Prostaglandin Synthetase Inhibitors from the African Medicinal Plant <i>Ozoroa mucronata</i>

Kubo, Isao; Kim, Mujo; Naya, Keizo; Komatsu, Sakae; Yamagiwa, Yoshiro; Ohashi, Kinji; Sakamoto, Yoshitaka; Hirakawa, Saori; Kamikawa, Tadao

doi:10.1246/cl.1987.1101

Cited by 41 publications

(34 citation statements)

References 13 publications

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“…1 for structures) (Kubo et al, 1993a). Their fully saturated derivative analogue, 6-pentadecylsalicylic acid (4) referred to as anacardic acid (C 15:0 ), was not isolated from A. occidentale but rather isolated as a prostaglandin synthetase inhibitor from an African medicinal plant Ozoroa mucronata (Anacardiaceae) together with anacardic acid (C 15:1 ) (Kubo et al, 1987). (7) and 5-pentadecylresorcinol (8) which are referred to as cardol (C 15:3 ), cardol (C 15:2 ), cardol (C 15:1 ) and cardol (C 15:0 ) for simplicity, were isolated from A. occidentale (Kubo et al, 1993a).…”

Section: Resultsmentioning

confidence: 99%

“…Although CNSL is available in greater tonnage, it is neglected in commercial terms, and there is thus considerable potential for its further exploitation. In addition, anacardic acid (C 15:1 ) (3) and anacardic acid (C 15:0 ) (4) were previously isolated in quantities as prostaglandin synthetase inhibitors from an African medicinal plant Ozoroa mucronata (Anacardiaceae) (Kubo et al, 1987). The same anacardic acids were also isolated as cytotoxic principles against six human cancer cell lines from another African medicinal plant O. insignis (Rea et al, 2003).…”

Section: Discussionmentioning

confidence: 99%

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Multifunctional cytotoxic agents from Anacardium occidentale

Kubo

Nitoda

Tocoli

et al. 2010

Phytotherapy Research

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The effects of anacardic acids and cardols isolated from the cashew nut and apple Anacardium occidentale (Anacardiaceae) on murine B16-F10 melanoma cells were tested. Although anacardic acids and cardols were found to inhibit tyrosinase, a key enzyme in melanin synthesis, melanogenesis in melanocytes was not suppressed in cultured cells but rather enhanced. Both anacardic acids and cardols exhibited moderate cytotoxicity.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Multifunctional cytotoxic agents from Anacardium occidentale

Kubo

Nitoda

Tocoli

et al. 2010

Phytotherapy Research

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“…A influência da cadeia alquílica no mecanismo de proteção é semelhante ao efeito proposto para a cadeia isoprênilica do tocoferol (Correia et al, 2006). O ácido anacárdico exibe propriedades moluscicida (Kubo et al, 1986), antitumoral (Itokawa et al, 1987;Kubo et al, 1993), antimicrobiana (Himejima & Kubo, 1991), inibidor de prostaglandina sintase (Kubo et al, 1987) e lipooxigenase (Grazzini et al, 1991).…”

Section: Introductionunclassified

Fenóis totais, atividade antioxidante e constituintes químicos de extratos de Anacardium occidentale L., Anacardiaceae

Chaves¹,

Lopes²,

Lopes³

et al. 2010

Rev. bras. farmacogn.

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RESUMO:O presente artigo relata o isolamento e identificação do palmitato, oleato e linoleato de sitosterila, sitosterol, estigmasterol, 3-O-β-D-galactopiranosídeo do sitosterol, 3-O-β-Dgalactopiranosídeo do estigmasterol, 3-O-β-D-glicopiranosídeo do sitosterol e uma mistura de ácidos anacárdicos (monoeno e dieno) do extrato etanólico de cascas do caule de Anacardium occidentale L., Anacardiaceae, bem como do sitosterol, estigmasterol, lupeol, β-amirina, catequina e epicatequina do extrato etanólico do tegumento da castanha de caju in natura. Os extratos EtOH da casca e do tegumento foram avaliados quanto ao conteúdo de fenóis totais e atividade antioxidante. O extrato etanólico das cascas do caule apresentou maior conteúdo de compostos fenólicos e percentual de atividade antioxidante.Unitermos: Anacardium occidentale, catequinas, esteroides, fenóis totais, atividade antioxidante. ABSTRACT: "Total phenolics, antioxidant activity and chemical constituents from extracts ofAnacardium occidentale L., Anacardiaceae". This paper describes the isolation and identification of a mixture of sitosteryl ester derivatives of fatty acids (palmitic, oleic and linoleic), sitosterol, stigmasterol, sitosterol-3-O-β-galactopyranoside, stigmasterol-3-O-β-galactopyranoside, sitosterol-3-O-β-glucopyranoside and a mixture of anacardic acids (monoene and diene) from stem bark of Anacardium occidentale L., Anacardiaceae, as well as sitosterol, stigmasterol, lupeol, β-amyrin, catechin and epicatechin from in natura cashew nut testa. Ethanol extracts from stem bark and testa were analyzed for antioxidant activity and total phenol content. The ethanol extract from stem bark exhibited the maximum of antioxidant activity and phenol content.

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“…Me0 23 Urushiol [21], w-Phenylalkyle [22], Anacard-und Ginkgosauren [ 181 [23] sowie einige der physiologisch sehr aktiven Alk(en)ylbenzochinone [24-261. Bei den aus Plectranthus albidus isolierten Phenolen und Pyrocatecholen ist die gemeinsame Synthese-Strategie aufgrund der Arylalkanon-Struktur vorgegeben. Ahnliches trifft fur die [n]-Gingerole zu, welche durch regioselektive Aldol-Kondensation aufgebaut werden [20]; im Gegensatz zur Herstellung von 1 wird in [20] das Enolat des Arylketons an homologe Alkanale addiert.…”

Section: Me0unclassified

Synthese von Alkylphenolen und ‐pyrocatecholen aus Plectranthus albidus (Labiatae)

Bürgi

Liu

Rüedi

1993

Helvetica Chimica Acta

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In the preceding paper, we described the isolation and structure elucidation of a series of even-numbered phenol-or pyrocatechol-derived 1 -arylalkane-5-ones. To establish the assigned structures unambiguously and to have larger quantities available for physiological testing, the following compounds were prepared: in the alkylphenol series, 1-(4-hydroxyphenyl)tetradecan-5-one (2a), 1-(4-hydroxyphenyl)hexadecan-5-one (2b), and 1-(4hydroxyphenyl)octadecan-5-one (2c); in the alkylcatechol series, 1 -(3',4-dihydroxyphenyl)decan-5-one (3a; not isolated as a natural compound), 1-(3',4-dihydroxyphenyl)dodecan-5-one (3b), 1-(3',4'-dihydroxyphenyl)tetradecan-5-one (3c), 1-(3',4'-dihydroxyphenyl)hexadecan-5-one (3d), I-(3',4-dihydroxyphenyl)octadecan-5-one (3e), and 1-(3',4-dihydroxyphenyl)icosan-S-one (30 ; in the alkenylphenol series, (2)-1-(4-hydroxyphenyI)octadec-l3en-5-one (4a) and (E)-l-(4-hydroxyphenyl)octadec-13-en-5-one (4b); in the alkenylcatechol series, (E,E)-l-(3',4'-dihydroxypheny1)deca-1,3-dien-S-one (1) and ( Z ) -1-(3',4'-dihydroxyphenyl)octadec-13-en-5-one (5). All compounds proved to be identical with the previously assigned structures. Compound 1 was synthesized by regioselective aldol condensation of heptan-2-one with (E)l-(3',4'-dimethoxyphenyl)prop-2-enal(6d; Scheme I ) , the phenols 2a+ and the catechols 3a-f by addition of the corresponding alkyl Grignard reagent to 5-(4'-methoxypheny1)or 5-(3',4'-dimethoxyphenyl)pentanal(17~ and 18c, resp.; Scheme 4 ) , and the olefins 4a, 4b and 5 from 17c or 18c oia the 9-0 -silyl-protected 13-(4'-methoxyphenyl)-or 13-(3',4'-dimethoxyphenyl)tridecanals (26 and 27, resp.) and Wittig olefination as the key steps (Scheme 5 ) .

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Prostaglandin Synthetase Inhibitors from the African Medicinal Plant Ozoroa mucronata

Abstract: Two prostaglandin synthetase inhibitory anacardic acids were isolated from O. mucronata. The structures of these inhibitors were established by spectroscopic means. Efficient syntheses of these two via directive metallation were reported.

Cited by 41 publications

References 13 publications

Multifunctional cytotoxic agents from Anacardium occidentale

Multifunctional cytotoxic agents from Anacardium occidentale

Fenóis totais, atividade antioxidante e constituintes químicos de extratos de Anacardium occidentale L., Anacardiaceae

Synthese von Alkylphenolen und ‐pyrocatecholen aus Plectranthus albidus (Labiatae)

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