The Use of Carbon-13 Nuclear Magnetic Resonance Spectroscopy in Natural Products Chemistry

Wehrli, Félix W.; Nishida, Toshiaki

doi:10.1007/978-3-7091-3265-4_1

Cited by 32 publications

(20 citation statements)

References 580 publications

(395 reference statements)

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“…The fractions F4, F-13 and F-51 are composed of a mixture of cardanols (1a+1b), cardols (2a+2b) and anacardic acid (3), respectively ( Figure 1). The NMR 1 H and 13 C data coincides with that found in other studies [16,18].…”

Section: Resultssupporting

confidence: 91%

Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

et al. 2008

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Propolis is a sticky, gummy, resinous substance collected by honeybees (Apis mellifera L.) from various plant sources, which has excellent medicinal properties. This paper describes the isolation and identification of triterpenoids and anacardic acid derivatives from Brazilian propolis and their antibacterial activity. Their structures were elucidated by ¹H and 13C NMR, including uni- and bidimensional techniques; in addition, comparisons were made with data from academic literature. These compounds were identified as: cardanols (1a + 1b), cardols (2a + 2b), monoene anacardic acid (3), a-amirine (4), b-amirine (5), cycloartenol (6), 24-methylene-cycloartenol (7) and lupeol (8). The determination of the position of the double bond after a reaction with Dimethyl disulfide (DMDS) is described for the phenol derivatives. The ethanolic extract was tested in vitro for antimicrobial activity by using the disc diffusion method and it showed significant results against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Shigella spp.

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Section: Resultssupporting

confidence: 91%

Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

et al. 2008

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“…9-Oxofuranoeremophilanes with a cis A/B ring stereochemistry (Guerreiro and Pietra, 1982;Tada et al, 1981;Flamm et al, 1976;Wehrly and Nishida, 1979), such as 6␤-acetoxy-1,10␤-epoxy-9-oxofuranoeremophilane, had a carbonyl carbon chemical shift of ca. 180-181 ppm, while those 6-oxo cis compounds, as 10␤H-6-oxofuranoeremophilane and 1, 10␤-epoxy-6-oxofuranoeremophilane, at 197.3-199.8 ppm.…”

Section: Resultsmentioning

confidence: 99%

Toxic Furanoeremophilanes from Senecio bonariensis

Pomilio

Jares

1997

International Journal of Pharmacognosy

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“…Os compostos conhecidos como acetato de a-amirina (2) (Seo et al, 1975;Bandeira et al, 2007;Zanon et al, 2008), cicloartenona (5) (Davies et al, 1992), sitostenona (6) (Wehrli & Nishida, 1979; e ácido ursólico (7) (Connolly & Hill, 1991;Mahato & Kundu, 1994;Montenegro et al, 2006) foram identificados através da comparação dos dados de RMN obtidos com os da literatura.…”

Section: Resultsunclassified

Triterpenos de Guettarda grazielae M: R.V. Barbosa (Rubiaceae)

Lima¹,

Moura²,

Lemos³

et al. 2009

Rev. bras. farmacogn.

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RESUMO:O presente trabalho descreve o isolamento e a identificação estrutural de seis triterpenos (acetato de a-amirina, cicloartenona, 3b,19a,23-triidroxi-urs-12-eno e os ácidos ursólico, 6b,19a,23-tetraidroxi-urs-12-en-28-óico), além de um fitoesteróide (sitostenona) de extratos das folhas, cascas do caule e caule de Guettarda grazielae M.R.V. Barbosa (Rubiaceae). Os compostos isolados, exceto o ácido 3-b-O-b-D-glicopiranosilquinóvico, estão sendo descritos pela primeira vez no gênero Guettarda e foram identificados com base na análise de dados espectrais de RMN, incluindo APT e DEPT, bem como pela comparação com dados da literatura.Unitermos: Guettarda grazielae, Rubiaceae, triterpenos.ABSTRACT: "Triterpenes from Guettarda grazielae M.R.V. Barbosa (Rubiaceae)". This work describes the isolation and structural identification of six triterpenes (a-amyrin acetate, cycloartenone, 3b,19a,23-trihydroxyurs-12-ene, and ursolic, 3-b-O-b-D-glucopyranosylquinovic, 3b,6b,19a,23-tetrahydroxyurs-12-en-28-oic acids), beside a phytosteroid (sitostenone) from leaves, stem barks and stems of Guettarda grazielae (Rubiaceae). All isolated compounds, except 3-b-O-b-D-glucopyranosylquinovic acid, are being described for the first time in the genus Guettarda and were identified on basis of the spectral NMR data, including APT and DEPT, as well as by comparison with data of the literature.

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The Use of Carbon-13 Nuclear Magnetic Resonance Spectroscopy in Natural Products Chemistry

Cited by 32 publications

References 580 publications

Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

Anacardic acid derivatives from Brazilian propolis and their antibacterial activity

Toxic Furanoeremophilanes from Senecio bonariensis

Triterpenos de Guettarda grazielae M: R.V. Barbosa (Rubiaceae)

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