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SUBSTANCES
Contents:
Introduction
History of lichen substances
Primary and Secondary metabolites
Biosynthetic pathways
Methods of determination of lichen substances
Activities of lichen substances
Conclusion
References
3
Algae Cyanobacteria
Nature: Eukaryotic algae Nature: Oxygenic photosynthetic
bacteria
Crustose
6
Contin..
Foliose
7
Contin..
Fruticose
8
Contin..
Squamulose
9
Contin..
Filamentous
10
Contin..
Leprose
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Lichen substances
Fungus absorb
moisture and
nutrients from
Fungus utilizing these
atmosphere
carbohydrates
produces secondary
metabolites
Supplied to
algae
Supplied to
fungus
Algae due to
photosynthetic
apparatus produces
carbohydrates
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Types of metabolites:
Include proteins, amino
acids, polyols, carotenoids,
polysaccharides, and
Primary metabolites vitamins
Primary metabolites:
Common intracellular products occurring in lichens
include proteins, amino acids, polyols, carotenoids,
polysaccharides, and vitamins, which are bound in the
cell walls and the protoplasts, are often water-soluble,
and can be extracted with boiling water .
Some of these products are synthesized by the fungus
and some by the alga.
Most of the intracellular products isolated from lichens
are nonspecific, and also occur in free-living fungi,
algae and in higher green plants
15
Secondary Metabolites:
The majority of organic compounds found in lichens are secondary
metabolites of the fungal component, which are deposited on the
surface of the hyphae rather than within the cells and are also called
as lichen acids.
These products are usually insoluble in water and can only be
extracted with organic solvents.
More than 800 secondary metabolites are known from lichens,
most are unique to these organisms
These metabolites are not absolutely essential for the survival and
growth of lichens . However, it is important that they may help to
protect the thalli against herbivores, pathogens, competitors and
external abiotic factors, such as UV irradiation ( e.g. lichen
derieved phenolic compounds including depsides , depsidones,
usnic acid derivates are effective UV- absorbing compounds)
16
Contin..
In many cases of axenic cultures, mycobionts can
produce secondary substances that are different from the
secondary metabolites found in symbiosis (Brunauer et al
2007)
For example natural lichen
Cont…
2. Mevalonic acid Pathway:
17% of total compounds are produced by this
pathway
include carotenes (β-carotene, γ-carotene,
xanthophylls, violoxanthin), sterols (ergosterol,
fungisterol, β-sitosterol) and triterpenes.
3. Shikimic acid Pathway:
Small portion of secondary metabolites by this.
Includes terphenylquinones and pulvinic acid
derivatives
19
Cont…
The genera of lichens best known for their
production of pulvinic acid pigments Stictaceae
family.
Algal symbionts are frequently blue green rather
than green. Lichens with green algae generally
show very low nitrogen content unless they grow
on high nitrogen substrates. Although nitrogen
metabolism in lichens is poorly understood. In
contrast to green algae, many blue green algae
show much enhanced nitrogen content.
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Source: Identification of
lichen substances (A
book)
21
Cont..
The present study investigates nineteen lichen species
belonging to eleven genera (Flavopunctelia, Flavoparmelia,
Cladonia, Parmelia, Umbilicaria, Xanthoria, Ochrolechia,
Hyperphyscia, Hypogymnia, Dermatocarpon and
Parmotrema) of Himalayan region (Abbottabad) Pakistan.
Spot test results showed the presence of different lichen
substances (gyrophoric, lecanoric acid, umbilicaric acids,
usnic acid, atranorin, chloroatranorin, salazinic acid and
parietin)
(Hussain et al 2019)
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One dimensional
the development of Two dimensional
chromatogram in only one development of
direction is quiet chromatogram using
satisfactory for the another solvent at right
separation of many angle to the first occurs
mixtures.
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GC-MS
Xanthones, anthraquinones, dibenzofurans,
terpenes and pulvinic acid derivatives which
lack thermolabile ester groups can be
studied by GCMS
24
Cont...
Thin layer Chromatography (TLC):
The best micro-chemical methods for the systematic
botanist due to its sensitivity, rapidity, general applicability
and simplicity. Lichen compounds identified using TLC
visualization and crystallography (Parizadeh et al 2017)
25
Cont..
High performance liquid chromatography (HPLC):
used to identify and quantify characteristic substances in
oakmoss(a type of light green to green-black fungal
lichen) products.
bonded reverse phase columns are used
Samples are dissolved in methanol and injected into the
appropriate portion column through which an appropriate
solvent is passed under high pressure.
UV detector
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Antiviral,
Antimicrobial /
cytotoxic and Antioxidant
Antifungal
anti-tumour activity
activity
activity
Anti-herbivore
Antipyretic and
and insecticidal Allelopathy analgesic drugs
activity
Antiviral activity:
Anethyl acetate-soluble fraction of the crude
methanolic extract of Ramalina farinacea can be
used as a broad-spectrum antiviral agent against
RNA and DNA viruses.
Ramalina
farinacea
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Ramalina
celastri
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Conti..
Epanorin (EP) is a secondary metabolite of
the Acarospora lichenic species.
Epanorin has:
antimicrobial activity
UV-absorption properties
inhibits cancer cell growth
(Moreno et al 2019)
Acarospora lichenic specie
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Antioxidant activity:
Antioxidants(Antioxidants are the substances which
interfere with the oxidation process by reacting with
free radicals, chelating free catalytic metals and also by
acting as oxygen scavengers.)
Lichens synthesize secondary lichen metabolites
which show strong antioxidant activity.
Some depsides, such as atranorin (extracted from
Placopsis sp.), divaricatic acid (extracted from
Protousnea malacea), depsidones, pannarin (extracted
from Psoroma pallidum) showed antioxidant activity.
32
Conti..
Methanol extracts of
Xanthoparmelia
camtschadalis and its
extracted lichen
compounds such as
salazinic acid, stictic
acid, and usnic acid
protected human
astrocytes from hydrogen
peroxide-induced damage
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Allelopathy:
Lichen secondary metabolites affect the
growth and development of neighboring
lichens, mosses, algae and vascular plants, as
well as microorganisms and can function as
allelopathic agents called allelochemicals.
It was reported that allelopathic compounds
are released into the environment and might
Growth
Growth of of mossess
mossess
influence photosynthesis, respiration, Hedwigia
Hedwigia ciliata
ciliata and
and
transpiration, protein and nucleic acid Anomodon
Anomodon attenu-atum
attenu-atum
synthesis, membrane ion transport, and and
and the
the liverwort
liverwort
permeability of other organisms. Porella
Porella platyphylla
platyphylla
found
found toto be
be inhibited
inhibited
by
by lichen
lichen Porpidia
Porpidia
albocaerulescens.
albocaerulescens.
35
Conti..
Physciosporin, isolated from Pseudo-cyphellaria
coriacea ((Yang et al 2015), atranorin isolated from
Everniastrum vexans (Zhou et al 2017) identified as an
effective compound and showed significant inhibitory
activity in migration and invasion assays against human
lung cancer cells.
Cont..
Sixteen compounds were isolated from lichen Usnea
longissima (useanol, lecanorin, 3'-methylevernic acid,
evernic acid, barbatinic acid, dimethyldibenzofuran,
orcinol,, methyl orsellinate, methyl everninate, 2-
hydroxy-4-methoxy-3,6-dimethyl benzoic acid, ethyl
everninate,ethyl 2,4-dihydroxy
methylbenzoate.. etc)
(Paul et al 2019)
Usnea longissima
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Conclusion:
Lichens usually are very slow growing organisms and
must be protected against lower and higher plants, the
lichen substances are active, protective and antibiotic
substances.
Many lichens grow under extreme conditions
concerning change of temperature, humidity and
intensity of light. Recent studies has shown that plants
under stress conditions are able to synthesize so called
stress-metabolites and it is likely that lichens respond
to such extreme changes in their environment by the
synthesis of large amount of stress metabolites.
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References:
Boustie, J., Grube, M., 2005. Lichens-a promising source of bioactive
secondary metabolites. Plant Genet Resour. 3 (2): 273-287.
Dayan, F.E., Romagni, J.G., 2001. Lichens as a potential source of
pesticides. Outlook Pestic. 12: 229 – 232.
Feuerer, T.,Hawksworth, D.L., 2007. Biodiversity of lichens, including a
world-wide Analysis of checklist data based on Takhtajan’s floristic regions.
Biodivers Conserv. 16: 85
Lawrey JD (1986). Biological role of lichen- Bacillus subtilis, Proteus
vulgaris, Aeromonas substances. J Bryol. 89(2):111-122
Muller K (2002). Pharmaceutically relevant metabolites from lichens.
Applied Microbiology and Biotechnology. 56: 9-16
Ranković, B. and Kosanić, M., 2019. Lichens as a potential source of
bioactive secondary metabolites. In Lichen secondary metabolites (pp. 1-29)
Rowe, J.G., Saenz, M.T., Garcia M.D., (1999). Some lichen products have
antimicrobial activity. Zeitschrift für Naturforschung. 54(7-8): 605-609.