Xanthones

Structural formula of 9 H -xanthone.

Xanthones are aromatic oxo compounds that are derived from the ring system of xanthene and are naturally the coloring substances of some plants. They are therefore secondary plant substances that are produced in plants as color, fragrance and flavor.

description

Mangostin , a polyphenol from the mangosteen fruit .

The basic substance of all xanthones is 9 H - xanthone with the empirical formula C ₁₃ H ₈ O ₂ . Apart from its importance as dyes and antibiotics some xanthones as are Mangostin (also mangosteen or mangosteen ) by marketers of such products as so-called phytonutrients ( gr. Φυτόν, plant, nutrient , nutrient), respectively. The 9 H -xanthone is used as a selectively acting insecticide against moth larvae.

Mangosteen fruit

Natural occurrence

A natural source of about 40 of the currently 210 known xanthones are exotic fruits from the tropical regions that grow within the 20th parallel , for example the fruits of the mangosteen ( Garcinia mangostana ). Many sac fungi (mostly lichen-forming Lecanoromycetes ) and Central European Gentiana ( gentian ) and Aphloia species also produce xanthones. Some xanthones such as cervinomycin (from Streptomyces cervinus ) and lysolipin (from Streptomyces violaceoniger ) are natural antibiotics produced by bacteria ( Streptomyces ) .

Medical importance

Xanthones have only been investigated in Asian and American studies since the mid-1970s. Certain xanthones, primarily polyphenols such as mangosteen (also mangostin ) act in the body antioxidant (i.e., in function as highly efficient., Free radical scavengers against free radicals ); this results in antibacterial, antibiotic, anti-hepatotoxic, anti-allergic and antifungal properties in some xanthones. The halogenated xanthone derivative lysolipin , which was first described in 1975, has both antibiotic effects against a wide variety of bacteria and anti-tumor activity.

A study published in December 2011 investigated the effects of xanthones from the mangosteen fruit in chemopreventive cancer treatment. Original conclusion of the study: "The study determines the observed anti-cancer effect of the xanthones, whereby the remarkable potential as an anti-cancer agent is confirmed."

The similar cervinomycin was first described in 1986 and is being tested as a potential drug in clinical studies in the form of triacetylcervinomycin . Cervinomycin and lysolipin have a ring structure similar to that of tetracycline (from Streptomyces aureofaciens ).

Individual evidence

↑ Steiner, LF & Summerland, SA (1943): Xanthone as an ovicide and larvicide for the codling moth. In: Journal of economic entomology. Vol. 36, pp. 435-439.
^ Wissenschaft-Online-Lexika: Entry on Xanthones in the Lexicon of Medicinal Plants and Drugs , accessed June 19, 2008.
↑ ^a ^b AKIRA NAKAGAWA, SATOSHI OMURA u. a .: Structure of cervinomycin, a novel xantone antibiotic active against anaerobe and mycoplasma .. In: The Journal of Antibiotics. 40, 1987, p. 301, doi : 10.7164 / antibiotics.40.301 .
^ ^A ^b H. Drautz, W. Keller-Schierlein, H. zahner: Metabolic products of microorganisms , in Archives of Microbiology , pp. 175-190, Volume 106, Number 3 / January 1975. doi : 10.1007 / BF00446521 .
^ YP Tang, PG Li et al. a .: Effect of a mangosteen dietary supplement on human immune function: a randomized, double-blind, placebo-controlled trial. In: Journal of medicinal food. Volume 12, number 4, August 2009, pp. 755-763, doi : 10.1089 / jmf.2008.0204 . PMID 19697997 .
^ SA Dahanukar et al .: Pharmacology of Medical Plants and Natural Products. In: Indian Journal of Pharmacology . 2000, p. 96.
↑ W. Mahabusarakam, J. Proudfoot and a .: Inhibition of lipoprotein oxidation by prenylated xanthones derived from mangostin. In: Free radical research. Volume 33, Number 5, November 2000, pp. 643-659, PMID 11200095 .
^ A. Hornung: Halogenases from Actinomycetes. (PDF; 5.9 MB) Dissertation, University of Freiburg i. B., 2005, p. 81.
↑ T. Shan, Q. Ma et al. a .: Xanthones from mangosteen extracts as natural chemopreventive agents: potential anticancer drugs. In: Current molecular medicine. Volume 11, Number 8, December 2011, pp. 666-677, PMID 21902651 . PMC 3237908 (free full text).

[1] Steiner, LF & Summerland, SA (1943): Xanthone as an ovicide and larvicide for the codling moth. In: Journal of economic entomology. Vol. 36, pp. 435-439.

[2] Wissenschaft-Online-Lexika: Entry on Xanthones in the Lexicon of Medicinal Plants and Drugs , accessed June 19, 2008.

[nagakawa-3] AKIRA NAKAGAWA, SATOSHI OMURA u. a .: Structure of cervinomycin, a novel xantone antibiotic active against anaerobe and mycoplasma .. In: The Journal of Antibiotics. 40, 1987, p. 301, doi : 10.7164 / antibiotics.40.301 .

[springer-4] A ^b H. Drautz, W. Keller-Schierlein, H. zahner: Metabolic products of microorganisms , in Archives of Microbiology , pp. 175-190, Volume 106, Number 3 / January 1975. doi : 10.1007 / BF00446521 .

[PMID19697997-5] YP Tang, PG Li et al. a .: Effect of a mangosteen dietary supplement on human immune function: a randomized, double-blind, placebo-controlled trial. In: Journal of medicinal food. Volume 12, number 4, August 2009, pp. 755-763, doi : 10.1089 / jmf.2008.0204 . PMID 19697997 .

[6] SA Dahanukar et al .: Pharmacology of Medical Plants and Natural Products. In: Indian Journal of Pharmacology . 2000, p. 96.

[PMID11200095-7] W. Mahabusarakam, J. Proudfoot and a .: Inhibition of lipoprotein oxidation by prenylated xanthones derived from mangostin. In: Free radical research. Volume 33, Number 5, November 2000, pp. 643-659, PMID 11200095 .

[Hornung-8] A. Hornung: Halogenases from Actinomycetes. (PDF; 5.9 MB) Dissertation, University of Freiburg i. B., 2005, p. 81.

[PMID21902651-9] T. Shan, Q. Ma et al. a .: Xanthones from mangosteen extracts as natural chemopreventive agents: potential anticancer drugs. In: Current molecular medicine. Volume 11, Number 8, December 2011, pp. 666-677, PMID 21902651 . PMC 3237908 (free full text).