Chevalone C analogues and globoscinic acid derivatives from the fungus Neosartorya spinosa KKU-1NK1.

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 isolated from the fungus Neosartorya spinosa. Their structures were established based on spectroscopic data analyses. The theoretical ECD spectra of epimers, 2S,4S-spinosate and 2S,4R-spinosate were calculated to support the experimental results of their CD spectra. 1-hydroxychevalone C exhibited antimycobacterial activity against Mycobacterium tuberculosis with a MIC value of 26.4 μM. 1-Acetoxychevalone C and tryptoquivaline showed antimalarial activity against Plasmodium falciparum with IC50 values of 6.67 and 2.65 μM, respectively. In addition, 1-hydroxychevalone C, 1-acetoxychevalone C, 1,11-dihydroxychevalone C and quinadoline A showed cytotoxicity against KB and NCI-H187 cancer cell lines with IC50 values in the range of 32.7-103.3 μM.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Rajachan OA,Kanokmedhakul K,Sanmanoch W,Boonlue S,Hannongbua S,Saparpakorn P,Kanokmedhakul S

doi

10.1016/j.phytochem.2016.09.008

subject

Has Abstract

pub_date

2016-12-01 00:00:00

pages

68-75

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(16)30192-3

journal_volume

132

pub_type

杂志文章
  • Dietary phytoestrogens and health.

    abstract::The interest in the potential health effects of dietary phytoestrogens has increased with the findings that hormone replacement therapy is not as safe or effective as previously thought. This review summarizes the dietary sources of the phytoestrogens; isoflavonoids, stilbenes, coumestans and lignans. It also examines...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2004.03.005

    authors: Cornwell T,Cohick W,Raskin I

    更新日期:2004-04-01 00:00:00

  • Dimeric bisindole alkaloids from the stem bark of Strychnos nux-vomica L.

    abstract::Strychnos nux-vomica L. (Loganiaceae) is famous for its monomeric alkaloid content, such as strychnine, a convulsant poison. The stem bark of the tree is traditionally used to treat intermittent fever in South East Asia. In various studies, it appeared that dimeric indolo-monoterpenic alkaloids possess a promising act...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.11.002

    authors: Jonville MC,Dive G,Angenot L,Bero J,Tits M,Ollivier E,Frédérich M

    更新日期:2013-03-01 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

  • 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

  • Phytoceramides and acylated phytosterol glucosides from Pterospermum acerifolium Willd. seed coat and their osteogenic activity.

    abstract::Phytochemical investigation of seed coats of Pterospermum acerifolium afforded two phytoceramides (1, 2) and two acylated phytosterol glucosides (3, 4) together with five known compounds (5-9). Their structures were elucidated on the basis of extensive spectroscopic analysis using 1D, 2D NMR and Mass spectrometry. Com...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.06.005

    authors: Dixit P,Chand K,Khan MP,Siddiqui JA,Tewari D,Ngueguim FT,Chattopadhyay N,Maurya R

    更新日期:2012-09-01 00:00:00

  • Steroidal glycosides and cardenolide glycosides from Asclepias fruticosa.

    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

    authors: Warashina T,Noro T

    更新日期:1994-09-01 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

  • Effects of exogenous auxin and ethylene on the Arabidopsis root proteome.

    abstract::The phytohormones, auxin and ethylene, together control a wide range of physiological and developmental processes in plants. The lack of knowledge regarding how the underlying signaling processes are reflected at the protein level represents a major gap in understanding phytohormone signaling, including that mediated ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.08.007

    authors: Slade WO,Ray WK,Williams PM,Winkel BS,Helm RF

    更新日期:2012-12-01 00:00:00

  • Infraspecific variability in the essential oil composition of Cistus monspeliensis leaves.

    abstract::The leaf essential oils of Cistus monspeliensis plants growing wild on calcareous and siliceous soils in Provence (South of France) were analysed by GC and GC-MS. Qualitative and quantitative differences are noted in the essential oil composition between the Cistus populations from the two soil types. For chemotaxonom...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00460-4

    authors: Robles C,Garzino S

    更新日期:2000-01-01 00:00:00

  • Phenylpropanoid glycosides from Smilax glabra.

    abstract::Five phenylpropanoid esters of sucrose glycosides, trivially named smiglasides A-E, were isolated from the rhizomes of Smilax glabra. Their structures were elucidated on the basis of spectroscopic studies. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00522-1

    authors: Chen T,Li JX,Xu Q

    更新日期:2000-04-01 00:00:00

  • Is the C:N ratio a reliable indicator of C allocation to primary and defence-related metabolisms in tomato?

    abstract::Plant growth and defence are both fuelled by compounds synthesized from a common pool of carbon and nitrogen, implying the existence of a competition for carbon and nitrogen allocation to both metabolisms. The ratio of carbon to nitrogen (C:N) of an organ is often regarded as a convenient indicator of growth and quali...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.12.003

    authors: Royer M,Larbat R,Le Bot J,Adamowicz S,Robin C

    更新日期:2013-04-01 00:00:00

  • Allosteric substrate inhibition of Arabidopsis NAD-dependent malic enzyme 1 is released by fumarate.

    abstract::Plant mitochondria can use L-malate and fumarate, which accumulate in large levels, as respiratory substrates. In part, this property is due to the presence of NAD-dependent malic enzymes (NAD-ME) with particular biochemical characteristics. Arabidopsis NAD-ME1 exhibits a non-hyperbolic behavior for the substrate L-ma...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.11.009

    authors: Tronconi MA,Wheeler MC,Martinatto A,Zubimendi JP,Andreo CS,Drincovich MF

    更新日期:2015-03-01 00:00:00

  • An anti-staphylococcal acylphloroglucinol from Hypericum foliosum.

    abstract::An investigation into the antibacterial properties of Hypericum foliosum Aiton. (Guttiferae) has led to the isolation of a new bioactive acylphloroglucinol natural product which by NMR spectroscopy and mass spectrometry was characterised as 1,3,5-trihydroxy-6-[2''',3'''-epoxy-3'''-methyl-butyl]-2-[2''-methyl-butanoyl]...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.04.024

    authors: Gibbons S,Moser E,Hausmann S,Stavri M,Smith E,Clennett C

    更新日期:2005-06-01 00:00:00

  • Dual metabolomics: a novel approach to understanding plant-pathogen interactions.

    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

    authors: Allwood JW,Clarke A,Goodacre R,Mur LA

    更新日期:2010-04-01 00:00:00

  • Triterpenoid saponins from Dianthus chinensis.

    abstract::Two novel triterpenoid saponins, dianchinenoside C [23-O-beta-D-glucopyranosyl 3 beta, 16 alpha-dihydroxyolean-12-ene 23 alpha, 28 beta-dioic acid 28-O-beta-D-glucopyranoside] and dianchinenoside D [3 beta, 16 alpha-dihydroxyolean-12-ene 23 alpha, 28 beta-dioic acid 28-O-beta-D-glucopyranosyl [1-->6)-beta-D-glucopyran...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)90599-5

    authors: Li HY,Koike K,Ohmoto T

    更新日期:1994-02-01 00:00:00

  • Diels-Alder type adducts from Morus cathayana.

    abstract::Two natural Diels-Alder type adducts, cathayanon A (1) and cathayanon B (2), resembling sanggenon C (4) and O (3), were isolated from the root bark of Morus cathayana. Their structures were elucidated on the basis of spectroscopic evidence. The structure of 1 was confirmed by the results of X-ray crystallographic anal...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00171-6

    authors: Shen RC,Lin M

    更新日期:2001-08-01 00:00:00

  • Acylated cyanidin 3-sambubioside-5-glucosides in three garden plants of the Cruciferae.

    abstract::Seven acylated cyanidin 3-sambubioside-5-glucosides were isolated from the flowers of three garden plants in the Cruciferae. Specifically, four pigments were isolated from Lobularia maritima (L.) Desv., together with a known pigment, as well as, three pigments from Lunaria annua L., and two known pigments from Cheiran...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.05.001

    authors: Tatsuzawa F,Saito N,Shinoda K,Shigihara A,Honda T

    更新日期:2006-06-01 00:00:00

  • Cassane diterpenoids from the stem of Caesalpinia pulcherrima.

    abstract::Cassane diterpenoids: pulcherrin A, pulcherrin B, pulcherrin C, neocaesalpin P, neocaesalpin Q and neocaesalpin R, together with eight known compounds: isovouacapenol C, 6beta-cinnamoyl-7beta-hydroxy-vouacapen-5alpha-ol, pulcherrimin E, pulcherrimin C, alpha-cadinol, 7-hydroxycadalene, teucladiol and bonducellin were ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.12.006

    authors: Pranithanchai W,Karalai C,Ponglimanont C,Subhadhirasakul S,Chantrapromma K

    更新日期:2009-01-01 00:00:00

  • Gibberellin oxidase activities in Bradyrhizobium japonicum bacteroids.

    abstract::Bradyrhizobium japonicum bacteroids isolated from root nodules of soybean (Glycine max.) plants converted the gibberellin (GA) precursor [(14)C1]GA12 into several products identified by combined gas chromatography-mass spectrometry as [(14)C1]GA24, [(14)C1]GA9, [(14)C1]GA15, GA9 17-nor-16-one and unidentified products...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.11.013

    authors: Méndez C,Baginsky C,Hedden P,Gong F,Carú M,Rojas MC

    更新日期:2014-02-01 00:00:00

  • Iridoids from Caryopteris x clandonensis.

    abstract::In continuation of our phytochemical studies on Caryopteris x clandonensis (Lamiaceae), three further iridoids were isolated from the methanolic extract of the stems. Their structures were established by 1D and 2D NMR and MS analysis as a C-6 epimer of 8-O-acetylharpagide (6-epi-8-O-acetylharpagide), a derivative of h...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00069-8

    authors: Hannedouche S,Stanislas E,Moulis C,Fourasté I

    更新日期:2000-08-01 00:00:00

  • Oleanane-type triterpenes of Embelia schimperi leaves.

    abstract::An investigation of an ethyl acetate extract of Embelia schimperi leaves has led to the isolation of 10 oleanane-type triterpenes characterized as 3beta,16alpha-di-O-acetyl-13beta, 28-epoxyoleanane (1), 3beta-acetyl-16-oxo-13beta, 28-epoxyoleanane (2), 3beta-acetyl-16alpha-hydroxy-13beta, 28-epoxyoleanane (3), 3beta-a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.07.025

    authors: Manguro LO,Okwiri SO,Lemmen P

    更新日期:2006-12-01 00:00:00

  • Dihydroagarofuran alkaloid and triterpenes from Maytenus heterophylla and Maytenus arbutifolia.

    abstract::The antimicrobially active EtOH extracts of Maytenus heterophylla yielded a new dihydroagarofuran alkaloid,1beta-acetoxy-9alpha-benzoyloxy-2beta,6alpha-dinicotinoyloxy-beta-dihydroagarofuran, together with the known compounds beta-amyrin, maytenfolic acid, 3alpha-hydroxy-2-oxofriedelane-20alpha-carboxylic acid, lup-20...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00277-1

    authors: Orabi KY,Al-Qasoumi SI,El-Olemy MM,Mossa JS,Muhammad I

    更新日期:2001-10-01 00:00:00

  • A sterol with an unusual side chain from Anoectochilus koshunensis.

    abstract::A new sterol with a non-conventional side chain has been isolated from the whole plant of Anoectochilus koshunensis, together with four known sterols, a megastigmane glucoside and 2'-deoxyadenosine. The structure of the new sterol was elucidated as 26-methylstigmasta-5,22,25, (27)-trien-3 beta-ol based on chemical and...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)89743-5

    authors: Ito A,Yasumoto K,Kasai R,Yamasaki K

    更新日期:1994-08-01 00:00:00

  • Transformations of testosterone and related steroids by Botrytis cinerea.

    abstract::Botrytis cinerea (strain AM235) was used to investigate the transformations of testosterone and related steroids. It was found that the position and stereochemistry of the introduced hydroxyl group, as well as the yield of products, depended on the structure of the substrate. Botrytis cinerea converts the examined sub...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00490-9

    authors: Huszcza E,Dmochowska-Gładysz J

    更新日期:2003-01-01 00:00:00

  • Isolation and structure elucidation of tetrameric procyanidins from unripe apples (Malus pumila cv. Fuji) by NMR spectroscopy.

    abstract::Procyanidins are plant secondary metabolites widely consumed and known to have various physiological functions, but their bioavailability and mechanism of action are still unclear especially for larger oligomers. One of the reasons is scarce information about the detailed structure of oligomeric procyanidins. As for a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.07.011

    authors: Nakashima S,Oda C,Masuda S,Tagashira M,Kanda T

    更新日期:2012-11-01 00:00:00

  • Interconverting flavonostilbenes with antibacterial activity from Sophora alopecuroides.

    abstract::Five flavonostilbenes (alopecurones H, I, J, K and L) and five known ones were isolated from roots of Sophora alopecuroides, in addition to ten other phenolic compounds. A non-enzymatic interconversion of the lavandulyl-substituted flavonostilbenes was observed among alopecurones A, H, I, and K through a Wessely-Moser...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.02.022

    authors: Wan CX,Luo JG,Ren XP,Kong LY

    更新日期:2015-08-01 00:00:00

  • Glucosinolates, flea beetle resistance, and leaf pubescence as taxonomic characters in the genus Barbarea (Brassicaceae).

    abstract::Glucosinolate content of leaves and roots, diversity in leaf pubescence, and resistance to two near-isogenic lines of the flea beetle Phyllotreta nemorum with or without an R-gene, were determined for 27 accessions of 7 Barbarea taxa, i.e. B. stricta, B. orthoceras, B. intermedia, B. verna, B. vulgaris var. vulgaris, ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00750-1

    authors: Agerbirk N,Ørgaard M,Nielsen JK

    更新日期:2003-05-01 00:00:00

  • An optimized protocol for metabolome analysis in yeast using direct infusion electrospray mass spectrometry.

    abstract::A method for the global analysis of yeast intracellular metabolites, based on electrospray mass spectrometry (ES-MS), has been developed. This has involved the optimization of methods for quenching metabolism in Saccharomyces cerevisiae and extracting the metabolites for analysis by positive-ion electrospray mass spec...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00713-6

    authors: Castrillo JI,Hayes A,Mohammed S,Gaskell SJ,Oliver SG

    更新日期:2003-03-01 00:00:00

  • Iridoid glycosides and cucurbitacin glycoside from Neopicrorhiza scrophulariiflora.

    abstract::Three iridoid glycosides, picrorosides A (1), B (2) and C (3), and a cucurbitacin glycoside, scrophoside A (4), were isolated from the rhizomes of Neopicrorhiza scrophulariiflora (Scrophulariaceae), along with two known iridoid glycosides, picrosides I (5) and II (6), and three known cucurbitacin glycosides (7-9). The...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.09.015

    authors: Kim IH,Uchiyama N,Kawahara N,Goda Y

    更新日期:2006-12-01 00:00:00

  • Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum.

    abstract::A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [alph...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.05.024

    authors: Adhikari U,Mateu CG,Chattopadhyay K,Pujol CA,Damonte EB,Ray B

    更新日期:2006-11-01 00:00:00