Crystal and molecular structure of lapachenole

Reibenspies, Joseph H.; Willams, Howard J.; Ortiz, Claudio; Scott, A. Ian; Suarez, Mauricio; Domínguez, Xorge A.

doi:10.1007/bf01185395

Cited by 6 publications

(6 citation statements)

References 4 publications

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“…Compound 5 is levorotatory, and, according to the calculated optical rotation, its absolute configuration was assigned as (3S, 4R, 4′S). The known compounds were identified as 6-methoxy-7,8benzocoumarin (6), 9 α-dunnione, 10 dunnione, 10 8-hydroxy-dunnione, 10 lapachenole, 11 8-methoxylapachenole, 4 tectoquinone, 12 7-hydroxytectoquinone, 13 dunniol, 14 aggregatin E, 15 cedrol, 16 oleanolic acid, 17 and halleridone. 18 Compound 6 had been synthesized, 9,19 but its NMR data were not reported.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Naphthochromenes and Related Constituents from the Tubers of Sinningia allagophylla

et al. 2016

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Chemical investigation of the tubers of Sinningia allagophylla led to the isolation of two new chromenes, (2S)-12-hydroxylapachenole (1) and (3R)-3,4-dihydro-3-hydroxy-4-oxo-8-methoxylapachenole (2), and three new dimeric chromenes, allagophylldimers A-C (3-5). Thirteen known compounds, 6-methoxy-7,8-benzocoumarin (6), lapachenole, 8-methoxylapachenole, tectoquinone, 7-hydroxytectoquinone, dunniol, α-dunnione, dunnione, 8-hydroxydunnione, aggregatin E, cedrol, oleanolic acid, and halleridone, were also identified. 6-Methoxy-7,8-benzocoumarin (6) has been isolated for the first time from a natural source.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Naphthochromenes and Related Constituents from the Tubers of Sinningia allagophylla

et al. 2016

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“…[9][10][11][12] Em particular, a mistura de ésteres esteroidais foi confirmada através do espectro de massas, obtido pela técnica de eletrospray (ESI) no modo positivo, que apresentou picos em m/z 675,60 (6), 677,47 (4 e 5) e 679 ,49 (3).…”

Section: Resultsunclassified

Estudo químico de Sinningia allagophylla guiado por testes de atividade antiproliferativa

Riva¹,

Barison²,

Stefanello³

et al. 2012

Quím. Nova

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Recebido em 18/9/11; aceito em 5/12/11; publicado na web em 28/2/12 CHEMICAL STUDY OF Sinningia allagophylla GUIDED BY ANTIPROLIFERATIVE ACTIVITY ASSAYS. Activity guided fractionation of Sinningia allagophylla (Mart.) Wiehler ethanolic extract yielded a new benzochromene 8-methoxylapachenol, besides seven known compounds: lapachenol, sitosteryl oleate, sitosteryl linoleate, stigmasteryl oleate, stigmasteryl linoleate, dunniol and tectoquinone. Extract, fractions, and compounds lapachenol, 8-methoxylapachenol, and dunniol were tested in vitro against human cancer cell lines U251 (glioma, CNS), MCF-7 (breast), NCI-ADR/RES (drug-resistant ovarian), 786-0 (kidney), NCI-H460 (lung, no small cells), PC-3 (prostate), OVCAR-3 (ovarian), HT-29 (colon), K562 (leukemia) and against VERO, a normal cell line. The most active compound was dunniol, which inhibited the growth of U251, MCF-7, NCI-ADR/RES, OVCAR-3 and K562 cell lines.Keywords: Sinningia allagophylla; Gesneriaceae; antiproliferative activity. INTRODUÇÃOSinningia (Gesneriaceae) é um gênero de plantas ornamentais encontrado nas regiões tropicais do Novo Mundo. Atualmente são reconhecidas 68 espécies, a maioria ocorrendo em território brasileiro.1 Sinningia allagophylla (Mart.) Wiehler é uma erva anual, de tubérculo perene, largamente espalhada no Brasil (rgiões centro-oeste, sul e sudeste), Argentina, Paraguai e Uruguai.2 É conhecida como batata-do-campo ou batata-de-perdiz, sendo empregada na medicina popular como febrífugo, diurético, depurativo, emoliente e tônico. O câncer é uma doença com elevado índice de mortalidade, que atinge anualmente milhões de pessoas ao redor do mundo. Embora tenha havido muito progresso na quimioterapia do câncer, muitos tumores ainda são de difícil remissão, tornando necessária a procura de novos agentes antitumorais. As plantas superiores constituem uma rica fonte de novas substâncias, que podem ser úteis contra neoplasias.8 Como parte de um projeto que visa a procura de substâncias com atividade citotóxica de plantas brasileiras, foi realizado o estudo fitoquímico de S. allagophylla guiado por ensaios de atividade antiproliferativa contra linhagens de células tumorais humanas. RESULTADOS E DISCUSSÃOO extrato etanólico dos tubérculos de S. allagophylla foi testado contra oito linhagens de células tumorais, apresentando um fraco efeito antiproliferativo in vitro, exceto para a linhagem de células K-562 (leucemia), que teve o seu crescimento totalmente inibido com uma concentração (TGI) de 5,13 µg mL -1 (Tabela 1). Por essa razão, esse extrato foi submetido à partição com hexano, diclorometano, acetato de etila e 1-butanol e as respectivas frações foram avaliadas frente a células tumorais e uma linhagem de células normais (VERO). A maior atividade foi observada na fração em hexano, a qual inibiu o crescimento de seis linhagens de células tumorais, com valores de TGI variando entre 15,5-32,7 µg mL -1 , mas foi inativa frente à linhagem VERO (células normais, TGI > 250 µg mL -1 ). Pôde ser notado que a linhagem K562 foi menos susceptíve...

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“…8ML is a new compound described by our group and a derivative from lapachenol . However, to our knowledge, no pharmacological activity has been ascribed to lapachenol.…”

Section: Discussionmentioning

confidence: 99%

Antinociceptive and Anti‐inflammatory Activities of the Ethanolic Extract, Fractions and 8‐Methoxylapachenol from Sinningia allagophylla Tubers

Barbosa

Mori

Riva

et al. 2013

Basic Clin Pharma Tox

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This study investigated the antinociceptive and anti-inflammatory activities of the ethanolic extract (EESAl), fractions and the compound 8-methoxylapachenol (8ML) obtained from the tubers of Sinningia allagophylla. Male Swiss mice were treated with EESAl (3-300 mg/kg) or vehicle by oral route (p.o.) 1 hr before the injection of formalin 2.5% or carrageenan (Cg) into the hind paw. EESAl (3-30 mg/kg) reduced the inflammatory phase of the nociceptive behaviour induced by formalin (around 65% for all doses). EESAl (3-300 mg/kg, p.o.) also reduced Cg-induced mechanical hyperalgesia and oedema in a dose-dependent fashion but did not change the hot-plate latency or the motor performance of the animals. Oral administration of petroleum ether fraction (PE, 3 mg/kg), but not in the methanolic fraction (30 mg/kg), reduced both Cg-induced oedema and hyperalgesia. Compound 8ML isolated from PE (1.8 mg/kg, p.o.) abolished Cg-induced hyperalgesia but also did not change hotplate latency or motor performance of the animals. 8ML administration into the paw (0.75-750 pg) dose-dependently reduced Cg-induced hyperalgesia. 8ML (750 pg) also blocked the hyperalgesia induced by tumour necrosis factor (TNF-a), interleukin1b (IL-1b) and prostaglandin E 2 (PGE 2 ) but failed to change the hyperalgesia induced by cytokine-induced neutrophil chemoattractant-1 (CINC-1) and dopamine (Dopa). These results suggest that EESAl has an important antinociceptive and anti-inflammatory activity, the former one related, at least in part, to the reduction in the hyperalgesia. Similarly, 8ML reduced Cg-induced oedema and mechanical hyperalgesia and seems to act in peripheral sites and on the prostaglandin rather than on the sympathetic component of the Cg-inflammatory hyperalgesia.Gesneriaceae is a pantropical family of ornamental plants, with 135 genera, among these Sinningia. Sinningia genus comprises 68 species, distributed in South America, mainly in Brazil [1]. Sinningia allagophylla (Martius) Wiehler is a shrub species with the popular names of clove field, field-potato or potato-of-Partridge and is considered medicinal in Brazil. The tubers are used as an emollient and tonic, while the flowers and leaves are used as febrifuge, diuretic and cleanser [2].Studies on chemical composition of Sinningia species showed the presence of flavonoids on Sinningia cardinalis [3], ethylcyclohexane derivatives and anthraquinones in Sinningia speciosa [4] and anthraquinones and aromatic compounds with a new skeleton named aggregatins A-D in Sinningia aggregata [5]. In Sinningia allagophylla, lapachenol, 8ML, anthraquinones and naphthoquinones were found [6]. Naphthoquinones and anthraquinones are classes of natural compounds commonly associated with anti-inflammatory and antinociceptive properties. For example, vitamin K3 derivatives, plumbagin and emodin among others, are known naphthoquinones and anthraquinones, which share these properties [7][8][9].Traditionally, non-steroidal anti-inflammatory drugs are the class of compounds most widely used to t...

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Crystal and molecular structure of lapachenole

Cited by 6 publications

References 4 publications

Naphthochromenes and Related Constituents from the Tubers of Sinningia allagophylla

Naphthochromenes and Related Constituents from the Tubers of Sinningia allagophylla

Estudo químico de Sinningia allagophylla guiado por testes de atividade antiproliferativa

Antinociceptive and Anti‐inflammatory Activities of the Ethanolic Extract, Fractions and 8‐Methoxylapachenol from Sinningia allagophylla Tubers

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