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1 Wiadomości Chemiczne

1 2015

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Naturalne i syntetyczne analogi strukturalne jononów

Grabarczyk M., Wińska K., Mączka W.

Wiadomości Chemiczne

2015

[Z] 69, 11-12

997--1018

Both plants and animals in the process of evolution gained the ability to produce compounds that affect their existence in the wild. These compounds may affect the organisms producing them, and may also be used by completely different individuals. Among huge number of molecules characterized by extremely essential features are, among others, ionones and their derivatives. Ionones are ketones composed of 13 carbon atoms. They are found in many essential oils being the products of degradation of carotenoids. Both they and their structural analogues can play various biological functions such as being deterrent to other individuals or, conversely, atractant. Compounds found in plants, containing like ionone carbon skeleton, and having in their structure additional hydroxyl groups or epoxide ring (4)–(23) often exhibit allelopathic activity [1–15] (Fig. 2–5). Marine animals may in turn use them as ichtyotoxic compounds (27) and (28) [19] (Fig. 7). A compound called luciferin Latia (29) is responsible for the bioluminescent properties of marine snail [20] (Fig. 8). Plants used for centuries in traditional folk medicine of different countries are a source of glycoside derived α- and β-ionone (37)–(55) [22–31] (Fig. 11–14). These compounds may also be used in modern medicine, inter alia, in the regulation of neurodegenerative diseases or for the treatment of osteoporosis. Because of the potential biological properties of structural analogs of ionones they are also obtained by chemical synthesis (56)–(69) [32–39] (Fig. 15–18) or biotransformation (70)–(89) [40–47] (Fig. 19–25), and then subjected to careful examination of their biological activities. By applying these methods we can also obtain a molecules whose acquisition from natural sources is unprofitable. We have received such derivatives which have no counterpart in nature.