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au:Lima, Mary Anne S.

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Aspergillus niger: A Hundred Years of Contribution to the Natural Products Chemistry
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Lima, Mary Anne S.

; Oliveira, Maria da Conceição F. de

; Pimenta, Antônia T. Á.

; Uchôa, Paula K. S.

Journal of the Brazilian Chemical Society

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oct 2019, Volume 30 N. 10 Pages 2029 - 2059

Abstract: En | Text: En | PDF: En

Aspergillus niger is a phytopathogenic fungus responsible for the plant disease called “black mold”, and it is considered the most versatile microorganism for producing acids, proteins, and enzymes of industrial value, besides a variety of compounds of pharmacological interest. This review presents a century of contribution of A. niger in the natural products chemistry under two different perspectives: (i) an overview of the structural diversity of secondary metabolites produced by A. niger from different habitats and their biological activities; (ii) a general discussion of the enzymatic potential of A. niger on the selective biotransformation of terpenes, highlighting the most uncommon microbial transformations.

https://doi.org/10.21577/0103-5053.20190080 2452 downloads

New flavone and other compounds from Tephrosia egregia: assessing the cytotoxic effect on human tumor cell lines
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Teixeira, Maria V.S.

; Lima, Jefferson Q.

; Pimenta, Antônia T.A.

; Silva, Francisca R.L. da

; Oliveira, Maria da Conceição F. de

; Pereira, Italo G.

; Costa-Junior, Dilailson C.

; Ribeiro, Paulo R.V.

; Santiago, Gilvandete M.P.

; Lima, Mary Anne S.

; Braz-Filho, Raimundo

; Bezerra, Mirna M.

; Montenegro, Raquel C.

; Rocha, Danilo D.

; Moraes, Maria Elisabete A. de

; Medeiros, Aline C. de

; Arriaga, Angela M.C.

Revista Brasileira de Farmacognosia

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jun 2018, Volume 28 N. 3 Pages 333 - 338

Abstract: En | Text: En | PDF: En

ABSTRACT The organic extracts from stems, roots and leaves of Tephrosia egregia Sandwith, Fabaceae, provided a new flavone, 5-hydroxy-8-(1",2"-epoxy-3"-hydroxy-3"-methylbutyl)-7-methoxyflavone (1), in addition to eleven known compounds: pongaflavone (2), praecansone B (3), 12a-hydroxyrotenone (4), praecansone A, 2',6'-dimethoxy-4',5'-(2",2"-dimethyl)-pyranochalcone, pongachalcone, maackiain, β-sistosterol and its glucoside, p-cumaric acid and cinnamic acid. The structures of all compounds were established on the basis of spectroscopic methods, mainly 1D and 2D NMR and HRESIMS, involving comparison with literature data. Cytotoxicity of compounds 1–4 was evaluated against AGP-01 (cancerous ascitic fluid), HCT-116 (colon adenocarcinoma), HL-60 (leukemia), PC-3 (prostate carcinoma), SF-295 (glioblastoma) and SKMEL 28 (melanoma) cell lines.

https://doi.org/10.1016/j.bjp.2018.03.008 525 downloads

New Epimeric Spirostanol and Furostanol-Type Steroidal Saponins from Cestrum laevigatum L.
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Ribeiro, Paulo R. V.

; Braz-Filho, Raimundo

; Araújo, Ana J.

; Costa-Lotufo, Letícia V.

; Souza, Luciana G. S.

; Nobre Junior, Hélio V.

; Silva, Cecília R. da

; Andrade Neto, João B. de

; Silveira, Edilberto R.

; Lima, Mary Anne S.

Journal of the Brazilian Chemical Society

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dec 2016, Volume 27 N. 12 Pages 2170 - 2180

Abstract: En | Text: En | PDF: En

Four new epimeric spirostanol and furostanol-type steroidal saponins, (25R,S)-5α-spirostan-2α,3β-diol 3-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl-(1→4)-β-D-galactopyranoside, (25R,S)-5α-spirostan-2α,3β-diol 3-O-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→4)-β-D-galactopyranoside, 26-O-β-D-glucopyranosyl-(25R,S)-5α-furost-20-ene,2α,3β-diol 3-O-β-D-galactopyranoside and 26-O-β-D-glucopyranosyl-(25R,S)-5α-furost-20-ene,2α,3β-diol 3-O-β-D-galactopyranosyl-(1→4)-β-D-galactopyranoside, in addition to the known (25R,S)-5α-spirostan-2α,3β-diol 3-O-β-D-galactopyranoside, were isolated from Cestrum laevigatum. Compounds were submitted to cytotoxic activity assays using colorectal adenocarcinoma (HCT-116), human promyelocytic leukemia (HL-60), ovarian carcinoma (OVCAR-8), glioma (SF-295) human cancer cell lines, and the antimicrobial activity was evaluated against Candida parapsilosis, C. albicans, C. krusei, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis.

https://doi.org/10.5935/0103-5053.20160109 921 downloads

NOVOS FLAVONOIDES DE Margaritopsis carrascoana COM ATIVIDADE ANTIOXIDANTE
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Nascimento, Raimundo Regivaldo G.

; Monteiro, Jackelyne A.

; Pimenta, Antônia Torres A.

; Trevisan, Maria Teresa S.

; Braz-Filho, Raimundo

; Souza, Elnatan Bezerra de

; Silveira, Edilberto R.

; Lima, Mary Anne S.

Química Nova

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jan 2015, Volume 38 N. 1 Pages 60 - 65

Abstract: Pt | Text: Pt | PDF: Pt

EtOH extracts of the stems and leaves of Margaritopsis carrascoana were found to contain new flavonoids luteolin 7-O-{β-D-apiofuranosil-(1→6)-[β-Lrhamnopyranosyl-( 1→2)]-β-D-glucopyranosyl} (5) and luteolin 7-O-{α-L-rhamnopyranosyl-(1→6)-[β-L-rhamnopyranosyl- (1→2)]-β-D-glucopyranosyl} (6), in addition to the known dihydrodehydrodiconiferyl alcohol 4-O-b-D-glucopyranoside (1), luteolin 7-O-b-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl (2), luteolin 7-O-[b-D-apiofuranosyl-(1→6)]-β-D-glucopyranoside (3), and chrysoeriol 7-O-[b-D-apiofuranosyl-(1→6)]-β-D-glucopyranoside (4). All isolated compounds presented higher antioxidant activities than the controls, BHT and quercetin, while the extract of the stems showed strong AChE inhibition.

https://doi.org/10.5935/0100-4042.20140289 1835 downloads

Trachylobane and kaurane diterpenes from Croton floribundus spreng
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Uchôa, Paula Karina S.

; Silva Jr., José Nunes da

; Silveira, Edilberto Rocha

; Lima, Mary Anne S.

; Braz-Filho, Raimundo

; Costa-Lotufo, Letícia Veras

; Araújo, Ana Jérsia

; Moraes, Manoel Odorico de

; Pessoa, Claudia do Ó

Química Nova

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2013, Volume 36 N. 6 Pages 778 - 782

Abstract: En | Text: En | PDF: En

A new trachylobane diterpene ent-trachyloban-18,19-diol (1) was isolated from root bark of Croton floribundus, along with known diterpenes ent-trachyloban-19-oic acid (2), 15b-hydroxy-ent-trachyloban-19-oic acid (3), ent-trachyloban-19-ol (4), ent-kaur-16-en-19-oic acid (5), ent-kaur-16-ene-6a,19-diol (6) and ent-16a-hydroxykaur-11-en-19-oic acid (7). ent-trachyloban-18,19-diol (1) was submitted to derivatization reactions affording four new compounds (8-11). Cytotoxic activity of diterpenes 1, 3, 4, 7-11 against three human cancer cell lines was evaluated. No compounds showed cytotoxic potential with IC50 values greater than 25 mg/mL. Compound 6 was evaluated against five human cancer cell lines, showing moderate effect against three cancer cell lines, MDA-MB-435, HCT-8 and HCT-116, with IC50 values of 14.32, 13.47 and 12.1 mg/mL, respectively.

2458 downloads

New flavonoids and coumarins from Platymiscium floribundum Vogel
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Veloso, Pérsio A.

; Pimenta, Antonia T. A.

; Francisco M. de, Sousa

; Falcão, Maria José C.

; Gramosa, Nilce V.

; Silva Junior, José Nunes da

; Silveira, Edilberto R.

; Lima, Mary Anne S.

Journal of the Brazilian Chemical Society

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jul 2012, Volume 23 N. 7 Pages 1239 - 1243

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

Dois novos flavonoides, 3,4,10-tri-hidróxi-9-metoxi-pterocarpano and 2',4'-di-hidróxi-4'-metoxi-β-hidroxichalcanonol, foram isolados a partir de Platymiscium floribundum, em adição a homopterocapina, 2',4',4-tri-hidroxichalcona, 7,3',5'-tri-hidroxiflavanona, 7,3'-di-hidróxi-8,5'-di-metoxiisoflavanona, 8-hidróxi-5,6,7-tri-metoxicumarina, 6-hidróxi-7,8-di-metoxicumarina, 6,7,8-tri-metoxicumarina, 6,7-di-metoxicumarina, 8-hidróxi-6,7-di-metoxicumarina, 3β-acetóxi-28-hidróxi-olean-12-eno, 1,2,3-tri-metoxi-5-alilbenzeno, 3,4-di-metoxicinamaldeído, e β-sitosterol e estigmasterol como mistura. A caracterização estrutural de todos os compostos foi estabelecida com base em métodos espectroscópicos, particularmente ressonância magnética nuclear (RMN) 1D e 2D e comparação com dados da literatura.

Two new flavonoids, 3,4,10-trihydroxy-9-methoxypterocarpan and 2',4'-dihydroxy-4-methoxy-b-hydroxychacanonol, were isolated from Platymiscium floribundum, in addition to the homopterocarpin, 2',4',4-trihydroxychalcone, 7,3',5'-trihydroxyflavanone, 7,3'-dihydroxy-8,5'-dimethoxyisoflavanone, 8-hydroxy-5,6,7,-trimethoxycoumarin, 6-hydroxy-7,8-dimethoxycoumarin, 6,7,8-trimethoxycoumarin, 6,7-dimethoxycoumarin, 8-hydroxy-6,7-dimethoxycoumarin, 3β-acetoxy-28-hydroxyolean-12-ene, 1,2,3-trimethoxy-5-allyl-benzene, 3,4-dimethoxycinnamaldehyde, and β-sitosterol and stigmasterol as a mixture. Structural characterization of all compounds was established on the basis of spectroscopic methods, particularly 1D and 2D nuclear magnetic resonance (NMR) and comparison with data from literature.

3672 downloads

Sensitive method for determination of piplartine, an alkaloid amide from Piper species, in rat plasma samples by liquid chromatography-tandem mass spectrometry
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Bezerra, Daniel P.

; Pessoa, Cláudia

; Moraes, Manoel O.

; Costa-Lotufo, Letícia V.

; Rubio Gouvea, Dayana

; Jabor, Valquíria A. Polisel

; Lopes, Norberto Peporine

; Borges, Keyller Bastos

; Lima, Mary Anne S.

; Silveira, Edilberto R.

Química Nova

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2012, Volume 35 N. 3 Pages 460 - 465

Abstract: En | Text: En | PDF: En

Piplartine (PPTN) is an alkaloid amide found in Piper species that presents different activities. PPTN determination in rat plasma is necessary to better understand its biological effects. The aim of this study was to develop a sensitive LC-MS/MS method for the determination of PPTN in rat plasma. The performance criteria for linearity, sensitivity, precision, accuracy, recovery, and stability have been assessed and were within the recommended guidelines. The validated method proved to be suitable in a pilot study of PPTN kinetic disposition in rat plasma after a single intraperitoneal dose, and represents an appropriate tool to further pharmacokinetic studies.

2651 downloads

Alkaloid and other chemical constituents from Psychotria stachyoides Benth.
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Pimenta, Antonia T. A.

; Uchôa, Daniel E. A.

; Braz-Filho, Raimundo

; Silveira, Edilberto R.

; Lima, Mary Anne S.

Journal of the Brazilian Chemical Society

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nov 2011, Volume 22 N. 11 Pages 2216 - 2219

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

Os extratos orgânicos das folhas e raízes de Psychotria stachyoides forneceram o novo alcaloide indólico monoterpênico glicosilado N-desmetil-correantosida, além de bizantionosida B, α-amirina, éter metílico da alizarina, rubiadina, escopoletina, ácido barbinévico e uma mistura deβ-sitosterol e estigmasterol glicosilados. A caracterização estrutural dos compostos isolados foi estabelecida com base na espectroscopia no infravermelho (IR), espectrometria de massa (MS) e particularmente ressonância magnética nuclear (RMN) 1D e 2D.

The organic extracts of leaves and roots of Psychotria stachyoides provided the new glucoside monoterpenoid indole alkaloid N-demethylcorreantoside, besides bizantionoside B, α-amyrin, alizarine methyl-ether, rubiadine, scopoletin, barbinevic acid and a mixture of β-sitosterol and stigmasterol glucosides. The structural characterization of the isolates was established based on infrared spectroscopy (IR), mass spectrometry (MS) and, particularly, 1D and 2D nuclear magnetic resonance (NMR).

2666 downloads

Antifungal iridoids, triterpenes and phenol compounds from Alibertia myrciifolia Sprunge Ex. Schum
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Luciano, João Henrique S.

; Lima, Mary Anne S.

; Silveira, Edilberto Rocha

; Vasconcelos, Ilka Maria

; Fernandes, Georgia Sampaio

; Souza, Elnatan Bezerra de

Química Nova

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2010, Volume 33 N. 2 Pages 292 - 294

Abstract: En | Text: En | PDF: En

The new iridoid glucoside 10-O-vanilloyl-geniposidic acid has been isolated from the aerial parts of Alibertia myrciifolia along with hydroxyhopanone, 3α,22-dihydroxyhopane, ursolic acid, luteolin-3´,4´-dimethyl ether, caffeic acid and geniposidic acid. The structures of the isolated compounds were determined by means of mass spectrometry and nuclear magnetic resonance spectral analyses. The antifungal activities of the iridoids 10-O-vanilloyl-geniposidic acid and geniposidic acid were evaluated against the phytopathogenic fungi strains Colletotrichum gloeosporioides, Fusarium solani and Aspergillus niger.

3332 downloads

10.

Pterocarpans and a novel flavanone from harpalyce brasiliana roots
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Araújo, Renata M. de

; Lima, Mary Anne S.

; Silveira, Edilberto R.

Journal of the Brazilian Chemical Society

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2009, Volume 20 N. 5 Pages 935 - 938

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

A nova '(-)-7,8,3',4'-tri-hidróxi-8-(3'',7''-dimetil-octa-2'',6''-dienoil)-flavanona foi isolada a partir do extrato etanólico das raízes de Harpalyce brasiliana, juntamente com os pterocarpanos conhecidos (-)-2-geranil-3-hidróxi-8,9-metilenodioxipterocarpano, harpalicina, medicarpina, maackiaina e as cabenegrinas A-I e A-II. Os metabólitos isolados foram caracterizados com base nos seus dados espectroscópicos, principalmente RMN uni e bidimensional.

The novel (-)-7,8,3',4'-trihydroxy-8-(3'',7''-dimethyl-octa-2'',6''-dienoyl)-flavanone was isolated from the EtOH extract from the roots of Harpalyce brasiliana (Leguminosae) together with the known pterocarpans (-)-2-geranyl-3-hydroxy-8,9-methylenedioxypterocarpan, harpalicin, medicarpin, maackiain and cabenegrins A-I and A-II. The isolated metabolites were characterized on the basis of spectroscopic data, mainly 1D and 2D NMR.

2208 downloads

11.

Flavonoids and triterpenes from the nest of the stingless bee Trigona spinipes
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Freitas, Marinalva O.

; Ponte, Flávio A. F.

; Lima, Mary Anne S.

; Silveira, Edilberto R.

Journal of the Brazilian Chemical Society

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2008, Volume 19 N. 3 Pages 532 - 535

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

No nordeste do Brasil, a abelha-sem-ferrão Trigona spinipes perfura o tronco de espécimens cultivados de Eucalyptus citriodora para a produção de exudatos. A investigação química do extrato etanólico do ninho de T. spinipes permitiu o isolamento dos triterpenos cicloartanos ácido magniferólico e ácido 3b-hidroxi-24-metilenocicloartan-26-óico, além dos flavonóides 3’-metil-quercetina, sakuranetina, éter 7-metil campferol, tricetina e éter 7-metil aromadendrina como compostos majoritários. O isolamento de sakuranetina, éter 7-metil campferol e éter 7-metil aromadendrina do ninho de T. spinipes e do exudato de Eucalyptus citriodora, sugere esta espécie como origem botânica dos constituintes do ninho destas abelhas-sem-ferrão no nordeste do Brasil. A caracterização estrutural dos compostos isolados foi realizada utilizando-se métodos espectrométricos e comparação com dados da literatura.

In the Northeast of Brazil the stingless bee Trigona spinipes Fabricius injures the tree bark of cultivated Eucalyptus citriodora specimens in order to make them exudate. The chemical investigation of the ethanol extract of an entire nest of T. spinipes allowed the isolation of the cycloartane triterpene magniferolic acid and 3b-hydroxy-24-methylenecicloartan-26-oic acid, besides the flavonoids 3’-methyl quercetin, sakuranetin, kaempferol 7-methyl ether, tricetin and aromadendrin 7-methyl ether as the main compounds. The isolation of sakuranetin, kaempferol 7-methyl ether, and aromadendrin 7-methyl ether from both Trigonas spinipes'nest and the exudate from Eucalyptus, may suggest this species as a botanical origin of the nest constituents of these stingless bee in the Northeast of Brazil. The structural characterization of the isolated compounds was accomplished by spectrometric means and comparison with the literature data.

4609 downloads

12.

Insecticidal activity of 2-tridecanone against the cowpea weevil Callosobruchus maculatus (Coleoptera: Bruchidae)
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Braga, Yussef F.B.

; Grangeiro, Thalles B.

; Freire, Eder A.

; Lopes, Helano L.

; Bezerra, José N. S.

; Andrade-Neto, Manoel

; Lima, Mary Anne S.

Anais da Academia Brasileira de Ciências

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mar 2007, Volume 79 N. 1 Pages 35 - 39

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

O efeito dos vapores da 2-tridecanona sobre o caruncho do feijão-de-corda (Callosobruchus maculatus) foi avaliado. Sementes de feijão-de-corda infestados com insetos adultos foram expostas a diferentes doses de 2-tridecanona isolada de Pilocarpus microphyllus, uma espécie nativa do Nordeste do Brasil. O monoterpeno puro foi utilizado nas diluições 1:10, 1:100 e 1:1000 (v/v). Os parâmetros da biologia do inseto foram analisados em função da resposta a doses decrescentes de 2-tridecanona: número de ovos postos por fêmea, percentagem de eclosão de ovos, percentagem de emergência de adultos, peso dos adultos recém-emergidos, tempo médio de desenvolvimento e número total de ovos emergidos. Diferenças significativas (P < 0.05) entre as doses de 2-tridecanona testadas foram observadas, para quatro dos seis parâmetros biológicos analisados. Os resultados obtidos indicaram que a 2-tridecanona é tóxica para C. maculatus, reduzindo significativamente (P < 0.05) o número de insetos emergidos após a infestação. Esse efeito foi causado principalmente pela significativa redução observada na eclosão dos ovos expostos ao vapor da substância.

The effect of 2-tridecanone vapor on the cowpea weevil (Callosobruchus maculatus) development was determined. Seeds of cowpea were infested with adults and exposed to different doses of 2-tridecanone isolated from Pilocarpus microphyllus Stapf ex Holm, a plant species native from northeastern Brazil. The pure monoterpene was evaluated both undiluted as well as in the dilutions 1:10, 1:100 and 1:1,000 (v/v). The following parameters of the cowpea weevil life cycle were analyzed in response to decreasing doses of 2-tridecanone: number of eggs laid, percentage of egg hatching on seeds, percentage of adult emergence, adult weight at emergence, mean developmental time and number of adults emerged. Vapor of 2-tridecanone caused a significant (P < 0.05) reduction in the number of eggs laid, in the percentage of eggs hatched and in the number of emerged adults in infested seeds. The fumigant insecticidal effect of 2-tridecanone was mainly due to its ovicidal activity.

3192 downloads

13.

A Labdane diterpene from the aerial parts of Egletes viscosa less
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Silva-Filho, Francisco Artur e

; Lima, Mary Anne S.

; Bezerra, Antonio Marcos E.

; Braz Filho, Raimundo

; Silveira, Edilberto R.

Journal of the Brazilian Chemical Society

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2007, Volume 18 N. 7 Pages 1374 - 1378

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

Um novo labdano glicosilado, 8alfa-hidroxilabd-14(15)-eno-13(S)-O-beta-D-ribopiranosídeo, foi isolado das partes aéreas de Egletes viscosa Less, juntamente com o 13-epi-esclareol, barbatol, tarapacol, espinasterol, ternatina e triacontano. As estruturas dos compostos isolados foram elucidadas pelo uso de métodos espectrométricos e preparação de derivados químicos.

A new labdane glycoside, 8alpha-hydroxylabd-14(15)-ene-13(S)-O-beta-D-ribopyranoside, was isolated from the aerial parts of Egletes viscosa Less, along with 13-epi-sclareol, barbatol, tarapacol, spinasterol, ternatin and triacontane. The structures of the isolated compounds were elucidated by the use of spectrometric methods and preparation of chemical derivatives.

1713 downloads

14.

Compostos polifenólicos do kino de Eucalyptus citriodora
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Freitas, Marinalva Oliveira

; Lima, Mary Anne S.

; Silveira, Edilberto R.

Química Nova

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2007, Volume 30 N. 8 Pages 1926 - 1929

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

Phytochemical analysis of the kino of Eucalyptus citriodora led to the isolation of 1-O,2-O-digaloil-6-O-trans -p-cumaroil-beta-D-glucopyranoside, 1-O-trans-p-cumaroil-6-O -cinamoil-beta-D-glucopyranoside, alpha and beta 6-O-trans-p-cumaroil-D-glucopyranoside, 7-methylaromadendrin-4'-O-6''- trans-p-cumaroil-beta-D-glucopyranoside, aromadendrin, aromadendrin-7-methyl-ether, naringenin, sakuranetin, kaempferol-7-methyl-ether and galic acid. Structural elucidation of the isolated compounds was established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift correlated NMR pulse sequences (¹H,¹H-COSY, HMQC, HMBC).

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Diterpenes from Erythroxylum barbatum
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Santos, Cláudio C. dos

; Lima, Mary Anne S.

; Braz Filho, Raimundo

; Silveira, Edilberto R.

Journal of the Brazilian Chemical Society

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dec 2006, Volume 17 N. 7 Pages 1304 - 1308

Abstract: Pt En | Text: Pt En | PDF: Pt | PDF: En

Das raízes de Erythroxylum barbatum foram isolados dois novos diterpenos ent- rosan-1-ona-5alfa,15ksi,16-triol (1) e ent-11alfa-acetoxi-devadarano-15ksi,16-diol (2), além do ent-devadarano-15ksi,16-diol (erythroxidiol X, 3) e do procesterol. Investigação do lenho do caule forneceu o ent-devadarano-11alfa,15ksi,16-triol (erythroxitriol Q, 4), o ent-devadarano-7beta,15ksi,16-triol (hidroxidevadarool, 5), o beta-sitosterol e seu glicosídeo. A caracterização estrutural, inclusive a estereoquímica relativa dos compostos, foi estabelecida com base em métodos espectroscópicos, particularmente RMN uni e bidimensional, e comparação com dados da literatura.

Two new diterpenes ent-rosan-1-one-5alpha,15xi,16-triol (1) and ent-11alpha-acetoxy-devadarane-15xi,16-diol (2) were isolated from roots of Erythroxylum barbatum, in addition to the known diterpenes ent-devadarane-15xi,16-diol (erythroxydiol X, 3) and procesterol. Investigation of the trunk heartwood furnished the ent-devadarane-11alpha,15xi,16-triol (erythroxytriol Q, 4), ent-devadarane-7beta,15xi,16-triol (hydroxydevadarool, 5), beta-sitosterol and its glucoside. Structural characterization, including the relative stereochemistry of all compounds, was established on the basis of spectroscopic methods, particularly 1D and 2D NMR, and comparison with data from literature.

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