Falcarindiol CAS NO.55297-87-5

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General tips：For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
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Chemical Properties of (Z)-Falcarindiol

Source of (Z)-Falcarindiol

The roots of Daucus carota

Preparing Stock Solutions of (Z)-Falcarindiol

References on (Z)-Falcarindiol

Bioassay-directed isolation of falcarindiol and isoacetovanillon from Pycnocycla caespitosa based on KCl-induced contraction in rat uterus smooth muscles.[Pubmed:28626483]

Res Pharm Sci. 2017 Jun;12(3):249-256.

Hydroalcoholic extract and essential oil of aerial parts of Pycnocycla caespitosa have spasmolytic activity on rat ileum contractions. The objective of this research was to separate fractions of total hydroalcoholic extract of P. caespitosa guided by their spasmolytic activity on rat uterus. Aerial parts of P. caespitosa were extracted with ethanol. The concentrated extract was subjected to column chromatography and thin layer chromatography (TLC) for isolation fractions, then one of the bioactive fractions was subjected to further isolation to find its active components. Five fractions were obtained (Fr.1-Fr.5) and their anti-spasmodic activities were examined on uterus contraction induced by KCl (80 mM) and compared with ritodrine. In addition, spasmolytic effect of Fr.4 (one of the bioactive fractions) was determined on rat uterus induced by oxytocin (0.0005 IU/mL) and compared with ritodrine. Hydroalcoholic extract of P. caespitosa (0.032-2 mg/mL) reduced the responses to KCl but the inhibitory effect was not complete with 2 mg/mL extract in the bath. Four fractions (Fr.1, Fr.2, Fr.3 and Fr.4) (32-500 mug/mL) inhibited rat uterus contractions on the uterus while Fr.4 was slightly more active than others (IC50 = 146 +/- 23 mug/mL). Falcarindiol and isoacetovanillone were identified from Fr.4 using phytochemical methods including high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) and TLC. In conclusion, in this research bioactivity guided technique was successfully used for separation of active fraction of P. caespitosa. Falcarindiol and isoacetovanillone were identified from the active fraction which inhibited both tonic and rhythmic contractile responses in rat isolated uterus.

The Dietary Constituent Falcarindiol Promotes Cholesterol Efflux from THP-1 Macrophages by Increasing ABCA1 Gene Transcription and Protein Stability.[Pubmed:28919859]

Front Pharmacol. 2017 Sep 1;8:596.

We report increased cholesterol efflux from macrophages in the presence of falcarindiol, an important dietary constituent present in commonly used vegetables and medicinal plants. Falcarindiol (3-20 muM) increased cholesterol efflux from THP-1-derived macrophages. Western blot analysis showed an increased protein level of ABCA1 upon falcarindiol exposure. Quantitative real-time PCR revealed that also ABCA1 mRNA level rise with falcarindiol (10 muM) treatment. The effect of falcarindiol on ABCA1 protein as well as mRNA level were counteracted by co-treatment with BADGE, an antagonist of PPARgamma. Furthermore, falcarindiol significantly inhibited ABCA1 protein degradation in the presence of cycloheximide. This post-translational regulation of ABCA1 by falcarindiol occurs most likely by inhibition of lysosomal cathepsins, resulting in decreased proteolysis and extended protein half-life of ABCA1. Taken together, falcarindiol increases ABCA1 protein level by two complementary mechanisms, i.e., promoting ABCA1 gene expression and inhibiting ABCA1 protein degradation, which lead to enhanced cholesterol efflux.

Bupleurum chinense Roots: a Bioactivity-Guided Approach toward Saponin-Type NF-kappaB Inhibitors.[Pubmed:28902374]

Planta Med. 2017 Oct;83(14-15):1242-1250.

The roots of Bupleurum chinense have a long history in traditional medicine to treat infectious diseases and inflammatory disorders. Two major compounds, saikosaponins A and D, were reported to exert potent anti-inflammatory activity by inhibiting NF-kappaB. In the present study, we isolated new saikosaponin analogues from the roots of B. chinese interfering with NF-kappaB activity in vitro. The methanol-soluble fraction of the dichloromethane extract of Radix Bupleuri was subjected to activity-guided isolation yielding 18 compounds, including triterpenoids and polyacetylenes. Their structures were determined by spectroscopic methods as saikogenin D (1), prosaikogenin D (2), saikosaponins B2 (3), W (4), B1 (5), Y (6), D (7), A (8), E (9), B4 (10), B3 (11), and T (12), saikodiyne A (13), D (14), E (15) and F (16), falcarindiol (17), and 1-linoleoyl-sn-glycero-3-phosphorylcholine (18). Among them, 4, 15, and 16 are new compounds, whereas 6, previously described as a semi-synthetic compound, is isolated from a natural source for the first time, and 13-17 are the first reports of polyacetylenes from this plant. Nine saponins/triterpenoids were tested for inhibition of NF-kappaB signaling in a cell-based NF-kappaB-dependent luciferase reporter gene model in vitro. Five of them (1, 2, 4, 6, and 8) showed strong (> 50%, at 30 microM) NF-kappaB inhibition, but also varying degrees of cytotoxicity, with compounds 1 and 4 (showing no significant cytotoxicity) presenting IC50 values of 14.0 microM and 14.1 microM in the cell-based assay, respectively.

Nonvolatile Chemical Constituents from the Leaves of Ligusticopsis wallichiana (DC.) Pimenov & Kljuykov and Their Free Radical-Scavenging Activity.[Pubmed:29484213]

J Anal Methods Chem. 2018 Feb 1;2018:1794650.

Different plant parts of Ligusticopsis wallichiana (family: Apiaceae) are widely used as traditional medicines. Although many volatile constituents are already identified from the leaves of L. wallichiana, there is no detailed report on the nonvolatile constituents. In the present study, we aimed to isolate and identify the major chemical constituents from the leaves. Bhutkesoside A (1), falcarindiol (2), ferulic acid (3), cnidioside A (4), quercetin 3-O-beta-D-glucopyranoside (5), rutin (6), 4'-O-methylquercetin 3-O-beta-D-glucopyranoside (7), scopoletin (8), umbelliferone (9), eugenol 4-O-beta-D-glucopyranoside (10) and pumilaside A (11) were isolated from the 70% MeOH extract. The structures of isolated compounds were elucidated on the basis of (1)H- and (13)C-NMR spectroscopic data. Compounds 4-11 are reported for the first time from L. wallichiana. Compounds 5 and 6 showed potent free radical-scavenging activity.

Correlations between Polyacetylene Concentrations in Carrot (Daucus carota L.) and Various Soil Parameters.[Pubmed:28231155]

Foods. 2016 Aug 31;5(3). pii: foods5030060.

This study assessed the concentrations of three falcarinol-type polyacetylenes (falcarinol, falcarindiol, falcarindiol-3-acetate) in carrots and the correlations between these and different soil traits. A total of 144 carrot samples, from three different harvests taken a single season, were analysed in terms of their polyacetylene concentrations and root development. On one of the harvesting occasions, 48 soil samples were also taken and analysed. The chemical composition of the soil was found to influence the concentrations of falcarinol-type polyacetylenes in carrots. When the total soil potassium level was 200 mg/100 g soil, the concentration of falcarindiol (FaDOH) in the carrot samples was 630 mug/g DW, but when carrots were grown in soil with a total potassium level of 300 mg/100 g soil, the FaDOH concentration in the carrots fell to 445 mug/g DW. Carrots grown in soils generally low in available phosphorus exhibited higher levels of falcarindiol if the soil was also low in available magnesium and calcium. The concentrations of polyacetylenes in carrots were positively correlated with total soil phosphorus level, but negatively correlated with total soil potassium level. Of the three polyacetylenes analysed, FaDOH concentrations were influenced most by changes in soil chemical composition.

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