Sanggenone D

CAS# 81422-93-7

Sanggenone D

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Chemical structure

Sanggenone D

3D structure

Chemical Properties of Sanggenone D

Cas No. 81422-93-7 SDF Download SDF
PubChem ID 442459 Appearance Powder
Formula C40H36O12 M.Wt 708.71
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-[(1R,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8,10a-tetrahydroxy-5a-(3-methylbut-2-enyl)-[1]benzofuro[3,2-b]chromen-11-one
SMILES CC1=CC(C(C(C1)C2=C(C=C(C=C2)O)O)C(=O)C3=C(C=C(C=C3)O)O)C4=C(C=C5C(=C4O)C(=O)C6(C(O5)(C7=C(O6)C=C(C=C7)O)CC=C(C)C)O)O
Standard InChIKey XETHJOZXBVWLLM-ZGXWVFFRSA-N
Standard InChI InChI=1S/C40H36O12/c1-18(2)10-11-39-27-9-6-22(43)16-31(27)52-40(39,50)38(49)35-32(51-39)17-30(46)34(37(35)48)26-13-19(3)12-25(23-7-4-20(41)14-28(23)44)33(26)36(47)24-8-5-21(42)15-29(24)45/h4-10,13-17,25-26,33,41-46,48,50H,11-12H2,1-3H3/t25-,26-,33-,39?,40?/m1/s1
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 Sanggenone D

The root bark of Morus alba L.

Biological Activity of Sanggenone D

Description1. Sanggenones D, B, O,G show an antifungal activity with IC50 values between 10 and 123 microM. 2. Sanggenones(sanggenones C, D) represent a new scaffold of positive GABAA receptor modulators. 3. Sanggenones D, C and kazinol B inhibit COX-2 activity (ic 50 = 73-100 μM). 4. Sanggenone D has anti-inflammatory activity, it can inhibit NO production from lipopolysaccharide (LPS)-induced RAW 264.7 cells at > 10 uM; inhibition of nitric oxide production was mediated by suppression of iNOS enzyme induction but not by direct inhibition of iNOS enzyme activity.
TargetsGABA Receptor | COX | NOS | NO

Sanggenone D Dilution Calculator

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Preparing Stock Solutions of Sanggenone D

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.411 mL 7.0551 mL 14.1101 mL 28.2203 mL 35.2754 mL
5 mM 0.2822 mL 1.411 mL 2.822 mL 5.6441 mL 7.0551 mL
10 mM 0.1411 mL 0.7055 mL 1.411 mL 2.822 mL 3.5275 mL
50 mM 0.0282 mL 0.1411 mL 0.2822 mL 0.5644 mL 0.7055 mL
100 mM 0.0141 mL 0.0706 mL 0.1411 mL 0.2822 mL 0.3528 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 Sanggenone D

Venturia inaequalis-inhibiting Diels-Alder adducts from Morus root bark.[Pubmed:17061817]

J Agric Food Chem. 2006 Nov 1;54(22):8432-6.

In organic apple orcharding there is a continuous need for natural fungicides effective against Venturia inaequalis (Cooke) Winter, the causal agent of apple scab. In this study an in vitro assay is presented for determining the germination inhibitory potential of extracts and pure compounds. From a screening of plant extracts, the methanol extract of Morus root bark revealed distinct V. inaequalis inhibiting qualities, which were subjected to a bioguided fractionation. Among the isolated metabolites [moracins M (1), O/P (2), kuwanon L (3), and sanggenons D (4), B (5), G (6), O (7), E (8), and C (9)] all the Diels-Alder adducts (3-9) showed an antifungal activity with IC50 values between 10 and 123 microM. The in vitro activity of the most active fraction (A5, IC50 39.0 +/- 4.2 microg/mL) was evaluated in vivo, confirming a distinct antifungal activity against V. inaequalis for the tested natural material.

HPLC-based activity profiling--discovery of sanggenons as GABAA receptor modulators in the traditional Chinese drug Sang bai pi (Morus alba root bark).[Pubmed:22294264]

Planta Med. 2012 Mar;78(5):440-7.

EtOAc extracts from two batches of Morus alba root bark (Sang bai pi) potentiated gamma-aminobutyric acid (GABA)-induced chloride influx in Xenopus oocytes, which transiently expressed GABA (A) receptors of the subunit composition alpha(1)beta(2)gamma(2S). With the aid of HPLC-based activity profiling of the extract from the first batch, activity was traced to a peak subsequently identified as sanggenon G (3). The second batch had a different phytochemical profile, and HPLC-based activity profiling led to the identification of sanggenon C (4) and a stereoisomer of sanggenon D (2) as positive GABA (A) receptor modulators. The structurally related compound kuwanon L (1) was inactive. The sanggenons represent a new scaffold of positive GABA (A) receptor modulators.

Effects of prenylated flavonoids and biflavonoids on lipopolysaccharide-induced nitric oxide production from the mouse macrophage cell line RAW 264.7.[Pubmed:11105561]

Planta Med. 2000 Oct;66(7):596-600.

Certain flavonoid derivatives possess anti-inflammatory activity in vitro and in vivo. Besides their antioxidative properties and effects on the arachidonic acid metabolism including cyclooxygenase/lipoxygenase inhibition, some flavones and flavonols were previously found to show inhibitory activity on nitric oxide production by inducible nitric oxide synthase (iNOS; NOS type 2) through suppression of iNOS induction. As part of our continuing investigations, the effects of unique and minor flavonoids (prenylated flavonoids and biflavonoids) on nitric oxide production from lipopolysaccharide-induced macrophage cell line (RAW 264.7) were evaluated in order to establish their inhibitory activity on NO production and correlate this action with their in vivo anti-inflammatory potential. Among the derivatives tested, prenylated compounds including morusin, kuwanon C, and sanggenon D and biflavonoids such as bilobetin and ginkgetin were found to inhibit NO production from lipopolysaccharide (LPS)-induced RAW 264.7 cells at > 10 microM. Inhibition of nitric oxide production was mediated by suppression of iNOS enzyme induction but not by direct inhibition of iNOS enzyme activity. An exception was echinoisoflavanone that inhibited iNOS enzyme activity (IC50 = 83 microM) and suppressed iNOS enzyme induction as well. While most prenylated derivatives showed cytotoxicity to RAW cells at 10-100 microM, all biflavonoids tested were not cytotoxic. Since nitric oxide (NO) produced by inducible NO synthase (iNOS) plays an important role in inflammatory disorders, inhibition of NO production by these flavonoids may contribute, at least in part, to their anti-inflammatory and immunoregulating potential in vivo.

Effects of naturally occurring prenylated flavonoids on enzymes metabolizing arachidonic acid: cyclooxygenases and lipoxygenases.[Pubmed:11705451]

Biochem Pharmacol. 2001 Nov 1;62(9):1185-91.

Prenylated flavonoids are chemical entities having an isoprenyl, a geranyl, a 1,1-dimethylallyl, and/or a lavandulyl moiety as part of their flavonoid backbone structure. In this study, the effects of 19 naturally occurring prenylated flavonoids, isolated from medicinal plants, on cyclooxygenase (COX)-1 and COX-2 and on 5-lipoxygenase (5-LOX) and 12-LOX were investigated using [14C]arachidonic acid as a substrate. The homogenates of bovine platelets and polymorphonuclear leukocytes were used as COX-1, 12-LOX, and 5-LOX enzyme sources; the homogenate of aspirin-pretreated lipopolysaccharide-induced RAW 264.7 cells was used for the COX-2 enzyme source. Among the 19 prenylated flavonoids, morusin, kuwanon C, sanggenon B, sanggenon D and kazinol B inhibited COX-2 activity (ic(50) = 73-100 microM), but the potencies were far less than that of NS-398 (ic(50) = 2.9 microM). In contrast, many prenylated flavonoids, such as kuraridin, kuwanon C and sophoraisoflavanone A, inhibited COX-1 activity. Of the COX-1 inhibiting prenylated flavonoids, kuraridin, kurarinone, and sophoraflavanone G, all having a C-8 lavandulyl moiety, showed potent activity (ic(50) = 0.1 to 1 microM) comparable to that of indomethacin (ic(50) = 0.7 microM). Most of the prenylated flavonoids tested inhibited 5-LOX activity with ic(50) values ranging from 0.09 to 100 microM. Of these, only kuwanon C, papyriflavonol A and sophoraflavanone G showed inhibitory activity against 12-LOX at low concentration ranges (ic(50) = 19-69 microM) comparable to that of NDGA (ic(50) = 2.6 microM). Our results suggest that the position and the nature of the prenyl substitution greatly influence in vitro biological activities of these molecules.

Description

Sanggenon D is a Diels-Alder-type adduct from Chinese crude drug root bark of Morus cathayana. Sanggenon D possesses antioxidant and inhibits Pancreatic lipase (PL) with the an IC50 of 0.77 μM.

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