Carbon-13 nmr shifts and C—H coupling constants of deoxybenzoins and related acetophenones

Jha, Hem Chandra; Zilliken, F.; Offermann, Werner; Breitmaier, Eberhard

doi:10.1139/v81-329

Cited by 16 publications

(3 citation statements)

References 7 publications

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“…Engl. Ochnaceae lead to the identification of the triterpenes friedelin (1) (Mahato & Kundu, 1994) and 3β-friedelinol (2) (Salazar et al, 2000), the isoflavone 4',5,7-trimethoxyisoflavone (3) (Jha et al, 1980;Wang, 2005) and the flavone 4',5-dihydroxy-3',5',7-trimethoxyflavone (4) (Zahir et al, 1996) and two glycosides 5 and 6 identified sitosteryl and stigmasteryl 3-O-β-D-glucopyranosides (Chaurasia & Wichth, 1987) …”

Section: Resultsmentioning

confidence: 99%

Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae

Nascimento¹,

Guilhon²,

Arruda³

et al. 2009

Rev. bras. farmacogn.

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RESUMO: "Biflavonas e triterpenóides isolados de Ouratea castaneifolia (DC.) Engl., Ochnaceae". O presente trabalho trata da investigação química das folhas e caule da espécie Ouratea castaneifolia (DC.) Engl., sobre a qual não há registros de estudos químicos ou farmacológicos anteriores. O estudo fitoquímico clássico dos extratos orgânicos do caule e das folhas de O. castaneifolia foi aliado à técnica da cromatografia líquida de alta eficiência (CLAE) e resultou na identificação de dezessete metabólitos: sete triperpenos (friedelina, 3β-friedelinol, α-amirina, β-amirina, lupeol, taraxerol e germanicol), quatro esteróides (sitosterol, estigmasterol e os glucosídeos sitosteril 3-O-β-D-glicopiranosídeo e estigmasteril 3-O-β-D-glicopiranosídeo), uma isoflavona (5,7,4´-trimetoxiisoflavona), uma flavona (5,4´-diidroxi-7,3´,5´-trimetoxiflavona), quatro biflavonas (amentoflavona, 7,7"-O-dimetil-amentoflavona, heveaflavona e tetrametilamentoflavona). A identificação das substâncias foi feita com base na análise de espectros de RMN de 1 H, 13 C e técnicas bidimensionais. As classes dos metabólitos identificados estão de acordo com aquelas citadas em estudos químicos do gênero Ouratea.Unitermos: Ouratea castaneifolia, Ochnaceae, biflavonas, flavonóide, terpenóide.ABSTRACT: This paper presents the chemical investigation of the leaves and stems of Ouratea castaneifolia (DC.) Engl.. There are no chemical or pharmacological studies with this species. Classic phytochemical investigation of the organic extracts together with high pressure liquid chromatography (HPLC) procedures lead to the identification of seventeen metabolites: seven triterpenes (friedelin, 3β-friedelinol, α-amyrin, β-amyrin, lupeol, germanicol and taraxerol), four steroids (sitosterol, stigmasterol and the glycosides sitosteryl 3-O-β-D-glucopyranoside and stigmasteryl 3-O-β-D-glucopyranoside), one isoflavone (5,7,4'-trimethoxyisoflavone), one flavone (5,4'-dihydroxy-7,3',5'-trimethoxyflavone) and four biflavones (amenthoflavone, 7,7"-O-dimethylamenthoflavone, heveaflavone and tetramethylamenthoflavone). The structures of the compounds were established by the analysis of 1 H, 13 C NMR spectra including bidimensional techniques. The classes of the identified metabolites are in agreement with previous studies of the Ouratea genus.Keywords: Ouratea castaneifolia, Ochnaceae, biflavones, flavonoid, terpenoid.triglycerides and chloroisoflavones were also reported from this genus (Velandia et al., 1998a and 1998b;Carvalho et al., 2000;Manga et al., 2001;Mbing et al., 2003a and2003b; Felício et al., 2004;Estevam et al., 2005). Some biflavonoids, as well as extracts of the Ouratea species showed important biological activities, as was previously published (Suzart et al., 2007).Ouratea castaneifolia (DC.) Engl. Ochnaceae Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae

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Section: Resultsmentioning

confidence: 99%

Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae

Nascimento¹,

Guilhon²,

Arruda³

et al. 2009

Rev. bras. farmacogn.

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“…The substitution patterns presented can be classified into 2,4-dioxygenated (1-7), 3,4-dioxygenated (8, 9), 2,5dioxygenated (10), 2,3,4-trioxygenated (11)(12)(13)(14)(15)(16), 2,4,5-trioxygenated (17)(18)(19)(20), and 2,4,6-trioxygenated (21)(22)(23)(24)(25) series of DOBs with various rings B. DOB 13 was found to be a new compound, and the NMR spectral data of 24 (29) were the first presented. DOBs 1, 3, and 4 were synthesized by W€ ah€ al€ a et al (20), and the data of 5 and 18 were reported previously in a NMR spectral study by Jha et al (30) (20).…”

Section: Methodsmentioning

confidence: 99%

“…1.41 g, 52%; R f = 0.40 (EtOAc/acetone/ n -hexane = 2:0.5:7.5); colorless needles (MeOH), mp 110 °C; 1 H NMR (CDCl 3 , 400 MHz, 25 °C) δ 3.79, 3.83 (each 3H, s, OMe), 4.15 (2H, s, CH 2 ), 6.42 (1H, d, J = 2.4 Hz, H-3), 6.44 (1H, dd, J = 2.4, 8.8 Hz, H-5), 6.88 (2H, d, J = 8.8 Hz, H-3′,5′), 7.19 (2H, d, J = 8.8 Hz, H-2′,6′), 7.75 (1H, d, J = 8.8 Hz, H-6), 12.74 (1H, s, C-2 OH); 13 C NMR (CDCl 3 , 100 MHz, 25 °C) δ 43.9 (CH 2 ), 55.3 (OMe), 55.5 (OMe), 101.0 (C-3), 107.8 (C-5), 113.1 (C-1), 114.2 (C-3′,5′), 126.3 (C-1′), 130.3 (C-2′,6′), 132.0 (C-6), 158.7 (C-4′), 165.8 (C-4), 166.1 (C-2), 202.3 (CO); EI-MS m / z 272 [M] + , 151 .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Structure−Activity Relationship Study of Deoxybenzoins on Relaxing Effects of Porcine Coronary Artery

Huang

et al. 2010

J. Agric. Food Chem.

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Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC50=3.30 μM (Emax=100%, n=7) and 2,4-dihydroxy-4'-methoxydeoxybenzoin EC50=3.70 μM (Emax=100%, n=5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure-activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H≥p-OMe>p-OH>o-OMe>m,p-diOMe≥m-OMe.

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Compounds derived from acetic acid

Martin¹

2005

Handbook of Hydroxyacetophenones: Preparation and Physical Properties

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Carbon-13 nmr shifts and C—H coupling constants of deoxybenzoins and related acetophenones

Cited by 16 publications

References 7 publications

Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae

Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae

Synthesis and Structure−Activity Relationship Study of Deoxybenzoins on Relaxing Effects of Porcine Coronary Artery

Compounds derived from acetic acid

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