Clerodendrins from Clerodendron trichotomum and their feeding stimulant activity for the turnip sawfly

Kawai, Kunji; Amano, Takashi; Nishida, Ritsuo; Kuwahara, Yasumasa; Fukami, Hiroshi

doi:10.1016/s0031-9422(98)00431-2

Cited by 35 publications

(23 citation statements)

References 10 publications

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“…Thus, the compound was deduced to possess the structure given by formula IId. A 2,3-dihydroxy-6,18-diacetyl derivative (II: R= H) was prepared by a mild hydrolysis of clerodendrin B (IIa) with potassium carbonate in methanol (Kawai et al 1998), the mass and 1 H NMR spectra of which coincided with those of IId isolated from A. rosae ruficornis. Compound IId is a novel clerodendrin analog which could not be detected from accounted for 80-90% of total clerodendrins.…”

Section: Identification Of Clerodendrin Analogs In Body Tissuesmentioning

confidence: 99%

“…They feed selectively on the glandular trichomes distributed densely on the leaf surface (Shimokawa & Kitano 1989). Clerodendrins B, D and H have been characterized as the specific feeding stimulants for the sawfly Kawai et al 1998). The insects sequester the bitter principles in their body tissues as defense substances by pharmacophagously feeding on the leaf tissues (Nishida & Johki 1989;Nishida & Fukami 1990).…”

Section: Introductionmentioning

confidence: 99%

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Pharmacophagous acquisition of clerodendrins by the turnip sawfly ( Athalia rosae ruficornis ) and their role in the mating behavior

et al. 1999

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Adults of the turnip sawfly, Athalia rosae ruficornis (Tenthredinidae: Hymenoptera), frequently visit a plant, Clerodendron trichotomum (Verbenaceae), and feed pharmacophagously on the glandular trichomes on the leaf surface. A series of neo-clerodane diterpenoids (e.g. clerodendrins B and D) contained in glandular organs on the leaf surface stimulate feeding of the sawflies (both males and females). The adults fed selectively on the trichomes were found to sequester a series of the bitter-tasting diterpenes (clerodendrin D, ajugachin A, athaliadiol) in the body tissues, which suggested their primary role as defense substances against predators. Females fed on Clerodendron leaves or on clerodendrin B or D were more successful in mating than unfed females. Thus, females seem to obtain an advantage in mating success through the acquisition of the defensive principles from the Clerodendron plant.

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Section: Identification Of Clerodendrin Analogs In Body Tissuesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Pharmacophagous acquisition of clerodendrins by the turnip sawfly ( Athalia rosae ruficornis ) and their role in the mating behavior

et al. 1999

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“…The dried leaf and stem of C. trichotomum, known as 'Chou Wu Tong', exhibits diverse pharmacological activities such as blood pressure reduction, sedation, soothing, and paralysis activity (Huang, 1993;Ahn, 1998). Several flavonoids (Okigawa et al, 1970;Morita et al, 1977), diterpenes (Kato et al, 1971;Kawai et al, 1998;, blue pigments (Iwadare et al, 1974), sterols (Kawano et al, 1967), and phenylpropanoid glycosides (Sakurai and Kato, 1983;Kim et al, 2001) have been isolated from C. trichotomum. Activity studies have revealed antihypertensive and antioxidant effects (Chae et al, 2005), as well as an inhibitory effect on human immunodeficiency virus (HIV)-1 integrase activity (Kim et al, 2001) by C. trichotomum.…”

Section: Various Pathogenic Bacteria Including Escherichia Coli Andmentioning

confidence: 99%

Antibacterial Activity of Triterpenoids from Clerodendron trichotomum

Choi¹,

Cho²,

Lee³

et al. 2012

Journal of Applied Biological Chemistry

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The aim of this research was to investigate the antibacterial activity of Clerodendron trichotomum. Antibacterial activities of the n-hexane, methylene chloride (MC), ethyl acetate, and n-butanol fractions from C. trichotomum were tested against Staphylococcus aureus, Escherichia coli, and Helicobacter pylori. The n-hexane and MC fractions showed antibacterial activity against H. pylori at a concentration of 1.7 mg/mL and showed inhibition zones of 10 and 11 mm in disc assay, respectively. Further testing of 22-dehydroclerosterol and β-amyrin (each 3.4 mg/mL) from the MC fraction of C. trichotomum revealed moderate antibacterial effects against E. coli, S. aureus, and H. pylori. In particular, β-amyrin showed clear zones of 12 and 13 mm against E. coli and H. pylori, respectively, suggesting its potential as an antibacterial agent. The active compounds from C. trichotomum might provide a promising therapeutic agent against infections by E. coli, S. aureus, and H. pylori.

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“…(1) Its S-enantiomer is used for the preparation of a COX-2 specific inhibitor, [4] while its R-enantiomer forms part of several biologically active natural products, such as the clerodendrins, [5,6,7] protoveratrine A [8,9] and germinalinine. [10] (2) The synthesis of I via the enantioselective addition of cyanide to the prochiral butanone and subsequent hydrolysis involves a daunting stereodifferentiation between a methyl and an ethyl group (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Linum usitatissimum Hydroxynitrile Lyase Cross‐Linked Enzyme Aggregates: A Recyclable Enantioselective Catalyst

et al. 2008

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An immobilized form of the hydroxynitrile lyase from Linum usitatissimum (LuHNL) as crosslinked enzyme aggregate (CLEA) with high specific activity (303.5 U/g) and recovery (33%) was developed. Molecular imprinting using 2-butanone as additive in the immobilization process improved the synthetic activity of the biocatalyst. LuCLEA could be partially recycled for the synthesis of (R)-2-butanone cyanohydrin on a preparative scale over two batches. The enantioenriched cyanohydrin obtained was further hydrolyzed to give (R)-2-hydroxy-2-methylbutyric acid in 85% yield (from 2-butanone) and 87% ee.

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Clerodendrins from Clerodendron trichotomum and their feeding stimulant activity for the turnip sawfly

Cited by 35 publications

References 10 publications

Pharmacophagous acquisition of clerodendrins by the turnip sawfly ( Athalia rosae ruficornis ) and their role in the mating behavior

Pharmacophagous acquisition of clerodendrins by the turnip sawfly ( Athalia rosae ruficornis ) and their role in the mating behavior

Antibacterial Activity of Triterpenoids from Clerodendron trichotomum

Linum usitatissimum Hydroxynitrile Lyase Cross‐Linked Enzyme Aggregates: A Recyclable Enantioselective Catalyst

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