- Biosynthesis of chloroplastidic and extrachloroplastidic terpenoids in liverwort cultured cells: 13C serine as a probe of terpene biosynthesis via mevalonate and non-mevalonate pathways
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Two terpenoid biosynthetic pathways, the mevalonate and non-mevalonate (glyceraldehyde phosphatepyruvate) routes, were examined by feeding 13C-labeled serines ([1-13C]- and [3-13C]-) to the cultured cells of the liverwort, Heteroscyphus planus. The labeling patterns observed in the isoprenoid unit of the biosynthetically 13C-labeled stigmasterol corresponded to those expected from the mevalonate pathway, while those of the phytyl side chain corresponded to those from the non-mevalonate pathway. Thus, serine is a potential probe to determine the origin of terpenoid biosynthesis, in either the mevalonate or non-mevalonate pathway.
- Itoh, Daisuke,Kawano, Kyouhei,Nabeta, Kensuke
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- Chemical constituents of aquatic fern Azolla nilotica
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Two new components, (24R)-6β-hydroxy-24-ethyl-cholest-4-en-3-one and phytyl-3,7,11,15-tetramethyl-2-hexadecanenate were isolated from the whole plants of aquatic fern Azolla nilotica. Their structures were established by spectroscopic techniques and chemical correlation. Some typical triterpenoids of ferns were also detected.
- Arai, Yoko,Nakagawa, Tomomi,Hitosugi, Mari,Shiojima, Kenji,Ageta, Hiroyuki,Abdel-Halim, Osama Basher
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p. 471 - 474
(2007/10/03)
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- 1,3,5-nonatriene derivatives, their preparation and their use
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1,3,5-Nonatriene derivatives of formula: STR1 in which R1 and R2, together with the carbon atom to which they are linked, form a carbonyl group, or each of R1 and R2 denotes alkoxy or R1 and R2 together form an alkylenedioxy radical, which may be made by reaction of a butadiene derivative of formula: STR2 in which R is alkyl or phenyl, with a butanal ketoacetal of 10 formula: STR3 followed by reaction of the product with a halomethyltriphenylphosphonium halide, are useful intermediates e.g. for the production of phytol.
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- SELECTIVE REDUCTION OF THE DISTANT DOUBLE BOND(S) IN GERANYL, FARNESYL AND GERANYL GERANYL DERIVATIVES.
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Selective addition of hydrogen chloride on the non-proximal double bond(s) of the title compounds followed by hydrogenolysis led to selective hydrogenation of these double bond(s).
- Julia, Marc,Roy, Pierre
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p. 4991 - 5002
(2007/10/02)
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- Synthesis of Phytone and Phytol through Prins Reaction of Norphytene and its Isomer
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Prins reaction on 2,6-dimethyloct-2-ene (IIa) using paraformaldehyde furnishes 2-isopropenyl-5-methylheptanol (IIIa) which on periodate oxidation or ozonolysis followed by Jones' oxidation gives the acid (Va).The latter (Va) upon pyrolysis affords 6-methyl-2-octanone (VIa).Similarly, norphytene isomer (IIb) furnishes phytone (VIb) through IIIb, IVb and Vb.Norphytene (Ib) on Prins reaction gives mainly E-phytol as one of the products.
- Kamath, S. V.,Rangaishenvi, M. V.,Phadke, A. S.,Kulkarni, Sheshgiri N.
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p. 1008 - 1009
(2007/10/02)
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- Synthesis of Phytol
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Ethyl 3,7,11-trimethyldodecanoate (IV), obtained from geranylacetone (II) by modified Wittig condensation with ethyl diethylphosphonoacetate followed by catalytic hydrogenation, on LAH reduction yields the carbinol (V).V on alkylation through its mesylate with ethyl monosodioacetoacetate and subsequent decarbethoxylation with alkoholic KOH affords 6,10,14-trimethylpentadecan-2-one (VIII).VIII on treatment with vinylmagnesium bromide followed by treatment with PTS in acetic anhydride and glacical acetic acid yields 3,7,11,15-tetramethyl-2(E)-hexadecen-1-ol acetate (X) which on saponification furnishes phytol (I).
- Vig, O. P.,Bari, S. S.,Vig, Rashmi,Dua, D. M.
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p. 453 - 455
(2007/10/02)
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