Elsevier

Phytochemistry

Volume 26, Issue 6, 1987, Pages 1845-1846
Phytochemistry

An oxindole from the roots of Capparis tomentosa

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Abstract

The structure of 3-hydroxy-3-methyl-4-methoxyoxindole isolated from the roots of Capparis tomentosa has been determined by spectrometric methods.

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There are more references available in the full text version of this article.

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  • Anti-inflammatory and anti-nociceptive property of Capparis tomentosa Lam. root extracts

    2020, Journal of Ethnopharmacology
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    Additionally, root and leaf parts of C. tomentosa have been used as a folkloric medicine for the treatment of evil eye, evil spirit, psychosis, and malaria alone or in combination with other plant species (Enyew et al., 2014; Suleman et al., 2018; Wubetu et al., 2018). Different phytochemicals including dipeptide derivatives, phytosterols (Akoto et al., 2008), oxindoles (alkaloids) (Dekker et al., 1987), and L-stachydrine (alkaloid) (Cornforth and Henry, 1952) have been reported from C. tomentosa root. However, the traditional use of C. tomentosa as an anti-inflammatory and anti-nociceptive remedy is not yet scientifically justified.

  • Absolute configuration assignment of oxindole derivatives by vibrational circular dichroism exciton coupling

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    The absolute configuration of (3S,14S)-3 and (3R,14S)-3 were independently determined using a time consuming protocol needed to compare the experimental vibrational circular dichroism (VCD) spectra with those calculated using DFT, which showed good agreement.2b In a continuation of our studies aimed at the determination of the absolute configuration of oxindole derivatives,3 we herein report that the absolute configuration of (3R)-2a–m and (3S)-2a–m can be assigned solely by VCD exciton coupling (VCDEC)4 by considering the bisignate couplets that originate from the through-space interaction of the C2 and C9 amide carbonyl groups. We also demonstrate that the absolute configurations of (3R)-2a–m and (3S)-2a–m can be assigned by this method independent of the chiral derivatizing amine used, thus avoiding the need of having an aromatic group that is capable of producing an efficient and space-oriented anisotropic effect to selectively affect substituents in the substrate.

  • Formal synthesis of (-)-flustramine B and its absolute configuration assignment by vibrational circular dichroism exciton chirality

    2015, Tetrahedron Asymmetry
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    The absolute configuration of (3R,14S)- and (3S,14S)-4 was independently determined using the time consuming protocol needed to compare experimental vibrational circular dichroism (VCD) spectra with those calculated using density functional theory, which showed good agreement.5 In continuation of our studies aimed at the synthesis of flustramines6 and the determination of the absolute configuration of indole and oxindole derivatives,4,7 we herein report that the absolute configuration of (3R,14S)- and (3S,14S)-6-bromooxindolylacetylphenyloxazolidinones 4, 6, 13a–c, and (3R)- and (3S)-amides 14, an intermediate in the formal synthesis of flustramine,3b can be assigned solely by VCD exciton chirality (VCDEC)8 considering the bisignate couplets that originate from the through-space interaction of the C2 and C9 amide carbonyl groups. The absolute configuration in both diastereomers was also assigned when comparing specific VCD bands in the (3R,14S)- and (3S,14S)-4, 6, 13a–c series.

  • Absolute configuration assignment of 3-oxindolylacetyl-4- phenyloxazolidinone derivatives

    2011, Tetrahedron Asymmetry
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    One advantage of the present methodology is that once the absolute configuration at C3 in the oxindolyl moiety has been achieved, the CDA could be recovered after hydrolysis of the corresponding oxazolidinone. Although aryloxazolidinones are versatile chiral auxiliaries and have been used for the synthesis of indole derivatives, enolate alkylations, Michael additions, β-lactams, alkene acylation, cyclopropanations, Wittig olefination, and Diels–Alder reactions,4 their use as a CDA has scarcely been explored. Pirkle and Simmons have achieved the absolute configuration assignment of primary amines by 1H NMR via the formation of allophanate derivatives in which the aryl ring causes specific shielding on the substituents of the amine5a moiety, while Pridgen and De Brosse have carried out the relative stereochemical assignments of some N-[α-hetero-β-hydroxy(acetoxy)-β-(substituted-phenyl)-1′-oxopropyl]-2-oxazolidinones.5b

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Part 5 in the series “Studies of South African Medicinal Plants”. For Part 4 see S. Afr. J. Chem. (1987) (submitted for publication).

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