T. Maoka / Phytochemistry 70 (2009) 920–923
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Britton, G., 1998. Overview of carotenoid biosynthesis. In: Britton, G., Liaaen-Jensen,
S., Pfander, H. (Eds.), Carotenoids, vol. 3. Birkhäuser Verlag, Basel, pp. 13–147.
Britton, G., Liaaen-Jensen, S., Pfander, H., 2004. Carotenoids Handbook. Birkhäuser
Verlag, Basel.
Clough, J.M., Pattenden, G., 1979. Naturally occurring poly-cis carotenoids.
Stereochemistry of poly-cis lycopene and its congeners in ‘Tangella’ tomato
fruits. J. Chem. Soc. Chem. Commun. 61, 616–619.
Clough, J.M., Pattenden, G., 1983. Stereochemical assignment of prolycopene and
other poly-Z-isomeric carotenoids in fruits of the tangerine tomato Lycopersicon
esculentum var. ‘Tangella’. J. Chem. Soc. Perkin Trans. 1, 3011–3018.
Englert, G., 1979. Homonuclear overhauser 1H NMR. Experiments on the carotenoid
pigments lycopene and prolycopene. Helv. Chim. Acta 62, 1497–1500.
Englert, G., 1995. NMR spectroscopy. In: Britton, G., Liaaen-Jensen, S., Pfander, H.
(Eds.), Carotenoids, vol. 1B. Birkhäuser Verlag, Basel, pp. 147–160.
Englert, G., Brown, B.O., Moss, G.P., Weedon, B.C.L., Britton, G., Goodwin, T.W.,
Simpson, K.L., Williams, J.H., 1979. Prolycopene, a tetra-cis carotene with two
hindered cis double bonds. J. Chem. Soc. Chem. Commun. 54, 545–547.
Hengartner, U., Bernhard, K., Meyer, K., Englert, G., Glinz, E., 1992. Synthesis,
isolation, and NMR-spectroscopic characterization of fourteen (Z)-isomers of
lycopene and of some acetylenic didehydro- and tetradehydrolycopene. Helv.
Chim. Acta 75, 1848–1865.
3.7. (all E)-Celaxanthin
Reddish crystals; UV–vis (Et2O) 455 (shoulder), 484, 516 nm;
EIMS (probe) 70 eV, m/z 550 (M+, rel. int. 100%), 532 (M+-H2O,
18%), 458 (25%), 444 (20%); 236 (35%), 209 (45%), 159 (55%), 130
(46%), 91 (55%); For 1H and 13C NMR spectroscopic assignments,
see Table 1; CD (Et2O): k nm (De) 220 (0), 241 (+1.0), 260 (0),
309 (-7.4), 340 (0), 377 (+2.5), 400 (0).
3.8. (30Z, 50Z)-Torulene (2)
Reddish crystals; UV–vis (Et2O) 465, 490 (shoulder) nm; HRE-
IMS (m/z) 534.4221 [M+] (C40H54, calc. for 534.4226); EI MS (probe)
70 eV, 534 (M+, rel. int. 100%), 442 (18%), 428 (15%); 236 (20%), 209
(45%), 157 (58%), 130 (44%), 91 (50%). UV–vis (Et2O) 465, 490
(shoulder) nm; 1H NMR d (in CDCl3 at 500 MHz) 1.03 (6H, s, H-
16, 17), 1.46 (2H, m, H-2), 1.62 (2H. m, H-3), 1.72 (3H, s, H-18),
1.80 (3H, s, H-160, H-170), 1.90 (3H, s H-190), 1.97 (9H, s, H-19, 20,
200), 2.00 (3H, s, H-180), 2.02 (2H, t, J = 7 Hz, H-4), 6.01 (1H, d,
J = 11.5 Hz, H-40), 6.03 (1H, d, J = 11.5 Hz, H-60), 6.11 (1H, d,
J = 11.5 Hz, H-20), 6.14 (1H, d, J = 16 Hz, H-8), 6.15 (1H, d,
J = 16 Hz, H-7), 6.16 (1H, d, J = 11.5 Hz, H-10), 6.20 (1H, d,
J=11.5 Hz, H-100), 6.26 (2H, m, H-14, 140), 6.27 (1H, d, J = 15 Hz,
H-80), 6.28 (1H, dd, J = 11.5, 11.5 Hz, H-30), 6.49 (1H, dd, 15,
11.5 Hz H-70), 6.63 (4H, overlapped, H-11, 110, 15, 150).
Isaacson, T., Ronen, G., Zamir, D., Hirschberg, J., 2002. Cloning of tangerine from
tomato reveals
a carotenoid isomerase essential for the production of b-
carotene and xanthophylls in plants. Plant Cell 14, 333–342.
Isaacson, T., Ohad, I., Beyer, P., Hirschberg, J., 2004. Analysis in vitro of the enzyme
CRTISO establishes a poly-cis-carotenoid biosynthesis pathway in plants. Plant
Physiol. 136, 4246–4255.
Maoka, T., 2009. Recent progress in structural studies of carotenoids in animals and
plants. Archiv. Biochem. Biophys. 483, 191–195.
Maoka, T., Akimoto, N., Ishiguro, K., Yoshinaga, M., Yoshimoto, M., 2007. Carotenoids
with
a 5,6-dihydro-5,6-dihydroxy-b-end group, from yellow sweet potato
‘‘Benimasari”, Ipomoea batatas LAM. Phytochemistry 68, 1740–1745.
Maoka, T., Akimoto, N., Kuroda, Y., Hashimoto, K., Fujiwara, Y., 2008. Structure of a
I2 catalyzed isomerization of 2 resulted in a bathochromic shift
of 15 nm (UV–vis (Et2O) 480 and 512 nm), with the isomerization
products being the same as for I2 catalyzed isomerization products
of (all E)-torulene. These were confirmed by HPLC on ODS with
CHCl3–MeOH (1:9) as eluant.
series of cycloaddition product of carotenoids with
a-tocopherol, named
pittosporumxanthins, from the seeds of Pittosporum tobira. J. Nat. Prod. 71,
622–627.
Pattenden, G., Robson, D.C., 1987. Total synthesis of prolycopene. Tetrahedron Lett.
28, 5751–5754.
Pattenden, G., Robson, D.C., 2006. Total synthesis of prolycopene, a novel 7,9,70,90-
tetra-cis(Z) carotenoid and main pigment of the tangerine tomato Lycopersicon
esculentum. Tetrahedron 62, 7477–7483.
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