Coumarins X: Spectral Studies on Some Linear Furanocoumarins

Lee, Kuo‐Hsiung; Soine, Taito O.

doi:10.1002/jps.2600580606

Cited by 55 publications

(17 citation statements)

References 8 publications

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“…Therefore, the structures of compounds were determined as osthole (1) (Sajjadi et al, 2009), isoimperatorin (2) (Liu et al, 2004), oxypeucedanin (3) (Ivie, 1978), psoralen (4) (Lin, 2007), oxypeucedanin hydrate (5) (Ivie, 1978), gosferol (6) (Adebajo & Reisch, 2000), oxypeucedanin methnolate (7) (Abyshev et al, 1973), and pranferol (8) (Kuznetsova et al, 1966) (Figure 1). Regarding 1 H-NMR spectra, the chemical shifts assigned to the C3, C4, C2 0 , and C3 0 protons are characteristic of the (Lee & Soine, 1969). The upfield position of H-8 in contrast to H-5 aromatic proton is related to the diamagnetic shift of an aromatic proton adjacent to an oxygen atom (Lee & Soine, 1969).…”

Section: Structure Elucidation Of Pure Compoundsmentioning

confidence: 99%

“…Regarding 1 H-NMR spectra, the chemical shifts assigned to the C3, C4, C2 0 , and C3 0 protons are characteristic of the (Lee & Soine, 1969). The upfield position of H-8 in contrast to H-5 aromatic proton is related to the diamagnetic shift of an aromatic proton adjacent to an oxygen atom (Lee & Soine, 1969). Gem-dimethyls of C-5 substitutes usually show different chemical shifts because of the anisotropic effect due to the 3,4 double bond (Lee & Soine, 1969).…”

Section: Structure Elucidation Of Pure Compoundsmentioning

confidence: 99%

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Antiviral and cytotoxic evaluation of coumarins fromPrangos ferulacea

Shokoohinia

Sajjadi

Gholamzadeh

et al. 2014

Pharmaceutical Biology

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Context: Prangos ferulacea (L.) Lindl. (Apiaceae) is a perennial plant found in the Middle-East, where it is commonly used as an antispasmodic and anti-inflammatory agent. It is a rich source of coumarins. Objective: To purify several coumarins from P. ferulacea and to screen their cytotoxicity and antiherpes activity. Materials and methods: Acetone extract of roots of P. ferulacea was subjected to several chromatographic separations to render pure coumarins (1-8). Anti-herpes virus effects of 1-7 were evaluated at concentration 2.5, 5, and 10 mgmL À1 , on a confluent monolayer of Vero cells infected with 25 PFU of HSV1. Cytotoxic effects of 1 and 2 were evaluated on an A2780S cell line using the MTT assay. The cells were exposed to a series of concentrations of coumarins (0.01-2.5 mM, 37 C, 72 h). Results: Compounds 1-8 were identified as osthole, isoimperatorin, oxypeucedanin, psoralen, oxypeucedanin hydrate, gosferol, oxypeucedanin methnolate, and pranferol. This is the first report of occurrence of 4 and 7 in this plant. Compound 1 showed a viability of 9.41% ± 2.4 at 2.5 mM on A2780S cells (IC 50 ¼ 0.38 mM). The cell survival of 2 at 2.5 mM was 46.86% ± 5.5 with IC 50 equal to 1.1 mM. Discussion and conclusion: Compound 1 shows cytotoxic effects on the A2780S cell line. Compound 2 is a cyclooxygenase-2 inhibitor and the A2780S cell line does not express COX-2 which may interpret the non-toxic effect of the compound on this cell line. None of the tested compounds showed an anti-HSV effect at non-toxic concentrations.

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Section: Structure Elucidation Of Pure Compoundsmentioning

confidence: 99%

Section: Structure Elucidation Of Pure Compoundsmentioning

confidence: 99%

Antiviral and cytotoxic evaluation of coumarins fromPrangos ferulacea

Shokoohinia

Sajjadi

Gholamzadeh

et al. 2014

Pharmaceutical Biology

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“…That the prenyloxy group was attached to C-5, rather than C-8, was indicated because the methyls gave two signals rather than a broad 6H singlet in the lower field strength (100 MHz) instrument (Murray et al, 1982). Thus, compound 1 was suggested to be isoimperatorin (cnidin) (Lee and Soine, 1969); the 13C NMR spectra confirmed this identification (Sasaki et al, 1980;Abyshev et al, 1982).…”

Section: Resultsmentioning

confidence: 52%

“…The EIMS signal for the M+ at m / z 300, thirty mass units higher than compound 1, suggested that compound 2 was 8-methoxyisoimperatorin (cnidilin); the spectral data was identical to that published for cnidilin (Lee and Soine, 1969;Sasaki et al, 1980). The molecular weight of compound 3 (CIMS MH+ m/z 271) was identical to that of compound 1 (isoimperitorin), but the Rf value on TLC was lower.…”

Section: Resultsmentioning

confidence: 74%

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Bioactive furanocoumarins from the berries of Zanthoxylum americanum

Saqib

Hui

Anderson

et al. 1990

Phytotherapy Research

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Crude extracts of the berries of Zanthoxylum americanum showed significant lethality to brine shrimp larvae and exhibited cytotoxicity to human tumor cells. Activity-directed fractionation led to 5 furanocoumarias (cnidilin, imperatorin, isoimperatorin, psoralen, and xanthotoxin), the last three of which are bioactive in these bioassays. All were previously known as natural compounds but are new to this plant species.

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Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer's Disease and Type II Diabetes

Özek

Yur

Göğer

et al. 2019

Chemistry & Biodiversity

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Hexane extracts of Heracleum verticillatum, H. sibiricum, H. angustisectum, and H. ternatum were studied for their furanocoumarin content antioxidant potential and acetylcholinesterase and α‐amylase inhibitory activities. Quantification of the furanocoumarins was performed by 1H‐NMR. Pimpinellin was found to be the main component in the roots of all studied species. Bergapten and imperatorin were the major compounds in the fruits of H. sibiricum and H. verticillatum, respectively, while byakangelicol dominated in H. angustisectum and H. ternatum fruits. The leaf and fruit extracts of H. angustisectum demonstrated the highest DPPH radical scavenging activity and TEAC (IC50 0.58 mg/mL and 1.83 mm, respectively). The root extracts of H. verticillatum and H. angustisectum were found to be the most effective against acetylcholinesterase (IC50 0.30 and 0.34 mg/mL, respectively). The studied extracts were not active or demonstrated a weak inhibitory effect (%Inh. up to 29.7) towards α‐amylase.

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Coumarins X: Spectral Studies on Some Linear Furanocoumarins

Cited by 55 publications

References 8 publications

Antiviral and cytotoxic evaluation of coumarins fromPrangos ferulacea

Antiviral and cytotoxic evaluation of coumarins fromPrangos ferulacea

Bioactive furanocoumarins from the berries of Zanthoxylum americanum

Furanocoumarin Content, Antioxidant Activity, and Inhibitory Potential of Heracleum verticillatum, Heracleum sibiricum, Heracleum angustisectum, and Heracleum ternatum Extracts against Enzymes Involved in Alzheimer's Disease and Type II Diabetes

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