Abstract:
:The role and fate of Jasmonoyl-Phenylalanine (JA-Phe), an understudied conjugate in the jasmonate pathway remain to be unraveled. We addressed here the possibility of JA-Phe oxidative turnover by cytochrome P450s of the CYP94 family. Leaf wounding or fungal infection in Arabidopsis resulted in accumulation of JA-Phe, 12-hydroxyl (12OH-JA-Phe) and 12-carboxyl (12COOH-JA-Phe) derivatives, with patterns differing from those previously described for Jasmonoyl-Isoleucine. In vitro, yeast-expressed cytochromes P450 CYP94B1, CYP94B3 and CYP94C1 differentially oxidized JA-Phe to 12-hydroxyl, 12-aldehyde and 12-carboxyl derivatives. Furthermore, a new aldehyde jasmonate, 12CHO-JA-Ile was detected in wounded plants. Metabolic analysis of CYP94B3 and CYP94C1 loss- and gain-of-function plant lines showed that 12OH-JA-Phe was drastically reduced in cyp94b3 but not affected in cyp94c1, while single or double mutants lacking CYP94C1 accumulated less 12COOH-JA-Phe than WT plants. This, along with overexpressing lines, demonstrates that hydroxylation by CYP94B3 and carboxylation by CYP94C1 accounts for JA-Phe turnover in planta. Evolutionary study of the CYP94 family in the plant kingdom suggests conserved roles of its members in JA conjugate homeostasis and possibly in adaptative functions. Our work extends the range and complexity of JA-amino acid oxidation by multifunctional CYP94 enzymes in response to environmental cues.
journal_name
Phytochemistryjournal_title
Phytochemistryauthors
Widemann E,Grausem B,Renault H,Pineau E,Heinrich C,Lugan R,Ullmann P,Miesch L,Aubert Y,Miesch M,Heitz T,Pinot Fdoi
10.1016/j.phytochem.2015.06.027subject
Has Abstractpub_date
2015-09-01 00:00:00pages
388-399eissn
0031-9422issn
1873-3700pii
S0031-9422(15)30038-8journal_volume
117pub_type
杂志文章相关文献
PHYTOCHEMISTRY文献大全abstract::The essential oil from the leaves of Callicarpa japonica was analyzed by GC-MS, and 84 compounds were identified. The main constituents of the essential oil were spathulenol (18.1%), germacrene B (13.0%), bicyclogermacrene (11.0%), globulol (3.3%), viridiflorol (2.6%), alpha-guaiene (2.3%), and gamma-elemene (2.0%). T...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(02)00207-8
更新日期:2002-09-01 00:00:00
abstract::The glycosylation of lipophilic small molecules produces many important plant secondary metabolites. The majority of these are O-glycosides with relatively fewer occurring as glucose esters of aromatic or aliphatic acids. In particular, monoterpene acid glucose esters have much lower structural diversity and distribut...
journal_title:Phytochemistry
pub_type: 杂志文章,评审
doi:10.1016/j.phytochem.2011.08.026
更新日期:2011-12-01 00:00:00
abstract::Eleven oleanane-type triterpenoid glycosides, named gordonsaponins A-K, were isolated from the stems of Gordonia kwangsiensis. Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of all eleven were evaluated against five human tumor cell lines (HCT-8, Bel-7402, BGC-823, A54...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2012.08.019
更新日期:2013-01-01 00:00:00
abstract::From the aerial parts of Chrozophora obliqua, two phenylpropanoid glucosides: 4-O-methyl guaiacylglycerol 9-O-beta-glucopyranoside (1) and 4-O-methyl guaiacylglycerol 8-O-beta-glucopyranoside (2) together with syringin, benzyl alcohol glucoside, isorhamnetin-3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside and quer...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(01)00262-x
更新日期:2001-10-01 00:00:00
abstract::Investigation of a hairy root culture of Tripterygium wilfordii var. regelii transformed with Agrobacterium rhizogenes resulted in the isolation of new diterpenoid and sesquiterpenoid together with known triterpenoids. These structures were determined by spectroscopic analyses. ...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(98)00300-8
更新日期:1998-11-20 00:00:00
abstract::The bark of Garcinia merguensis yielded 10 xanthones, merguenone, 1,5-dihydroxy-6'-methyl-6'-(4-methyl-3-pentenyl)-pyrano(2',3':3,2)-xanthone, subelliptenone H, 8-deoxygartanin, rheediaxanthone A, morusignin G, 6-deoxyjacareubin, 1,3,5-trihydroxy-4,8-di(3-methylbut-2-enyl)-xanthone, rheediachromenoxanthone and 6-deoxy...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(02)00433-8
更新日期:2003-06-01 00:00:00
abstract::C6-aldehydes, such as (Z)-3-hexenal, (E)-2-hexenal, and n-hexanal, are volatile compounds formed by hydroperoxide lyase (HPL) and found in most terrestrial plants. They are fungicidal and bactericidal compounds, and are also signaling compounds to induce defense responses in plants. Transgenic plants having overexpres...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2008.04.023
更新日期:2008-08-01 00:00:00
abstract::One of the most well-characterised plant pathogenic interactions involves Arabidopsis thaliana and the bacteria Pseudomonas syringae pathovar tomato (Pst). The standard Pst inoculation procedure involves infiltration of large populations of bacteria into plant leaves which means that metabolite changes cannot be readi...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2010.01.006
更新日期:2010-04-01 00:00:00
abstract::Nine cycloartane triterpenoids, including two new derivatives 22,25-dihydroxy-cycloart-23E-en-3-one and 24-methylenecycloartane-3 beta,22-diol have been isolated from leaves of Guarea macrophylla. The structures were elucidated by interpretation of spectral data, mainly 1H and 13C NMR, including bidimensional analysis...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(02)00123-1
更新日期:2002-06-01 00:00:00
abstract::Activity guided fractionations led to the isolation of two antitumor compounds 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3 beta-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-beta-D-g...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(99)00128-4
更新日期:1999-08-01 00:00:00
abstract::In search for new or chemo-taxonomically relevant bioactive compounds from chemically unexplored Hypericum species, four previously undescribed natural products, named peplidiforones A-D were isolated and characterized from Hypericum peplidifolium A. Rich., together with six known compounds. The structures of all comp...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2016.02.003
更新日期:2016-04-01 00:00:00
abstract::A bioassay-guided fractionation of Agave offoyana leaves led to the isolation of five steroidal saponins (1-5) along with six known saponins (6-11). The compounds were identified as (25R)-spirost-5-en-2α,3β-diol-12-one 3-O-{α-l-rhamnopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyr...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2014.05.014
更新日期:2014-09-01 00:00:00
abstract::A new bidesmosidic triterpenoidal saponin of hederagenin was isolated from the ethanolic extract of the roots of Symphytum officinale L. Its structure was elucidated by using 1H NMR, 1H-1H COSY NMR, heteronuclear 1H-13C correlated spectroscopy (heteroCOSY), 13C NMR, DEPT, FAB mass spectrometry and chemical evidence as...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(00)97091-2
更新日期:1994-05-01 00:00:00
abstract::The chemical origin and biological role of distinct semen-like odor occasionally found in some flowers are very curious but remain scarcely studied. Here, we used direct ambient corona discharge ionization mass spectrometry (MS) to study the volatile chemical composition behind the semen-like odor emitted by the fresh...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2017.11.001
更新日期:2018-01-01 00:00:00
abstract::The bean aphid, Megoura crassicauda Mordvilko, feeds selectively on plants belonging to the genus Vicia (Fabaceae). However, it never infests the tiny vetch, V. hirsuta (L.) Gray. The aphid appeared to discriminate between host and non-host plants by tasting specific chemicals during penetration of its stylet into the...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2005.12.013
更新日期:2006-03-01 00:00:00
abstract::A novel minor triterpenoid saponin mimusin (3-O-[beta-D-glucopyranosyl- (1-->6)-beta-D-glucopyranosyl]-2 beta,3 beta,6 beta,23-tetrahydroxyolean- 12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L- rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside was isolated from the seeds o...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(96)00659-0
更新日期:1997-03-01 00:00:00
abstract::Radicinin is a phytotoxic and antibiotic metabolite produced by some phytopathogenic fungi. Precursor administration and cell-free experiments with deoxyradicinin and radicinin were carried out in Bipolaris coicis H13-3. When deoxyradicinin was administered to the fungus, radicinin and 3-epi-radicinin formed. When rad...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2011.11.010
更新日期:2012-03-01 00:00:00
abstract::In a study of 62 plant species of the Cretan flora for their phytotoxic activity, plants were extracted successively with CH2Cl2, MeOH and H2O. Phytotoxicity evaluation of the 240 extracts was performed against Lactuca sativa L. and Agrostis stolonifera L.. The MeOH extract of Bellis longifolia was the most phytotoxic...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2017.08.019
更新日期:2017-12-01 00:00:00
abstract::In the course of our screening for new bioactive natural products, a culture of Hypoxylon rickii, a xylariaceous ascomycete collected from the Caribbean island Martinique, was identified as extraordinary prolific producer of secondary metabolites. Ten metabolites of terpenoid origin were isolated from submerged cultur...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2015.06.002
更新日期:2015-09-01 00:00:00
abstract::Incubation of the diterpene 2beta-hydroxy-ent-13-epi-manoyl oxide with Gibberella fujikuroi afforded in good yield 2beta,6beta-dihydroxy-ent-13-epi-manoyl oxide, 2beta,12beta-dihydroxy-ent-13-epi-manoyl oxide and 2beta,20-dihydroxy-ent-13-epi-manoyl oxide, confirming that although ent-13-epi-manoyl oxide is a final me...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(02)00436-3
更新日期:2003-01-01 00:00:00
abstract::Inspired by the recently discovered phenomenon of "horizontal natural product transfer" we investigated the putative uptake of phenolic specialized metabolites. Umbelliferone was chosen for this case study, since this coumarin as well as its derivatives can easily be determined by HPLC analyses. Barley (Hordeum vulgar...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2018.10.032
更新日期:2019-01-01 00:00:00
abstract::Triterpene saponins 1-8 were isolated from the aerial parts of Gynostemma pubescens. Among them, compounds 1-4, 8 possess carboxylic groups at both C-21 and C-29, 5 contains a carboxylic group at C-21 and an aldehyde function at C-29, whereas 6 and 7 contain carboxylic groups at C-21 and hydroxymethylene groups at C-2...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2007.05.005
更新日期:2007-07-01 00:00:00
abstract::From the roots of various Stemona species four new dehydrotocopherols (chromenols) were isolated and their structures and stereochemistry elucidated by spectroscopic methods. The double bond between C-3 and C-4 proved to be a typical chemical character of the genus found in most of the species. Various C-methylations ...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2004.08.023
更新日期:2004-10-01 00:00:00
abstract::Dietary intake of proanthocyanidins (PAs) has been largely unknown because of the lack of reliable values for their content in foods. Recent development of an analytical method for PAs has allowed the quantification of individual oligomers and polymers. This method has been employed to analyze food samples collected u...
journal_title:Phytochemistry
pub_type: 杂志文章,评审
doi:10.1016/j.phytochem.2005.03.025
更新日期:2005-09-01 00:00:00
abstract::Two sulfur-containing compounds, (S)-2-amino-5-((R)-1-carboxy-2-((E)-3-(4-hydroxy-3-methoxyphenyl)allylthio)ethyl-amino)-5-oxopentanoic acid (1) and (S)-2-amino-5-((R)-1-(carboxymethylamino)-3-((E)-3-(4-hydroxyphenyl)allylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid (2), and one 1H-pyrrole-2-carboxylic acid deriva...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2010.08.014
更新日期:2010-12-01 00:00:00
abstract::Eleven indole alkaloids, comprising four corynanthean, two eburnane, one aspidofractinine, one secoleuconoxine, one andranginine, and two pauciflorine type alkaloids were isolated from the stem-bark and leaf extracts of Kopsia pauciflora. Their structures were determined using NMR and MS analyses. The catharinensine t...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2014.09.014
更新日期:2014-12-01 00:00:00
abstract::Four meroterpenoids, 1-hydroxychevalone C, 1-acetoxychevalone C, 1,11-dihydroxychevalone C, and 11-hydroxychevalone C and two ester epimers, 2S,4S-spinosate and 2S,4R-spinosate, together with seven known compounds, chevalones B, C, and E, tryptoquivaline, nortryptoquivaline, tryptoquivaline L, and quinadoline A were i...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2016.09.008
更新日期:2016-12-01 00:00:00
abstract::The glucosinolate content of various organs of the model plant Arabidopsis thaliana (L.) Heynh., Columbia (Col-0) ecotype, was analyzed at different stages during its life cycle. Significant differences were noted among organs in both glucosinolate concentration and composition. Dormant and germinating seeds had the h...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/s0031-9422(02)00549-6
更新日期:2003-02-01 00:00:00
abstract::Asclepias fruticosa afforded, in addition to five known pregnane glycosides and 11 known cardenolide glycosides, four new pregnane glycosides and eleven new cardenolide glycosides. Structures of these compounds were elucidated by spectroscopic methods and from chemical evidence. ...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/0031-9422(94)85029-1
更新日期:1994-09-01 00:00:00
abstract::The stem bark of Croton gratissimus (Euphorbiaceae) yielded four cembranolides, including the first reported example of a 2,12-cyclocembranolide, (+)-[1R*,2S*,7S*,8S*,12R*]-7,8-epoxy-2,12-cyclocembra-3E,10Z-dien-20,10-olide, whose structure was confirmed by means of single crystal X-ray analysis. This compound showed ...
journal_title:Phytochemistry
pub_type: 杂志文章
doi:10.1016/j.phytochem.2010.05.014
更新日期:2010-08-01 00:00:00