Potential of natural products as insect antifeedants

Jain, D. C.; Tripathi, Arun Kumar

doi:10.1002/ptr.2650070502

Cited by 19 publications

(7 citation statements)

References 81 publications

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“…The biological activity of ring D and rings B,D-seco limonoids of Meliaceae, and of gedunin ( 416 ) have also been summarized recently . Furthermore, the activities of natural limonoids from plants have been presented including the meliaceous limonoids as one of their discussion topics. ,− …”

Section: Biological Activities Of Meliaceous Limonoidsmentioning

confidence: 99%

“…Some mini-reviews related to limonoids from Meliaceae have been presented since 1966. For example, the chemistry, − biosynthesis, ,− and biological activities − of meliaceous limonoids were summarized in different years. It is noteworthy that some reviews emphasize the well-known azadirachtin ( 292 ) and aspects of its chemistry, − synthesis, , and bioactivities including antifeedant activity, − insecticidal activity, and insect-growth-regulating activity, ,, as well as its environmental behavior, and its physiological behavior properties. , In addition, the toxicity characteristics of azadirachtin and the mechanisms of its insecticidal action − were also reviewed.…”

Section: Background and Introductionmentioning

confidence: 99%

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Meliaceous Limonoids: Chemistry and Biological Activities

2011

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Section: Biological Activities Of Meliaceous Limonoidsmentioning

confidence: 99%

Section: Background and Introductionmentioning

confidence: 99%

Meliaceous Limonoids: Chemistry and Biological Activities

2011

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“…The genus Chisocheton belongs to the family Meliaceae, a subtropical and tropical plant family widely known for its insecticidal limonoid (tetranortriterpenoid) constituents (Jain and Tripathi, 1993;Roy and Saraf, 2006). Previous phytochemical studies on Chisocheton species have yielded a number of interesting compounds, including limonoids (Connolly et al, 1979;Gunning et al, 1994), antifungal meliacin-type compounds (Bordoloi et al, 1993), dammarane triterpenoids, with an inhibitory effect on EpsteinBarr virus activation (Inada et al, 1993), and spermidine alkaloids (Tzouros et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

A new sesquiterpene and other terpenoid constituents of Chisocheton penduliflorus

et al. 2008

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A new aromadendrane sesquiterpene, allo-aromadendrane-10alpha, 14-diol (3), was isolated from Chisocheton penduliflorus (Meliaceae), along with two known sesquiterpenes: allo-aromadendrane-10beta, 14-diol (2) and allo-aromadendrane-10beta, 13, 14-triol (7). Six dammarane triterpenoids, including cabraleadiol (1), eichlerialactone (4), cabraleahydroxylactone (5), cabralealactone (6), hollongdione (8) and dammaradienone (9), the coumarins scoparone and scopoletin, and vanillic acid were also isolated from the wood and leaves of this plant. Compounds 1-7 displayed antimycobacterial activity against Mycobacterium tuberculosis. Compounds 1, 4, 5 and 6 were weakly cytotoxic to a breast cancer (BC) cell line; whereas, compound 6 was moderately active against a small-cell lung cancer (NCI-H187) cell line.

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“…These attributes have also been seen in other neoclerodanes such as ajugatansin A1 ( 9 ), and tafricanin A ( 10 ). 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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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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Potential of natural products as insect antifeedants

Cited by 19 publications

References 81 publications

Meliaceous Limonoids: Chemistry and Biological Activities

Meliaceous Limonoids: Chemistry and Biological Activities

A new sesquiterpene and other terpenoid constituents of Chisocheton penduliflorus

Chemical methods for the synthesis and modification of neoclerodane diterpenes

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