Anhydrorutaretin, a new furanocoumarin and other minor constituents of Apium leptophyllum seeds

Sharma, B.R.; Rattan, Ram; Sharma, Perveen

doi:10.1016/0031-9422(80)80223-8

Cited by 2 publications

(5 citation statements)

References 6 publications

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“…Chemical shifts and coupling constants (J) obtained from 1D 1 H NMR spectrum Table 2. Heteronuclerar long-range coupling of 1 H- 13 C for the mixture of 7, 8 and 9 observed in HMBC spectrum, in CDCl 3 *…”

Section: Resultsmentioning

confidence: 96%

“…The known natural products marmesin (10), 1',2'dehydromarmesin (11), 8-methoxymarmesin (12), 1'hydroxy-3'-O-b-glucopyranosylmarmesin (13) and 2',4',4trihydroxy-3',3-diprenylchalcone (kanzonol C, 14) were identified through their 1 H and 13 C NMR spectral data, including the comparison with literature values for 10, 10,11 11, 12 12, named rutaretin methyl ether, 13 13 14 and 14. 15 The new peracetyl derivative 13a was also used to confirm the structure of 13 and to obtain the complete 1 H and 13 C NMR chemical shift assignments (see Experimental).…”

Section: Resultsmentioning

confidence: 99%

“…3b-O-b-Dglucopyranosylsitosterol was characterized by 1 H and 13 C NMR spectral data, including the data of its peracetyl derivative, and comparison with literature values. 16 The multiplicity of each carbon of the components present in the mixture of the cinnamic acid derivatives 3-(7-methoxy-2,2-dimethyl-2H-6-chromenyl)-(E)-propenoic acid (7), 3-(7-methoxy-2,2-dimethyl-2H-6-chromenyl) propanoic acid (8) and 3-(6-methoxybenzo[b]furan-5yl)propanoic acid (9) was deduced from the analysis of the HBBD-and DEPT- 13 C NMR (125 MHz) spectra (Table 1). This analysis in combination with the 1 ) allowed the deduction of the expanded molecular formulas: (C) 5 (COOH)(CH) 6 (CH 3 ) 2 (OMe)(O) for 7, (C) 5 (COOH)(CH) 4 (CH 2 ) 2 (CH 3 ) 2 (OMe)(O) for 8 and (C) 4 (COOH)(CH) 4 (CH 2 ) 2 (OMe)(O) for 9 ( Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…This precipitate was chromatographed on CC (neutral aluminum oxide) eluted with CH 2 Cl 2 and MeOH to afford a mixture of 4 and 5 (3.7 g) and 15 (6.0 mg). The residue obtained of the CH 2 Cl 2 solution was partitioned using hexane/MeOH Mixture of marmesin (10) and 1',2'-dehydromarmesin (11) IR n max /cm -1 : 3478, 1707, 1628, 1570, 1482, 1446, 1399, 1369, 1266, 1180, 1134 (KBr); 1 H (300 MHz) and 13…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…In this paper, we report the isolation of eleven additional compounds, eight known substances, and three new cinnamic acid derivatives: 3-(7-methoxy-2,2-dimethyl-2H-6-chromenyl)-(E)-propenoic acid (7), 3-(7-methoxy-2,2-dimethyl-2H-6-chromenyl)propanoic acid (8) and 3-(6-methoxybenzo[b]furan-5-yl)propanoic acid (9). The known substances are the coumarins marmesin (10), 1',2'dehydromarmesin (11), 8-methoxymarmesin (12) and 1'hydroxy-3'-O-b-glucopyranosylmarmesin (13), the chalcone 2',4',4-trihydroxy-3',3-diprenylchalcone (14), the steroids b-sitosterol and 3b-O-b-D-glucopyranosyl-sitosterol (daucosterol) and the triterpene b-amyrin. All substances were isolated from the roots of this species.…”

Section: Introductionmentioning

confidence: 99%

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Prenylated Coumarins, Chalcone and New Cinnamic Acid and Dihydrocinnamic Acid Derivatives from Brosimum gaudichaudii

Monteiro¹,

Mathias²,

Vieira³

et al. 2002

J. Braz. Chem. Soc.

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Três novos derivados naturais dos ácidos cinâmico e diidrocinâmico foram isolados das raízes de Brosimum gaudichaudii, além de mais quatorze substâncias naturais conhecidas (dez cumarinas, uma chalcona, os dois esteróides b-sitosterol e 3b-O-b-D-glicopiranosil-b-sitosterol e o triterpeno bamirina). As estruturas destas substâncias foram estabelecidas com base na análise de dados espectrais, inclusive experiências de RMN 2D e espectros de massas. O ácido 4-hidroxi-3-prenilcinâmico pode ser postulado como precursor para todas substancias aromáticas. As novas substâncias naturais são derivadas do precursor das cumarinas que perdeu a possibilidade de formar o anel lactônico devido a O-metilação. Three new natural cinnamic acid and dihydrocinnamic acid derivatives were isolated from the roots of Brosimum gaudichaudii, in addition to fourteen known substances (ten coumarins, one chalcone, b-sitosterol, 3b-O-b-D-glucopyranosylsitosterol and b-amyrin). The structures were established by spectral data, including analysis of 2D-NMR experiments and mass spectra. All aromatic compounds have 4-hydroxy-3-prenylcinnamic acid as a common precursor. The new substances are derived from a precursor of the coumarins, which through an O-methylation lost its ability to form the lactone ring.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Extraction and Isolationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Prenylated Coumarins, Chalcone and New Cinnamic Acid and Dihydrocinnamic Acid Derivatives from Brosimum gaudichaudii

Monteiro¹,

Mathias²,

Vieira³

et al. 2002

J. Braz. Chem. Soc.

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Estimation of total phenolics and flavonoidal contents as well as in vitro antioxidant potential of Apium leptophyllum Pers.

et al. 2013

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At present, major causes of diseases is oxidative stress affecting both metabolic and physiological functions of the body. That is why there is a great need for investigation of nutritious food supplements for counteracting these oxidative stresses. Therefore, the aim of study was to evaluate the therapeutic potential of Apium leptophyllum Pers. fruits by estimating total phenolic as well as flavonoidal contents and antioxidant values. The collected fruits were extracted separately using different solvents like methanol, ethanol and water. Total phenolic and flavonoid contents were measured from the respective extracts and correlated with their antioxidant values. The antioxidant properties of various fruit extracts (12.5, 25, 50, 100 and 150 μg/ml) were evaluated by DPPH, hydroxyl, nitric oxide and superoxide scavenging assay and compared with ascorbic acid as a standard. All the extracts of A. leptophyllum were found to be dose dependent inhibition against these free radicals. Among all these extracts, the methanolic one was found better in the scavenging activity and followed dose-dependent manner against DPPH, hydroxyl radical, nitric oxide, superoxide anions with minimum IC50 values of 97.9, 89.02, 135.37, 127.73 μg/ml, respectively, and also observed more significant (p<0.01) as compared with standard Furthermore, total phenolic and flavonoidal contents were found highest in methanolic extract. The results obtained in this study clearly indicate that the methanolic extract of A. leptophyllum may be used as a new potential source of natural nutritional supplement in food or pharmaceutical industries due to rich source of phenolic, flavonoidal contents as well as antioxidant property

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Anhydrorutaretin, a new furanocoumarin and other minor constituents of Apium leptophyllum seeds

Cited by 2 publications

References 6 publications

Prenylated Coumarins, Chalcone and New Cinnamic Acid and Dihydrocinnamic Acid Derivatives from Brosimum gaudichaudii

Prenylated Coumarins, Chalcone and New Cinnamic Acid and Dihydrocinnamic Acid Derivatives from Brosimum gaudichaudii

Estimation of total phenolics and flavonoidal contents as well as in vitro antioxidant potential of Apium leptophyllum Pers.

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