Oxypeucedanin methanolate

Anticholinesterase Compounds from Endemic Prangos uechtritzii.[Pubmed:36201258]

Chem Biodivers. 2022 Nov;19(11):e202200557.

In this study, the anticholinesterase effects of the extracts and isolated compounds from the roots of endemic Prangos uechtritzii Boiss & Hausskn (Apiaceae) are reported. A novel polyacetylenic compound; (+)-8-O-methyloplopantriol A along with two known polyacetylenes; (-)-panaxynol, (+)-falcarindiol and fifteen known coumarin derivatives; umbelliferone, 6-formylumbelliferone, suberosin, 7-demethylsuberosin, (+)-ulopterol, tamarin, psoralen, imperatorin, (+)-oxypeucedanin, (+)-oxypeucedanin hydrate, (+)-Oxypeucedanin methanolate, (+)-marmesin, (-)-prantschimgin, (+)-decursinol, and (-)-adicardin were isolated from the hexane (Pu-HE), chloroform (Pu-CE), and methanol (Pu-ME) extracts of P. uechtritzii roots. (-)-Panaxynol, (+)-falcarindiol, 6-formylumbelliferone, (+)-decursinol, and (-)-adicardin were obtained from the genus Prangos for the first time. (+)-8-O-Methyloplopantriol A inhibited both AChE (IC(50) =194.5+/-5.8 muM) and BChE (IC(50) =51.9+/-2.96 muM) enzymes. (+)-Falcarindiol, 6-formylumbelliferone, 7-demethylsuberosin, tamarin, and imperatorin also exhibited BChE-specific inhibitory activities (IC(50) =27.88-93.86 muM). (+)-Falcarindiol (IC(50) =27.88+/-0.91 muM) and imperatorin (IC(50) =30.89+/-1.40 muM) as the most active components could be led compounds to develop new BChE inhibitors with further research against Alzheimer's disease.

Antiproliferative and cytotoxic activities of furocoumarins of Ducrosia anethifolia.[Pubmed:31070540]

Pharm Biol. 2018 Dec;56(1):658-664.

CONTEXT: Phytochemical and pharmacological data on Ducrosia anethifolia (DC.) Boiss. (Apiaceae), an Iranian medicinal plant, are scarce; however, furocoumarins are characteristic compounds of D. anethifolia. OBJECTIVE: Our experiments identify the secondary metabolites of D. anethifolia and assess their antitumor and anti-multidrug resistance activities. MATERIALS AND METHODS: Pure compounds were isolated from the extract of aerial parts of the plant by chromatographic methods. Bioactivities were tested on multidrug resistant and sensitive mouse T-lymphoma cell lines. The inhibition of the cancer MDR efflux pump ABCB1 was evaluated by flow cytometry (at 2 and 20 microM). A checkerboard microplate method was applied to study the interactions of furocoumarins and doxorubicin. Toxicity was studied using normal murine NIH/3T3 fibroblasts. RESULTS: Thirteen pure compounds were isolated, nine furocoumarins namely, pabulenol (1), (+)-oxypeucedanin hydrate (2), oxypeucedanin (3), Oxypeucedanin methanolate (4), (-)-oxypeucedanin hydrate (5), imperatorin (6), isogospherol (7), heraclenin (8), heraclenol (9), along with vanillic aldehyde (10), harmine (11), 3-hydroxy-alpha-ionone (12) and 2-C-methyl-erythrytol (13). Oxypeucedanin showed the highest in vitro antiproliferative and cytotoxic activity against parent (IC(50) = 25.98 +/- 1.27, 40.33 +/- 0.63 microM) and multidrug resistant cells (IC(50) = 28.89 +/- 0.73, 66.68 +/- 0.00 microM), respectively, and exhibited slight toxicity on normal murine fibroblasts (IC(50) = 57.18 +/- 3.91 microM). DISCUSSION AND CONCLUSIONS: Compounds 2, 3, 5, 7, 10-13 were identified for the first time from the Ducrosia genus. Here, we report a comprehensive in vitro assessment of the antitumor activities of D. anethifolia furocoumarins. Oxypeucedanin is a promising compound for further investigations for its anticancer effects.

Bioactive coumarins from the roots and fruits of Ferulago trifida Boiss., an endemic species to Iran.[Pubmed:28954543]

Nat Prod Res. 2018 Nov;32(22):2724-2728.

Phytochemical analysis of the Ferulago trifida Boiss. from Apiaceae family led to the isolation and identification of suberosin (1), isoimperatorin (2), prantschimgin (3), oxypeucedanin (4), Oxypeucedanin methanolate (5), suberenol (6), 6-hydroxymethylherniarin (7), oxypeucedanin hydrate (8), ulopterol (9), bergapten (10), xanthotoxin (11), imperatorin (12) and grandivittin (13) from chloroform extracts of the roots (1-9) and fruits (1, 2, 8, 10-13) of this species. Oxypeucedanin methanolate and suberenol demonstrated a potent antioxidant power with 268.2 +/- 5.4 and 251.2 +/- 6.2 mmol FSE/100 g, respectively, compared by BHT (267.2 +/- 4.2 mmol FSE/100 g) in FRAP method. The potent antibacterial effects were found for Oxypeucedanin methanolate on S. epidermidis (IZ; 26 mm, MIC; 250 mug mL(-1)) an oxypeucedanin hydrate on K. pneumoniae (IZ: 21 mm, MIC: 250 mug mL(-1)). Moreover, suberosin showed higher preferential toxicity against MDA-MB-23 cells (IC(50): 0.21 mM, SI: 5.0), in comparison with tamoxifen (IC(50): 0.012 mM, SI: 2.45) in MTT assay.

[Chemical constituents from lipophilic parts in roots of Angelica dahurica var. formosana cv. Chuanbaizhi].[Pubmed:26552172]

Zhongguo Zhong Yao Za Zhi. 2015 Jun;40(11):2148-56.

The chemical constituents from lipophilic parts in the roots of Angelica dahurica var. formosana cv. Chuanbaizhi were studied in this paper. The compounds were separated and purified by repeated column chromatographic methods on silica gel and HPLC, and the chemical structures of compounds were determined by spectral data analyses. Twenty-nine compounds were obtained and identified as isoimperatorin (1), beta-sitosterol (2), imperatorin (3), bergapten (4), osthenol (5), xanthotoxin (6), isoimpinellin (7), dehydrogeijerin (8), phellopterin (9), isodemethylfuropinarine (10), 7-demethylsuberosin (11), alloimperatorin (12), xanthotoxol (13), isooxypeucedanin (14), alloisoimperatorin (15), demethylfuropinarine (16), 5-hydroxy-8-methoxypsoralen (17), Oxypeucedanin methanolate (18), pabulenol (19), byakangelicin (20), marmesin (21), (+) -decursinol (22), heraclenol (23), oxypeucedanin hydrate (24), marmesinin (25), ulopterol (26), erythro-guaiacylglycerol-beta-ferulic acid ether (27), threo-guaiacylglycerol-beta-ferulic acid ether (28), and uracil (29). Compounds 5, 8, 11, 18, 21-23, and 26-28 were obtained from the roots of title plant for the first time.

Phenylpropanoids and furanocoumarins as antibacterial and antimalarial constituents of the Bhutanese medicinal plant Pleurospermum amabile.[Pubmed:25230503]

Nat Prod Commun. 2014 Jul;9(7):957-60.

With the objective of determining safety and verifying the traditional uses of the Bhutanese medicinal plant, Pleurospermum amabile Craib & W. W. Smith, we investigated its crude extracts and the isolated phytochemicals for their biological activities. Four phenylpropanoids [(E)-isomyristicin (1), (E)-isoapiol (2), methyl eugenol (3) and (E)-isoelemicin (4)] and six furanocoumarins [psoralen (5), bergapten (6), isoimperatorin (7), isopimpinellin (8), oxypeucedanin hydrate (9) and Oxypeucedanin methanolate (10)] were isolated from this plant. Among the test samples, compound 10 showed weak antibacterial activity against Bacillus subtilis and best antimalarial activity against the Plasmodium falciparum strains, TM4/8.2 (chloroquine and antifolate sensitive) and K1CB1 (multidrug resistant). None of the test samples showed cytotoxicity. This study generated scientific data that support the traditional medical uses of the plant.