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Chemistry

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Also known as: Mangostin, 6147-11-1, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9h-xanthen-9-one, Mangostine, Alpha-mangostin, 95%, A-mangostin
Molecular Formula
C24H26O6
Molecular Weight
410.5  g/mol
InChI Key
GNRIZKKCNOBBMO-UHFFFAOYSA-N
FDA UNII
U6RIV93RU1

Mangostin
mangostin is a natural product found in Garcinia merguensis, Garcinia cowa, and other organisms with data available.
1 2D Structure

Mangostin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
2.1.2 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
2.1.3 InChI Key
GNRIZKKCNOBBMO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=CCC1=C(C2=C(C=C1O)OC3=C(C2=O)C(=C(C(=C3)O)OC)CC=C(C)C)O)C
2.2 Other Identifiers
2.2.1 UNII
U6RIV93RU1
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,3,6,7-tetrahydroxy-2,5-bis(3-methyl-2-butenyl)-9h-xanthen-9-one

2. 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2- Butenyl)-9h-xanthen-9-one

3. 7-o-methyl-4-desprenylcostatin

4. 7-o-methyl-gamma-mangostin

5. Alfa-mangostin

6. Alpha-mangosten

7. Gamma-mangostin

8. Mangostin

2.3.2 Depositor-Supplied Synonyms

1. Mangostin

2. 6147-11-1

3. 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9h-xanthen-9-one

4. Mangostine

5. Alpha-mangostin, 95%

6. A-mangostin

7. Nsc-30552

8. 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one

9. Nsc27593

10. Nsc30552

11. U6riv93ru1

12. Chembl323197

13. Chebi:67547

14. 1,3,6-trihydroxy-7-methoxy-2,8-diprenylxanthone

15. Tnp00140

16. 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9h-xanthen-9-one

17. Nsc-27593

18. Nsc-139154

19. 1,3,6-trihydroxy-7-methoxy-2,8-bis(3,3-dimethylallyl)xanthone

20. 9h-xanthen-9-one, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-

21. 1,3,6-trihydroxy-7-methoxy-2,8-di(3-methyl-2-butenyl)xanthone

22. 3,6,8-trihydroxy-2-methoxy-1,7-bis(3-methylbut-2-enyl)xanthen-9-one

23. 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)-9h-xanthen-9-one

24. Xanthen-9-one, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-

25. 7-o-methyl-4-desprenylcostatin

26. 9h-xanthen-9-one,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-

27. Xanthen-9-one,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-

28. .alpha.-mangosten

29. .alpha.-mangostin

30. Mfcd00135200

31. Nsc 27593

32. Nsc 30552

33. Nsc 139154

34. Spectrum_001726

35. Specplus_000574

36. Mangostin [mi]

37. Mangostin [inci]

38. Spectrum2_001620

39. Spectrum3_001297

40. Spectrum4_001911

41. Spectrum5_000622

42. Unii-u6riv93ru1

43. Bspbio_002933

44. Kbiogr_002529

45. Kbioss_002206

46. Bidd:er0576

47. Divk1c_006670

48. Schembl354735

49. Spectrum1504015

50. Spectrum1505128

51. 7-o-methyl-.gamma.-mangostin

52. Spbio_001659

53. Hsdb 8103

54. Kbio1_001614

55. Kbio2_002206

56. Kbio2_004774

57. Kbio2_007342

58. Kbio3_002153

59. Dtxsid00210420

60. Act09245

61. Bcp13253

62. Hy-n0328

63. Zinc5430812

64. Alpha-mangostin, >=98% (hplc)

65. 1,7-bis(3-methylbut-2-enyl)-3,6,8-trihydroxy-2-methoxyxanthen-9-one

66. Bdbm50214969

67. Ccg-36465

68. Nsc139154

69. S3804

70. 9h-xanthen-9-one,1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-

71. Akos015912806

72. Ac-6089

73. Cs-6435

74. Ds-3359

75. Sdccgmls-0066796.p001

76. 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-9h-xanthen-9-one

77. Ncgc00017251-01

78. Ncgc00017251-02

79. Ncgc00017251-03

80. Ncgc00017251-04

81. Ncgc00017251-05

82. Ncgc00095730-01

83. Ncgc00095730-02

84. Ncgc00095730-03

85. Ncgc00178385-01

86. Db-053898

87. Ft-0635997

88. M2793

89. N1590

90. N2590

91. 147m111

92. A833244

93. Q909638

94. Sr-05000002649

95. Q-100010

96. Sr-05000002649-1

97. Brd-k11991978-001-02-6

98. Brd-k11991978-001-03-4

99. 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)-9-xanthenone

100. 1,3,6-trihydroxy-7-methoxy-2,8-bis-(3-methyl-but-2-enyl)-xanthen-9-one

101. 2-methoxy-1,7-bis(3-methylbut-2-enyl)-3,6,8-tris(oxidanyl)xanthen-9-one

102. (c) Paragraph Sign-mangostin Pound>>alpha-mangostin; Nsc 139154; Nsc 27593; Nsc 30552

103. 1,3,6-trihydroxy-7-methoxy-2,8-bis-(3-methyl-2-buten-1-yl)-9h-xanthen-9-one

104. 9h-xanthen-9-one, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 410.5 g/mol
Molecular Formula C24H26O6
XLogP36.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass410.17293854 g/mol
Monoisotopic Mass410.17293854 g/mol
Topological Polar Surface Area96.2 Ų
Heavy Atom Count30
Formal Charge0
Complexity677
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

*Xanthones; Protein Kinase Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 2012)


/EXPERIMENTAL THERAPY/The mangosteen fruit has a long history of medicinal use in Chinese and Ayurvedic medicine. Recently, the compound a-mangostin, which is isolated from the pericarp of the fruit, was shown to induce cell death in various types of cancer cells in in vitro studies. This led us to investigate the antitumor growth and antimetastatic activities of a-mangostin in an immunocompetent xenograft model of mouse metastatic mammary cancer having a p53 mutation that induces a metastatic spectrum similar to that seen in human breast cancers. Mammary tumors, induced by inoculation of BALB/c mice syngeneic with metastatic BJMC3879luc2 cells, were subsequently treated with a-mangostin at 0, 10 and 20 mg/kg/day using mini-osmotic pumps and histopathologically examined. To investigate the mechanisms of antitumor ability by a-mangostin, in vitro studies were also conducted. Not only were in vivo survival rates significantly higher in the 20 mg/kg/day a-mangostin group versus controls, but both tumor volume and the multiplicity of lymph node metastases were significantly suppressed. Apoptotic levels were significantly increased in the mammary tumors of mice receiving 20 mg/kg/day and were associated with increased expression of active caspase-3 and -9. Other significant effects noted at this dose level were decreased microvessel density and lower numbers of dilated lymphatic vessels containing intraluminal tumor cells in mammary carcinoma tissues. In vitro, a-mangostin induced mitochondria-mediated apoptosis and G1-phase arrest and S-phase suppression in the cell cycle. Since activation by Akt phosphorylation plays a central role in a variety of oncogenic processes, including cell proliferation, anti-apoptotic cell death, angiogenesis and metastasis, we also investigated alterations in Akt phosphorylation induced by a-mangostin treatment both in vitro and in vivo. Quantitative analysis and immunohistochemistry showed that a-mangostin significantly decreased the levels of phospho-Akt-threonine 308 (Thr308), but not serine 473 (Ser473), in both mammary carcinoma cell cultures and mammary carcinoma tissues in vivo. Since lymph node involvement is the most important prognostic factor in breast cancer patients, the antimetastatic activity of a-mangostin as detected in mammary cancers carrying a p53 mutation in the present study may have specific clinical applications. In addition, a-mangostin may have chemopreventive benefits and/or prove useful as an adjuvant therapy, or as a complementary alternative medicine in the treatment of breast cancer.

Shibata M-A et al; BMC Medicine 9: 69 (2011) https://www.biomedcentral.com/1741-7015/9/69


/EXPERIMENTAL THERAPY/This study was conducted to examine the activity of alpha-mangostin against Candida albicans, the most important microorganism implicated in oral candidiasis. Its activity was compared to Clotrimazole and Nystatin. Results showed that alpha-mangostin was effective against C. albicans, the minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) were 1,000 and 2,000 ug/mL, respectively. The C. albicans killing activity of alpha-mangostin was more effective than Clotrimazole and Nystatin. The cytotoxicity of alpha-mangostin was determined and it was found that alpha-mangostin at 4,000 ug/mL was not toxic to human gingival fibroblast for 480 min. The strong antifungal activity and low toxicity of alpha-mangostin make it a promising agent for treatment of oral candidiasis.

PMID:19776506 Kaomongkolgit R et al; J Oral Sci. 51(3):401-6 (2009)


/EXPERIMENTAL THERAPY/ Alzheimer's disease (AD) is a progressive neurodegenerative disease characterized by the accumulation of beta-sheet-rich amyloid oligomers or fibrils which are associated with cellular toxicity in the brain. Inhibition of Abeta aggregation could be a viable therapeutic strategy for slowing and/or preventing the progress of AD. Here /the authors/ reported that a-mangostin (a-M), a polyphenolic xanthone derivative from mangosteen, concentration-dependently attenuated the neurotoxicity induced by Abeta-(1-40) or Abeta-(1-42) oligomers (EC(50) = 3.89 nM, 4.14 nM respectively) as observed by decreased cell viability and impaired neurite outgrowth in primary rat cerebral cortical neurons. Molecular docking and dynamics simulations demonstrated that a-M could potentially bind to Abeta and stabilize alpha-helical conformation. a-M was found to directly dissociate Abeta-(1-40) and Abeta-(1-42) oligomers by blotting with oligomer-specific antibodies. ThioflavinT fluorescence assay and electron microscopy imaging further demonstrated that a-M blocked the fibril formation as well as disturbed the pre-formed fibrils. Taken together, /these/ results indicate that a-M is capable /of/ inhibiting and dissociating the Abeta aggregation, which could contribute to its effect of attenuating Abeta oligomers-induced neurotoxicity. Thus, a-M could be a great potential candidate for AD treatment...

PMID:21958557 Wang Y et al; Neuropharmacology. 62 (2): 871-81 (2012)


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Mangostin manufacturers, exporters & distributors 1

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API | Excipient name

Mangostin

Synonyms

6147-11-1, 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9h-xanthen-9-one, Mangostine, Alpha-mangostin, 95%, A-mangostin, Nsc-30552

Cas Number

6147-11-1

Unique Ingredient Identifier (UNII)

U6RIV93RU1

About Mangostin

mangostin is a natural product found in Garcinia merguensis, Garcinia cowa, and other organisms with data available.

Mangostin Manufacturers

A Mangostin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Mangostin, including repackagers and relabelers. The FDA regulates Mangostin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Mangostin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Mangostin manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Mangostin Suppliers

A Mangostin supplier is an individual or a company that provides Mangostin active pharmaceutical ingredient (API) or Mangostin finished formulations upon request. The Mangostin suppliers may include Mangostin API manufacturers, exporters, distributors and traders.

click here to find a list of Mangostin suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Mangostin NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Mangostin as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Mangostin API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Mangostin as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Mangostin and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Mangostin NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Mangostin suppliers with NDC on PharmaCompass.

Mangostin GMP

Mangostin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Mangostin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Mangostin GMP manufacturer or Mangostin GMP API supplier for your needs.

Mangostin CoA

A Mangostin CoA (Certificate of Analysis) is a formal document that attests to Mangostin's compliance with Mangostin specifications and serves as a tool for batch-level quality control.

Mangostin CoA mostly includes findings from lab analyses of a specific batch. For each Mangostin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Mangostin may be tested according to a variety of international standards, such as European Pharmacopoeia (Mangostin EP), Mangostin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Mangostin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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