Synthesis of potent neuroprotective butenolides based on plant smoke derived 3,4,5-Trimethylfuran-2(5H)-one and 3-methyl-2H-furo[2,3-c]pyrone-2-one.

Abstract:

:Smoke derived karrikinolide and trimethylbutenolide exerted neuroprotective effects against monoamine oxidase and acetylcholinesterase. Synthesis of potent analogs was achieved. Sulphur substitution in the bicyclic ring structure of KAR1 displayed the most encouraging activity returning IC50 values of 13.75 ± 0.001 μM and 0.03 ± 0.02 μM for monoamine oxidase A and B and 0.08 ± 0.006 μM for acetylcholinesterase. Neuroprotective butenolides may be particularly useful in the treatment of depressive disorders, Alzheimer's and Parkinson's diseases.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Naidoo D,Pošta M,Roy A,Kulkarni M,Van Staden J

doi

10.1016/j.phytochem.2019.03.014

subject

Has Abstract

pub_date

2019-07-01 00:00:00

pages

187-194

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(18)30798-2

journal_volume

163

pub_type

杂志文章
  • Cytotoxic cycloartanes from Aglaia argentea.

    abstract::Aglaia argentea leaves yielded three new cycloartanes: argenteanones A and B, and argenteanol. The first two possess cytotoxic activity against KB cells (IC50 7.5 micrograms ml-1 and 6.5 micrograms ml-1 respectively). Structural elucidation was done by two-dimensional NMR spectroscopy. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00745-8

    authors: Omobuwajo OR,Martin MT,Perromat G,Sevenet T,Awang K,Païs M

    更新日期:1996-03-01 00:00:00

  • Involvement of calcium in ACC-oxidase activity from Cicer arietinum seed embryonic axes.

    abstract::Both in vivo and in vitro ACC-oxidase activities as well as ethylene production from embryonic axes of chickpea seeds were strongly inhibited by EGTA, a selective extracellular Ca2+ ion chelator, indicating that the influx of Ca2+ is important for enzymatic activity. EGTA inhibition was restored by exogenous Ca2+. Tre...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00591-3

    authors: Gallardo M,Gómez-Jiménez MC,Matilla A

    更新日期:1999-02-01 00:00:00

  • Triterpenoids from the stems and leaves of Schisandra incarnata.

    abstract::Six undescribed triterpenoids, schincarins A‒F, categorized as the preschisanartane (schincarin A), 3,4-secocycloartane (schincarins B‒D), 3,4; 9,10-disecocycloartane (schincarin E), and 3,4-secolanostane (schincarin F) classes, along with twelve known analogues, were obtained from the stems and leaves of Schisandra i...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112448

    authors: Zhou M,Peng X,Zhou J,Liu Y,Meng X,Ruan H

    更新日期:2020-09-01 00:00:00

  • Four tetracyclic oxindole alkaloids and a taberpsychine derivative from a Malayan Tabernaemontana.

    abstract::Four tetracyclic oxindole alkaloids, 7(R)- and 7(S)-geissoschizol oxindole (1 and 2), 7(R),16(R)- and 7(S),16(R)-19(E)-isositsirikine oxindole (3 and 4), in addition to a taberpsychine derivative, N(4)-demethyltaberpsychine (5), were isolated from the Malayan Tabernaemontana corymbosa and the structures were establish...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.06.010

    authors: Lim KH,Sim KM,Tan GH,Kam TS

    更新日期:2009-06-01 00:00:00

  • Response of prostaglandin content in the red alga Gracilaria verrucosa to season and solar irradiance.

    abstract::The influence of solar irradiance and seasons on prostaglandin (PG) and arachidonic acid (AA) content in the marine red alga Gracilaria verrucosa (Huds.) Papenf. (unattached form) was investigated. PGA(2), PGE(2), PGF(2), and 15-keto-PGE(2) were isolated from the alga, quantitatively analyzed as 4-methyl-7-methoxycoum...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00321-1

    authors: Imbs AB,Vologodskaya AV,Nevshupova NV,Khotimchenko SV,Titlyanov EA

    更新日期:2001-12-01 00:00:00

  • Isoflavonoids from the roots of Erythrina poeppigiana.

    abstract::Five isoflavonoids, 7,4'-dihydroxy-2'-methoxy-8-(gamma,gamma-dimethylallyl)isoflav-3-ene, 4'-hydroxy-2'-methoxy-6",6"-dimethylpyran[2",3":7,8]isoflav-3-ene, 5,7,4'-trihydroxy-2'-methoxy-5'-(gamma,gamma-dimethylallyl)isoflavanone, 5,4'-dihydroxy-7,2'-dimethoxy-5'-(gamma,gamma-dimethylallyl)isoflavanone and 3,9-dihydrox...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00164-4

    authors: Tanaka H,Oh-Uchi T,Etoh H,Shimizu H,Tateishi Y

    更新日期:2002-08-01 00:00:00

  • Chromenes of polyketide origin from Peperomia villipetiola.

    abstract::An extract of leaves and stems of Peperomia villipetiola has been found to contain myristicin (3-methoxy-4,5-methylenedioxy-allylbenzene) and seven chromenes, whose structures are methyl 5-hydroxy-7-methyl-2,2-dimethyl-2H-1-chromene-6-carboxylate (1), methyl 5-methoxy-7-methyl-2,2-dimethyl-2H-1-chromene-8-carboxylate ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.01.003

    authors: Malquichagua Salazar KJ,Delgado Paredes GE,Lluncor LR,Young MC,Kato MJ

    更新日期:2005-03-01 00:00:00

  • A benzoquinone and flavonoids from Cyperus alopecuroides.

    abstract::A benzoquinone, named alopecuquinone, was isolated from the ethanol extract of the inflorescences of Cyperus alopecuroides. Its structure was primarily elucidated by spectroscopic analysis including 1H, 13C NMR, APT, HMQC, 1H-1H COSY and CIMS. The known flavonoids, vicenin 2, orientin, diosmetin, quercetin 3,3'-dimeth...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00060-2

    authors: Nassar MI,Abdel-Razik AF,El-Khrisy Eel-D,Dawidar AA,Bystrom A,Mabry TJ

    更新日期:2002-06-01 00:00:00

  • Biologically active compounds and pharmacological activities of species of the genus Crocus: A review.

    abstract::The present article is the first comprehensive review on the chemical composition and pharmacological activities of the raw materials of Crocus species. In the present review, data on chemical constituents and pharmacological profile of Crocus sativus stigmas, as well as of other plant parts (perianth, stamens, leaves...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2019.02.004

    authors: Mykhailenko O,Kovalyov V,Goryacha O,Ivanauskas L,Georgiyants V

    更新日期:2019-06-01 00:00:00

  • Deposition of stearate-oleate rich seed fat in Mangifera indica is mediated by a FatA type acyl-ACP thioesterase.

    abstract::Although the mechanism of accumulation of C8-C16 saturated fatty acids in seed oils has been well-studied, the control of stearic (C18:0) acid deposition in high stearate seed fat is still unclear. We investigated the mechanism that regulates high level of stearate and oleate (C18:1) accumulation in mango (Mangifera i...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.11.004

    authors: Bhattacharjee A,Ghosh SK,Neogi K,Aich A,Willard B,Kinter M,Sen SK,Ghosh D,Ghosh S

    更新日期:2011-02-01 00:00:00

  • Alkaloids from Cynanchum komarovii with inhibitory activity against the tobacco mosaic virus.

    abstract::A pyrroloisoquinoline alkaloid, 2,3-dimethoxy-6-(3-oxo-butyl)-7,9,10,11,11a,12-hexahydrobenzo[f]pyrrolo[1,2-b]isoquinoline (1), whose structure was determined by spectroscopic methods, was isolated from the aerial parts of Cynanchum komarovii, together with two known alkaloids, 7-demethoxytylophorine (2) and 7-demetho...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00382-x

    authors: An T,Huang RQ,Yang Z,Zhang DK,Li GR,Yao YC,Gao J

    更新日期:2001-12-01 00:00:00

  • Composition of the epicuticular waxes coating the adaxial side of Phyllostachys aurea leaves: Identification of very-long-chain primary amides.

    abstract::The present study presents comprehensive chemical analyses of cuticular wax mixtures of the bamboo Phyllostachys aurea. The epicuticular and intracuticular waxes were sampled selectively from the adaxial side of leaves on young and old plants and investigated by gas chromatography-mass spectrometry and flame ionizatio...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.06.005

    authors: Racovita RC,Jetter R

    更新日期:2016-10-01 00:00:00

  • Polyacetylene glycosides from Pratia nummularia cultures.

    abstract::Two polyacetylene glycosides, lobetyol 9-O-glc(6)-(1)rha (pratialin-A) and lobetyol 9-O-glc(6)-(1)glc(6)-(1)glc (pratialin-B), were isolated from Pratia nummularia (Campanulaceae) callus and hairy root cultures and their chemical structures were determined by analysis of spectroscopic data. From the methanol extract o...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00669-6

    authors: Ishimaru K,Osabe M,Yan L,Fujioka T,Mihashi K,Tanaka N

    更新日期:2003-02-01 00:00:00

  • Sulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit.

    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

    authors: Zheng ZP,Ma J,Cheng KW,Chao J,Zhu Q,Chang RC,Zhao M,Lin ZX,Wang M

    更新日期:2010-12-01 00:00:00

  • Composition of cuticular waxes coating flag leaf blades and peduncles of Triticum aestivum cv. Bethlehem.

    abstract::The work herein presents comprehensive analyses of the cuticular wax mixtures covering the flag leaf blade and peduncle of bread wheat (Triticum aestivum) cv. Bethlehem. Overall, Gas Chromatography-Mass Spectrometry and Flame Ionization Detection revealed a wax coverage of flag leaf blades (16 μg/cm(2)) a third that o...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.05.003

    authors: Racovita RC,Hen-Avivi S,Fernandez-Moreno JP,Granell A,Aharoni A,Jetter R

    更新日期:2016-10-01 00:00:00

  • Targeted metabolite profiling provides a functional link among eucalypt taxonomy, physiology and evolution.

    abstract::Adaptation to aridity is considered a major factor in the evolution of the genus Eucalyptus. For the first time, targeted metabolite profiling has uncovered a quantitative yet discrete phytochemical link with eucalypt taxonomy. The distribution of cyclitols among Eucalyptus species, and a range of other Australian tre...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.11.027

    authors: Merchant A,Richter A,Popp M,Adams M

    更新日期:2006-02-01 00:00:00

  • Furofuran lignans display schistosomicidal and trypanocidal activities.

    abstract::Parasitic diseases continue to be a major worldwide health problem, and there is an urgent need for development of therapeutic drugs. This paper describes synthesis of dehydrodiferulic acid dilactone 1 and dehydrodisinapic acid dilactone 2 furofuran lignans by oxidative coupling of ferulic and sinapic acids, respectiv...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.08.010

    authors: Pereira AC,Esperandim VR,Ferreira da Silva D,Magalhães LG,Lima TC,Nanayakkara DN,Cunha WR,Bastos JK,Andrade e Silva ML

    更新日期:2014-11-01 00:00:00

  • Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae.

    abstract::In a chemosystematic investigation of tribe Veroniceae (Plantaginaceae), representatives of Camptoloma, Sibthorpia, Veronica subg. Pentasepalae and subg. Hebe, Veronicastrum, Wulfenia, and the related Ellisiophyllum and Globularia were examined for non-flavonoid glycosides. From the 14 species studied, 28 different ir...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.11.011

    authors: Taskova RM,Gotfredsen CH,Jensen SR

    更新日期:2006-02-01 00:00:00

  • Diversity of fatty acid composition of symbiotic dinoflagellates in corals: evidence for the transfer of host PUFAs to the symbionts.

    abstract::High diversity of fatty acid (FA) composition of endosymbiotic dinoflagellates of the Symbiodinium group (zooxanthellae) isolated from different cnidarian groups has been found. To explain this diversity, FA composition of the total lipids of pure symbiont fractions (SF) and host cell tissue fractions (HF) isolated fr...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.02.012

    authors: Imbs AB,Yakovleva IM,Dautova TN,Bui LH,Jones P

    更新日期:2014-05-01 00:00:00

  • Sequential oxidation of Jasmonoyl-Phenylalanine and Jasmonoyl-Isoleucine by multiple cytochrome P450 of the CYP94 family through newly identified aldehyde intermediates.

    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, ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.06.027

    authors: Widemann E,Grausem B,Renault H,Pineau E,Heinrich C,Lugan R,Ullmann P,Miesch L,Aubert Y,Miesch M,Heitz T,Pinot F

    更新日期:2015-09-01 00:00:00

  • Kaempferol triosides from Reseda muricata.

    abstract::A flavonoid trioside and its coumaryl ester together with seven known flavonoids and five phenolic acids were isolated from the leaves of Reseda muricata. Their structures were elucidated by spectroscopic methods including UV, FAB MS, 1H, 13C and 2D-NMR, DEPT, HMBC and HMQC experiments. The two compounds were identifi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00479-9

    authors: El-Sayed NH,Omara NM,Yousef AK,Farag AM,Mabry TJ

    更新日期:2001-06-01 00:00:00

  • Leishmanicidal effect of LLD-3 (1), a nor-triterpene isolated from Lophanthera lactescens.

    abstract::Leishmanicidal activity of 6alpha, 7alpha, 15beta, 16beta, 24-pentacetoxy-22alpha-carbometoxy-21beta,22beta-epoxy-18beta-hydroxy-27,30-bisnor-3,4-secofriedela-1,20 (29)-dien-3,4 R-olide (LLD-3 (1)) isolated from Lophanthera lactescens Ducke, a member of the Malpighiaceae, was demonstrated against intramacrophage amast...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.03.009

    authors: Danelli MG,Soares DC,Abreu HS,Peçanha LM,Saraiva EM

    更新日期:2009-03-01 00:00:00

  • Identification of phytochelatin-related peptides in maize seedlings exposed to cadmium and obtained enzymatically in vitro.

    abstract::An analytical strategy based on the sensitivity of electrospray tandem mass spectrometry following a simplified and reproducible sample preparation procedure was evaluated for the determination of Cd-induced phytochelatins (PC) and related peptides in four maize varieties. In addition to the three known families of PC...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00489-1

    authors: Chassaigne H,Vacchina V,Kutchan TM,Zenk MH

    更新日期:2001-04-01 00:00:00

  • Flavonoids from Ochna integerrima.

    abstract::Two biflavonoids namely, 2",3"-dihydroochnaflavone and 2",3"-dihydroochnaflavone 7"-O-methyl ether, and a flavonoid glycoside, 6-gamma,gamma-dimethylallyltaxifolin 7-O-beta-D-glucoside were isolated from the leaves of Ochna integerrima. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00409-x

    authors: Likhitwitayawuid K,Rungserichai R,Ruangrungsi N,Phadungcharoen T

    更新日期:2001-02-01 00:00:00

  • The current status of chemical systematics.

    abstract::Chemical systematics sets out to interpret the phylogenetic implications of the occurrence and distribution of secondary metabolites. In this review, a number of the major contributions from the 1960's and 1970's are identified and re-assessed in the light of recent evidence gained from DNA studies. It is shown that f...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2007.06.029

    authors: Waterman PG

    更新日期:2007-11-01 00:00:00

  • The destruxins: synthesis, biosynthesis, biotransformation, and biological activity.

    abstract::Destruxins, secondary metabolites first reported in 1961, are cyclic hexadepsipeptides composed of an alpha-hydroxy acid and five amino acid residues. The name "destruxin" is derived from "destructor" from the species Oospora destructor, the entomopathogenic fungus from which these metabolites were first isolated. Ind...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0031-9422(02)00016-x

    authors: Pedras MS,Irina Zaharia L,Ward DE

    更新日期:2002-03-01 00:00:00

  • Functional characterization of domains in AtTRB1, a putative telomere-binding protein in Arabidopsis thaliana.

    abstract::Telomeres are nucleoprotein structures ensuring the stability of eukaryotic chromosome ends. Two protein families, TRFL (TFL-Like) and SMH (Single-Myb-Histone), containing a specific telobox motif in their Myb domain, have been identified as potential candidates involved in a functional nucleoprotein structure analogo...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.04.001

    authors: Mozgová I,Schrumpfová PP,Hofr C,Fajkus J

    更新日期:2008-06-01 00:00:00

  • A benzoic acid glycoside from Geniostoma antherotrichum.

    abstract::Fractionation of an HIV-inhibitory organic extract of Geniostoma antherotrichum afforded a glycoside derivative, which has been characterized as 2-hydroxy-3-O-beta-D-glucopyranosyl-benzoic acid (1) on the basis of spectral analyses. The HIV-inhibitory activity of the extract was traced to polymeric tannins, while 1 wa...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00768-7

    authors: Rashid MA,Gustafson KR,Cardellina JH 2nd,Boyd MR

    更新日期:1996-03-01 00:00:00

  • Mechanisms of survival of necrotrophic fungal plant pathogens in hosts expressing the hypersensitive response.

    abstract::The hypersensitive response (HR), elicited when resistant hosts are infected by incompatible races of biotrophic fungi, has been researched extensively. New studies on host responses to necrotrophic fungi are beginning to show that when the HR occurs in hosts colonized by necrotrophs, fungal growth is accelerated rath...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0031-9422(01)00187-x

    authors: Mayer AM,Staples RC,Gil-ad NL

    更新日期:2001-09-01 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