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Mangostin

PubChem CID
5281650
Structure
Mangostin_small.png
Mangostin_3D_Structure.png
Mangostin__Crystal_Structure.png
Molecular Formula
Synonyms
  • alpha-Mangostin
  • Mangostin
  • 6147-11-1
  • 1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one
  • Mangostine
Molecular Weight
410.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2024-12-28
Description
Alpha-mangostin is a member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1, 3 and 6, a methoxy group at position 7, an oxo group at position 9 and prenyl groups at positions 2 and 8. Isolated from the stems of Cratoxylum cochinchinense, it exhibits antioxidant, antimicrobial and antitumour activities. It has a role as an antineoplastic agent, an antimicrobial agent, an antioxidant and a plant metabolite. It is a member of xanthones, a member of phenols and an aromatic ether.
Mangostin is a plant/plant extract used in some OTC (over-the-counter) products. It is not an approved drug.
alpha-Mangostin has been reported in Garcinia cowa, Garcinia merguensis, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Mangostin.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 2
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

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
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GNRIZKKCNOBBMO-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(=CCC1=C(C2=C(C=C1O)OC3=C(C2=O)C(=C(C(=C3)O)OC)CC=C(C)C)O)C
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C24H26O6
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 NSC Number

2.3.13 Pharos Ligand ID

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,3,6,7-tetrahydroxy-2,5-bis(3-methyl-2-butenyl)-9H-xanthen-9-one
  • 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2- butenyl)-9H-xanthen-9-one
  • 7-O-methyl-4-desprenylcostatin
  • 7-O-methyl-gamma-mangostin
  • alfa-mangostin
  • alpha-mangosten
  • alpha-mangostin
  • gamma-mangostin
  • mangostin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
410.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
6.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
410.17293854 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
410.17293854 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
96.2Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
30
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
677
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Color / Form

Faint yellow to yellow powder
Sigma-Aldrich; Product Search alpha-Mangostin (CAS NO. 6147-11-1). Available from, as of Dec. 27, 2012: https://www.sigmaaldrich.com/united-states.html

3.2.3 Melting Point

180 - 181 °C

3.2.4 Solubility

Soluble in methanol
Sigma-Aldrich; Product Search alpha-Mangostin (CAS NO. 6147-11-1). Available from, as of Dec. 27, 2012: https://www.sigmaaldrich.com/united-states.html

3.2.5 Stability / Shelf Life

Stable under normal temperatures and pressures.
Clearsynth Labs Material Safety Data Sheet alpha-Mangostin. Available from, as of February 27, 2013: https://www.clearsynth.com/docs/MSD-CS-N-01473.pdf

3.2.6 Decomposition

Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Clearsynth Labs Material Safety Data Sheet alpha-Mangostin. Available from, as of February 27, 2013: https://www.clearsynth.com/docs/MSD-CS-N-01473.pdf

3.2.7 Polymerization

Has not been reported.
Clearsynth Labs Material Safety Data Sheet alpha-Mangostin. Available from, as of February 27, 2013: https://www.clearsynth.com/docs/MSD-CS-N-01473.pdf

3.2.8 Collision Cross Section

181.86 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

196.96 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

211.32 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

209.13 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111
198.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

Source of Spectrum
AJC-8-131-AM
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2.2 MS-MS

1 of 8
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Spectra ID
Ionization Mode
Negative
Top 5 Peaks

351.0853 100

339.0887 48.83

311.0963 35.16

307.0301 32.94

377.139 23.13

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Spectra ID
Ionization Mode
Negative
Top 5 Peaks

409.164 100

394.1368 44.06

351.0846 37.54

339.0792 22.17

365.1031 20.59

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4.2.3 LC-MS

1 of 11
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Authors
Cuthbertson DJ, Johnson SR, Lange BM, Institute of Biological Chemistry, Washington State University
Instrument
Agilent 1200 RRLC; Agilent 6520 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
10 ev
Column Name
Agilent C8 Cartridge Column 2.1X30mm 3.5 micron (guard); Agilent SB-Aq 2.1x50mm 1.8 micron (analytical)
Retention Time
11.16
Precursor m/z
411.1802
Precursor Adduct
[M+H]+
Top 5 Peaks

355.1155 999

411.1725 190

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License
CC BY-SA
2 of 11
View All
Authors
Cuthbertson DJ, Johnson SR, Lange BM, Institute of Biological Chemistry, Washington State University
Instrument
Agilent 1200 RRLC; Agilent 6520 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
10 ev
Column Name
Agilent C8 Cartridge Column 2.1X30mm 3.5 micron (guard); Agilent SB-Aq 2.1x50mm 1.8 micron (analytical)
Retention Time
11.171
Precursor m/z
409.1656
Precursor Adduct
[M-H]-
Top 5 Peaks

409.1666 999

339.082 50

408.1451 48

351.0865 35

365.098 31

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License
CC BY-SA

4.3 IR Spectra

4.3.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Indofine Chemical Company, Inc.
Catalog Number
M-002
Lot Number
97072
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Indofine Chemical Company, Inc.
Catalog Number
M-002
Lot Number
97072
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 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.
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...
Wang Y et al; Neuropharmacology. 62 (2): 871-81 (2012)

8 Pharmacology and Biochemistry

8.1 Human Metabolite Information

8.1.1 Cellular Locations

Membrane

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Biochemical/physiological actions: antioxidant and anti-inflammatory; alpha-mangostin has been shown to induce apoptosis via the mitochondrial pathway, reduce cell proliferation, and inhibit tumorigenesis.
Sigma-Aldrich; Product Search alpha-Mangostin (CAS NO. 6147-11-1). Available from, as of Dec. 27, 2012: https://www.sigmaaldrich.com/united-states.html
Antibacterial, 100 ug/mL; antiseptic; fungicide; pesticide
USDA; Dr. Duke's Phytochemical and Ethnobotanical Databases. Plants with a chosen chemical. Mangostin. Washington, DC: US Dept Agric, Agric Res Service. Available from, as of Dec 27, 2012: https://www.ars-grin.gov/duke/
MEDICATION

9.2 Methods of Manufacturing

From various parts of the mangosteen tree (Garcina mangostana L., Guttiferae)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 991

9.3 General Manufacturing Information

a-Mangostin is an oxygenated heterocyclic xanthone with remarkable pharmacological properties, but poor aqueous solubility and low oral bioavailability hinder its therapeutic application. ...
Aisha AF et al; J Pharm Sci. 101 (2): 815-25 (2012)

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 95.3% (41 of 43) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 4.7% (2 of 43) of reports.
Pictogram(s)
Acute Toxic
Signal
Danger
GHS Hazard Statements
H301 (88.4%): Toxic if swallowed [Danger Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P316, P321, P330, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 43 reports by companies from 4 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 2 of 43 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 3 notifications provided by 41 of 43 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 3 (88.4%)

10.2 Fire Fighting

10.2.1 Fire Fighting Procedures

In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.
Clearsynth Labs Material Safety Data Sheet alpha-Mangostin. Available from, as of February 27, 2013: https://www.clearsynth.com/docs/MSD-CS-N-01473.pdf

10.3 Accidental Release Measures

10.3.1 Cleanup Methods

Clean up spills immediately... Sweep up, then place into a suitable container for disposal.
Clearsynth Labs Material Safety Data Sheet alpha-Mangostin. Available from, as of February 27, 2013: https://www.clearsynth.com/docs/MSD-CS-N-01473.pdf

10.3.2 Disposal Methods

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

10.3.3 Preventive Measures

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Clearsynth Labs Material Safety Data Sheet alpha-Mangostin. Available from, as of February 27, 2013: https://www.clearsynth.com/docs/MSD-CS-N-01473.pdf

10.4 Handling and Storage

10.4.1 Storage Conditions

Store in a well closed container.
Clearsynth Labs Material Safety Data Sheet alpha-Mangostin. Available from, as of February 27, 2013: https://www.clearsynth.com/docs/MSD-CS-N-01473.pd

10.5 Stability and Reactivity

10.5.1 Hazardous Reactivities and Incompatibilities

Strong oxidizing agents, strong bases
Clearsynth Labs Material Safety Data Sheet alpha-Mangostin. Available from, as of February 27, 2013: https://www.clearsynth.com/docs/MSD-CS-N-01473.pd

10.6 Regulatory Information

REACH Registered Substance

11 Toxicity

11.1 Toxicological Information

11.1.1 Interactions

Altered membrane integrity and inflammation play a key role in cardiovascular damage. /The authors/ investigated the salubrious effect of exogenously administered alpha-mangostin against beta-adrenergic cathecolamine-induced cardiovascular toxicity with special reference to membrane ATPases, lysosomal hydrolases and inflammatory mediators TNF-alpha and Cyclooxygenase-2 (COX-2) expressions in albino rats. Induction of rats with isoproterenol (150 mg/kg body wt, ip) for 2 days resulted in a significant increase in the activities of serum and cardiac lysosomal hydrolases (beta-d-glucuronidase, beta-d-galactosidase, beta-d-N-acetylglucosaminidase, acid phosphatase and cathepsin-D). A significant increase in cardiac levels of sodium, calcium with a decrease in the level of potassium paralleled by abnormal activities of membrane-bound phosphatases (Na(+)-K(+) ATPase, Ca(2+) ATPase and Mg(2+) ATPase) were observed in the heart of ISO-administered rats. Cardiac TNF-alpha and COX-2 expressions were assessed by Western blotting. Cardiac TNF-alpha and COX-2 expressions were significantly elevated in ISO-intoxicated rats. Pre-co-treatment with alpha-mangostin (200mg/kg body wt.) orally for 8 days significantly attenuated these abnormalities and restored the levels to near normalcy when compared to ISO intoxicated group of rats. In conclusion, alpha-mangostin preserves the myocardial membrane integrity and extenuates anomalous TNF-alpha and COX-2 expressions by mitigating ISO-induced oxidative stress and cellular damage effectively. Restoration of cellular normalcy accredits the cytoprotective role of alpha-mangostin.
Sampath PD, Vijayaragavan K; Exp Toxicol Pathol. 60 (4-5): 357-64 (2008)
Cisplatin (CDDP) is a chemotherapeutic agent that produces nephrotoxicity associated with oxidative/nitrosative stress. alpha-Mangostin (alpha-M) is a xanthone extracted from mangosteen with antioxidant and anti-inflammatory properties. The purpose of this study was to evaluate the renoprotective effect of alpha-M on the CDDP-induced nephrotoxicity. alpha-M was administered (12.5 mg/kg/day, i.g.) for 10 days (7 days before and 3 days after CDDP injection). On day 7, rats were treated with a single injection of CDDP (7.5 mg/Kg, i.p.); 3 days after the rats were killed. alpha-M attenuated renal dysfunction, structural damage, oxidative/nitrosative stress, decrease in catalase expression and increase in mRNA levels of tumour necrosis factor alpha and transforming growth factor beta. In conclusion the renoprotective effect of alpha-M on CDDP-induced nephrotoxicity was associated with the attenuation in oxidative/nitrosative stress and inflammatory and fibrotic markers and preservation of catalase activity.
Perez-Rojas JM et al; Free Radic Res. 43 (11): 1122-32 (2009)
alpha-Mangostin, isolated from the stem bark of Garcinia mangostana L., was found to be active against vancomycin resistant Enterococci (VRE) and methicillin resistant Staphylococcus aureus (MRSA), with minimum inhibitory concentration (MIC) values of 6.25 and 6.25 to 12.5 ug/mL, respectively. Our studies showed synergism between alpha-mangostin and gentamicin (GM) against VRE, and alpha-mangostin and vancomycin hydrochloride (VCM) against MRSA. Further studies showed partial synergism between alpha-mangostin and commercially available antibiotics such as ampicillin and minocycline. These findings suggested that alpha-mangostin alone or in combination with GM against VRE and in combination with VCM against MRSA might be useful in controlling VRE and MRSA infections.
Sakagami Y et al; Phytomedicine. 12 (3): 203-8 (2005)

11.1.2 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

11.1.3 Human Toxicity Excerpts

/ALTERNATIVE and IN VITRO TESTS/ /The authors/ examined the effects of six xanthones from the pericarps of mangosteen, Garcinia mangostana, on the cell growth inhibition of human leukemia cell line HL60. All xanthones displayed growth inhibitory effects. Among them, alpha-mangostin showed complete inhibition at 10 uM through the induction of apoptosis.
Matsumoto K et al; J Nat Prod. 66 (8): 1124-7 (2003)
/ALTERNATIVE and IN VITRO TESTS/ The oxidation of low density lipoprotein (LDL) may play an important role in atherosclerosis. /The authors/ investigated the possible antioxidant effects of mangostin, isolated from Garcinia mangostana, on metal ion dependent (Cu2+) and independent (aqueous peroxyl radicals) oxidation of human LDL. Mangostin prolonged the lagtime to both metal ion dependent and independent oxidation of LDL in a dose dependent manner over 5 to 50 uM as monitored by the formation of conjugated dienes at 234 nm (P < 0.001). There was no significant effect of mangostin on the rate at which conjugated dienes were formed in the uninhibited phase of oxidation. Levels of thiobarbituric reactive substances (TBARS) generated in LDL were measured 4 and 24 hours after oxidation with 5 uM Cu2+ in the presence or absence of 50 uM or 100 uM mangostin. /The authors/ observed an inhibition of TBARS formation with 100 uM mangostin at 4 hours (P = 0.027) but not at 24 hours (P = 0.163). Similar results were observed in the presence of 50 uM mangostin. Mangostin, at 100 uM, retarded the relative electrophoretic mobility of LDL at both 4 and 24 hours after Cu2+ induced oxidation. Mangostin (100 uM) significantly inhibited the consumption of alpha-tocopherol in the LDL during Cu2+ initiated oxidation over a 75 minute period (P < 0.001). From these results, /the authors/ conclude that mangostin is acting as a free radical scavenger to protect the LDL from oxidative damage in this in vitro system.
Williams P et al; Free Radic Res. 23 (2): 175-84 (1995)
/ALTERNATIVE and IN VITRO TESTS/ /The authors/ investigated the antiproliferative effects of four structurally similar prenylated xanthones, alpha-mangostin, beta-mangostin, gamma-mangostin, and methoxy-beta-mangostin, in human colon cancer DLD-1 cells. These xanthones differ in the number of hydroxyl and methoxy groups. Except for methoxy-beta-mangostin, the other three xanthones strongly inhibited cell growth at 20 uM and their antitumor efficacy was correlated with the number of hydroxyl groups. Hoechst 33342 nuclear staining and nucleosomal DNA-gel electrophoresis revealed that the antiproliferative effects of alpha- and gamma-mangostin, but not that of beta-mangostin, were associated with apoptosis. It was also shown that their antiproliferative effects were associated with cell-cycle arrest by affecting the expression of cyclins, cdc2, and p27; G1 arrest was by alpha-mangostin and beta-mangostin, and S arrest by gamma-mangostin. These findings provide a relevant basis for the development of xanthones as an agent for cancer prevention and combination therapy with anti-cancer drugs.
Matsumoto K et al; Bioorg Med Chem. 13 (21): 6064-9 (2005)
/ALTERNATIVE and IN VITRO TESTS/ Despite the progress in colon cancer treatment, relapse is still a major obstacle. Hence, new drugs or drug combinations are required in the battle against colon cancer. a-Mangostin and betulinic acid (BA) are cytotoxic compounds that work by inducing the mitochondrial apoptosis pathway, and cisplatin is one of the most potent broad spectrum anti-tumor agents. This study aims to investigate the enhancement of BA cytotoxicity by a-mangostin, and the cytoprotection effect of a-mangostin and BA on cisplatin-induced cytotoxicity on HCT 116 human colorectal carcinoma cells. Cytotoxicity was investigated by the XTT cell proliferation test, and the apoptotic effects were investigated on early and late markers including caspases-3/7, mitochondrial membrane potential, cytoplasmic shrinkage, and chromatin condensation. The effect of a-mangostin on four signalling pathways was also investigated by the luciferase assay. a-Mangostin and BA were more cytotoxic to the colon cancer cells than to the normal colonic cells, and both compounds showed a cytoprotective effect against cisplatin-induced cytotoxicity. On the other hand, a-mangostin enhanced the cytotoxic and apoptotic effects of BA. Combination therapy hits multiple targets, which may improve the overall response to the treatment, and may reduce the likelihood of developing drug resistance by the tumor cells. Therefore, a-mangostin and BA may provide a novel combination for the treatment of colorectal carcinoma. The cytoprotective effect of the compounds against cisplatin-induced cytotoxicity may find applications as chemopreventive agents against carcinogens, irradiation and oxidative stress, or to neutralize cisplatin side effects.
Aisha AF et al; Molecules. 17 (3): 2939-54 (2012)
For more Human Toxicity Excerpts (Complete) data for Mangostin (9 total), please visit the HSDB record page.

11.1.4 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ There is a need to characterize promising dietary agents for chemoprevention and therapy of prostate cancer (PCa). /The authors/ examined the anticancer effect of a-mangostin, derived from the mangosteen fruit, in human PCa cells and its role in targeting cell cycle-related proteins involved in prostate carcinogenesis. Using an 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, /the authors/ found that a-mangostin significantly decreases PCa cell viability in a dose-dependent manner. Further analysis using flow cytometry identified cell cycle arrest along with apoptosis. To establish a more precise mechanism of action, /the authors/ performed a cell free biochemical kinase assay against multiple cyclins/cyclin-dependent kinases (CDKs) involved in cell cycle progression; the most significant inhibition in the cell free-based assays was CDK4, a critical component of the G1 phase. Through molecular modeling, /the authors/ evaluated a-mangostin against the adenosine triphosphate-binding pocket of CDK4 and propose three possible orientations that may result in CDK4 inhibition. /The authors/ then performed an in vivo animal study to evaluate the ability of a-mangostin to suppress tumor growth. Athymic nude mice were implanted with 22Rv1 cells and treated with vehicle or a-mangostin (100 mg/kg) by oral gavage. At the conclusion of the study, mice in the control cohort had a tumor volume of 1190 cu mm, while the treatment group had a tumor volume of 410 cu mm (P < 0.01). The ability of a-mangostin to inhibit PCa in vitro and in vivo suggests a-mangostin may be a novel agent for the management of PCa.
Johnson JJ et al; Carcinogenesis. 33 (2): 413-9 (2012)
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ The purpose of this study was to examine whether crude alpha-mangostin (a major xanthone derivative in mangosteen pericarp (Garcinia mangostana)) has short-term chemopreventive effects on putative preneoplastic lesions involved in rat colon carcinogenesis. The crude preparation was obtained by simple recrystallization of an ethylacetate extract of mangosteen pericarps. A total of 33 five-week-old male F344 rats were randomly divided into 5 experimental groups. Rats in groups 1-3 were given a subcutaneous injection of 1,2-dimethylhydrazine (DMH)(40 mg/kg body weight) once a week for 2 weeks. Starting one week before the first injection of DMH, rats in groups 2 and 3 were fed a diet containing 0.02% and 0.05% crude alpha-mangostin, respectively, for 5 weeks. Rats in group 4 also received the diet containing 0.05% crude alpha-mangostin, while rats in group 5 served as untreated controls. The experiment was terminated 5 weeks after the start. Dietary administration of crude alpha-mangostin at both doses significantly inhibited the induction and/or development of aberrant crypt foci (ACF) (P<0.05 for 0.02% crude alpha-mangostin, P<0.01 for 0.05% crude alpha-mangostin), when compared to the DMH-treated group (group 1). Moreover, treatment of rats with 0.05% crude alpha-mangostin significantly decreased dysplastic foci (DF) (P<0.05) and beta-catenin accumulated crypts (BCAC) (P<0.05), to below the group 1 values. The proliferating cell nuclear antigen (PCNA) labeling indices of colon epithelium and focal lesions in groups 2 and 3 were also significantly lower than in group 1 and this effect occurred in a dose dependent manner of the crude alpha-mangostin. This finding that crude alpha-mangostin has potent chemopreventive effects in our short-term colon carcinogenesis bioassay system suggests that longer exposure might result in suppression of tumor development.
Nabandith V et al; Asian Pac J Cancer Prev. 5 (4): 433-8 (2004)
/ENDOCRINE MODULATION/ Severe developmental and reproductive disorders in wild animals have been linked to high exposure to persistent environmental chemicals with hormonal activity. These adverse effects of environmental estrogens have raised considerable concern and have received increasing attention. Although numerous chemicals with the capacity to interfere with the estrogen receptor (ER) have been identified, information on their molecular mechanism of action and their relative potency is rather limited. For the endometrium, the lack of information is due to the lack of a suitable experimental model. /The authors/ investigated the functions of phytoestrogens in an endometrial-derived model, RUCA-I rat endometrial adenocarcinoma cells. The cells were cultured on a reconstituted basement membrane to preserve their functional differentiation and estrogen responsiveness. /The authors/ assessed the relative binding affinity to the estrogen receptor of the selected phytoestrogens coumestrol, genistein, daidzein, and the putative phytoestrogen mangostin compared to estradiol by a competitive Scatchard analysis. The following affinity ranking was measured: 17beta-estradiol >>> coumestrol > genistein > daidzein >>> mangostin. In addition, /the authors/ investigated the capacity of these compounds to promote the increased production of complement C3, a well-known estradiol-regulated protein of the rat endometrium. All substances tested increased the production of complement C3, although different concentrations were necessary to achieve equivalent levels of induction compared to estradiol. Mechanistically /the authors/ were able to demonstrate that the increase of complement C3 production was mediated by primarily increasing its steady-state mRNA level. These findings indicate that RUCA-I cells represent a sensitive model system to elucidate relative potencies and functions of environmental estrogens in an endometrium-derived model.
Hopert AC et al; Environ Health Perspect. 106 (9): 581-6 (1998)
/ALTERNATIVE and IN VITRO TESTS/ 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...
Wang Y et al; Neuropharmacology. 62 (2): 871-81 (2012)
For more Non-Human Toxicity Excerpts (Complete) data for Mangostin (18 total), please visit the HSDB record page.

11.2 Ecological Information

11.2.1 Environmental Fate / Exposure Summary

Mangostin's production and use as an antibacterial may result in its release to the environment through various waste streams. Mangostin is found in the plant species Garcinia mangostana, Hydnocarpus octandra, and H. venenata. If released to air, an estimated vapor pressure of 9.4X10-15 mm Hg at 25 °C indicates mangostin will exist solely in the particulate phase in the atmosphere. Particulate-phase mangostin will be removed from the atmosphere by wet and dry deposition. Mangostin contains chromophores that absorb at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, mangostin is expected to have no mobility based upon an estimated Koc of 7.6X10+5. However, the estimated pKa values of mangostin are 3.68, 7.69 and 9.06, indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Biodegradation data in soil or water were not available. If released into water, mangostin is expected to adsorb to suspended solids and sediment based upon the estimated Koc. The estimated pKa values indicate mangostin will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process. An estimated BCF of 1600 suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to mangostin may occur through inhalation and dermal contact with this compound at workplaces where mangostin is produced or used. Exposure to mangostin among the general population may be limited to those administered drugs containing mangostin. (SRC)

11.2.2 Natural Pollution Sources

Mangostin is found in the plant species Garcinia mangostana(1,2), Hydnocarpus octandra, and H. venenata(2).
(1) USDA; Dr. Duke's Phytochemical and Ethnobotanical Databases. Plants with a chosen chemical. Mangostin. Washington, DC: US Dept Agric, Agric Res Service. Available from, as of Dec 27, 2012: https://www.ars-grin.gov/duke/
(2) ChemSpider; Structure-based Chemistry Information. rev. May 9, 2008. Mangostin. (CAS No. 6147-11-1) ChemZoo, Inc., info@chemspider.com, (919) 341-8375. Available from, as of Dec 27, 2012: https://www.chemspider.com

11.2.3 Artificial Pollution Sources

Mangostin's production and use as an antibacterial(1) may result in its release to the environment through various waste streams(SRC).
(1) USDA; Dr. Duke's Phytochemical and Ethnobotanical Databases. Plants with a chosen chemical. Mangostin. Washington, DC: US Dept Agric, Agric Res Service. Available from, as of Dec 27, 2012: https://www.ars-grin.gov/duke/

11.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7.6X10+5(SRC), determined from a structure estimation method(2), indicates that mangostin is expected to be immobile in soil(SRC). However, the estimated pKa values of mangostin are 3.68, 7.69 and 9.06(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Mangostin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.4X10-15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2012).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Dec. 27, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) SPARC; pKa/property server. Ver 4.6., Jan, 2012. Available from, as of Mar 24, 2013: https://archemcalc.com/sparc/
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7.6X10+5(SRC), determined from a structure estimation method(2), indicates that mangostin is expected to adsorb to suspended solids and sediment(SRC). The estimated pKa values of 3.68, 7.69 and 9.06(3) indicate mangostin will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(4), an estimated BCF of 1600(SRC), from an estimated log Kow of 7.71(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). Biodegradation data in water were not available(SRC, 2012).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Dec 27, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) SPARC; pKa/property server. Ver 4.6., Jan, 2012. Available from, as of Mar 24, 2013: https://archemcalc.com/sparc/
(4) Franke C et al; Chemosphere 29: 1501-14 (1994)
(5) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), mangostin, which has an estimated vapor pressure of 9.4X10-15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase mangostin may be removed from the air by wet and dry deposition(SRC). Mangostin contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Dec 27, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

11.2.5 Environmental Biodegradation

Biodegradation data in soil or water were not available. (SRC, 2013)

11.2.6 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of mangostin with photochemically-produced hydroxyl radicals has been estimated as 3.8X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 20.4 minutes at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Mangostin is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Mangostin contains chromophores that absorb at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)

11.2.7 Environmental Bioconcentration

An estimated BCF of 1600 was calculated in fish for mangostin(SRC), using an estimated log Kow of 7.71(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Dec 27, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

11.2.8 Soil Adsorption / Mobility

Using a structure estimation method based on molecular connectivity indices(1), the Koc of mangostin can be estimated to be 7.56X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that mangostin is expected to be immobile in soil. However, the estimated pKa values of mangostin are 3.68, 7.69 and 9.06(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2011. Available from, as of Dec 27, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) SPARC; pKa/property server. Ver 4.6., Jan, 2012. Available from, as of Mar 24, 2013: https://archemcalc.com/sparc/
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)

11.2.9 Volatilization from Water / Soil

The estimated pKa values of 3.68, 7.69 and 9.06(1) indicate mangostin will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water or moist soil surfaces is not expected to be an important fate process. Mangostin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.44X10-15 mm Hg (SRC), determined from a fragment constant method(2).
(1) SPARC; pKa/property server. Ver 4.6., Jan, 2012. Available from, as of Mar 24, 2013: https://archemcalc.com/sparc/
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.1. Jan, 2010. Available from, as of Dec 27, 2012: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm

11.2.10 Plant Concentrations

Mangostin plant concentration(1).
Species
Garcinia mangostana L.
Common name
Mangosteen, Mangostin
Part
Latex exudate
Concentration (ppm)
300,000-500,000
Species
Garcinia mangostana L.
Common name
Mangosteen, Mangostin
Part
Fruit
Concentration (ppm)
not quantified
(1) USDA; Dr. Duke's Phytochemical and Ethnobotanical Databases. Plants with a chosen chemical. Mangostin. Washington, DC: US Dept Agric, Agric Res Service. Available from, as of Dec 27, 2012: https://www.ars-grin.gov/duke/

11.2.11 Probable Routes of Human Exposure

Occupational exposure to mangostin may occur through inhalation and dermal contact with this compound at workplaces where mangostin is produced or used. Exposure to mangostin among the general population may be limited to those administered drugs containing mangostin. (SRC)

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Nature Journal References

13.7 Chemical Co-Occurrences in Literature

13.8 Chemical-Gene Co-Occurrences in Literature

13.9 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 KEGG: Lipid

18.4 KEGG: Phytochemical Compounds

18.5 ChemIDplus

18.6 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

18.7 ChEMBL Target Tree

18.8 UN GHS Classification

18.9 EPA CPDat Classification

18.10 CCSBase Classification

18.11 EPA DSSTox Classification

18.12 LOTUS Tree

18.13 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. BindingDB
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  9. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  10. European Chemicals Agency (ECHA)
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    1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-
    https://echa.europa.eu/substance-information/-/substanceinfo/100.208.637
    1,3,6-Trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen- (EC: 683-120-1)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213652
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  12. Hazardous Substances Data Bank (HSDB)
  13. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  14. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  15. ChEBI
  16. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  17. ChEMBL
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  21. NIST Mass Spectrometry Data Center
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  22. Japan Chemical Substance Dictionary (Nikkaji)
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  28. Metabolomics Workbench
  29. Nature Chemistry
  30. Pharos
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  31. Protein Data Bank in Europe (PDBe)
  32. RCSB Protein Data Bank (RCSB PDB)
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    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
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  33. SpectraBase
  34. Springer Nature
  35. Thieme Chemistry
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  40. Medical Subject Headings (MeSH)
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  41. GHS Classification (UNECE)
  42. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  43. PATENTSCOPE (WIPO)
CONTENTS