Semi-synthesis of a novel hybrid isoxazolidino withaferin via chemoselective and diastereoselective 1,3-dipolar nitrone cycloaddition reaction.

Abstract:

:A facile, atom-economic synthesis of isoxazilidino withaferin, a novel hybrid of withaferin A, has been accomplished via two-step reaction of nitrone synthesis followed by nitrone 1,3-dipolar cycloaddition. The reaction is highly chemoselective (preferential reaction only on one of the two double bonds present on withaferin A) and diastereoselective affording exclusively the cis-fused products. The structure was determined by detailed analysis of 1D, 2D NMR and mass spectral data.

journal_name

Nat Prod Res

journal_title

Natural product research

authors

Mandal R,Singh M,Krishnan AAV,Dahat YH,Bharitkar YP,Ravichandiran V,Hazra A

doi

10.1080/14786419.2019.1582045

subject

Has Abstract

pub_date

2020-08-01 00:00:00

pages

2208-2218

issue

15

eissn

1478-6419

issn

1478-6427

journal_volume

34

pub_type

杂志文章
  • Monoterpene glycosides from Indigofera hetrantha.

    abstract::Monoterpene glycosides have been isolated from the ethyl acetate soluble fraction of Indigofera hetrantha and their structures assigned to be 3,7-dimethyl-2(E),6-octadien-5-one-1-O-beta-D-6-O-acetylglucopyranoside (1) and 3,7-dimethyl-2(E), 6-octadien-5-one-1-O-[-beta-D-6''-O-acetylglucopyra-nosyl (1'' --> 6')-beta-D-...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786410801980097

    authors: Mehmood S,Aziz-Ur-Rahman,Ahmad Z,Afza N,Malik A,Ahmad H,Choudhary MI

    更新日期:2008-01-01 00:00:00

  • A novel hexanordammarane glycoside from the leaves and stems of Panax quinquefolium L.

    abstract::One novel hexanordammarane glycoside, ginsenoside R(10), was isolated from the leaves and stems of Panax quinquefolium L. as a minor constituent. It is the first time that a hexanordammarane glycoside isolated from the plant of Panax quinquefolium L. Its structure was elucidated as 3-O-β-D-glucopyranosyl-3β, 12β-dihyd...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2010.551768

    authors: Liu JP,Lu D,Li PY

    更新日期:2012-01-01 00:00:00

  • Anthraquinones, Cdc25B phosphatase inhibitors, isolated from the roots of Polygonum multiflorum Thunb.

    abstract::Three anthraquinones, Cdc25B phosphatase inhibitors, were isolated from the methanolic extract of the roots of Polygonum multiflorum Thunb. (Polygonaceae). Anthraquinones, physcion (1), emodin (2), and questin (3), inhibited the enzymatic activity of Cdc25B phosphatase with IC(50) values of 62.5, 30, and 34 microg mL(...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786410601012265

    authors: Choi SG,Kim J,Sung ND,Son KH,Cheon HG,Kim KR,Kwon BM

    更新日期:2007-05-20 00:00:00

  • Betula pendula Roth leaves: gastroprotective effects of an HPLC-fingerprinted methanolic extract.

    abstract::In this study, a methanolic extract of Betula pendula leaves (BLE) was investigated for its gastroprotective effects against 90% ethanol-induced ulcer in rats. Oral pretreatment of rats with BLE (100, 200 and 400 mg kg(- 1)) significantly reduced the incidence of gastric lesions induced by ethanol administration as co...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2012.740036

    authors: Germanò MP,Cacciola F,Donato P,Dugo P,Certo G,D'Angelo V,Mondello L,Rapisarda A

    更新日期:2013-01-01 00:00:00

  • Chemical composition and antioxidant activities of the essential oil from Nandina domestica fruits.

    abstract::The chemical composition and antioxidant activities of the essential oil from Nandina domestica fruits were studied for the first time. Twenty-two compounds, representing 82.79% of the oil, were identified from the oil. The major compounds were 3-hexen-1-ol (12.9%), linalool (12.3%), 2-methoxy-4-vinylphenol (9.9%), ol...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2015.1057584

    authors: Bi SF,Zhu GQ,Wu J,Li ZK,Lv YZ,Fang L

    更新日期:2016-01-01 00:00:00

  • Composition of the essential oil of Buddleja thyrsoides Lam. leaves from Brazil.

    abstract::This study is designed to examine the chemical composition of the essential oil obtained from Buddleja thyrsoides Lam leaves from south Brazil. Gas chromatography/mass spectrometry analysis resulted in the detection of 12 components, representing 91.4% of the total oil composition. Germacrene D (27.16%), 1,10-di-epi-C...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2012.740035

    authors: Mahlke JD,Boligon AA,Machado MM,Athayde ML

    更新日期:2013-01-01 00:00:00

  • Bioactive triterpenoids from Sambucus javanica Blume.

    abstract::A new triterpene, javablumine A (1) along with six known ones were isolated from the aerial parts of Sambucus javanica Blume. They were identified as 3β,23-dihydroxy-11α,12α-epoxy-urs-20(30)-en-28,13β-olide (1), ursolic acid (2), pomolic acid (3), oleanic acid (4), 2α-hydroxy-oleanolic acid (5), α-amyrin (6), and lupe...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2019.1596092

    authors: Chen F,Liu DL,Wang W,Lv XM,Li W,Shao LD,Wang WJ

    更新日期:2020-10-01 00:00:00

  • Plantagiolide F, a minor withanolide from Tacca plantaginea.

    abstract::A minor new withanolide, named plantagiolide F, was isolated from the whole plant of Tacca plantaginea (Hance). The structure of plantagiolide F was elucidated on the basis of spectroscopic methods including extensive 1- and 2-D NMR experiments. ...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786411003774304

    authors: Yang JY,Chen CX,Zhao RH,Hao XJ,Liu HY

    更新日期:2011-01-01 00:00:00

  • Topical anti-inflammatory constituents of lipophilic leaf fractions of Alchornea floribunda and Alchornea cordifolia.

    abstract::The leaves of Alchornea floribunda and Alchornea cordifolia are used traditionally as topical anti-inflammatory agents. In this study, two highly lipophilic fractions AFLF and ACLF isolated from A. floribunda and A. cordifolia leaves respectively were investigated for topical anti-inflammatory effects using xylene-ind...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2010.512272

    authors: Okoye FB,Osadebe PO,Nworu CS,Okoye NN,Omeje EO,Esimone CO

    更新日期:2011-12-01 00:00:00

  • Estimation of the influence of the environmental factors on the accumulation of phytochemicals and antioxidant capacity in the ivy leaves (Hedera helix L.).

    abstract::This study aimed at evaluating the impact of environmental factors on the accumulation of various components in Hedera helix L. folium collected from different European countries. The obtained results of studied samples showed that the antioxidant capacities were in the range of 0.027 to 0.688 mg/g. Contents of active...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2020.1843029

    authors: Bezruk I,Materiienko A,Gubar S,Proskurina K,Budanova L,Ivanauskas L,Georgiyants V

    更新日期:2020-11-04 00:00:00

  • Quantitative analysis of sulphated glycosaminoglycans content of Malaysian sea cucumber Stichopus hermanni and Stichopus vastus.

    abstract::Stichopus hermanni and Stichopus vastus are sea cucumber species from the Stichopodidae family within the coastal waters of Malaysia. The integument of these invertebrates is hypothesised to contain abundant glycosaminoglycans (GAGs). GAGs are divided into non-sulphated and sulphated GAGs. Sulphated GAGs have various ...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2010.545354

    authors: Masre SF,Yip GW,Sirajudeen KN,Ghazali FC

    更新日期:2012-01-01 00:00:00

  • (22E)-Ergosta-6,22-diene-3beta,5alpha,8alpha-triol: a new polyhydroxysterol isolated from Lentinus edodes (Shiitake).

    abstract::From the ethanolic extract of Lentinus edodes (Shiitake) eight known sterols were isolated and identified: ergosterol, ergosterol peroxide, (22E)-ergosta-5,7,9(11), 22-tetraen-3beta-ol, (22E)-ergosta-7,9(11),22-trien-3beta-ol, (22E)-ergosta-6,8,22-trien-3beta-ol, (22E)-norergosta-5,7,9,22-tetraen-3beta-ol, 3beta,5alph...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786410802038671

    authors: Rivera A,Benavides OL,Rios-Motta J

    更新日期:2009-01-01 00:00:00

  • New anthraquinone and eurotinone analogue from the seeds of Senna obtusifolia and their inhibitory effects on human organic anion transporters 1 and 3.

    abstract::A continuous phytochemical study on the seeds of Senna obtusifolia (Syn.: Cassia obtusifolia) led to the isolation of a new anthraquinone analogue, obtusifolin-2-O-β-D-(6'-O-α,β-unsaturated butyryl)-glucopyranoside (1) and a new eurotinone analogue, epi-9-dehydroxyeurotinone-β-D-glucopyranoside (2). Their structures w...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2018.1480621

    authors: Pang X,Wang LM,Zhang YC,Kang LP,Yu HS,Fan GW,Han LF

    更新日期:2019-12-01 00:00:00

  • Cytotoxic effect of pure compounds from Piper rivinoides Kunth against oral squamous cell carcinoma.

    abstract::The oral squamous cell carcinoma (OSCC) is the eighth more common cancer in men. The development of new and more efficient drugs is needed. Plants of the genus Piper are popularly used in the treatment of many diseases. This study evaluated the antitumor effect of extract, fraction and isolated compounds from leaves o...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2020.1831494

    authors: Fonseca ACCD,de Queiroz LN,Sales Felisberto J,Jessé Ramos Y,Mesquita Marques A,Wermelinger GF,Pontes B,de Lima Moreira D,Robbs BK

    更新日期:2020-10-14 00:00:00

  • Denigrins A-C: new antitubercular 3,4-diarylpyrrole alkaloids from Dendrilla nigra.

    abstract::Chemical diversity is vital to antitubercular drug discovery as it ensures a novel bioactivity profile. Marine sponges have so far provided more than 1000 new bioactive molecules. Ethyl acetate extract of the marine sponge Dendrilla nigra on bioactivity-guided screening yielded three new compounds denigrins A-C, with ...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2014.891112

    authors: Murali Krishna Kumar M,Devilal Naik J,Satyavathi K,Ramana H,Raghuveer Varma P,Purna Nagasree K,Smitha D,Venkata Rao D

    更新日期:2014-01-01 00:00:00

  • Development, characterisation, stability study and antileukemic evaluation of nanoemulsions containing Astrocaryum aculeatum extract.

    abstract::The objective of this work was to produce and characterise nanoemulsions containing tucumã extract and to evaluate the performance of the nanostructure and the free compound regarding antitumor activity, cytotoxicity, and oxidative metabolism in NB4/APL cells. The nanoemulsions showed adequate physicochemical characte...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2020.1862830

    authors: Copetti PM,Gündel SDS,de Oliveira PSB,Favarin FR,Ramos AP,Pintos FG,Pappis L,Gündel A,Machado AK,Ourique AF,Sagrillo MR

    更新日期:2020-12-24 00:00:00

  • Detection of flavonoids from Spinacia oleracea leaves using HPLC-ESI-QTOF-MS/MS and UPLC-QqQLIT-MS/MS techniques.

    abstract::Spinacia oleracea L. (Spinach) is a leafy vegetable which is considered to have a high nutritional value. Flavonoids in spinach were reported to act as antimutagenic property. Rapid detection of these flavonoids in Spinach was achieved by using HPLC-ESI-QTOF-MS/MS. Thirty six compounds were tentatively identified base...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2018.1489395

    authors: Singh A,Singh P,Kumar B,Kumar S,Dev K,Maurya R

    更新日期:2019-08-01 00:00:00

  • Studies on the chemical constituents of Phyllanthus emblica.

    abstract::Phytochemical investigations on Phyllanthus emblica have resulted in the isolation of the two new flavonoids, kaempferol-3-O-alpha-L-(6''-methyl)-rhamnopyranoside (1) and kaempferol-3-O-alpha-L-(6''-ethyl)-rhamnopyranoside (2). Their structures were determined on the basis of extensive spectroscopic studies including ...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786410601124664

    authors: Habib-ur-Rehman,Yasin KA,Choudhary MA,Khaliq N,Atta-ur-Rahman,Choudhary MI,Malik S

    更新日期:2007-07-20 00:00:00

  • Two new triterpenes from Alstonia scholaris flowers.

    abstract::In the context of our previous communication on phytochemical studies of the ethanolic extract of flowers of Alstonia scholaris of Pakistan origin, these have resulted in the isolation of two new triterpenoids. One is of the oleanane type, alstoprenyol, 3-β-hydroxy-28-β-acetoxy-5-olea triterpene (1), the other is of u...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2012.730046

    authors: Sultana N,Saify ZS,Saleem M,Kamal M

    更新日期:2013-01-01 00:00:00

  • Sesquiterpene-neolignans from Manglietia hookeri.

    abstract::The comet assay-guided fractionation of the twigs of Manglietia hookeri resulted in the isolation of three sesquiterpene-neolignans, including a new one 5-allyl-2-(4-allyl-phenoxy)-3-[7-(1-hydroxy-1-methyl-ethyl)-1, 4a-dimethyl-decahydro-naphthalen-1-yloxy]-phenol (1), and eudesobovatol A (2) and eudesobovatol B (3), ...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2015.1110703

    authors: Hu X,Sui X,Wang Y,Wang W,Wu H,Zhang F,Tan Y,Zhang F

    更新日期:2016-07-01 00:00:00

  • Neuroprotection of two C21 steroidal glycosides from Cynanchum auriculatum against H2O2-induced damage on PC12 cells.

    abstract::Neuroprotection under conditions of oxygen stress of two C21 steroidal glycosides, cynsaccatol Q (1) and saccatol K (2), isolated from Cynanchum auriculatum Royle ex Wight, and their potential mechanisms were studied using the model of H2O2-induced damage on PC12 cells in this paper. Experiments showed that compounds ...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2019.1636241

    authors: Zhang M,Wang D,Li B

    更新日期:2019-07-02 00:00:00

  • Bioactive compounds derived from the marine-derived fungus MCCC3A00951 and their influenza neuraminidase inhibition activity in vitro and in silico.

    abstract::Penicillium polonicum MCCC3A00951 is a fungus with influenza neuraminidase (NA) inhibition activity derived from a sediment of the mangrove forest of Zhangjiangkou in Fujian province, China. Chemical investigation on an ethyl acetate extract of its fermentation led to the isolation of a new compound, 7-hydroxy-3,10-de...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2020.1817015

    authors: Liu SZ,He FM,Bin YL,Li CF,Xie BY,Tang XX,Qiu YK

    更新日期:2020-09-14 00:00:00

  • Production of bioactive tryptamine derivatives by co-culture of marine Streptomyces with Bacillus mycoides.

    abstract::Tryptamine derivatives such as tryptamine and bacillamides were strong algicidal compounds promising in controlling harmful algae blooms, but their bioactivity and application researches were hindered by extremely low natural production rates. This study found an induced production of algicidal tryptamine derivatives ...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2015.1005619

    authors: Yu L,Hu Z,Ma Z

    更新日期:2015-01-01 00:00:00

  • Balanochalcone, a new chalcone from Balanophora laxiflora Hemsl.

    abstract::A new chalcone named as balanochalcone (1) together with eight known compounds, methyl caffeate (2), β-hydroxydihydrochalcone (3), methyl gallate (4), dimethyl-6,9,10-trihydroxybenzo[kl]xanthene-1,2-dicarboxylate (5), p-coumaric acid (6), quercetin (7), scopoletin (8) and pinoresinol (9) have been isolated from the et...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2017.1359172

    authors: Quang DN,So TC,Thanh NTP,Hoa LTP,Dien PH,Luong TM,Tung NQ,Long LD,Dai TD,Tien NQ

    更新日期:2018-04-01 00:00:00

  • Cytotoxicity, apoptosis-inducing effects and structure-activity relationships of four natural xanthones from Gentianopsis paludosa Ma in HepG2 and HL-60 cells.

    abstract::Four xanthones were isolated from Gentianopsis paludosa Ma and were identified by modern spectroscopic methods. Cytotoxicity of the four xanthones was tested on HepG2 cells and HL-60 cells by sulphorhodamine B (SRB) assay. Clonogenic survival assay, trypan blue exclusion method, AO/EB staining and DNA fragmentation as...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786410802497398

    authors: Ding L,Liu B,Zhang SD,Hou Q,Qi LL,Zhou QY

    更新日期:2011-04-01 00:00:00

  • Chemical constituents from Curcuma longa L. and their inhibitory effects of nitric oxide production.

    abstract::A new bisabolane-type sesquiterpenoid, turmerone Q (1), along with six known compounds (2-7), were isolated from the rhizomes of Curcuma longa L. The structural elucidation of the new compound was conducted using 1H NMR, 13C NMR, HSQC, HMBC and NOESY spectroscopic analyses. The absolute configuration of 1 was elucidat...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2017.1354185

    authors: Yuan T,Zhang C,Qiu C,Xia G,Wang F,Lin B,Li H,Chen L

    更新日期:2018-08-01 00:00:00

  • Psidium myrtoides O. Berg fruit and leaves: physicochemical characteristics, antifungal activity and chemical composition of their essential oils in different seasons.

    abstract::This paper aims to investigate, for the first time, physicochemical characteristics and antioxidant capacity of Psidium myrtoides ripe and unripe fruit. In addition, essential oil was extracted from fresh leaves (PM-EO) collected in dry and rainy seasons to investigate the influence of seasonality and, after that, to ...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2020.1844689

    authors: Dias ALB,Batista HRF,Sousa WC,Bailão EFLC,Rocha JD,Sperandio EM,Fernandes CC,Souchie EL,Miranda MLD

    更新日期:2020-11-09 00:00:00

  • Antiplasmodial activity of a novel diarylheptanoid from Siphonochilus aethiopicus.

    abstract::The Nigerian and South African varieties of Siphonochilus aethiopicus were examined for their phytochemical constituents. The ethyl acetate extract of the rhizomes of the South African variety yielded a novel diarylheptanoid, 2,3-diacetoxy-7-(3'',4''-dihydroxy-5''-methoxyphenyl)-1-(4'-hydroxy-3'-methoxyphenyl)-5-hepte...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786419.2020.1799358

    authors: Igoli NP,Al-Tannak NF,Ezenyi IC,Gray AI,Igoli JO

    更新日期:2020-07-27 00:00:00

  • Glaucocalyxin A: a review.

    abstract::Glaucocalyxin A is a natural ent-Kaurane diterpenoid. It has been widely studied for some important biological activities like cytotoxicity and anti-tumour, anti-bacterial, anti-oxidative, anti-coagulative, anti-thrombotic, immune and anti-neuroinflammatory activities. The aim of the present article is to review the a...

    journal_title:Natural product research

    pub_type: 杂志文章,评审

    doi:10.1080/14786419.2014.934235

    authors: Xiang Z,Wu X,Liu X,Jin Y

    更新日期:2014-01-01 00:00:00

  • A new anthraquinone from Galium verum L.

    abstract::A new anthraquinone (4) and three known anthraquinones (1-3) were isolated from Galium verum L. Their structures were identified as 1,3-dihydroxy-2-methylanthraquinone (1), physcion (2), 2-hydroxy-1,3-dimethoxyanthraquinone (3), 2,5-dihydroxy-1,3-dimethoxyanthraquinone (4) by means of chemical and spectroscopic analys...

    journal_title:Natural product research

    pub_type: 杂志文章

    doi:10.1080/14786410600921532

    authors: Zhao CC,Shao JH,Li X,Xu J,Wang JH

    更新日期:2006-09-01 00:00:00