derivatization Of Cinnamodialmentioning

confidence: 99%

Semi-synthetic Cinnamodial Analogues: Structural Insights into the Insecticidal and Antifeedant Activities of Drimane Sesquiterpenes Against the Mosquito Aedes aegypti

Manwill

Kalsi

et al. 2019

Preprint

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“…19−21 Other naturally occurring mosquito larvicidal quinones are anthraquinones, such as emodin (6-methyl-1,3,8-trihydroxyanthraquinone) from Cassia obtusifolia and tectoquinone (2-methylanthraquinone) from Cryptomeria japonica. 1,4,5,21 The larvicidal activity of lapachol isolated from C. antisyphilitica stem wood against A. aegypti larvae (third instar) was reported by Rodrigues et al 20 However, in this study, the larvicidal activities of lapachol isolated from T. avellanedae bark and its structurally related compounds against fourth instar larvae of A. aegypti, C. pipiens pallens, and O. togoi were investigated. Furthermore, the larvicidal activity of synthetic insecticide (pirimiphos-methyl) for comparison was evaluated against three mosquito species, and the results were different from those of the previous study.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 84%

Larvicidal Activity of the Active Constituent Isolated from Tabebuia avellanedae Bark and Structurally Related Derivatives against Three Mosquito Species

Kim

Jeon

Lee

2013

J. Agric. Food Chem.

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Mosquito larvicidal activities of active constituent isolated from Tabebuia avellanedae bark and its structurally related derivatives were examined against the fourth instar larvae of Aedes aegypti, Culex pipiens pallens, and Ochlerotatus togoi. The insecticidal constituent of T. avellanedae bark was isolated by chromatographic techniques and identified as 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione. On the basis of the 50% lethal concentration (LC50) values against C. pipiens pallens larvae, the most toxic compound was 1,4-naphthalenedione (1.26 mg/L), followed by 1,2-naphthalenedione (1.43 mg/L), 1,4-naphthalenediol (3.20 mg/L), 2-chloro-3-pyrrolidino-1,4-naphthalenedione (5.11 mg/L), 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (8.30 mg/L), and 2-chloro-3-morpholino-1,4-naphthalenedione (12.98 mg/L). Similar results against A. aegypti and O. togoi larvae were observed for 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione and its derivatives. According to the LC50 values against three mosquito species, these compounds were less toxic than pirimiphos-methyl. Nonetheless, naturally occurring T. avaellenedae bark-derived materials could be useful as a natural mosquito control agent.

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“…In the literature, quinones have been found to have larvicidal activities against several mosquito species. Examples include para ‐benzoquinones, naphthoquinones and anthraquinones . Interestingly, the halogenated naphthoquinones were found to be more active against A. aegypti than the non‐halogenated congeners .…”

Section: Resultsmentioning

confidence: 99%

Larvicidal spirobisnaphthalenes from the endophytic fungus Berkleasmium sp. against Aedes albopictus

Tian

Liu

et al. 2015

Pest Management Science

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Larvicidal activity of para-Benzoquinones

Cited by 16 publications

References 20 publications

Semi-synthetic Cinnamodial Analogues: Structural Insights into the Insecticidal and Antifeedant Activities of Drimane Sesquiterpenes Against the Mosquito Aedes aegypti

Semi-synthetic Cinnamodial Analogues: Structural Insights into the Insecticidal and Antifeedant Activities of Drimane Sesquiterpenes Against the Mosquito Aedes aegypti

Larvicidal Activity of the Active Constituent Isolated from Tabebuia avellanedae Bark and Structurally Related Derivatives against Three Mosquito Species

Larvicidal spirobisnaphthalenes from the endophytic fungus Berkleasmium sp. against Aedes albopictus

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