Structure–Activity Relationship Studies on the Mosquito Toxicity and Biting Deterrency of Callicarpenal Derivatives

Cantrell, Charles L.; Klun, J. A.; Pridgeon, Julia W.; Becnel, James J.; Green, Solomon; Fronczek, Frank R.

doi:10.1002/cbdv.200800291

Cited by 9 publications

(2 citation statements)

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“…These discoveries have implications for agriculture, as neoclerodane diterpenes, may have potential use as environmentally benign pest deterrents 16. One such example is callicarpenal ( 11 ), which has been shown to be a mosquito bite detterant17,18 and a repellant of the blacklegged tick, lxodes scapularis and the lone star tick, Amblyomma americanum 19…”

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confidence: 99%

Chemical methods for the synthesis and modification of neoclerodane diterpenes

Lozama

Prisinzano

2009

Bioorganic & Medicinal Chemistry Letters

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Diterpenes are a structural class of molecules that are derived from four isoprene subunits and are widespread throughout nature. A number of neoclerodane diterpenes have been found to have biological activity but a limited number of chemical investigations have been conducted. Recently, the neoclerodane diterpene, salvinorin A (12) has been investigated due to its unique pharmacological profile. This review will discuss the chemical methods used to chemically modify and synthesize 12. Keywords diterpene; neoclerodane; salvinorin A; Salvia divinorumTerpenes are a wide variety of 10-carbon skeletons formed from the coupling of two isoprene subunits.1 They are ubiquitous in nature as they are used as biosynthetic building blocks in many living organisms including plants and animals.1 There are many different types of terpenes and they are classified by their structure.1 Diterpenes are one class that possess a core 20-carbon skeleton and are found in many different plant families and some animals. 1 They are biosynthesized by two different pathways, the mevalonic acid pathway (MVA) or the deoxyxylulose phosphate pathway (DOXP). 2-5 Diterpenes are of interest as many have been found to have biological activity. Some biologically active diterpenes include taxol (1), cafestol (2) and kahweol (3) (Figure 1). Diterpenes 1-3, isolated from Taxus brevifolia 6 and Coffea arabica respectively, 7,8 all display anticancer properties.One type of structural class of diterpenes are clerodanes which are found in many different plant families and contain four contiguous stereocenters contained in a cis or trans decalin (4). 9,10 Various clerodane diterpenes have been isolated and displayed biological activity. These include columbin (5), isolated from the roots of Calumbae radix ,11 which has cancer chemo-preventive properties 12 and clerocidin (6), isolated from Oidiodendron truncatum ,13 which has shown antibiotic activity. 13 Terpentecin (7), a microbial clerodane diterpene from © 2009 Elsevier Ltd. All rights reserved. Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Despite their biological properties, few synthetic works have been published on neoclerodane diterpenes. 9,20-22 One neoclerodane diterpene that has been investigated recently is salvinorin A (12). Neoclerodane 12 is isolated from the leaves of Salvia divinorum, and has shown to have hallucinogenic effects. [23][24][25][26] However, 12 is unlike classical hallucinogens, as it does not interact with the 5-HT 2A receptor. 25,27 Rather, 12 is a selective κ opioid agonist. 28 This was the first report of a neoclerodane d...

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confidence: 99%

Chemical methods for the synthesis and modification of neoclerodane diterpenes

Lozama

Prisinzano

2009

Bioorganic & Medicinal Chemistry Letters

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“…135 Newer chemicals have shown promise in deterring ticks; they include eugenol, isolongifolenone, callicarpenal derivatives, and 2-undecanone. [138][139][140][141] In a recent study from Connecticut, both protective clothing and tick repellents were shown to significantly reduce the incidence of acute LD. 142 However, from 2002 to 2004 in three health districts of that state, the rate of residents who either avoided wooded areas or tucked their pants into socks decreased.…”

Section: Repellents and Other Protective Behaviormentioning

confidence: 98%

Lyme disease

Bhate

Schwartz

2011

Journal of the American Academy of Dermatology

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Toxicity of Thiophenes from Echinops transiliensis (Asteraceae) against Aedes aegypti (Diptera: Culicidae) Larvae

Nakano

Alı

Rehman

et al. 2014

Chemistry & Biodiversity

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Structureactivity relationships of nine thiophenes, 2,2': 5',2″-terthiophene (1), 2-chloro-4-[5-(penta-1,3-diyn-1-yl)thiophen-2-yl]but-3-yn-1-yl acetate (2), 4-(2,2'-bithiophen-5-yl)but-3-yne-1,2-diyl diacetate (3), 4-[5-(penta-1,3-diyn-1-yl)thiophen-2-yl]but-3-yne-1,2-diyl diacetate (4), 4-(2,2'-bithiophen-5-yl)-2-hydroxybut-3-yn-1-yl acetate (5), 2-hydroxy-4-[5-(penta-1,3-diyn-1-yl)thiophen-2-yl]but-3-yn-1-yl acetate (6), 1-hydroxy-4-[5-(penta-1,3-diyn-1-yl)thiophen-2-yl]but-3-yn-2-yl acetate (7), 4-(2,2'-bithiophen-5-yl)but-3-yne-1,2-diol (8), and 4-[5-(penta-1,3-diyn-1-yl)thiophen-2-yl]but-3-yne-1,2-diol (9), isolated from the roots of Echinops transiliensis, were studied as larvicides against Aedes aegypti. Structural differences among compounds 3, 5, and 8 consisted in differing AcO and OH groups attached to C(3″) and C(4″), and resulted in variations in efficacy. Terthiophene 1 showed the highest activity (LC50 , 0.16 μg/ml) among compounds 1-9, followed by bithiophene compounds 3 (LC50 , 4.22 μg/ml), 5 (LC50 , 7.45 μg/ml), and 8 (LC50 , 9.89 μg/ml), and monothiophene compounds 9 (LC50 , 12.45 μg/ml), 2 (LC50 , 14.71 μg/ml), 4 (LC50 , 17.95 μg/ml), 6 (LC50 , 18.55 μg/ml), and 7 (LC50 , 19.97 μg/ml). These data indicated that A. aegypti larvicidal activities of thiophenes increase with increasing number of thiophene rings, and the most important active site in the structure of thiophenes could be the tetrahydro-thiophene moiety. In bithiophenes, 3, 5, and 8, A. aegypti larvicidal activity increased with increasing number of AcO groups attached to C(3″) or C(4″), indicating that AcO groups may play an important role in the larvicidal activity.

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Structure–Activity Relationship Studies on the Mosquito Toxicity and Biting Deterrency of Callicarpenal Derivatives

Cited by 9 publications

References 13 publications

Chemical methods for the synthesis and modification of neoclerodane diterpenes

Chemical methods for the synthesis and modification of neoclerodane diterpenes

Lyme disease

Toxicity of Thiophenes from Echinops transiliensis (Asteraceae) against Aedes aegypti (Diptera: Culicidae) Larvae

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