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Monterey Bay Aquarium Research Institute
Marine Botany

Caloplaca coralloides

Chemistry

Types of Lichen Compounds:

One special feature of lichens is the diversity of chemical products they produce. These products can be split up into intracellular and extracellular products. Some of the types of intracellular products found in lichens are carbohydrates, free amino acids, vitamins (generally in lower quantities than in higher green plants) and sometimes carotenoids. Many of the carbohydrates found in lichens are unique to lichens, or found only rarely in other plants. For example, lichenin is the main component of the cell walls of hyphae in lichens and is uncommon in other plants however, it is found in oat seeds (Hale, 103).

However, it is the extracellular products of lichens that are really exciting. Most of these compounds are weak phenolic acids made only by lichenized fungi. However, some compounds, such as endocrocin, parietin, other anthraquinones, polyporic and thelephoric acids and terphenylquinones are also made in small quantities by un-lichenized fungi.

These phenolic acids produced by lichens are related to tannins.

Cool Ways Lichens Use these Compounds:

Many of the extracellular compounds that lichens produce are “secondary” compounds, meaning that they are not used directly in metabolism. Lichens produce over 600 of these secondary compounds and they can produce large quantities of them – up to 5% of the lichen’s body weight (Brodo, 42). The isolated fungal component can produce some of these compounds, but only in tiny amounts.

Depsides, depsidones and fatty acids occur mostly in the medulla where they coat hyphae with insoluble crystalline material that helps repel water and maintain airspaces within the lichen. This is important for efficient gas exchange for photosynthesis.

Substances deposited on the cortex of the lichen often act as sunscreens or taste bad and act as deterrents to herbivory.

Other lichen substances function to inhibit growth of organisms that compete for resources. For example, some of these compounds can inhibit the growth of soil fungi or the germination of seeds of vascular plants. This can give lichens an important edge because they are generally slow-growing.

Color Tests:

Many of these unique lichen substances are used to identify lichens. Color tests for this purpose were developed in 1870’s. The first chemicals used were KOH and Ca(ClO)2, used individually or sequentially (K followed by C). These two are still the simplest way to use chemicals to help with lichen identification, and they often provide very useful information. Later para-phenylenediamine was added as another useful reagent and microcrystal tests were developed to help identify the lichen acids. Currently, people also use more recent techniques such as thin layer chromatography and high pressure liquid chromatography. Color tests are useful in identifying most lichens, but are particularly necessary for identifying crusts, which often do not have much visible morphological information that can be used for identification.

Many extracellular lichen substances have characteristic colors, which they impart to the lichen. For example, orange and yellow lichens often contain anthraquinones, pulvic acid derivatives or usnic acid in their cortex. In Caloplaca, the orange cortical pigment is parietin (an anthraquinone), which reacts deep red/purple with KOH.


chemical structure of parietin anthraquinone
image progression showing parietin in C. coralloides interacting with KOH


Extracellular lichen substances are sometimes categorized by the biosynthetic pathways through which they are synthesized. Quinones are synthesized in the acetate-malonate pathway.

Other compounds that C. coralloides has in small amounts are emodin, fallacinal, parietinic acid and teloschistin.

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2005 Megan Kelso

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