Potential of natural peptidic compounds as leads for novel pesticides

Bland, John M.; Edwards, Jesse; Eaton, Scott R.; Lax, Alan R.

doi:10.1002/ps.2780390414

Cited by 13 publications

(9 citation statements)

References 15 publications

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“…1), has not led to a simpler molecule with acceptable activity (e.g. Edwards et al ., 1988 ; Bland et al ., 1993 ). The herbicidal activity of glufosinate (phosphinothricin) is better than that of structural analogues ( Lydon & Duke, 1999) The evolutionary process often appears to have optimized biological activity.…”

Section: Advantages and Weaknessesmentioning

confidence: 99%

Natural products as sources of herbicides: current status and future trends

2000

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Although natural product-based discovery strategies have not been as successful for herbicides as for other pesticides or pharmaceuticals, there have been some notable successes. Phosphinothricin, the biosynthetic version of glufosinate, and bialaphos are phytotoxic microbial products that have yielded commercial herbicides. Cinmethylin, a herbicidal analogue of cineole, has been sold in Europe and Asia. The triketone herbicides are derivatives of the plant-produced phytotoxin leptospermone. These products represent only a small fraction of commercialized herbicides, but they have each introduced a novel molecular target site for herbicides. Analysis of the literature reveals that phytotoxic natural products act on a large number of unexploited herbicide target sites. The pesticide industry's natural product discovery eorts have so far concentrated on microbially derived phytotoxins, primarily from non-pathogenic soil microbes, involving the screening of large numbers of exotic isolates. Plant pathogens usually produce potent phytotoxins, yet they have received relatively little attention. Even less eort has been made to discover plant-derived phytotoxins. Bioassay-directed isolation has been the preferred method of discovery after a producing organism is selected. This laborious approach often leads to rediscovery of known compounds. Modern tandem separation/chemical characterization instrumentation can eliminate much of this problem by identi®cation of compounds before they are bioassayed.

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Section: Advantages and Weaknessesmentioning

confidence: 99%

Natural products as sources of herbicides: current status and future trends

2000

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“…As an alternative to higher natural production, we have undertaken extensive structure activity relationship studies utilizing computer modelling to guide synthetic efforts at simpler more readily synthesized molecules which retain both the potent activity and the desired specificity (75). In numerous analogues synthesized and tested none of the compounds has demonstrated greater activity than the parent molecule (8,9,13).…”

Section: Figure 1 Structure Of Tentoxin [Cyclo(n-methylalanyl-leucylmentioning

confidence: 92%

“…Structure activity studies have led us to speculate that the composition and conformation of the leucyl-dehydophenylalanyl portion of tentoxin are essential for its activity (8)(9)(10)(11)13). We have undertaken to produce simpler compounds whose conformations at this position match the parent compound.…”

Section: A βmentioning

confidence: 96%

Biorational Control of Weeds and Fungi with Peptides

Lax

Bland

Shepherd

1993

Natural and Engineered Pest Management Agents

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Tentoxin is a cyclic tetrapeptide produced by the fungus Alternaria alternata that disrupts chloroplast development in most of the major weed species in soybean and johnsongrass in corn while having no effect on either of these crop species. The major impediment to the development of tentoxin as a herbicide is its limited availability because of low biosynthetic yields. Iturins are a family of cyclic octapeptides having a unique β-amino acid, iturinic acid, incorporated into the peptide backbone. Iturins have a broad antifungal activity, but low biosynthetic yields may limit their commercialization. Chemical synthesis of both molecules is possible and the production of analogues has led to meaningful structure/activity relationships. To date no analog has provided greater activity or specificity than the parent molecule for either of the two agents. Molecular genetic manipulation is considered the best strategy for the increase in production of both of these compounds for cost effective synthesis. Success of cloning of the biosynthetic genes may determine the eventual deployment of these biorational pesticides.The cost of pest control in agriculture is staggering; direct costs of pesticides are estimated to be at least $20 billion annually, with unestimated indirect costs making the exact amount impossible to accurately state. Recent popular concern for the environment and legislation toward banning some of the more traditional pesticide compounds has led to the development of new strategies for the control of pests which include microbes as biological control organisms and the use of the biorational approach in which natural products provide a basis for the This chapter not subject to U.S.

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“…Insect neuropeptides, which are present in interneurons and motor neurons as well as neurosecretory cells, play an important role during an insect's life and therefore can be considered as bioinsecticides for potential application in pest control. [2][3][4][5] The insect kinins, which share the highly conserved C-terminal pentapeptide sequence Phe 1 -Xaa 2 -Yaa 3 -Trp 4 -Gly 5 -NH 2 (Xaa 2 = His, Asn, Ser, or Tyr and Yaa 3 = Ser, Pro, or Ala) are one class of insect neuropeptides with multifunctions including the regulation of hindgut contraction, diuresis and modulation of digestive enzyme release. [6][7][8][9] However, several shortcomings, such as susceptibility to both exoand endo-peptidases in hemolymph and tissues of insects, need to be overcome for insect kinins before they can be applied in pest control.…”

Section: Introductionmentioning

confidence: 99%

“…[17][18][19][20][21][22] The hydrolysis of the insect kinins by particular peptidases leads to their reduced activity or inactivity in vivo. There are two susceptible hydrolysis sites in the core pentapeptide sequence Phe 1 -Tyr 2 -Pro 3 -Trp 4 -Gly 5 -NH 2 . The first site is between Pro 3 and the Trp 4 residue, susceptible to cleavage by angiotensin converting enzyme (ACE) from the housefly and neprilysin (NEP).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, aphicidal activity and conformation of novel insect kinin analogues as potential eco‐friendly insecticides

Zhang

Ling

et al. 2020

Pest Management Science

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BACKGROUND The discovery of ecofriendly insecticides through a new strategy for aphid control is important because of the substantial resistance and unexpected eco‐toxicity to honeybees caused by traditional insecticides. The insect kinins, a class of multifunctional insect neuropeptides, are considered for potential application in pest control. In our previous work we developed several series of insect kinin analogues and found a promising lead II‐1 with good aphicidal activity. To seek further eco‐friendly aphicides, the optimization of II‐1 is carried out in this study. RESULTS Fifteen novel Yaa3 modified analogues based on the lead II‐1 were synthesized. The aphicidal tests indicated that IV‐3, IV‐5 and IV‐10 exhibited significant activity against the soybean aphid Aphis glycines with LC50 values of 0.0029, 0.0072 and 0.0086 mmol L–1, respectively, higher than that of lead II‐1 and the commercial Pymetrozine. The molecular modeling results showed that analogues II‐1, IV‐3, IV‐5, IV‐7 and IV‐10 formed a β‐turn‐like conformation, while the conformation of analogues IV‐1, IV‐2 and IV‐9 seemed to be linear. Some structural elements favorable for the activity were proposed based on the conformation‐activity relationship of the analogues. CONCLUSION Insect kinin analogues derived from lead II‐1 by modifying the hydrolysis site Yaa3 with natural, sterically hindered α‐ and β‐amino acids showed great potential as eco‐friendly insecticides. Inspiringly, the most active analogue IV‐3 can be a candidate for further development. The β‐turn‐like conformation and the orientation of the aromatic rings of the side chain of Phe2 and Trp4 may be critical factors beneficial to activity. © 2019 Society of Chemical Industry

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Potential of natural peptidic compounds as leads for novel pesticides

Cited by 13 publications

References 15 publications

Natural products as sources of herbicides: current status and future trends

Natural products as sources of herbicides: current status and future trends

Biorational Control of Weeds and Fungi with Peptides

Synthesis, aphicidal activity and conformation of novel insect kinin analogues as potential eco‐friendly insecticides

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