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Chrysosplenol D

CAS# 14965-20-9

Chrysosplenol D

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Quality Control of Chrysosplenol D

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Chemical structure

Chrysosplenol D

3D structure

Chemical Properties of Chrysosplenol D

Cas No. 14965-20-9 SDF Download SDF
PubChem ID 5280699 Appearance Yellow powder
Formula C18H16O8 M.Wt 360.3
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,6,7-trimethoxychromen-4-one
SMILES COC1=C(C(=C2C(=C1)OC(=C(C2=O)OC)C3=CC(=C(C=C3)O)O)O)OC
Standard InChIKey BYWLLSQTJBXAPV-UHFFFAOYSA-N
Standard InChI InChI=1S/C18H16O8/c1-23-12-7-11-13(14(21)17(12)24-2)15(22)18(25-3)16(26-11)8-4-5-9(19)10(20)6-8/h4-7,19-21H,1-3H3
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.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Chrysosplenol D

The herbs of Artemisia annua L.

Biological Activity of Chrysosplenol D

DescriptionChrysosplenol D, an efflux pump inhibitor that can potentiate the activity of commercially important antibiotics and antimalarials. Chrysosplenol D has anti-inflammatory, antimalarial, antibacterial and antifungal activities; it also exerts its anti-proliferative effect on tsFT210 cells through inhibiting cell cycle and inducing apoptosis, it may as a new cell cycle inhibitor.
TargetsNF-kB | JNK | IkB | IL Receptor | IKK | Antifection
In vitro

Antimalarial activity of Artemisia annua flavonoids from whole plants and cell cultures.[Pubmed: 24213368 ]

Plant Cell Rep. 1992 Nov;11(12):637-40.

Cell suspension cultures developed from Artemisia annua exhibited antimalarial activity against Plasmodium faldparum in vitro both in the n-hexane extract of the plant cell culture medium and in the chloroform extract of the cells.
METHODS AND RESULTS:
Trace amounts of the antimalarial sesquiterpene lactone artemisinin may account for the activity of the n-hexane fraction but only the methoxylated flavonoids artemetin, chrysoplenetin, chrysosplenol-D and cirsilineol can account for the activity of the chloroform extract. These purified flavonoids were found to have IC50 values at 2.4 - 6.5 × 10(-5)M against P. falciparum in vitro compared with an IC50 value of about 3 × 10(-8)M for purified artimisinin.
CONCLUSIONS:
At concentrations of 5 × 10(-6)M these flavonoids were not active against P. falciparum but did have a marked and selective potentiating effect on the antiplasmodial activity of artemisinin.

Antimicrobial flavonoids from Psiadia trinervia and their methylated and acetylated derivatives.[Reference: WebLink]

Phytochemistry, 1989, 28(9):2323-7.

From a dichloromethane extract and a hydrolysed methanolic extract from the leaves of Psiadia trinervia, 13 3-methylated flavonols have been isolated.
METHODS AND RESULTS:
Their structures were established by the usual spectroscopic methods (UV, EIMS, 1H and 13C NMR). Ayanin, casticin, chrysosplenol-D and 5,7,4′-trihydroxy-3,8-dimethoxyfiavone were responsible for the antifungal activity found in the preliminary screening. Chrysosplenol D, isokaempferide, 5,7,4′- trihydroxy-3,3′-dimethoxyflavone and 5,7,4′-trihydroxy-3,8-dimethoxyflavone displayed antibacterial activity. Twenty-nine derivatives were prepared by permethylation and selective methylation of the free hydroxyl group at C-5.
CONCLUSIONS:
The antimicrobial activities of the isolates and derivatives were determined by bioautographic assays using C. cucumerinum and B. cereus as test organisms.

In vivo

Flavonoids casticin and chrysosplenol D from Artemisia annua L. inhibit inflammation in vitro and in vivo.[Pubmed: 25891417]

Toxicol Appl Pharmacol. 2015 Apr 17.

The aim of our experiments was to investigate the anti-inflammatory properties of casticin and Chrysosplenol D, two flavonoids present in Artemisia annua L.
METHODS AND RESULTS:
Topical inflammation was induced in ICR mice using croton oil. Mice were then treated with casticin or Chrysosplenol D. Cutaneous histological changes and edema were assessed. ICR mice were intragastrically administrated with casticin or Chrysosplenol D followed by intraperitoneal injection of lipopolysaccharide (LPS). Mouse Raw264.7 macrophage cells were incubated with casticin or Chrysosplenol D. Intracellular phosphorylation was detected, and migration was assessed by trans-well assay. HT-29/NFκB-luc cells were incubated with casticin or Chrysosplenol D in the presence or absence of LPS, and NF-κB activation was quantified. In mice, administration of casticin (0.5, 1 and 1.5μmol/cm2) and Chrysosplenol D (1 and 1.5μmol/cm2) inhibited croton oil-induced ear edema (casticin: 29.39-64.95%; Chrysosplenol D: 37.76-65.89%, all P<0.05) in a manner similar to indomethacin (0.5, 1 and 1.5μmol/cm2; 55.63-84.58%). Casticin (0.07, 0.13 and 0.27mmol/kg) and Chrysosplenol D (0.07, 0.14 and 0.28mmol/kg) protected against LPS-induced systemic inflammatory response syndrome (SIRS) in mice (all P<0.05), in a manner similar to dexamethasone (0.03mmol/kg). Casticin and Chrysosplenol D suppressed LPS-induced release of IL-1 beta, IL-6 and MCP-1, inhibited cell migration, and reduced LPS-induced IκB and c-JUN phosphorylation in Raw264.7 cells. JNK inhibitor SP600125 blocked the inhibitory effect of Chrysosplenol D on cytokine release.
CONCLUSIONS:
The flavonoids casticin and Chrysosplenol D from A. annua L. inhibited inflammation in vitro and in vivo.

Protocol of Chrysosplenol D

Kinase Assay

A new α-glucosidase inhibitor from Achillea fragrantissima (Forssk.) Sch. Bip. growing in Egypt.[Pubmed: 24666348]

Direct synthesis of chrysosplenol D.[Pubmed: 18855445]

J Nat Prod. 2008 Nov;71(11):1961-2.

An aldol condensation and an Algar-Flynn-Oyamada oxidative cyclization were key steps in the direct synthesis of Chrysosplenol D, an efflux pump inhibitor that can potentiate the activity of commercially important antibiotics and antimalarials.

Nat Prod Res. 2014;28(11):812-8.

α-Glucosidase inhibitors (AGIs) represent a class of oral antidiabetic drugs that delay the absorption of ingested carbohydrates, reducing the postprandial glucose and insulin peaks to reach normoglycaemia.
METHODS AND RESULTS:
In this study, a bioassay-guided fractionation of the ethanolic extract of the aerial parts of Achillea fragrantissima (Forssk.) Sch. Bip. growing in Egypt led to the isolation of a new potent AGI; acacetin-6-C-(6″-acetyl-β-D-glucopyranoside)-8-C-α-L-arabinopyranoside (5) alongside with four known compounds: chondrillasterol (1), quercetin-3,6,7-trimethyl ether (chrysosplenol-D) (2), isovitexin-4'-methyl ether (3) and isovitexin (4). The structure of the new compound (5) was elucidated on the basis of its spectral data, including HR-FAB-MS, UV, (1)H NMR, (13)C NMR, (1)H-(1)H COSY, HSQC and HMBC. The new compound (5) exhibited the most significant α-glucosidase inhibitory activity (IC₅₀ 1.5 ± 0.09 μg/mL).
CONCLUSIONS:
Under the assay conditions, all the tested compounds were more potent than the positive control acarbose (IC50 224 ± 2.31 μg/mL).

Cell Research

Flavonoids from Vitex trifolia L. inhibit cell cycle progression at G2/M phase and induce apoptosis in mammalian cancer cells.[Pubmed: 16087636 ]

J Asian Nat Prod Res. 2005 Aug;7(4):615-26.

Six flavonoids, persicogenin (1), artemetin (2), luteolin (3), penduletin (4), vitexicarpin (5) and Chrysosplenol D (6), have been isolated for the first time as new cell cycle inhibitors from Vitex trifolia L., a Chinese folk medicine used to treat cancers, through a bioassay-guided separation procedure. They were identified by spectroscopic methods.
METHODS AND RESULTS:
The inhibitory effects of 1-6 on the proliferation of mammalian cancer cells have been evaluated by the SRB (sulforhodamine B) method and their effects on cell cycle and apoptosis investigated by flow cytometry with the morphological observation under light microscope and by agarose-gel electrophoresis to detect internucleosomal DNA fragmentation. Compounds 1-6 inhibited the proliferation of mouse tsFT210 cancer cells with the IC50s (microg ml(-1)) > 100 (inhibition rate at 100 microg ml(-1), 47.9%) for 1, >100 (inhibition rate at 100 microg ml(-1), 49.6 %) for 2, 10.7 for 3, 19.8 for 4, 0.3 for 5, and 3.5 for 6. Flow cytometric investigations for 1-6 demonstrated that 1-5 mainly inhibited cell cycle at the G2/M phase in a dose-dependent manner with a weak induction of apoptosis on the tsFT210 cells, while 6 induced mainly apoptosis of the same tsFT210 cells also in a dose-dependent manner together with a weak inhibition of the cell cycle at the G0/G1 and G2/M phases, demonstrating that 1-6 exert their anti-proliferative effect on tsFT210 cells through inhibiting cell cycle and inducing apoptosis. In contrast to the cell cycle G2/M phase inhibitory main effect on tsFT210 cells, 5 induced mainly apoptosis on human myeloid leukemia K562 cells with a weak inhibition of the cell cycle at the G2/M phase.
CONCLUSIONS:
The present result provides flavonoids 1-6 as new cell cycle inhibitors and 1 and 4 as new anticancer flavonoids, which not only provide the first example of cell cycle G2/M phase inhibitory and apoptosis-inducing constituents of V. trifolia L. but also explain the use of Vitex trifolia L. by Chinese people to treat cancers.

Chrysosplenol D Dilution Calculator

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Preparing Stock Solutions of Chrysosplenol D

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7755 mL 13.8773 mL 27.7546 mL 55.5093 mL 69.3866 mL
5 mM 0.5551 mL 2.7755 mL 5.5509 mL 11.1019 mL 13.8773 mL
10 mM 0.2775 mL 1.3877 mL 2.7755 mL 5.5509 mL 6.9387 mL
50 mM 0.0555 mL 0.2775 mL 0.5551 mL 1.1102 mL 1.3877 mL
100 mM 0.0278 mL 0.1388 mL 0.2775 mL 0.5551 mL 0.6939 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Chrysosplenol D

Flavonoids from Vitex trifolia L. inhibit cell cycle progression at G2/M phase and induce apoptosis in mammalian cancer cells.[Pubmed:16087636]

J Asian Nat Prod Res. 2005 Aug;7(4):615-26.

Six flavonoids, persicogenin (1), artemetin (2), luteolin (3), penduletin (4), vitexicarpin (5) and chrysosplenol-D (6), have been isolated for the first time as new cell cycle inhibitors from Vitex trifolia L., a Chinese folk medicine used to treat cancers, through a bioassay-guided separation procedure. They were identified by spectroscopic methods. The inhibitory effects of 1-6 on the proliferation of mammalian cancer cells have been evaluated by the SRB (sulforhodamine B) method and their effects on cell cycle and apoptosis investigated by flow cytometry with the morphological observation under light microscope and by agarose-gel electrophoresis to detect internucleosomal DNA fragmentation. Compounds 1-6 inhibited the proliferation of mouse tsFT210 cancer cells with the IC50s (microg ml(-1)) > 100 (inhibition rate at 100 microg ml(-1), 47.9%) for 1, >100 (inhibition rate at 100 microg ml(-1), 49.6 %) for 2, 10.7 for 3, 19.8 for 4, 0.3 for 5, and 3.5 for 6. Flow cytometric investigations for 1-6 demonstrated that 1-5 mainly inhibited cell cycle at the G2/M phase in a dose-dependent manner with a weak induction of apoptosis on the tsFT210 cells, while 6 induced mainly apoptosis of the same tsFT210 cells also in a dose-dependent manner together with a weak inhibition of the cell cycle at the G0/G1 and G2/M phases, demonstrating that 1-6 exert their anti-proliferative effect on tsFT210 cells through inhibiting cell cycle and inducing apoptosis. In contrast to the cell cycle G2/M phase inhibitory main effect on tsFT210 cells, 5 induced mainly apoptosis on human myeloid leukemia K562 cells with a weak inhibition of the cell cycle at the G2/M phase. The present result provides flavonoids 1-6 as new cell cycle inhibitors and 1 and 4 as new anticancer flavonoids, which not only provide the first example of cell cycle G2/M phase inhibitory and apoptosis-inducing constituents of V. trifolia L. but also explain the use of Vitex trifolia L. by Chinese people to treat cancers.

Direct synthesis of chrysosplenol D.[Pubmed:18855445]

J Nat Prod. 2008 Nov;71(11):1961-2.

An aldol condensation and an Algar-Flynn-Oyamada oxidative cyclization were key steps in the direct synthesis of Chrysosplenol D, an efflux pump inhibitor that can potentiate the activity of commercially important antibiotics and antimalarials.

Flavonoids casticin and chrysosplenol D from Artemisia annua L. inhibit inflammation in vitro and in vivo.[Pubmed:25891417]

Toxicol Appl Pharmacol. 2015 Aug 1;286(3):151-8.

BACKGROUND: The aim of our experiments was to investigate the anti-inflammatory properties of casticin and Chrysosplenol D, two flavonoids present in Artemisia annua L. METHODS: Topical inflammation was induced in ICR mice using croton oil. Mice were then treated with casticin or Chrysosplenol D. Cutaneous histological changes and edema were assessed. ICR mice were intragastrically administrated with casticin or Chrysosplenol D followed by intraperitoneal injection of lipopolysaccharide (LPS). Mouse Raw264.7 macrophage cells were incubated with casticin or Chrysosplenol D. Intracellular phosphorylation was detected, and migration was assessed by trans-well assay. HT-29/NFkappaB-luc cells were incubated with casticin or Chrysosplenol D in the presence or absence of LPS, and NF-kappaB activation was quantified. RESULTS: In mice, administration of casticin (0.5, 1 and 1.5mumol/cm(2)) and Chrysosplenol D (1 and 1.5mumol/cm(2)) inhibited croton oil-induced ear edema (casticin: 29.39-64.95%; Chrysosplenol D: 37.76-65.89%, all P<0.05) in a manner similar to indomethacin (0.5, 1 and 1.5mumol/cm(2); 55.63-84.58%). Casticin (0.07, 0.13 and 0.27mmol/kg) and Chrysosplenol D (0.07, 0.14 and 0.28mmol/kg) protected against LPS-induced systemic inflammatory response syndrome (SIRS) in mice (all P<0.05), in a manner similar to dexamethasone (0.03mmol/kg). Casticin and Chrysosplenol D suppressed LPS-induced release of IL-1 beta, IL-6 and MCP-1, inhibited cell migration, and reduced LPS-induced IkappaB and c-JUN phosphorylation in Raw264.7 cells. JNK inhibitor SP600125 blocked the inhibitory effect of Chrysosplenol D on cytokine release. CONCLUSIONS: The flavonoids casticin and Chrysosplenol D from A. annua L. inhibited inflammation in vitro and in vivo.

Antimalarial activity of Artemisia annua flavonoids from whole plants and cell cultures.[Pubmed:24213368]

Plant Cell Rep. 1992 Nov;11(12):637-40.

Cell suspension cultures developed from Artemisia annua exhibited antimalarial activity against Plasmodium faldparum in vitro both in the n-hexane extract of the plant cell culture medium and in the chloroform extract of the cells. Trace amounts of the antimalarial sesquiterpene lactone artemisinin may account for the activity of the n-hexane fraction but only the methoxylated flavonoids artemetin, chrysoplenetin, chrysosplenol-D and cirsilineol can account for the activity of the chloroform extract. These purified flavonoids were found to have IC50 values at 2.4 - 6.5 x 10(-5)M against P. falciparum in vitro compared with an IC50 value of about 3 x 10(-8)M for purified artimisinin. At concentrations of 5 x 10(-6)M these flavonoids were not active against P. falciparum but did have a marked and selective potentiating effect on the antiplasmodial activity of artemisinin.

A new alpha-glucosidase inhibitor from Achillea fragrantissima (Forssk.) Sch. Bip. growing in Egypt.[Pubmed:24666348]

Nat Prod Res. 2014;28(11):812-8.

alpha-Glucosidase inhibitors (AGIs) represent a class of oral antidiabetic drugs that delay the absorption of ingested carbohydrates, reducing the postprandial glucose and insulin peaks to reach normoglycaemia. In this study, a bioassay-guided fractionation of the ethanolic extract of the aerial parts of Achillea fragrantissima (Forssk.) Sch. Bip. growing in Egypt led to the isolation of a new potent AGI; acacetin-6-C-(6''-acetyl-beta-D-glucopyranoside)-8-C-alpha-L-arabinopyranoside (5) alongside with four known compounds: chondrillasterol (1), quercetin-3,6,7-trimethyl ether (chrysosplenol-D) (2), isovitexin-4'-methyl ether (3) and isovitexin (4). The structure of the new compound (5) was elucidated on the basis of its spectral data, including HR-FAB-MS, UV, (1)H NMR, (13)C NMR, (1)H-(1)H COSY, HSQC and HMBC. The new compound (5) exhibited the most significant alpha-glucosidase inhibitory activity (IC(5)(0) 1.5 +/- 0.09 mug/mL). Under the assay conditions, all the tested compounds were more potent than the positive control acarbose (IC50 224 +/- 2.31 mug/mL).

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