Cassane diterpenes from Plathymenia reticulata

Leal, R. de S.; Lima, Mary Anne Sousa; Silveira, Edilberto R.

doi:10.1590/s0103-50532003000100019

Cited by 11 publications

(8 citation statements)

References 8 publications

(13 reference statements)

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“…The 3rd ring of 1 retained chair conformation, whereas the β‐oriented hemiketal hydroxyl forced the 3rd ring to adopt a boat conformation in 2 . However, conformation of 1 seems highly abundant in nature13–17 but that of 2 was found to be new and was reported in our previous publication; the relative stereochemistry was assigned on the basis of ROESY correlations 11. The heat of formation was calculated (using semiempirical computational methods PM3) to be − 273.689482 kcal/mol for 1 and − 265.42087 kcal/mol for 2 .…”

Section: Resultsmentioning

confidence: 84%

“…Due to the anticancer activity of both 1 and 2, we were interested in differentiate these two epimeric compounds by MS. Several cassane type diterpenes have been reported in literature mentioning their importance 13–17. But only a few research works have reported on the fragmentation of cassane type diterpenes 17. A full scan LC‐ESI‐MS of these two compounds showed different mass patterns (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Fragmentation patterns of newly isolated cassane butenolide diterpenes and differentiation of stereoisomer by tandem mass spectrometry

Kanojiya

Yadav

2008

J. Mass Spectrom.

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Different stereoisomers of active molecules often cause different physiological responses and hence pose a challenge for their identification. This study involves perceptive fragmentation behavior of newly isolated cassane butenolides, caesalpinolide A [1] and caesalpinolide B [2] (epimeric at the hemiketal position) by tandem MS. The electrospray ionization-mass spectrometry (ESI-MS)/collision-induced dissociation (CID; ESI-MS(2) and ESI-IT-MS(n)) were investigated. The effect of orientations of hemiketal hydroxyl at C-12 was clearly observed in the mass spectrum. Tandem mass spectra of 1, 1(A) or 2, 2(A) show stereospecific fragmentation resulting in significant abundance dissimilarity of [MH - H(2)O](+) as well as differences in fragmentation pathway. Both of these pathways seem to be influenced by the stereochemistry of the molecule. The differentiation can be clearly visualized from the [M + H - H(2)O](+)/[M + H](+) ratio of the two isomers where beta-isomer 2 was found to be five times higher than that of alpha-isomer 1 in full scan liquid chromatography-electrospray ionization mass spectrometry(LC-ESI-MS). In high-energy CID, the mass fingerprint of 1, 2, 1(A), and 2(A) was found to be different from one another.

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Section: Resultsmentioning

confidence: 84%

Section: Resultsmentioning

confidence: 99%

Fragmentation patterns of newly isolated cassane butenolide diterpenes and differentiation of stereoisomer by tandem mass spectrometry

Kanojiya

Yadav

2008

J. Mass Spectrom.

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“…Observou-se um sinal adicional em δ C 51,8 correspondente à metoxila e que o sinal da carbonila foi deslocado para δ C 179,3, caracterizando o éster 25,26 . Os dados de RMN observados para 3a foram semelhantes aos registrados na literatura para o vinhaticoato de metila 24,27 . Os mapas de contornos HMQC e HMBC possibilitaram atribuir os deslocamentos químicos do ácido vinhaticóico (3) e do seu derivado metilado, vinhaticoato de metila (3a), Tabela 1.…”

Section: Tabela 1 Dados De Rmn 1 H (500 Mhzunclassified

“…Seu derivado metilado, vinhaticoato de metila, encontra-se descrito em Caesalpinia crista 32 , em Plathymenia reticulata e P. foliosa (Leguminosae-Mimosoideae) 24,27,33 .…”

Section: Tabela 1 Dados De Rmn 1 H (500 Mhzunclassified

Terpenos e ácidos graxos de Dipteryx lacunifera Ducke

et al. 2007

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Federal do Alagoas, 57072-970 Maceió -AL, BrasilRecebido em 6/10/06; aceito em 1/2/07; publicado na web em 28/5/07 TERPENES AND FATTY ACIDS FROM Dipteryx lacunifera Ducke. This paper describes the isolation of the furanocassane-type diterpene, named vinhaticoic acid, along with β-farnesene and spatulenol from fruit shells of D. lacunifera. Structural determinations were accomplished by chemical derivatization and spectral analysis, including 1D and 2D NMR and X-ray crystallography. The fatty portion was extracted from the fruit kernels, transesterfied and analysed by HRGC/MS. Oleic acid (75.8 ± 4.3%) was the major component. Essential oil extracted from the fruit shells of D. lacunifera was analysed by HRGC/MS and nine sesquiterpenes were identified; β-farnesene (48.6%) and spatulenol (21.61%) were the major constituents.Keywords: Dipteryx lacunifera; vinhaticoic acid; fatty acids. INTRODUÇÃOO gênero Dipteryx, pertencente à tribo Dipterygeae, família Leguminosae-Papilionoideae, é constituído por 14 espécies que se destacam por serem utilizadas como plantas medicinais. São encontradas nas regiões amazônica, nordeste e central do Brasil, na Venezuela e na América Central (Costa Rica e Panamá). Algumas frutificam precocemente aos 4 anos, em matas de terras firmes e planas, podendo atingir 50 m de altura [1][2][3][4] .Quimicamente as espécies do gênero Dipteryx acumulam cumarinas, isoflavonas, triterpenóides, ácidos graxos e diterpenóides furanocassanos 2,3,5-9 . A D. odorata é a mais estudada; suas sementes são ricas em cumarinas, importantes na indústria de cosméti-cos e perfumaria, além de serem comercializadas para distúrbios vasculares e linfáticos 10 e exibirem atividade farmacológica no sistema muscular 2 . As cascas apresentam cumarinas, lupeol, β-farneseno, betulina e ésteres metílicos de ácidos graxos 8,9,11 e o óleo essencial das flores é rico em germacreno D e espatulenol 12 . Pesquisas recentes, realizadas com as sementes de D. odorata, resultaram no isolamento de vários constituintes químicos, dentre eles um novo diterpenóide furanocassano, uma nova isoflavolignana e a chalcona isoliquiritigenina que exibe um alto potencial preventivo contra câncer em glândulas mamárias de ratos 6 .Dipteryx lacunifera Ducke, sinonímia Coumarouna lacunifera, conhecida popularmente como castanha de burro e garampara, é encontrada na região meio-norte do Brasil (Maranhão e Piauí) 4 . Esta espécie produz um fruto, cuja amêndoa é comestível, comercializado em feiras livres do município de Bom Jesus-PI, com o nome de fava de morcego. Em trabalho anterior, de Mendes e Silveira 2 , foram identificados ácidos graxos, β-farneseno e dois diterpenos furanocassanos nos frutos desta espécie.Este artigo relata pela primeira vez a composição química do óleo essencial das cascas do fruto de D. lacunifera e, adicionalmente, descreve também os constituintes fixos do extrato hexânico das cascas do fruto e do óleo das amêndoas, visando contribuir para o conhecimento da constituição química desta espécie. O estudo fitoquímico do extrato hex...

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“…The medicinal potential of P. reticulata as anti-inflammatory [4], antimicrobial [5, 6], and depurative of blood [7] is also highlighted by the inherent presence of tannins, flavonoids [5], and cassane diterpenes in its constitution [3]. …”

Section: Introductionmentioning

confidence: 99%

Assessment of Cytotoxicity, Fetotoxicity, and Teratogenicity ofPlathymenia reticulataBenth Barks Aqueous Extract

Albuquerque

Belo

Santos

et al. 2013

BioMed Research International

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Scientific assessment of harmful interactions of chemicals over the entire reproductive cycle are divided into three segments based on the period: from premating and mating to implantation (I), from implantation to major organogenesis (II), and late pregnancy and postnatal development (III). We combined the segments I and II to assess Plathymenia reticulata aqueous extract safety. In order to investigate reproductive toxicity (segment I), pregnant rats received orally 0.5 or 1.0 g/kg of extract, daily, during 18 days. These concentrations were determined by a preliminary in vitro LD50 test in CHO-k1 cells. A control group received deionized water. The offspring was removed at the 19th day, by caesarean, and a teratology study (segment II) was carried out. The corpora lutea, implants, resorptions, live, and dead fetuses were then counted. Placenta and fetuses were weighted. External and visceral morphology were provided by the fixation of fetuses in Bouin, whereas skeletal analysis was carried out on the diaphanizated ones. The increase in the weights of placenta and fetuses was the only abnormality observed. Since there was no sign of alteration on reproduction parameters at our experimental conditions, we conclude that P. reticulata aqueous extract is safe at 0.5 to 1.0 g/kg and is not considered teratogenic.

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Cassane diterpenes from Plathymenia reticulata

Cited by 11 publications

References 8 publications

Fragmentation patterns of newly isolated cassane butenolide diterpenes and differentiation of stereoisomer by tandem mass spectrometry

Fragmentation patterns of newly isolated cassane butenolide diterpenes and differentiation of stereoisomer by tandem mass spectrometry

Terpenos e ácidos graxos de Dipteryx lacunifera Ducke

Assessment of Cytotoxicity, Fetotoxicity, and Teratogenicity ofPlathymenia reticulataBenth Barks Aqueous Extract

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