Subnudatones A and B, new trans-decalin polyketides from the cultured lichen mycobionts of Pseudopyrenula subnudata.

Abstract:

:Chemical investigation of the cultured polyspore-derived mycobionts of a Pseudopyrenula subnudata lichen led to the isolation of two new compounds, subnudatones A and B (1 and 2), together with four known compounds, 1-(2-hydroxy-1,2,6-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethanone (3), libertalide C (4), aspermytin A (5), and 6,7-dimethoxy-4-hydroxymellin (6). Their chemical structures were elucidated by extensive 1D and 2D NMR analysis and high resolution mass spectroscopy, and comparisons were made with the literature. The absolute configuration of 1 was defined unambiguously using single crystal X-ray crystallography. Compound 1 represents the first dimeric decalin polyketide to be found in nature. The in vitro cytotoxicity of 1 against two cancer cell lines (K562 and MCF-7) was evaluated. Compound 1 showed moderate cytotoxic activity with IC50 values of 23.5 ± 1.0 and 51.9 ± 1.4 μM, respectively.

journal_name

Fitoterapia

journal_title

Fitoterapia

authors

Duong TH,Nguyen HH,Le TT,Tran TN,Sichaem J,Nguyen TT,Nguyen TP,Mai DT,Nguyen HH,Le HD

doi

10.1016/j.fitote.2020.104512

subject

Has Abstract

pub_date

2020-04-01 00:00:00

pages

104512

eissn

0367-326X

issn

1873-6971

pii

S0367-326X(20)30094-0

journal_volume

142

pub_type

杂志文章
  • New metabolites of acteoside identified by ultra-performance liquid chromatography/quadrupole-time-of-flight MS(E) in rat plasma, urine, and feces.

    abstract::Acteoside, which belongs to the family of phenylethanoid glycosides (PhGs), has extensive biological activities, including strong antioxidant, anti-inflammatory, hepatoprotect, and cell apoptosis regulation. Like other PhGs compounds, the fate of acteoside in the gut for both parent polyphenols and their degradation p...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2016.05.004

    authors: Su D,Li W,Xu Q,Liu Y,Song Y,Feng Y

    更新日期:2016-07-01 00:00:00

  • Seladoeflavones A-F, six novel flavonoids from Selaginella doederleinii.

    abstract::Six new flavonoids, seladoeflavones A-F (1-6), were isolated from the whole herbs of Selaginella doederleinii, together with one known flavonoid (7). Their structures including absolute configuration were characterized on the basis of extensive spectroscopic methods including NMR, HRMS, and electronic circular dichroi...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2016.11.014

    authors: Zou Z,Xu K,Xu P,Li X,Cheng F,Li J,Yu X,Cao D,Li D,Zeng W,Zhang G,Tan G

    更新日期:2017-01-01 00:00:00

  • Cinnamaldehyde and its derivatives, a novel class of antifungal agents.

    abstract::The last few decades have seen an alarming rise in fungal infections, which currently represent a global health threat. Despite extensive research towards the development of new antifungal agents, only a limited number of antifungal drugs are available in the market. The routinely used polyene agents and many azole an...

    journal_title:Fitoterapia

    pub_type: 杂志文章,评审

    doi:10.1016/j.fitote.2016.05.016

    authors: Shreaz S,Wani WA,Behbehani JM,Raja V,Irshad M,Karched M,Ali I,Siddiqi WA,Hun LT

    更新日期:2016-07-01 00:00:00

  • Acute toxicity and diuretic studies of Rungia repens aerial parts in rats.

    abstract::Ethanolic extract of Rungia repens aerials parts (300 and 600 mg/kg p.o) showed diuretic activity in rats. The acute toxicity, orally evaluated in mice, was found to be higher than 3000 mg/kg. ...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2005.11.007

    authors: Basu SK,Arivukkarasu R

    更新日期:2006-02-01 00:00:00

  • Antimicrobial activity of Hymenodictyon parvifolium.

    abstract::Methanol extract of the stem bark of Hymenodictyon parvifolium was tested for its antifungal and antibacterial activity. The extract was found to have inhibitory effect against all the pathogens tested. ...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/s0367-326x(02)00176-4

    authors: Kariba RM

    更新日期:2002-10-01 00:00:00

  • A new steroidal saponin from Solanum sisymbriifolium roots.

    abstract::Isonuatigenin-3-O-beta-solatriose (1) was isolated from the roots of Solanum sisymbriifolium. Its structure was determined by spectroscopic methods. ...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2005.04.008

    authors: Ferro EA,Alvarenga NL,Ibarrola DA,Hellión-Ibarrola MC,Ravelo AG

    更新日期:2005-09-01 00:00:00

  • Ginsenoside Rd stimulates the differentiation and mineralization of osteoblastic MC3T3-E1 cells by activating AMP-activated protein kinase via the BMP-2 signaling pathway.

    abstract::As part of our search for biologically active anti-osteoporotic agents that enhance the differentiation and mineralization of osteoblastic MC3T3-E1 cells, we identified the ginsenoside Rd as the most active compound among ginsenosides. In this study, we showed that Rd stimulates osteoblastic differentiation and minera...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2011.10.017

    authors: Kim DY,Park YG,Quan HY,Kim SJ,Jung MS,Chung SH

    更新日期:2012-01-01 00:00:00

  • Monitoring the antioxidant activity of extracts originated from various Serratula species and isolation of flavonoids from Serratula coronata.

    abstract::The antioxidant effect of aqueous methanolic herb extracts of Serratula coronata, S. wolffii and S. tinctoria was investigated using both enzyme-dependent and enzyme-independent systems. The extracts displayed concentration-dependent inhibition of lipid peroxidation. Flavonoids and ecdysteroids present in the extracts...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2003.12.009

    authors: Báthori M,Zupkó I,Hunyadi A,Gácsné-Baitz E,Dinya Z,Forgó P

    更新日期:2004-03-01 00:00:00

  • Determination of dehydroevodiamine in Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography and classification of the samples by using hierarchical clustering analysis.

    abstract::A simple, sensitive and accurate liquid chromatographic method with photodiode-array detection was developed for determination of dehydroevodiamine with detection wavelength at 368 nm and column temperature at 30 degrees C. The separation was carried out on an Agilent Zorbax SB-C(18) column (250 mm x 4.6 mm, 5 microm)...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2009.05.017

    authors: Zhao Y,Zhou X,Chen HG,Gong XJ,Cai ZW,Zhou CY

    更新日期:2009-10-01 00:00:00

  • Effect of quercetin on platelet spreading on collagen and fibrinogen and on multiple platelet kinases.

    abstract::alpha(2)beta(1) and alpha(IIb)beta(3) integrins, that support platelet adhesion to collagen and fibrinogen, respectively, share common signaling molecules. The effect of quercetin on platelet static adhesion to collagen and fibrinogen was assessed and correlated with its kinase inhibitory activity. Quercetin strongly ...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2009.08.006

    authors: Navarro-Núñez L,Lozano ML,Martínez C,Vicente V,Rivera J

    更新日期:2010-03-01 00:00:00

  • Caesalpinone A, a new type of gorgonane sesquiterpenoid containing an unprecedented 1,15-bridge, from the pods of Caesalpinia spinosa Kuntze.

    abstract::Caesalpinone A (1), a new type of gorgonane sesquiterpenoid containing an unprecedented 1,15-bridge, along with ten known sesquiterpenoids (2-11) were isolated from the pods of Caesalpinia spinosa Kuntze (Tara). The structure of caesalpinone A was elucidated based on its 1D and 2D NMR spectra. The absolute configurati...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2016.06.012

    authors: Mu W,Tang H,Li Y,He D,Ma R,Wang L

    更新日期:2016-07-01 00:00:00

  • Structure of a novel diterpenoid ester, fritillahupehin from bulbs of Fritillaria hupehensis Hsiao and K.C. Hsia.

    abstract::A new diterpenoid ester, fritillahupehin (1) together with three known fatty acids: palmitic acid (2), lignoceric acid (3) and azelaic acid (4) were isolated from the bulbs of Fritillaria hupehensis Hsiao and K.C. Hsia. The structure of fritillahupehin has been established to be ent-kauran-16beta-yl lignocerate by mea...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/s0367-326x(02)00085-0

    authors: Ruan H,Zhang Y,Wu J,Deng S,Sun H,Fujita T

    更新日期:2002-07-01 00:00:00

  • A novel water-soluble alpha-(1-->4)-glucan from the root of Cudrania tricuspidata.

    abstract::CTPS-01, a water-soluble polysaccharide, was obtained from the root of Cudrania tricuspidata and estimated to have an average molecular weight of 5.9 x 10(3) and to be composed of glucose residues, solely. It contains an average repeating unit of decasaccharide, having a backbone consisting of 1,4-linked alpha-D-gluco...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2007.03.007

    authors: Shi L,Fu YL,Chen KS

    更新日期:2007-06-01 00:00:00

  • New monoterpene glycosides from Paeonia lactiflora.

    abstract::Three new monoterpene glycosides named 4-O-methyl-paeoniflorin (1), isopaeoniflorin (2), and isobenzoylpaeoniflorin (3), together with two known monoterpene glycosides, paeoniflorin (4) and benzoylpaeoniflorin (5), were isolated from the roots of Paeonia lactiflora. Their structures were established on the basis of sp...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2007.11.001

    authors: Braca A,Kiem PV,Yen PH,Nhiem NX,Quang TH,Cuong NX,Minh CV

    更新日期:2008-02-01 00:00:00

  • Composition and alpha-amylase inhibitory effect of essential oils from Cedrus libani.

    abstract::The inhibitory activity of alpha-amylase and the phytochemical composition of Cedrus libani essential oils obtained from wood, leaves and cones were investigated. The C. libani woods oil exhibit an IC(50) value of 0.14 mg/ml, whereas the leaves and cones oils were devoid of any significant activity. ...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2007.03.006

    authors: Loizzo MR,Saab AM,Statti GA,Menichini F

    更新日期:2007-06-01 00:00:00

  • Five novel naphthylisoquinoline alkaloids with growth inhibitory activities against human leukemia cells HL-60, K562 and U937 from stems and leaves of Ancistrocladus tectorius.

    abstract::Two new 7,6'-coupled naphthylisoquinolines, namely ancistrotectorines A (1) and B (2), two new 5,3'-coupled naphthylisoquinolines, namely ancistrotectorines C (3) and D (4), and one new 7,8-coupled naphthylisoquinoline, namely ancistrotectorine E (5), together with 9 known naphthylisoquinoline alkaloids, hamatine (6),...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2013.09.010

    authors: Jiang C,Li ZL,Gong P,Kang SL,Liu MS,Pei YH,Jing YK,Hua HM

    更新日期:2013-12-01 00:00:00

  • New cycloartane triterpenes from bioactive extract of propolis from Pitcairn Island.

    abstract::Dichloromethane extract of propolis (DCME) originating from Pitcairn Island demonstrated potent cytotoxicity against triple-negative MDA-MB-231 human breast carcinoma cells. The results from MTT assay showed that DCME inhibits the growth of the cancer cells in a dose- and time-dependent manner and upon the cell growth...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2018.05.024

    authors: Georgieva K,Trusheva B,Uzunova V,Stoyanova T,Valcheva V,Popova M,Tzoneva R,Bankova V

    更新日期:2018-07-01 00:00:00

  • Constituents of the pericarp of Glyptopetalum sclerocarpum.

    abstract::Two new compounds, 6-oxo-20-hydroxy-20-epi-tingenol (1) and 2R*,3R*,5S*-trihydroxy-6R*-nonadecyltetrahydropyran-4-one (2), were isolated from the pericarp of Glyptopetalum sclerocarpum along with other 10 constituents. ...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2004.04.012

    authors: Sotanaphun U,Lipipun V,Bavovada R

    更新日期:2004-09-01 00:00:00

  • Naphthofuranone derivatives and other constituents from Pachira aquatica with inhibitory activity on superoxide anion generation by neutrophils.

    abstract::Two new naphthofuranone derivatives, 11-hydroxy-2-O-methylhibiscolactone A (1) and O-methylhibiscone D (2), have been isolated from the stems of Pachira aquatica, together with 18 known compounds (3-20). The structures of two new compounds were determined through spectroscopic and MS analyses. Among the isolated compo...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2016.12.008

    authors: Cheng LY,Liao HR,Chen LC,Wang SW,Kuo YH,Chung MI,Chen JJ

    更新日期:2017-03-01 00:00:00

  • High performance liquid chromatographic analysis and anticancer potential of Oplopanax horridus: comparison of stem and berry extracts.

    abstract::Oplopanax horridus or devil's club is a herbal medicine distributed in North America. The constituents and pharmacological activities of O. horridus (OPH) are largely unknown. In this study, we assayed OPH stem and berry extracts using high performance liquid chromatography (HPLC). The anticancer potentials of extract...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2009.08.003

    authors: Wang CZ,Aung HH,Mehendale SR,Shoyama Y,Yuan CS

    更新日期:2010-03-01 00:00:00

  • Chemical constituents of Swertia yunnanensis and their anti-hepatitis B virus activity.

    abstract::Four new triterpenoids, sweriyunnangenin A (1), sweriyunnanosides A (2), B (3) and C (4), along with nineteen known compounds (5-23) were isolated from Swertia yunnanensis. Based on extensive spectroscopic analyses (1D- and 2D-NMR, HRESIMS, UV, IR, [α]D), the structures of sweriyunnangenin A (1), sweriyunnanosides A (...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2013.05.023

    authors: Cao TW,Geng CA,Jiang FQ,Ma YB,He K,Zhou NJ,Zhang XM,Zhou J,Chen JJ

    更新日期:2013-09-01 00:00:00

  • Isolation, characterization and acetylcholinesterase inhibitory activity of alkaloids from roots of Stemona sessilifolia.

    abstract::Two new alkaloids, named stenine A (1) and stenine B (2), along with the known compounds neostenine (3), stenine (4) and neotuberostemonine (5), were isolated from the roots of Stemona sessilifolia. Their structures were elucidated by 1D- and 2D-NMR spectra and X-ray single-crystal diffraction experiment. Anti-acetylc...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2013.06.010

    authors: Lai DH,Yang ZD,Xue WW,Sheng J,Shi Y,Yao XJ

    更新日期:2013-09-01 00:00:00

  • A new alpha-methylene gamma-lactone sesquiterpene from Hedyosmum arborescens.

    abstract::A new sesquiterpene lactone, 7alpha,10alpha-epoxy-1alpha(H),5alpha(H)-guaia-3,11(13)-dien-8alpha,12-olide, was isolated from the leaves of Hedyosmum arborescens. The structure of this unusual 7,10-epoxy-guaianolide was determined by spectroscopic methods, particularly one- and two-dimensional 1H and 13C NMR. ...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2005.06.006

    authors: Bercion S,Couppe de K Martin MA,Baltaze JP,Bourgeois P

    更新日期:2005-12-01 00:00:00

  • New megastigmane sesquiterpene and indole alkaloid glucosides from the aerial parts of Bupleurum chinense DC.

    abstract::A new megastigmane sesquiterpene glucoside named chaihuxinoside A (1), and a new indole diglucoside named chaihuxinoside B (9) were isolated from the aerial parts of Bupleurum chinense DC. along with eight known compounds. Structures of two new compounds were elucidated by a combination of chemical and spectroscopic m...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2008.09.007

    authors: Kuang H,Sun S,Yang B,Xia Y,Feng W

    更新日期:2009-01-01 00:00:00

  • Urinary metabolites of isorhynchophylline in rats and their neuroprotective activities in the HT22 cell assay.

    abstract::Isorhynchophylline is one of the major alkaloids from the Uncaria hook possessing the effects of lowered blood pressure, vasodilatation and protection against ischemia-induced neuronal damage. However, the metabolic pathway of isorhynchophylline has not been fully reported yet. In this paper, the metabolism of isorhyn...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2014.05.022

    authors: Chen F,Qi W,Sun J,Simpkins JW,Yuan D

    更新日期:2014-09-01 00:00:00

  • A new norneohopane caffeate from Filicium decipiens.

    abstract::Investigation of the dichloromethane extract of the stem of Filicium decipiens yielded a new natural product, 24-norneohopa-4(23),22(29)-diene-3beta,6beta,7beta-triol 7-caffeate (1). ...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/s0367-326x(01)00296-9

    authors: Jayasinghe UL,Bandara AG,Hara N,Fujimoto Y

    更新日期:2001-11-01 00:00:00

  • Strictosidinic acid, isolated from Psychotria myriantha Mull. Arg. (Rubiaceae), decreases serotonin levels in rat hippocampus.

    abstract::Psychotria is a complex genus whose neotropical species are known by the presence of glucosidic monoterpene indole alkaloids. These compounds are able to display a large range of effects on the central nervous system, such as anxiolytic, antidepressant, analgesic, and impairment of learning and memory acquisition. The...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2012.04.013

    authors: Farias FM,Passos CS,Arbo MD,Barros DM,Gottfried C,Steffen VM,Henriques AT

    更新日期:2012-09-01 00:00:00

  • New C-methylated flavonoids and α-pyrone derivative from roots of Talinum triangulare growing in Nigeria.

    abstract::The first chemical examination of roots of the traditionally used medicinal plant Talinum triangulare (Portulacaceae) from Nigeria led to the isolation of two new C-methylated flavonoids, 5,6-dimethoxy-7-hydroxy-8-methyl-flavone (1), 5,6-dimethoxy-8-methyl-2-phenyl-7H-1-benzopyran-7-one (2), and one new α-pyrone deriv...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2016.01.002

    authors: Umeokoli BO,Muharini R,Okoye FB,Ajiwe VI,Akpuaka MU,Lin W,Liu Z,Proksch P

    更新日期:2016-03-01 00:00:00

  • Cytotoxic activity of lignans from Hibiscus cannabinus.

    abstract::The antimicrobial and cytotoxic activities of six lignans isolated from the core and bark acetone extracts of Hibiscus cannabinus have been investigated. Two compounds (2 and 3) showed strong cytotoxic activity against HeLa, Hep-2 and A-549 cell lines while compound 5 showed moderate activity on HeLa cells when they w...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2007.03.010

    authors: Moujir L,Seca AM,Silva AM,López MR,Padilla N,Cavaleiro JA,Neto CP

    更新日期:2007-07-01 00:00:00

  • Berberine hydrochloride attenuates cyclooxygenase-2 expression in rat small intestinal mucosa during acute endotoxemia.

    abstract::The effect of berberine hydrochloride (BBR) on inducible cyclooxygenase-2 (COX-2) in small intestinal mucosa and related mechanisms was investigated in a rat model of acute endotoxemia. The results showed that lipopolysaccharide (LPS) increased COX-2 expression, whereas SB202190 and BBR curtailed it. LPS increased pho...

    journal_title:Fitoterapia

    pub_type: 杂志文章

    doi:10.1016/j.fitote.2011.05.013

    authors: Feng AW,Yu C,Mao Q,Li N,Li QR,Li JS

    更新日期:2011-10-01 00:00:00