Plants and Lichens

Only three macrolides have been isolated from lichens (Table VII). On the other hand, plants produce about 700 macrolides (Table VIII), but most of them are macrodiolides or macrotriolides such as tannins and alkaloids (e.g., pyrroliz-idines). Their biosynthetic pathways are quite different from polyketide macrolides. A small group of monolactone macrolides has up to 19-membered ring lactones. Some of them have a musky odor. 

Ring size Structural characteristic Number of reported compounds Example  

9 Macrodiolide 1 l,3-Di-0-[3,4-bis-(3,4-dihydroxyphenyl)-cyclobutane-1,2-dicarbonyl]-4,5-di-0-caffeoylquinic acid (133) 

Aspicilin (Fig. 21, 118) was the first macrolide isolated from lichens. It is an 

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Casselman, K. L. Craft of the Dyer Color from Plants and Lichen, 2nd ed. Dover Publications, Inc. New York, 1993. 

D Kuehnelt, J Lintschinger, W Goessler. Arsenic compounds in terrestrial organisms IV Green plants and lichens from an old arsenic smelter site in Austria. Appl Or-ganomet Chem 14 411-420, 2000. 

C30H30O, Mr 426.73, needles, mp. 267-269 °C, [aJu -27.8 (CHCI3). A pentacyclic " triterpene widely distributed in many higher plants and lichens it can be obtained as the main component from the cork of the cork oak (Quercus suber, Fagaceae) by extraction with hot ethanol. F. has diuretic activity. 

Casselman KL (1993) Craft of the Dyer. Colour from Plants and Lichens, 2nd edn. Dover Publ Inc, New York... 

H02C(CH2)2C02H. Colourless prisms m.p. 182 C, b.p. 235°C. Occurs in amber, algae, lichens, sugar cane, beets and other plants, and is formed during the fermentation of sugar, tartrates, malates and other substances by a variety of yeasts, moulds and bacteria. Manufactured by the catalytic reduction of maleic acid or by heating 1,2-dicyanoethane with acids or alkalis. Forms an anhydride when heated at 235°C. Forms both acid and neutral salts and esters. Used in the manufacture of succinic anhydride and of polyesters with polyols. 

To date, 152 species of flowering plants belonging to 46 different families, as well as a few species of mushrooms, mosses, ferns, and lichens, have been screened. Extracts from 20 seed plants have shown enough inhibitory activity to warrant further study. Leaf extracts of members of three families, Liliaceae, Pinaceae, and Labiateae, show a high incidence of antiviral agents. Several members of the Capri-foliaceae, on the other hand, contain virus-stimulating agents. 

The natural dyes industry was also a large, sophisticated, and worldwide employer. Master dyers made a wide range of reasonably fast colors and handed down secret dye recipes to their apprentices. Europe s two staple dyes were madder red from the Mediterranean and indigo blue from India. Other natural dyes included violet from lichens dark red from the forget-me-not family brown from African aloe plants and black from tumorlike... 

Fumaric acid, a metabolite of many fungi, lichens moss and some plants, and mainly used as the diacid component in alkyd resins, is produced commercially to some extent by fermentation of glucose in Rhizopus arrhizus yet productivity improvements appear essential for the product to be an option for replacing its petrochemical production by catalytic isomerization of maleic acid. 

Terpenoids are found in all parts of higher plants and occur in mosses, liverworts, algae and lichens. Terpenoids of insect and microbial origins have also been found. 

This widespread occurrence of apiose5 has not been substantiated by Beck.248 In lower plants (1 lichen, 3 mosses, 8 ferns, and 5 Gymnosperms), he detected no apiose. Beck also found no apiose in any of the plants representing families tested by Duff and Knight,5 except the Lemnaceae and Zosteraceae. It should be noted that Duff and Knight5 (also, unpublished data of Duff) did not originally find apiose in all species of any one family in which a member contained apiose, except when some species were re-examined more closely. 

Besides playing a vital role in the oxidation-reduction processes of living organisms, quinones occur widely as natural pigments found mainly in plants, fungi, lichens, marine organisms, and insects (see alizarin, Section 28-4A, as representative of a natural anthraquinone-type dye). 

The former are mostly derived from plants [vegetabty colours) and may be contained in woods (e.g., campeachy, Brazil wood, sandalwood, yellow wood, fustic), barks (quercitron), roots [madder, turmeric), leaves (indigo, woad), flowers [safflower), fruit (Persian berries) and lichens [archil). Far fewer are animal colours [cochineal, kermes). 

The simplest quinones are o- and p-benzoquinone [(3) and (4) respectively]. This quinonoid structural feature is widespread in naturally occurring compounds isolated from moulds, fungi, lichens, plants and insects,52 which include not only substituted benzoquinones but also substituted polycyclic quinones [i.e. the substituted analogues of, for example, 1,2-naphthoquinone (5), 9,10-anthraquinone (6), and 9,10-phenanthraquinone (7)]. 

Organohalogens are present in many terrestrial environments sediments, soils, plants, fungi, lichen, volcanoes, biomass combustion, bacteria, insects, and higher organisms. The high concentration and dispersal of chloride in minerals, soils,... 

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