Abstract
The history of natural products is virtually the history of organic chemistry itself. Even at the end of the Twentieth Century, Nature still surprises us by the revelation of hitherto unknown structural types of molecule, and so it is no surprise that the nomenclature of natural products encompasses and exemplifies many of the problems that apply to organic compounds generally, often in an empirical and somewhat chaotic form. To add to the difficulties imposed by the sheer structural diversity of natural product molecules, there exist some genuine philosophical differences between different ‘user groups’ as to how the nomenclature should be organized and systematized, except in the case of structurally rather homogeneous classes such as carbohydrates and lipids.
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Notes and References
This can be appreciated by asking oneself the hypothetical question what would happen if, by some extraordinary combination of circumstances, the structure of methane were to be found to be CH5 not CH4. The substance found in natural gas, etc. would retain the name methane and the textbooks would report that, before 1997, methane was thought to be CH4 but is now known to have a different structure. However, if a similar thing were to happen to hexane, we would have to say that the substance with a boiling point of 68.95°C that was formerly thought to be hexane has now been shown to be something else, and that the real hexane has some other set of properties; in other words, the name stays with the structure of six carbons in a straight chain. This scenario is far-fetched, but analogous situations arise with some frequency in natural product chemistry.
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A search of the Dictionary of Natural Products database in 1997 revealed that at least 500 natural products, or 0.4% of the known total, were mentioned as having had their structures revised (including stereochemical revisions). This does not include historical revisions during the classical period of structure determination, or other cases where the DNP entry does not mention that the now-accepted structure is a revision. The current rate of publication of structure revisions of less well-known natural products would suggest that the proportion of incorrect structures in the literature, including those for which corrections have not yet been published, is at least 1%.
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This is without even taking into account whether the semi-systematic nucleus ‘flavone’ is allowable. Substitution of the up-to-date CAS alternatives for the flavone names given in this statement results in intractable complexity.
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Buckingham, J. (1998). Natural Products. In: Thurlow, K.J. (eds) Chemical Nomenclature. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4958-7_7
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