Nomenclature of carotenoids

IUPAC Commission on the Nomenclature of Organic Chemistry (CNOC) and IUPAC-IUB Commission on Biochemical Nomenclature (CBN) (1975). Nomenclature of carotenoids (Rules approved 1974). Pure Appl. Chem. 41 107-131. 

Tentative rules for the nomenclature of carotenoids /. Biol Chem. (1972) 247, 2633-2643 Revision, Biochemistry (1975) 14, 1803 Pure Appl Chem. (1975) 41, 407-431... 

Nomenclature of Carbohydrates http //www.chcm.qinul.ac.Lik/iupac/2carb/ Nomenclature of Carotenoids http //www.chcin.qmul.ac.uk/iiipac/carot/ Nomenclature and Symbols for Folic Acid and Related Compounds http //www. chem.qmul.ac.uk/iupac/misc/folic.html... 

IUPAC-IUB. IUPAC commission on the nomenclature of organic chemistry and IUPAC-IUB commission on biochemical nomenclature tentative rules for the nomenclature of carotenoids. Biochemistry 10 4827-4837, 1971. 

Moss GP. lUPAC-IUB loint commission biochemical nomenclature (ICBN). Nomenclature of Carotenoids, http //www.chem.qmul. ac. uk/iupac/carot/. 

Eine im Jahre 1946 veroffentlichte Nomenklatur fiir Carotinoide [B. L. Wehm-hoff , Nomenclature of Carotenoid Pigments", Chem. and Engin. News 24, 1235 (1946)] bezieht sich nur auf die natiirlichen Eigmente der Begriff, Carotinoide" wurde nicht klar umgrenzt. 

Isler 0(1971) Carotenoids. Birkhauser Verlag, Basel and Stuttgart lUPAC and lUB (1971) lUPAC commission on the nomenclature of organic chemistry and lUPAC-IUB commission on biochemical nomenclature Tentative rules for the nomenclature of carotenoids. Biochemistry 10 4827-4837 lUPAC and lUB (1975) Nomenclature of carotenoids (Recommendations 1974). Biochemistry 14 1803-1804 Jablonski A Z (1935) Uber den Mechanismus des Photo-lumineszenz von Farbstoffphosphoren. Zs Phys 94 38 6 Jackson JB and Crofts AR (1969) The high energy state in chromatophores from Rhodopseudomonas sphaeroides. FEBS Lett 4 185-189... 

In 1972 tentative rules for the nomenclature of carotenoids were adopted by the lUPAC Commission on the Nomenclature of Organic Chemistry and the lUPAC-IUB Commission on Biochemical Nomenclature. These were revised in 1975. The names given to carotenoids are based on the stem name carotenes, and the numbering of the carbon atoms is as shown in (I). In this chapter the appropriate semisystematic names are given, along with the common names for carotenoids. 

Nomenclature of carotenoids (Rules approved 1974). London Butterworths. 1974. 

In the semisystematic nomenclature of carotenoids the end group first in the Greek alphabet shown on the left and its carbons take the unprimed numerals... 

Ito, M., Iwata, T., and Tsukida, K. (1982). Heterocycles 19, 1385-1389. lUPAC Nomenclature of Carotenoids (1973). Pure Appl. Chem. 41, 407-431. lUPAC Nomenclature of Organic Chemistry (1979). Section E, Appendix 2, pp. 486-490. Per-gamon, Oxford. 

Davies (1976) has reviewed the new system of nomenclature of carotenoids. Figure 1 shows the basic structure and numbering system for (3-, a-, and y-carotenes and for cryptoxanthin, the major carotenoids contributing to the vitamin A activity in animal and human foods. Apocarotenoids are compounds that have been shortened by removal of at least one end of the molecule beyond a designated location. In general, they have less biological activity than P-carotene (see Table I). 

Rules for the nomenclature of carotenoids (semi-systematic names) were approved by the International Union of Pure and Applied Chemistry (lUPAC) in 1974 (Weedon and Moss, 1995). However, because they are familiar and... 

Some 117 naturally occurring apo-carotenoids, 88 of which have been fully identified and another 6 naturally occurring seco-carotenoids have been referenced as carotenoids, thus representing around 15% of the carotenoids numbered to date (see Figure 3.3.1). This subfamily of carotenoids would be even larger if we consider the retinoids andnorisoprenoids. However, these compounds are excluded by nomenclature rules that dictate that they are not deemed to be carotenoids because of the absence of two central methyl groups (at C20 and C20 ). Retinoic acid, retinal. 

Some amendments to the IUPAC-IUB rules for carotenoid nomenclature have been made, in particular to include the 7-ring end-group (1) and some C37 (trinor) carotenoids.1 Rules have also been presented for the nomenclature of quinones with isoprenoid side-chains.2... 

Other Commissions on Nomenclature of the lUPAC have not been inactive. In biochemistry reports have been made on steroids (II), amino acids (12), vitamins (8), and carotenoids (7). A report on the nomenclature of macro-molecular compounds has been approved (6). 

International Union of Pure and Applied Chemistry, /. Am. Chem. Soc. 82, 5575-84 (I960) Definitive rules for the nomenclature of amino acids, steroids, vitamins, and carotenoids (lUPAC). 

The Nomenclature of the Carotenoid Pigments. Report of the Committee on Biochemical Nomenclature of the National Research Council, accepted by the Committee on Nomenclature, Spelling, and Pronunciation of the American Chemical Society. No charge. 

Carotenoids. A preliminary report on nomenclature of the carotenoids, drawn by the Committee on Biochemical Nomenclature of the National Research Council of the United States, was published in 1946 (11). P. Karrer, president of the commission at that time, with this report as a basis, presented a project to the commission (9) containing a few modifications and extensions of the American draft. KarrePs (5) text was discussed at the London conference in 1947 at a meeting held by the joint commissions for nomenclature of organic chemistry and biological chemistry. A few slight modifications were made, and this new text was adopted by the Council of the Union in 1947. It has been published by several periodicals (5) since that time. 

Palmer LS (1934) The biological and chemical nomenclature of the carotenoids. Science 79 488 90 PearlsteinRM( 1982) Chlorophyll singletexcitons. In Govindjee (ed) Photosynthesis. Vol I, Energy Conversion by Plants and Bacteria, pp 293-330. Academic Press, New York Perrin F (1926) Polarisation de la lumiere de fluorescence. Vie moyenne des molecules dans I etat excitb. J Physique 7 390-401... 

Many carotenoids have trivial names. However all carotenoids have been named semisystematically based on lUPAC-IUB nomenclature (lUPAC Commission on Nomenclatme of Organic Chemistry and the lUPAC-IUB Commission on Biochemical Nomenclature, 1975 Weedon and Moss, 1995). The structure of the end groups and carbon numberings of carotenoids within photosynthetic bacteria are illustrated in Fig. 1. A list of these names and the structures of all known naturally occurring carotenoids, and references giving data for each compound... 

Fig. I. Structure of the end groups and carbon numberings of carotenoids within photosynthetic bacteria based on lUPAC-IUP nomenclature (1975).

The I.U.P.A.C.-I.U.B. tentative nomenclature for carotenoids has been widely published. Recent progress in carotenoid and related fields has appeared in the proceedings of the Phytochemical Society Symposium held in Liverpool in 1970. In particular, advances in carotenoid chemistry are surveyed by Liaaen-Jensen the distribution and taxonomic significance of algal carotenoids by Goodwin and studies on abscisic acid by Milborrow. A symposium on sporopollenin has been published which includes a discussion on its possible origin from carotenoids. The properties of yeast pigments are summarized in a chapter written by Chichester and co-workers." The obituary of Professor P. Karrer outlines some of his many contributions to carotenoid chemistry. Advances in the biosynthesis of carotenoids and polyterpenoids are dealt with in the next chapter. 

According to the new lUPAC nomenclature for carotenoids (98) the cis-trans convention is still used to denote geometrical isomerism of the polyene chain. However, the EjZ designations may also be used, especially when the prefixes cis and tram might lead to ambiquity (98). 

In photosynthetically active chloroplasts, the carotenoids are found as part of photosynthetic pigment-protein complexes (PPCs) in the thylakoid membranes. The core complex, CCI, contains one /3-carotene molecule per 40 chlorophyll a, whereas the light-harvesting complex LHCI is associated with lutein, violaxanthin, and neoxanthin. /3-Carotene is also located in CCII, ° while LHCII contains xanthophylls." The separation, identification, and nomenclature of the PPCs has been discussed in detail in several recent reviews. ... 

Table 1 Chemical Nomenclature and Provitamin A Activity of Some Common Carotenoids of Plant Foods...

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