α-Mangostin
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| Category | Bioactive by-products |
| Catalog number | BBF-04170 |
| CAS | 6147-11-1 |
| Molecular Weight | 410.46 |
| Molecular Formula | C24H26O6 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04170 | 1 g | $367 | In stock |
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Add to cartDescription
It was isolated from Garcinia mangostana Linn (Guttiferae). It is an anti-inflammatory agent. It can inhibit the activity of COX-2, an inhibitor of mutant IDH1 (IDH1-R132H).
Specification
| Synonyms | 1,3,6-Trihydroxy-7-methoxy-2,8-bis(3,3-dimethylallyl)xanthone; α-Mangosten; NSC 139154; NSC 27593; NSC 30552 |
| Storage | Store at 2-8°C |
| IUPAC Name | 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one |
| Canonical SMILES | CC(=CCC1=C(C=C2C(=C1O)C(=O)C3=C(C(=C(C=C3O2)O)OC)CC=C(C)C)O)C |
| InChI | InChI=1S/C24H26O6/c1-12(2)6-8-14-16(25)10-19-21(22(14)27)23(28)20-15(9-7-13(3)4)24(29-5)17(26)11-18(20)30-19/h6-7,10-11,25-27H,8-9H2,1-5H3 |
| InChI Key | GNRIZKKCNOBBMO-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Crystals |
| Boiling Point | 640.1±55.0°C at 760 Torr |
| Melting Point | 180-181°C |
| Flash Point | 220.3±25.0 °C |
| Density | 1.265±0.06 g/cm3 |
| Solubility | Soluble in DMSO (37 mg/mL) |
Reference Reading
1.In vivo Antimalarial Activity of α-Mangostin and the New Xanthone δ-Mangostin.
Upegui Y;Robledo SM;Gil Romero JF;Quiñones W;Archbold R;Torres F;Escobar G;Nariño B;Echeverri F Phytother Res. 2015 Aug;29(8):1195-201. doi: 10.1002/ptr.5362. Epub 2015 May 5.
Based on the previously reported in vitro antiplasmodial activity of several xanthones from Garcinia mangostana, two xanthones, α-mangostin and a new compound, δ-mangostin, were isolated from mangosteen husk, and the in vitro antiplasmodial and cytotoxic effects were determined. α-Mangostin was more active against the resistant Plasmodium falciparum chloroquine-resistant (FCR3) strain (IC50 = 0.2 ± 0.01 μM) than δ-mangostin (IC50 = 121.2 ± 1.0 μM). Furthermore, the therapeutic response according to the administration route was evaluated in a Plasmodium berghei malarial murine model. The greatest therapeutic response was obtained with intraperitoneal administration; these xanthones reduced parasitemia by approximately 80% with a daily dose of 100 mg/kg administered twice a day for 7 days of treatment. Neither compound was effective by oral administration. Noticeable toxicological effects were not observed. In addition to the antimalarial effect of these xanthones isolated from G. mangostana husk, the availability of larger amounts of husk raw material to purify the bioactive xanthones is advantageous, permitting additional preclinical assays or chemical transformations to enhance the biological activity of these substances.
2.Altered mRNA expression related to the apoptotic effect of three xanthones on human melanoma SK-MEL-28 cell line.
Wang JJ;Zhang W;Sanderson BJ Biomed Res Int. 2013;2013:715603. doi: 10.1155/2013/715603. Epub 2013 Sep 23.
We previously demonstrated that α-mangostin, γ-mangostin, and 8-deoxygartanin have significant cytotoxic effects on human melanoma SK-MEL-28 cell line. The current study revealed the underlying mechanisms. α-Mangostin (7.5 μg/mL) activated caspase activity, with a 3-fold and 4-fold increased caspase 8 and 9 activity, respectively. The molecular mechanisms were investigated by qRT-PCR for mRNA related to cell cycle arrest in G1 phase (p21(WAF1) and cyclin D1), apoptosis (cytochrome C, Bcl-2, and Bax), and survival pathways (Akt1, NFκB, and IκBα). α-Mangostin significantly upregulated mRNA expression of cytochrome C and p21(WAF1) and downregulated that of cyclin D1, Akt1, and NFκB. γ-Mangostin significantly downregulated mRNA expression of Akt1 and NFκB and upregulated p21(WAF1) and IκBα. 8-Deoxygartanin significantly upregulated the mRNA expression of p21(WAF1) and downregulated that of cyclin D1 and NFκB. The three xanthones significantly inhibited the mRNA expression of the BRAF V600E mutation. Moreover, α-mangostin and γ-mangostin significantly downregulated Akt phosphorylation at Ser473. In conclusion, the three xanthones induced an inhibitory effect on SK-MEL-28 cells by modulating the molecular targets involved in the apoptotic pathways.
3.The mode of inhibitory action of alpha-mangostin, a novel inhibitor, on the sarcoplasmic reticulum Ca(2+)-pumping ATPase from rabbit skeletal muscle.
Furukawa K;Shibusawa K;Chairungsrilerd N;Ohta T;Nozoe S;Ohizumi Y Jpn J Pharmacol. 1996 Aug;71(4):337-40.
alpha-Mangostin, the principal ingredient of the fruit hull of Garcinia mangostana, caused a concentration-dependent decrease in the activities of both Ca(2+)-ATPase and Ca(2+)-transport of the sarcoplasmic reticulum from rabbit skeletal muscle with an IC50 value of 5 microM. Neither Ca2+ release nor other enzyme activities were affected by alpha-mangostin. Kinetic analysis of the inhibitory effects of alpha-mangostin on Ca(2+)-ATPase suggests that the inhibition of the ATPase is a noncompetitive-type with respect to ATP or Ca2+. alpha-Mangostin may become a useful pharmacological tool for clarifying the physiological functions of Ca(2+)-pumping ATPase and sarcoplasmic reticulum.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
