41720-91-6Relevant articles and documents
STRESS COMPOUNDS IN THE LEAVES OF NICOTIANA UNDULATA INDUCED BY TMV INOCULATION
Uegaki, Reiko,Kubo, Susumu,Fujimori, Takane
, p. 365 - 368 (1988)
In leaves of Nicotiana undulata inoculated with TVM, 19 sesquiterpenoids were detected as stress compounds.Among them, dehydrocarissone, capsidiol 3-acetate, aubergenone, 4-epi-aubergenone, trans-dihydrocarissone, 1,2-dehydro-α-cyperone and 3-epi-3-hydroxysolavetivone are novel tobacco stress compounds.Key Word Index - Nicotiana undulata; Solanaceae; tobacco; sesquiterpenoid; stress compounds.
Structural and biosynthetic studies on eremophilenols related to the phytoalexin capsidiol, produced by Botrytis cinerea
Suárez, Ivonne,da Silva Lima, Gesiane,Conti, Raphael,Pinedo, Cristina,Moraga, Javier,Barúa, Javier,de Oliveira, Ana Ligia L.,Aleu, Josefina,Durán-Patrón, Rosa,Macías-Sánchez, Antonio J.,Hanson, James R.,Tallarico Pupo, M?nica,Hernández-Galán, Rosario,Collado, Isidro G.
, p. 10 - 18 (2018)
A thorough study of the fermentation broth of three strains of Botrytis cinerea which were grown on a modified Czapek-Dox medium supplemented with 5 ppm copper sulphate, yielded five undescribed metabolites. These metabolites possessed a sesquiterpenoid (+)-4-epi-eremophil-9-ene carbon skeleton which was enantiomeric to that of the phytoalexin, capsidiol. The isolation of these metabolites when the fungus was stressed, suggests that they may be potential effectors used by B. cinerea to circumvent plant chemical defences against phytopathogenic fungi. The biosynthesis of these compounds has been studied using 2H and 13C labelled acetate.
SYNTHESIS OF (+)-5-EPI-ARISTOLOCHENE AND (+)-1-DEOXYCAPSIDIOL FROM CAPSIDIOL
Whitehead, Ian M.,Ewing, David F.,Threlfall, David R.,Cane, David E.,Prabhakaran, P. C.
, p. 479 - 482 (2007/10/02)
(+)-5-epi-Aristolochene, a common precursor of the phytoalexins capsidiol and debneyol, was synthesized from capsidiol (ex.Capsicum annum) via (+)-1-deoxycapsidiol.It is identical (TLC, GC, GC-MS, 1H NMR) with the enzymic product from cell-free preparations from elicitor-treated suspension cultures of Nicotiana tabacum incubated with either 14C>isopentenyl pyrophosphate or E,E-3H2>farnesyl pyrophosphate.The (+)-1-deoxycapsidiol was identical (GC, MS, 13C and 1H NMR) to a natural sample previously obtained from elicitor-treated fruits of C. annum.An isomer of 1-deoxycapsidiol, formed during the synthesis of this compound, was identified as 4-epi-eremophila-1(10),11-diene.
