Carbon-13 magnetic resonance spectroscopy of coumarins. Carbon-13-proton long-range couplings

C-j, Chang; Hg, Floss; Steck, Warren

doi:10.1021/jo00428a014

Cited by 66 publications

(28 citation statements)

References 3 publications

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“…Isolation and identification of antibacterial substances Three compounds were isolated from the hydrophobic fraction of lemon peel extract and identified as 8-geranyloxypsolaren, 5-geranyloxypsolaren, and 5-geranyloxy-7-methoxycoumarin by MS, 1 H-NMR, and 13 C-NMR analyses ( The spectral properties of the isolated compounds were consistent with those described in the literature (Dreyer and Huey 1973;Herpol-Borremans et al 1985;Chang et al 1997;Murakami et al 1999). …”

Section: Resultssupporting

confidence: 77%

Isolation and extraction of antimicrobial substances against oral bacteria from lemon peel

Miyake

Hiramitsu²

2011

J Food Sci Technol

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We have isolated 4 antibacterial substances that were active against the oral bacteria that cause dental caries and periodontitis, such as Streptococcus mutans, Prevotella intermedia, and Porphyromonas gingivalis, from lemon peel, a waste product in the citrus industry. The isolated substances were identified as 8-geranyloxypsolaren, 5-geranyloxypsolaren, 5-geranyloxy-7-methoxycoumarin, and phloroglucinol 1-β-D-glucopyranoside (phlorin) upon structural analyses. Among these, 8-Geranyloxypsolaren, 5-geranyloxypsolaren, and 5-geranyloxy-7-methoxycoumarin exhibited high antibacterial activity. These 3 compounds were effectively extracted using ethanol and n-hexane, whereas phlorin was extracted with water. Further, the above 3 compounds were present in lemon essential oil and abundantly present in the residue produced upon the cooling treatment of concentrated lemon essential oil.

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Section: Resultssupporting

confidence: 77%

Isolation and extraction of antimicrobial substances against oral bacteria from lemon peel

Miyake

Hiramitsu²

2011

J Food Sci Technol

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“…Many of them also, have been synthesized and studied for their pharmacological activities [1][2][3][4]. A literature survey revealed numerous reports on the antiproliferative and antitumor activities of a variety of coumarin compounds [5].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical synthesis of new coumarin derivatives of potential biological significance

Amani

Nematollahi

2012

Journal of Electroanalytical Chemistry

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“…Oleanolic acid (2) and ursolic acid (3) were identified by comparison of their spectral data with values reported in the literature [27,28].…”

Section: Resultsmentioning

confidence: 99%

Hypoglycemic activity of constituents from Astianthus viminalis in normal and streptozotocin-induced diabetic mice

Gutierrez¹,

Solís

Baez³

et al. 2009

J Nat Med

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Astianthus viminalis has been used as a medicinal plant for a long time owing to its many physiological actions such as anti-inflammatory and antidiabetic activities. A new tetracyclic triterpenoid 3beta,19alpha-dihydroxyurs-12,20(21)-diene-28-oic acid (1), known constituents oleanolic acid (2) and ursolic acid (3), and the coumarins 7,8-dimethoxycoumarin (4) and 7-methoxycoumarin (5) were isolated from the chloroform extract of the leaves of A. viminalis. The structure and relative configurations of 1 were determined by spectroscopic methods (1H- and 13C-NMR, IR, and MS) and 2D-NMR experiments. The hypoglycemic ingredients of A. viminalis were characterized as compounds 1-3. The hypoglycemic effect of the isolated natural product 1 was investigated in normoglycemic and streptozotocin (STZ)-induced diabetic mice. All effects were compared with those of tolbutamide. Triterpenoid 1 showed potent hypoglycemic and hypolipidemic effects in the STZ-induced diabetic mice. Continuous administration of 1 (30 mg/kg, orally) led to significant decrease in the level of glucose, triglycerides, total cholesterol, LDL, and VLDL in the diabetic mice, whereas the level of HDL did not alter significantly in any of the groups studied.

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Carbon-13 magnetic resonance spectroscopy of coumarins. Carbon-13-proton long-range couplings

Cited by 66 publications

References 3 publications

Isolation and extraction of antimicrobial substances against oral bacteria from lemon peel

Isolation and extraction of antimicrobial substances against oral bacteria from lemon peel

Electrochemical synthesis of new coumarin derivatives of potential biological significance

Hypoglycemic activity of constituents from Astianthus viminalis in normal and streptozotocin-induced diabetic mice

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