What are Xanthones?

Xanthones are organic compounds, powerful phytonutrients found in few plants and are composed of stable carbon-structure molecules. They have been demonstrated to be effective in inhibiting inflammation as well as serve as potent antioxidants in combating free radical damage.

There have been about 200 xanthones found in nature so far and research continue to identify more. Some tropical fruits contain Xanthones such as the Mangosteen which contains 40 different Xanthones which is believed to be one of the highest concentrations of xanthones in any eatable source.

"Xanthones show considerable biological activity, and it is surprising that none of them so far have an established use in medicine." - Taylor and Frost, Phytochemical Dictionary, 1983

Xanthones are though to be the most portent source of anti-oxidants, much more powerful than vitamin C and vitamin E. Some doctors refer to Xanthones as Super Antioxidants.

A Xanthone is an organic compound with the molecular formula C13H8O2.

Xanthones are comprised of planar-six carbon molecules in a conjugated ring system consisting of a backbone molecule and various chemical groups attached to it. The backbone consists of two benzene rings bridged through a carbonyl group and oxygen. Each ring is connected in a fused formation not allowing free rotation about the carbon-carbon bonds. This unique backbone along with type and position of the attached chemical groups define specific functionality (properties) of xanthones and have been shown to have extensive biological and pharmacological activities such as very powerful anti-oxidant properties.

Details

CAS number : [90-47-1]
SMILES : O=C2C3=C(C=CC=C3) / OC1=CC=CC=C12
Molecular formula : C13H8O2
Molar mass : 196.19 g/mol
Appearance : off-white solid
Melting point : 174C (447 K)
Boiling point : 351C (624 K)
Solubility in water : sl. sol. in hot water

I was able to find this list of Xanthones. I will keep looking to complete it and in the meantime if you know more, please let me know with the source of information and I will add to this list.

• BR-xanthone A


• BR-xanthone B


• Calabaxanthone


• Garcinone A


• Garcinone B


• Garcinone C


• Garcinone D


• Garcinone E


• Gamma-Mangostin


• Garcimangosone A


• Garcimangosone B


• Garcimangosone C


• 1-Isomangostin


• 3-Isomangostin


• 1-Isomangostin hydrate


• 3-Isomangostin hydrate


• Gartanin


• Demethylcalabaxanthone


• Maclurin


• Mangostenone


• Mangostanin


• Mangostanol


• Mangostin


• Mangostinone


• Mangostinone A


• Mangostinone B


• a-Mangostin


• b-Mangostin


• g-Mangostin


• Norathriol


• Tovophyllin


• Tovophyllin A


• Tovophyllin B


• Trapezifolixanthone

Study Overview

A pre-clinical, preliminary 28-day study of [a product with Xanthones] identified the bioavailability of xanthones to determine how many xanthones the body actually absorbs and the pathway they travel. A validated xanthone analysis method was used to measure the quantities of the alpha-mangostin xanthone found in blood plasma.

Researchers

Researchers have implemented safety studies, initiated analytical work and validation, established pharmacokinetics and oversees all clinical work.

Charles River Laboratories, a pre-clinical lab that was established in 1947. It is world renowned for its research models in safety, pharmacokinetics, and in-vitro work. It employs 7,500 employees, including 500 researchers that include PhDs, MDs and DVMs.

Methods

The validated plasma method used LC-MS/MS technique to identify and quantify the amounts of alpha-mangostin in the plasma. This new analysis can quantify levels as low as 1 nanogram per ml (ng/ml).

Results

The preliminary research demonstrates that the body absorbs xanthones in low dosages and that very high levels of xanthone consumption actually result in decreased absorption efficiency. In addition, preliminary results showed long-term daily consumption of [a juice with Xanthones] increases the levels of xanthones in the blood.

More specifically, the study showed the following regarding alpha-mangostin:

- In approximately 3.5 hours, the xanthone has been absorbed during digestion.
- Females have a more efficient absorption rate than males.
- Long-term consumption of [a juice with Xanthones] causes a blood loading effect.
- Alpha-mangostin is absorbed the way nature intended, at very low doses of consumption, such as the amount contained in [a juice with Xanthones].
- At very high levels, the absorption efficiency of the xanthone decreases.

This study allows for a solid foundation for future clinical trials. Also, these preliminary findings show artificially inflating a product with xanthone extracts does not add any value.

The peer-reviewed, single lab validated High Performance Liquid Chromatography (or HPLC) analysis of selected xanthones in mangosteen fruit study was published in the June 2007 issue of the Journal of Separation Science. The study utilized AOAC protocols. AOAC International is a not-for-profit scientific association that sets standard methods, allowing consumers to have confidence in analytical results obtained from scientific analysis.

An 80:20 acetone/water mixture was used to extract the xanthones from dried, ground whole mangosteen fruit rind. A total of six xanthones were purified by preparative HPLC, utilizing the same solvent system and UV detection as for the analytical method. Each compound has unique UV absorption spectra that allows for easy identification of the xanthone found naturally in the mangosteen fruit.

The study establishes a credible scientific method for testing and measuring xanthones. Six specific xanthones have been identified, and their relative response factors determined. Although additional xanthones are in the process of being identified and measured, this research ensures a more consistent and reliable marketing of mangosteen products to consumers relative to xanthone content claims.

The science facts about the Xanthones are only are a very early stage as only 15% of all the Xanthones properties have been studied. However, some very promising research shows that the Xanthones can have the following properties:

• Anti-Fatigue - Helps boost energy
• Anti-Inflammatory - Helps prevent and reduce inflammation
• Anti-Aging
• Helps prevent cancer - According to a preliminary study, six xanthones have been found to be capable of killing cancer cells
• Helps lower blood pressure
• Helps lower blood sugar
• Helps prevent infections - Bacteria, Microbes, Viruses, Fungus.
• Anti-Diarrheal - In folk medicine, the pericarp of the mangosteen (most potent source of xanthones) has been used for centuries to effectively treat dysentery
• Anti-Parkinson, Anti-Alzheimer - Helps prevent dementia
• Anti-allergenic - Helps with allergies
• Eye Care - Helps prevents cataracts and glaucoma
• Helps protect the heart and cardiovascular system

Remember that the research on Xanthones is only at an early stage and this list is for general information only. The best source of details about any of the above information or any other medical information is the PubMed website. Se below for some extracts.

Induction of apoptosis by xanthones from mangosteen in human leukemia cell lines.

Matsumoto K, Akao Y, Kobayashi E, Ohguchi K, Ito T, Tanaka T, Iinuma M, Nozawa Y. Gifu International Institute of Biotechnology, 1-1 Naka-Fudogaoka, Kakamigahara, Gifu 504-0838, Japan. kmatsumoto@giib.or.jp. PMID: 12932141 [PubMed - indexed for MEDLINE]

We 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 microM through the induction of apoptosis.

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Antimycobacterial activity of prenylated xanthones from the fruits of Garcinia mangostana.

Suksamrarn S, Suwannapoch N, Phakhodee W, Thanuhiranlert J, Ratananukul P, Chimnoi N, Suksamrarn A. Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok, Thailand. sunit@swu.ac.th. PMID: 12843596 [PubMed - indexed for MEDLINE]

Prenylated xanthones, isolated from the fruit hulls and the edible arils and seeds of Garcinia mangostana, were tested for their antituberculosis potential. Alpha- and beta-mangostins and garcinone B exhibited strong inhibitory effect against Mycobacterium tuberculosis with the minimum inhibitory concentration (MIC) value of 6.25 microg/ml. Tri- and tetra-oxygenated xanthones with di-C5 units or with a C5 and a modified C5 groups are essential for high activities. Substitution in the A and C rings has been shown to modify the bioactivity of the compounds.

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Garcinone E, a xanthone derivative, has potent cytotoxic effect against hepatocellular carcinoma cell lines.

Ho CK, Huang YL, Chen CC. Department of Medical Research & Education, Veterans General Hospital, Taipei, ROC. PMID: 12451486 [PubMed - indexed for MEDLINE]

Treatment of hepatocellular carcinomas (HCCs) with chemotherapy has generally been disappointing and it is most desirable to have more effective new drugs. We extracted and purified 6 xanthone compounds from the rinds (peel) of the fruits of Garcinia mangostana L., using partitioned chromatography and then tested the cytotoxic effects of these compounds on a panel of 14 different human cancer cell lines including 6 hepatoma cell lines, based on the MTT method. Several commonly used chemotherapeutic agents were included in the assay to determine the relative potency of the potential new drugs. Our results have shown that one of the xanthone derivatives which could be identified as garcinone E has potent cytotoxic effect on all HCC cell lines as well as on the other gastric and lung cancer cell lines included in the screen. We suggest that garcinone E may be potentially useful for the treatment of certain types of cancer.

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Inhibition of cyclooxygenase and prostaglandin E2 synthesis by gamma-mangostin, a xanthone derivative in mangosteen, in C6 rat glioma cells.

Nakatani K, Nakahata N, Arakawa T, Yasuda H, Ohizumi Y. Department of Pharmaceutical Molecular Biology, Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Aramaki, Aoba-ku, 980-8578, Sendai, Japan. PMID: 11754876 [PubMed - indexed for MEDLINE]

The fruit hull of mangosteen, Garcinia mangostana L., has been used for many years as a medicine for treatment of skin infection, wounds, and diarrhea in Southeast Asia. In the present study, we examined the effect of gamma-mangostin, a tetraoxygenated diprenylated xanthone contained in mangosteen, on arachidonic acid (AA) cascade in C6 rat glioma cells. gamma-Mangostin had a potent inhibitory activity of prostaglandin E2 (PGE2) release induced by A23187, a Ca2+ ionophore. The inhibition was concentration-dependent, with the IC50 value of about 5 microM. gamma-Mangostin had no inhibitory effect on A23187-induced phosphorylation of p42/p44 extracellular signal regulated kinase/mitogen-activated protein kinase or on the liberation of [14C]-AA from the cells labeled with [14C]-AA. However, gamma-mangostin concentration-dependently inhibited the conversion of AA to PGE2 in microsomal preparations, showing its possible inhibition of cyclooxygenase (COX). In enzyme assay in vitro, gammamangostin inhibited the activities of both constitutive COX (COX-1) and inducible COX (COX-2) in a concentration-dependent
manner, with the IC50 values of about 0.8 and 2 microM, respectively. Lineweaver-Burk plot analysis indicated that gammamangostin competitively inhibited the activities of both COX-1 and -2. This study is a first demonstration that gamma-mangostin, a xanthone derivative, directly inhibits COX activity.

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Inhibitory effects of crude alpha-mangostin, a xanthone derivative, on two different categories of colon preneoplastic lesions induced by 1, 2-dimethylhydrazine in the rat.

Asian Pac J Cancer Prev. 2004 Oct-Dec;5(4):433-8. Nabandith V, Suzui M, Morioka T, Kaneshiro T, Kinjo T, Matsumoto K, Akao Y, Iinuma M, Yoshimi N. Tumor Pathology Division, Faculty of Medicine, University of the Ryukyus, Okinawa 903-0215, Japan. PMID: 15546251 [PubMed - indexed for MEDLINE]

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 alphamangostin 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 betacatenin 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.

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Preferential target is mitochondria in alpha-mangostin-induced apoptosis in human leukemia HL60 cells.

Matsumoto K, Akao Y, Yi H, Ohguchi K, Ito T, Tanaka T, Kobayashi E, Iinuma M, Nozawa Y. Gifu International Institute of Biotechnology, 1-1 Naka-Fudogaoka, Kakamigahara, Gifu 504-0838, Japan. kmatsumo@giib.or.jp. PMID: 15498656 [PubMed - indexed for MEDLINE]

Our previous study has shown that alpha-mangostin, a xanthone from the pericarps of mangosteen, induces caspase-3-dependent apoptosis in HL60 cells. In the current study, we investigated the mechanism of apoptosis induced by alpha-mangostin in HL60 cells. Alpha-mangostin-treated HL60 cells demonstrated caspase-9 and -3 activation but not -8, which leads us to assume that alpha-mangostin may mediate the mitochondrial pathway in the apoptosis. Parameters of mitochondrial dysfunction including swelling, loss of membrane potential (deltapsim), decrease in intracellular ATP, ROS accumulation, and cytochrome c/AIF release, were observed within 1 or 2 h after the treatment. On the other hand, alpha-mangostin-treatment did not affect expression of bcl-2 family proteins and activation of MAP kinases. These findings indicate that alpha-mangostin preferentially targets mitochondria in the early phase, resulting in indication of apoptosis in HL60 cells. Furthermore, we examined the structure-activity
relationship between xanthone derivatives including alpha-mangostin and the potency of deltapsim-loss in HL60 cells. Interestingly, replacement of hydroxyl group by methoxy group remarkably decreased its potency. It was also shown that the cytotoxicity substantially correlated with deltapsim decrease. These results indicate that alpha-mangostin and its analogs would be candidates for preventive and therapeutic application for cancer treatment.

Information herein is not intended to be taken as medical advice. No therapeutic or medical claims are either implied or made. Do not alter any medical treatment or the use of medications without the permission of your medical care provider.