Studies on the Synthesis of Sesquiterpene Lactones, 12. Synthesis of (+)-Colartin, (+)-Arbusculin A and Their C-4 Epimers and Their Biological Activities

Ando, Masayoshi; Isogai, Koji; Azami, Hidenori; Hirata, Naomi; Yanagi, Yoshikazu

doi:10.1021/np50076a015

Cited by 31 publications

(21 citation statements)

References 7 publications

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“…In a re cent report, the antiinflammatory activity of A. inculta ex tract, without testing any pure compound, was associated with the presence of flavonoids and sesquiterpene lac tones in the extract (4). Several flavonoids (7 10) and some oxygenated sesquiterpenes and sesquiterpene hydrocarbons (11)(12)(13) are known for their antiinflamma tory potential. In the light of the available literature, there is a need to explore different properties of santonin and related terpenoids that may help in understanding the mechanism of the antiinflammatory activity common to several Compositae plants.…”

mentioning

confidence: 99%

Studies on the Antiinflammatory, Antipyretic and Analgesic Activities of Santonin

Alharbi

Qureshi

Ahmed

et al. 1994

Japanese Journal of Pharmacology

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ABSTRACT-Santonin, a sesquiterpene lactone, commonly found in the plants of the family Compositae was found to show significant antiinflammatory activity on acute inflammatory processes. The activity profile of santonin closely resembled that of a standard non-steroidal antiinflammatory drug, diclofenac sodium. It also showed a significant inhibitory effect on granuloma formation; however, this effect of san tonin was less pronounced as compared to diclofenac sodium. Santonin caused a significant antipyretic effect in mice, which was found to be independent of the route of administration of the drug. It also increas ed the hot plate reaction time of treated mice, similar to morphine.

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confidence: 99%

Studies on the Antiinflammatory, Antipyretic and Analgesic Activities of Santonin

Alharbi

Qureshi

Ahmed

et al. 1994

Japanese Journal of Pharmacology

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“…Therefore, in order to elucidate the structures of these two compounds, the EOs were separated on a silica gel column (Sephadex LH-20), followed by semi-preparative HPLC, which yielded four sesquiterpenes. Peaks 5 and 19 structures were then verified as β-selinene and feropodin after comparison with 1D NMR data reported in the literature, and the absolute configuration of feropodin was further determined using 2D NMR spectra (Ando et al, 1991;Chu et al, 2011). Surprisingly, costunolide (peak 20) and 11,13-dihydrocostunolide (peak 18) were segregated in the EOs.…”

Section: Yield and Compositions Of Eos From The Aerial Part Of A Nakaiimentioning

confidence: 88%

Insecticidal Terpenes From the Essential Oils of Artemisia nakaii and Their Inhibitory Effects on Acetylcholinesterase

et al. 2021

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Essential oils (EOs) are often the source of insecticidal substances of high efficiency and low toxicity. From gas chromatograph-mass spectrometer, column chromatography, and nuclear magnetic resonance spectra analyses, twenty terpenes were identified from the EOs of Artemisia nakaii. These comprised mostly monoterpenes (49.01%) and sesquiterpenes (50.76%). The terpenes at the highest concentrations in the EOs of A. nakaii were feropodin (200.46 ± 1.42 μg/ml), (+)-camphor (154.93 ± 9.72 μg/ml), β-selinene (57.73 ± 2.48 μg/ml), and 1,8-cineole (17.99 ± 1.06 μg/ml), calculated using area normalization and external standards. The EOs were tested for biological activity and showed strong fumigant toxicity and significant antifeedant activity against the larvae of Spodoptera litura. Furthermore, the monoterpenes 1,8-cineole and (+)-camphor displayed significant fumigant activity against S. litura, with LC50 values of 7.00 ± 0.85 and 18.16 ± 2.31 μl/L, respectively. Antifeedant activity of the sesquiterpenes feropodin and β-selinene was obvious, with EC50 values of 12.23 ± 2.60 and 10.46 ± 0.27 μg/cm2, respectively. The EOs and β-selinene were also found to inhibit acetylcholinesterase, with IC50 values of 37.75 ± 3.59 and 6.88 ± 0.48 μg/ml, respectively. These results suggest that monoterpenes and sesquiterpenes from the EOs of A. nakaii could potentially be applied as a botanical pesticides in the control of S. litura.

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“…A large number of pseudoguaianolides, 4,5-secopseudoguaianolides, guaianolides, and 4,5-secoguaianolides have been shown to exhibit biological activities, including antitumoral [23], root-growth and germination inhibitory activities [24][25][26][27], as well as preventive or curative activities against phytopatogenic fungi [24,26]. Shimoma et al [28] reported the regio-and stereoselective synthesis of common synthetic intermediates via kinetic resolution with Lipase PS, (Fig.…”

Section: Herbicidesmentioning

confidence: 99%

Biocatalysis Applied to the Synthesis of Agrochemicals

Aleu¹,

Bustillo²,

Hernández-Galán³

et al. 2006

COC

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Studies on the Synthesis of Sesquiterpene Lactones, 12. Synthesis of (+)-Colartin, (+)-Arbusculin A and Their C-4 Epimers and Their Biological Activities

Cited by 31 publications

References 7 publications

Studies on the Antiinflammatory, Antipyretic and Analgesic Activities of Santonin

Studies on the Antiinflammatory, Antipyretic and Analgesic Activities of Santonin

Insecticidal Terpenes From the Essential Oils of Artemisia nakaii and Their Inhibitory Effects on Acetylcholinesterase

Biocatalysis Applied to the Synthesis of Agrochemicals

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