CHAPTER 10
Terpenoids: Structure and Distribution *
w. SANDERMANN
Federal Research Station for Forestry and Forest Products,
ReinbeklHamburg, Germany
I. Scheme of Terpenoid Structure
II. Structure and Distribution of Terpenoids
A. Hemiterpene Compounds
B. Terpenes
C. Sesquiterpenes
D. Diterpenes
E. Triterpenes
References .
503
507
507
508
509
509
510
586
I. Scheme of Terpenoid Structure
The parent compounds of the terpenes and terpenoids are multiples
of an unsaturated isopentane unit (Table I). Up to diterpenes, the carbon skeletons are lined up one next to the other, but the synthesis of
tri- and tetraterpenes is achieved through the dimerization of precursors half their size. Mo'no- and sesquiterpenes often occur as hydrocarbons. By oxidation, these can be converted to alcohols, oxides,
ketones, aldehydes, acids, and lactones. Triterpene compounds are
known almost exclusively in the form of their oxygen derivatives. In
certain cases the original terpenoid is hydrogenated ( phytol) or dehydrogenated ( carotenoids ). Still other alterations in the original
terpenoids lead, by way of oxidative degradation, to numerous steroid
derivatives (bile acids, sex hormones, etc.); and by reaction with other
compounds, to mixed terpenoids (alkaloids of the delphinium, aconitum,
solanum, and veratrum groups, vitamins E and K, certain coumarins,
and the like).
As one can see from Scheme I and Chapter 11 on metabolism of
terpenoids, the isopentane units ( "active isoprene") are always aligned
according to (Ia). The "irregularly" constructed coupling (Ib) which is
found in some terpenoids, can be formed only through secondary
changes. These playa part in certain mono-, sesqui-, and diterpenes. By
~ Translated from the German by Dr. Herbert S. Heineman, University of
Pittsburgh School of Medicine.
503
Terpenoids: Structure and Distribution *
w. SANDERMANN
Federal Research Station for Forestry and Forest Products,
ReinbeklHamburg, Germany
I. Scheme of Terpenoid Structure
II. Structure and Distribution of Terpenoids
A. Hemiterpene Compounds
B. Terpenes
C. Sesquiterpenes
D. Diterpenes
E. Triterpenes
References .
503
507
507
508
509
509
510
586
I. Scheme of Terpenoid Structure
The parent compounds of the terpenes and terpenoids are multiples
of an unsaturated isopentane unit (Table I). Up to diterpenes, the carbon skeletons are lined up one next to the other, but the synthesis of
tri- and tetraterpenes is achieved through the dimerization of precursors half their size. Mo'no- and sesquiterpenes often occur as hydrocarbons. By oxidation, these can be converted to alcohols, oxides,
ketones, aldehydes, acids, and lactones. Triterpene compounds are
known almost exclusively in the form of their oxygen derivatives. In
certain cases the original terpenoid is hydrogenated ( phytol) or dehydrogenated ( carotenoids ). Still other alterations in the original
terpenoids lead, by way of oxidative degradation, to numerous steroid
derivatives (bile acids, sex hormones, etc.); and by reaction with other
compounds, to mixed terpenoids (alkaloids of the delphinium, aconitum,
solanum, and veratrum groups, vitamins E and K, certain coumarins,
and the like).
As one can see from Scheme I and Chapter 11 on metabolism of
terpenoids, the isopentane units ( "active isoprene") are always aligned
according to (Ia). The "irregularly" constructed coupling (Ib) which is
found in some terpenoids, can be formed only through secondary
changes. These playa part in certain mono-, sesqui-, and diterpenes. By
~ Translated from the German by Dr. Herbert S. Heineman, University of
Pittsburgh School of Medicine.
503