Deciphering the chemical origin of the semen-like floral scents in three angiosperm plants.

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 flowers of Photinia serrulata, Castanopsis sclerophylla and Stemona japonica without any chemical pretreatment. Chemical identification was performed using high-resolution MS analysis in combination with tandem MS analysis and whenever possible was confirmed by the analysis of standard reference compounds. A total of 19 compounds, mostly belonging to nitrogenous volatiles, were identified in P. serrulata, C. sclerophylla, and S. japonica flowers, 1-pyrroline, 1-piperideine, 2-pyrrolidone, and phenethylamine being common in all the three studied species. Several lines of evidence indicate that the major component responsible for the semen-like odor is most likely 1-pyrroline. 1-Pyrroline is most probably formed via the oxidative deamination of putrescine, as indicated by the observation of signal from 4-amino-butanal intermediate. Flower visitation observations suggest that the released volatiles serve to attract dipterans, including Syrphidae, Calliphoridae, and Muscidae. On the analytical side, the comparison of our results to earlier studies also indicate that compared to the traditional GC-MS approach the direct corona discharge ionization mass spectrometry provides more sensitive detection of VOCs with high proton affinity, in particular volatile amines, and therefore can be used to complement traditional GC-MS approach for the highest chemical coverage of VOC analysis.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Zhang X,Chingin K,Zhong D,Luo L,Frankevich V,Chen H

doi

10.1016/j.phytochem.2017.11.001

subject

Has Abstract

pub_date

2018-01-01 00:00:00

pages

137-145

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(17)30341-2

journal_volume

145

pub_type

杂志文章
  • Comparative phytochemical analysis of four Mexican Nymphaea species.

    abstract::Four Mexican Nymphaea species, N. ampla, N. pulchella, N. gracilis and N. elegans belonging to subgenera Brachyceras were analyzed. In this work two 5-glycosyl isoflavones, 7,3',4'-trihydroxy-5-O-beta-D-(2''-acetyl)-xylopyranosylisoflavone (1) and 7,3',4'-trihydroxy-5-O-alpha-L-rhamnopyranosylisoflavone (2), were isol...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.02.027

    authors: Marquina S,Bonilla-Barbosa J,Alvarez L

    更新日期:2005-04-01 00:00:00

  • Sesquiterpene lactones and their precursors as chemosystematic markers in the tribe Cichorieae of the Asteraceae.

    abstract::This review summarizes all reports on sesquiterpene lactones and their immediate precursors from the Cichorieae (Lactuceae) tribe of the Asteraceae. A total of 360 compounds have been reported from this tribe. The reported substances belong to three classes of sesquiterpenoids: guaianolides (243 compounds), eudesmanol...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2008.06.013

    authors: Zidorn C

    更新日期:2008-09-01 00:00:00

  • Norditerpene and diterpene alkaloids from Aconitum variegatum.

    abstract::Aerial parts of Aconitum variegatum L. from the Pyrenees furnished four norditerpene alkaloids, 16 beta-hydroxycardiopetaline, 8-ethoxysachaconitine, 14-acetylgenicunine B, N-deethyl-N-19-didehydrosachaconitine, five diterpene alkaloids 15-veratroyldictizine, 15-veratroyl-17-acetyldictizine, 15-veratroyl-17-acetyl-19-...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.01.019

    authors: Díaz JG,Ruiza JG,Herz W

    更新日期:2005-04-01 00:00:00

  • The structures of antioxidant and cytotoxic agents from natural source: anthraquinones and tannins from roots of Rumex patientia.

    abstract::A new anthraquinone glycoside, emodin-6-O-beta-D-glucopyranoside, and a new simple halogenated flavan-3-ol, 6-chlorocatechin, have been isolated from the roots of Rumex patientia L. together with seven known phenolic compounds. Their structures were elucidated on the basis of spectroscopic methods. Cytotoxic effects a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00337-5

    authors: Demirezer LO,Kuruüzüm-Uz A,Bergere I,Schiewe HJ,Zeeck A

    更新日期:2001-12-01 00:00:00

  • Antimicrobial metabolites produced by an intertidal Acremonium furcatum.

    abstract::In a screening for antimicrobial metabolites, amides of D-allo- and L-isoleucine derivatives were isolated from the culture of a marine strain of Acremonium furcatum. Structural elucidation of these compounds was performed by analysis of spectroscopic data and confirmed by synthesis. All of the compounds, natural and ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.07.028

    authors: Gallardo GL,Butler M,Gallo ML,Rodríguez MA,Eberlin MN,Cabrera GM

    更新日期:2006-11-01 00:00:00

  • Indole alkaloids of Psychotria as multifunctional cholinesterases and monoamine oxidases inhibitors.

    abstract::Thirteen Psychotria alkaloids were evaluated regarding their interactions with acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and monoamine oxidases A and B (MAO-A and MAO-B), which are enzymatic targets related with neurodegenerative diseases. Two quaternary β-carboline alkaloids, prunifoleine and 14-oxop...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.11.015

    authors: Passos CS,Simões-Pires CA,Nurisso A,Soldi TC,Kato L,de Oliveira CM,de Faria EO,Marcourt L,Gottfried C,Carrupt PA,Henriques AT

    更新日期:2013-02-01 00:00:00

  • African Cucurbita pepo L.: properties of seed and variability in fatty acid composition of seed oil.

    abstract::Pumpkin (Cucurbita pepo) seeds are used locally in Eritrea to treat tapeworm. Seeds were found to be rich in oil (approximately 35%), protein (38%), alpha-tocoferols (3 mg/100 g) and carbohydrate content (approximately 37%). The physico-chemical properties and fatty acid composition of the seed oil were examined. The ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00610-x

    authors: Younis YM,Ghirmay S,al-Shihry SS

    更新日期:2000-05-01 00:00:00

  • Tumor promoting diterpenes from Euphorbia leuconeura L.

    abstract::Diterpene esters of the phorbol and ingenol types are known to be highly active tumor promoting agents that typically occur in members of the Euphorbiaceae. In the present work, Euphorbia leuconeura, a rare indoor plant, is analyzed for its tumor promoting potential. Latex as well as total leaf extracts exhibited Epst...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00016-3

    authors: Vogg G,Mattes E,Rothenburger J,Hertkorn N,Achatz S,Sandermann H Jr

    更新日期:1999-05-01 00:00:00

  • Induction of acid phosphatase transcripts, protein and enzymatic activity by simulated herbivory of hybrid poplar.

    abstract::Herbivory and wounding upregulate a large suite of defense genes in hybrid poplar leaves. A strongly wound- and herbivore-induced gene with high similarity to Arabidopsis vegetative storage proteins (VSPs) and acid phosphatase (AP) was identified among genes strongly expressed during the poplar herbivore defense respo...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.01.001

    authors: Veljanovski V,Major IT,Patton JJ,Bol E,Louvet S,Hawkins BJ,Constabel CP

    更新日期:2010-04-01 00:00:00

  • Isolation and identification of lateral bud growth inhibitor, indole-3-aldehyde, involved in apical dominance of pea seedlings.

    abstract::A lateral bud growth inhibitor was isolated from etiolated pea seedlings and identified as indole-3-aldehyde. The indole-3-aldehyde content was significantly higher in the diffusates from explants with apical bud and indole-3-acetic acid treated decapitated explants, in which apical dominance is maintained, than in th...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00400-4

    authors: Nakajima E,Nakano H,Yamada K,Shigemori H,Hasegawa K

    更新日期:2002-12-01 00:00:00

  • A chlorinated coumarinolignan from the African medicinal plant, Mondia whitei.

    abstract::The unusual chlorinated coumarinolignan, 5-chloropropacin, along with several other known compounds have been isolated from the roots of Mondia whitei. The structure of the chlorinated coumarinolignan was determined by NMR and mass spectroscopic analyses. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.11.012

    authors: Patnam R,Kadali SS,Koumaglo KH,Roy R

    更新日期:2005-03-01 00:00:00

  • Chalcones and other constituents of Dorstenia prorepens and Dorstenia zenkeri.

    abstract::The twigs of Dorstenia prorepens furnished the digeranylated chalcone, 5,3'-(3,7-dimethyl-2,6-octadienyl)-3,4, 2',4'-tetrahydroxychalcone while Dorstenia zenkeri yielded the 3',4'-(3-hydroxy-2,2-dimethyldihydropyrano)-4,2'-dihydroxychalcone and a bichalcone. 4-Hydroxylonchocarpin was found in both plants. D. prorepens...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00483-6

    authors: Abegaz BM,Ngadjui BT,Dongo E,Ngameni B,Nindi MN,Bezabih M

    更新日期:2002-04-01 00:00:00

  • Diterpenes from the berries of Juniperus excelsa.

    abstract::From the hexane extract of berries of Juniperus excelsa, one new and four known diterpenes were isolated besides a known sesquiterpene. The structures of the known diterpenes were identified as isopimaric, isocommunic, (-)ent-trans communic and sandracopimaric acids, along with the sesquiterpene 4a-hydroxycedrol and t...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00675-x

    authors: Topçu G,Erenler R,Cakmak O,Johansson CB,Celik C,Chai HB,Pezzuto JM

    更新日期:1999-04-01 00:00:00

  • Defensive strategies in Geranium sylvaticum. Part 1: organ-specific distribution of water-soluble tannins, flavonoids and phenolic acids.

    abstract::A combination of high-resolution mass spectrometry and modern HPLC column technology, assisted by diode array detection, was used for accurate characterization of water-soluble polyphenolic compounds in the pistils, stamens, petals, sepals, stems, leaves, roots and seeds of Geranium sylvaticum. The organs contained a ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.05.013

    authors: Tuominen A,Toivonen E,Mutikainen P,Salminen JP

    更新日期:2013-11-01 00:00:00

  • Intermediates in the oxidative pathway from torulene to torularhodin in the red yeasts Cystofilobasidium infirmominiatum and C. capitatum (Heterobasidiomycetes, Fungi).

    abstract::Two red Cystofilobasidium spp. isolated from spring sap-flows of Betula pendula were analysed for their carotenoid content. In Cystofilobasidium infirmominiatum, three unusual pigments were detected and identified by structure elucidation as oxidised torulene derivatives. These included 16'-hydroxytorulene and torular...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.05.019

    authors: Herz S,Weber RW,Anke H,Mucci A,Davoli P

    更新日期:2007-10-01 00:00:00

  • Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia.

    abstract::Five cucurbitacins, kuguacins A-E (1-5), together with three known analogues, 3beta,7beta,25-trihydroxycucurbita-5,(23E)-diene-19-al (6), 3beta,25-dihydroxy-5beta,19-epoxycucurbita-6,(23E)-diene (7), and momordicine I (8), were isolated from roots of Momordica charantia. Structures of 1-5 were elucidated by NMR and MS...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.10.020

    authors: Chen J,Tian R,Qiu M,Lu L,Zheng Y,Zhang Z

    更新日期:2008-02-01 00:00:00

  • Characterization of the 1-aminocyclopropane-1-carboxylic acid (ACC) oxidase multigene family of Malus domestica Borkh.

    abstract::Two 1-aminocyclopropane-1-carboxylic acid (ACC) oxidase (ACO) genes have been cloned from RNA isolated from leaf tissue of apple (Malus domestica cv. Royal Gala). The genes, designated MD-ACO2 (with an ORF of 990bp) and MD-ACO3 (966bp) have been compared with a previously cloned gene of apple, MD-ACO1 (with an ORF of ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.01.002

    authors: Binnie JE,McManus MT

    更新日期:2009-02-01 00:00:00

  • Production of (+)-5-deoxystrigol by Lotus japonicus root culture.

    abstract::Lotus japonicus roots, cultured in a modified B5 medium, produced and secreted germination stimulants that induced Striga hermonthica seed germination. The germination-inducing activity was detected both in the roots and the culture filtrate. Following bioassay-guided purification procedures, an active compound was is...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.06.011

    authors: Sugimoto Y,Ueyama T

    更新日期:2008-01-01 00:00:00

  • Heterologous expression of the plant proteins strictosidine synthase and berberine bridge enzyme in insect cell culture.

    abstract::The heterologous expression of cDNAs encoding the alkaloid biosynthetic enzymes, strictosidine synthase [EC 4.3.3.2] from Rauvolfia serpentina and the berberine bridge enzyme [(S)-reticuline: oxygen oxidoreductase (methylene-bridge-forming), EC 1.5.3.9] from Eschscholtzia californica, has been achieved in a cell cultu...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)94763-0

    authors: Kutchan TM,Bock A,Dittrich H

    更新日期:1994-01-01 00:00:00

  • Neolignan and flavonoid glycosides in Juniperus communis var. depressa.

    abstract::Two neolignan glycosides (junipercomnosides A and B) were isolated from aerial parts of Juniperus communis var. depressa along with two known neolignan glycosides and seven flavonoid glycosides. The structures of the isolated compounds were determined by spectral analysis, in particular by 2D-NMR analysis. The signifi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2003.10.025

    authors: Nakanishi T,Iida N,Inatomi Y,Murata H,Inada A,Murata J,Lang FA,Iinuma M,Tanaka T

    更新日期:2004-01-01 00:00:00

  • Distribution of morphinan and benzo[c]phenanthridine alkaloid gene transcript accumulation in Papaver somninferum.

    abstract::The opium poppy Papaver somniferum L. produces the antimicrobial benzo[c]phenanthridine alkaloid sanguinarine and the narcotic analgesic morphinan alkaloid morphine. Transcripts of three genes of alkaloid biosynthesis in P. somniferum in developing seedlings, mature plants and plant cell suspension culture were monito...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00600-7

    authors: Huang FC,Kutchan TM

    更新日期:2000-03-01 00:00:00

  • Secoiridoids from Gentiana siphonantha.

    abstract::Repeated fractionations of the methanol extract of the subterranean parts (rhizomes and roots) of Gentiana siphonantha afforded two new and five known secoiridoids, in addition to the widespread plant constituents beta-sitiosterol, daucosterol and oleanolic acid. The structures of the new acyl secoiridoid glycosides w...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(97)00225-2

    authors: Tan RX,Kong LD

    更新日期:1997-11-01 00:00:00

  • Chrysin and other leaf exudate flavonoids in the genus Pelargonium.

    abstract::In a chemotaxonomic survey of 57 Pelargonium species, leaf exudate flavonoids were detected in 35% of the sample, mostly in trace amounts. However, chrysin and a related C-methylflavanone were identified as major leaf surface constituents of P. crispum, and a mixture of quercetin and kaempferol mono-, and di- and trim...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(97)00514-1

    authors: Williams CA,Harborne JB,Newman M,Greenham J,Eagles J

    更新日期:1997-12-01 00:00:00

  • Evolutionary changes in defensive specialized metabolism in the genus Hordeum.

    abstract::Plants have developed defensive specialized metabolites over the course of evolution. In the genus Hordeum, which includes the important cereal crop barley, specialized metabolites such as hordatines, benzoxazinones, and gramine have been identified. Hordeum species are classified into four clades, H, Xu, Xa, and I. T...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.05.004

    authors: Ube N,Nishizaka M,Ichiyanagi T,Ueno K,Taketa S,Ishihara A

    更新日期:2017-09-01 00:00:00

  • Pestalopyrones A-D, four tricyclic pyrone derivatives from the endophytic fungus Pestalotiopsis neglecta S3.

    abstract::Four undescribed pyrone derivatives, pestalopyrones A-D, containing unusual tricyclic 5/6/6 polycyclic skeletons, were isolated from the ethyl acetate extract of the endophytic fungus Pestalotiopsis neglecta S3 derived from the fresh stems of Rubia podantha Diels (Rubiaceae). Their planar structures were elucidated ma...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112505

    authors: Feng L,Han J,Wang J,Zhang AX,Miao YY,Tan NH,Wang Z

    更新日期:2020-11-01 00:00:00

  • Guaianolide sesquiterpenes from Pulicaria crispa (Forssk.) Oliv.

    abstract::A phytochemical study of the asteraceous herb Pulicaria crispa (Forssk.) Oliv. resulted in the characterisation of three guaianolide sesquiterpenes, 2alpha,4alpha-dihydroxy-7alphaH,8alphaH,10alphaH-guaia-1(5),11(13)-dien-8beta,12-olide (1), 1alpha,2alpha-epoxy-4beta-hydroxy-5alphaH,7alphaH,8alphaH,10alphaH-guaia-11(13...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.03.012

    authors: Stavri M,Mathew KT,Gordon A,Shnyder SD,Falconer RA,Gibbons S

    更新日期:2008-06-01 00:00:00

  • Applicability of ISSR and DAMD markers for phyto-molecular characterization and association with some important biochemical traits of Dendrobium nobile, an endangered medicinal orchid.

    abstract::Dendrobium nobile is an important medicinal orchid having profound importance in traditional herbal drug preparations and pharmacopeias worldwide. Due to various anthropogenic pressures the natural populations of this important orchid species are presently facing threats of extinction. In the present study, genetic an...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.06.022

    authors: Bhattacharyya P,Kumaria S,Tandon P

    更新日期:2015-09-01 00:00:00

  • Leaf sheath cuticular waxes on bloomless and sparse-bloom mutants of Sorghum bicolor.

    abstract::Leaf sheath cuticular waxes on wild-type Sorghum bicolor were approximately 96% free fatty acids, with the C28 and C30 acids being 77 and 20% of these acids, respectively. Twelve mutants with markedly reduced wax load were characterized for chemical composition. In all of the 12 mutants, reduction in the amount of C28...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00153-9

    authors: Jenks MA,Rich PJ,Rhodes D,Ashwort EN,Axtell JD,Din CK

    更新日期:2000-07-01 00:00:00

  • Lycophlegmariols A-D: cytotoxic serratene triterpenoids from the club moss Lycopodium phlegmaria L.

    abstract::Lycopodium serratene triterpenoids, along with an abietane-type diterpene were isolated from the methanol extract of club moss Lycopodium phlegmaria L. The structures of these hitherto unknown lycopodium terpenoids were elucidated on the basis of spectroscopic analysis. Pentacyclic triterpenoids, 21β-hydroxy-serrat-14...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.01.006

    authors: Wittayalai S,Sathalalai S,Thorroad S,Worawittayanon P,Ruchirawat S,Thasana N

    更新日期:2012-04-01 00:00:00

  • Caudatan A, an undescribed human kidney-type glutaminase inhibitor with tetracyclic flavan from Ohwia caudata.

    abstract::Human kidney-type glutaminase (KGA) is an important target that is often over expressed in many cancer cells but very few effective inhibitors of this enzyme have yet reached clinical trials. Caudatan A and caudatan B, two undescribed tetracyclic flavans with an unusual ether bond between the C-4 and C-2' were isolate...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.04.013

    authors: Sun Y,Feng X,Liu X,Qian C,Che X,Cao F,Jin S,Meng D

    更新日期:2018-08-01 00:00:00