Vol 11, Issue 2, 2018
Online - 2455-3891
Print - 0974-2441
SYNTHESIS AND BIOLOGICAL PROPERTIES OF PHARMACEUTICALLY IMPORTANT
XANTHONES AND BENZOXANTHONE ANALOGS: A BRIEF REVIEW
POOJA BEDI, RICHA GUPTA, TANAY PRAMANIK*
Department of Chemistry, Faculty of Technology and Sciences, School of Chemical Engineering and Physical Science, Lovely Professional
University, Phagwara, Punjab, India. Email: Tanay.pramanik@gmail.com
Received: 06 September 2017, Revised and Accepted: 30 October 2017
ABSTRACT
Xanthones are one of the biggest classes of compounds in natural product chemistry. A number of xanthones have been isolated from natural sources
of higher plants such as fungi, ferns, and lichens. Synthetic analogs of xanthones have shown a large number of pharmacological properties such as
antioxidant, anti-inflammatory, antidiabetics, antihistamine, antitumoral, antiulcer, and algicidal. Moreover, they also find usages in photodynamic
therapy, laser technology, and dyes. This review lays stress on various solvents, catalyst and synthetic route for synthesis of xanthones, benzoxanthones
analogs. The review has also focused on the classifications of xanthone as well as extensively studied biological properties of the xanthones and
benzoxanthones analogs.
Keywords: Multicomponent reactions, Xanthones, Benzoxanthones, Biological properties.
INTRODUCTION
During the past few decades, there has been widespread interest in
multicomponent reactions (MCRs) due to their increasing importance
in organic and medicinal chemistry [1-3]. MCRs are the processes in
which three or more reactants are combined in a single step to yield
products by combining suitable portions of all the reactants. These
reactions are very effective in synthesizing highly functionalized small
organic molecules from easily available starting materials in a single step
and in short duration of time period. MCR also provides a higher overall
percentage of yield. Thus these reactions reduces labor by reducing a
number of synthetic operations such as extraction, purification, and
generates lesser amount of waste as compare to conventional multistep
reactions of a complex molecule [4-6]. A large number of MCRs are
already known, and the searches for new MCRs are still on. One such
reaction which belongs to MCR category is a synthesis of xanthones and
its derivatives with extended conjugation, i.e., Benzoxanthones.
Xanthones are naturally occurring polyphenolic compounds. Xanthone
nucleus is the main framework of large number of natural and synthetic
materials. These are parent of several natural yellow pigments.
These comprise an important class of oxygenated heterocycles.
Xanthone Skelton possesses good thermal oxidative and hydrolytic
stability, that’s why these are considered as structural motif in high
performance and engineering polymers [7]. Numerous derivatives
of xanthones are isolated from higher plants, fungi, and lichens [8].
However, the naturally occurring xanthones are limited to a fewer
number of substituent, so efforts are made to synthesize them from
their constituent fragments.
Xanthones and benzoxanthones constitute an important class
of biologically active heterocycles. Due to their remarkable
pharmacological and biological applications, their synthesis has drawn
great attention in the field of medicinal and pharmaceutical chemistry.
They possess antiviral [9], anti-inflammatory [10], antibacterial [11],
antimalarial [12], anti-HIV [13], antimicrobial, antioxidant, and
anticarcinogenic [14,15] activities. These are also used as an antagonist
for paralyzing action of zoxazolamine [16]. Furthermore, these
compounds can be used in photodynamic therapy [17], as dyes [18] in
laser technology [19] and in fluorescent materials which are sensitive
to pH for visualization of biomolecules [20].
Classification of xanthone
Naturally occurring xanthones are broadly classified into six categories:
1. Simple oxygenated xanthone.
2. Xanthone glycosides.
3. Prenylated xanthone.
4. Bisxanthones.
5. Xantholignoids.
6. Miscellaneous xanthones.
Simple oxygenated xanthone
These xanthones carry simple hydroxyl, methoxy, and methyl groups.
These are further subdivided into various categories such as mono,
di, tri, tetra, penta, and hexa oxygenated depending on the level of
oxygenation [21-23]. For example, 2-hydroxyxanthone (3), 2-hydroxy-
1-methoxyxanthone (4).
Xanthone glycosides
The xanthone in which sugar moiety is attached to xanthone nucleus
is called xanthone glycosides. These are further of two types,
i.e., C-glycosides and O-glycosides. In C-glycosides sugar moiety is
attached to xanthone nucleus by C-C bond whereas in O-glycosides
glycosidic linkage, i.e. C-O-C joins sugar moiety to xanthone. C-glycosides
are fewer in number as compare to O-glycosides. For example,
mangiferin (22) and isomangiferin are most common C-glycosides, and
Swertia japonica (24) and gentioside are few O-glycosides.
Prenylated xanthone
These are the xanthones in which 5-carbon unit such as isoprenyl
and 1,1-dimethylprop-2-enyl,3-hydroxy-3-methylbutyl [24-26]
is attached as a substituent to xanthone nucleus, for example,
© 2018 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (http://creativecommons.
org/licenses/by/4. 0/) DOI: http://dx.doi.org/10.22159/ajpcr.2018.v11i2.22426
Review Article