Pittosporumxanthins, cycloaddition products of carotenoids with α-tocopherol from seeds of Pittosporum tobira

Journal of Natural Products

Volumn 71, Issue 4, 2008, Pages 622-627

  Maoka, Takashi ^a   Akimoto, Naoshige ^b   Kuroda, Yoshihiro ^b,d   Hashimoto, Keiji ^c   Fujiwara, Yasuhiro ^c  

^a RESEARCH INSTITUTE FOR PRODUCTION DEVELOPMENT   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^d HIMEJI DOKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TOCOPHEROL; CAROTENOID; XANTHINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CYCLOADDITION; DRUG ISOLATION; DRUG STRUCTURE; MASS SPECTROMETRY; MOSHER METHOD; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PITTOSPORUM TOBIRA; SEED; TREE;

ALPHA-TOCOPHEROL; CAROTENOIDS; CIRCULAR DICHROISM; JAPAN; MOLECULAR STRUCTURE; ROSALES; SEEDS; STEREOISOMERISM;

PITTOSPORUM TOBIRA;

EID: 43249108822     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np070650h     Document Type: Article

References (15)

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6. 2n+2 at the alkyl terminal of the molecular ion of α-tocopherol and fragment ion at m/z 430 in the pittosporumxanthins produced in the source on MS1 were observed. These ions clearly revealed the structure of the isoprenoid chain of the α-tocopherol moiety in 1-8.
7. Englert, G., NMR Spectroscopy. In Carotenoids; Britton, G., Liaaen-Jensen, S., Pfander, H., Eds.; 1995; Birkhäuser Verlag; Basel, Vol. 1B; pp 147-160.
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9. The 1.1 ppm high-field shift at C-27″ (δ 24.4 for 1 and δ 23.3 for 2) and 1.7 ppm low-field shift at C-11″ (δ 39.0 for 1 and δ 40.7 for 2 at C-11″) in 2 indicated that the methyl group at C-27″ in 2 is oriented more axially to the pyran ring B than 1 (see ref 5).
10. Optimization of the conformations of pittosporumxanthins was carried out using molecular dynamics calculation software NMR graf Ver3.0 (Molecular Simulations, Inc., Waltham, MA). The calculation results showed that the hexaene (or heptaene) chain at C-11′ and diene chain at C-12′ were equatorial and that the dihedral angles between H-11′ and H-12′ were about 170° in 1, 3, 5, and 7 and about 180° in 2, 4, 6, and 8. The conformation of the pyran ring B was shown to be a half-chair for 1, 3, 5, and 7 and to be a half-boat for 2, 4, 6, and 8, and the methyl group C-27″ was oriented more axially in 2, 4, 6, and 8 than in 1, 3, 5, and 7.
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13. The configuration of naturally occurring α-tocopherol is (2R,4′R,8′R).
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