New C-19-modified geldanamycin derivatives: synthesis, antitumor activities, and physical properties study.

Abstract:

:Thiazinogeldanamycin (2) was identified from Streptomyces hygroscopicus 17997 at the late stage of the fermentation. The pH was firstly proposed as an important factor in the biosynthesis of it. It was verified that 2 was produced by direct chemical reactions between geldanamycin (1, GDM) and cysteine or aminoethanethiol hydrochloride at pH > 7 in vitro. The proposed synthesis pathway for compound 2 was also discussed. Eleven new C-19-modified GDM derivatives, including five stable hydroquinone form derivatives, were synthesized, most of which exhibited desirable properties such as lower cytotoxicity, increased water solubility, and potent antitumor activity. Especially, compounds 5 and 8 showed antitumor activities against HepG2 cell with IC50 values of 2.97-6.61 μM, lower cytotoxicity and at least 15-fold higher water solubility compared with 1 in pH 7.0 phosphate buffer.

journal_name

J Asian Nat Prod Res

authors

Liu YF,Zhong JJ,Lin L,Liu JJ,Wang YG,He WQ,Yang ZY

doi

10.1080/10286020.2016.1160896

subject

Has Abstract

pub_date

2016-08-01 00:00:00

pages

752-64

issue

8

eissn

1028-6020

issn

1477-2213

journal_volume

18

pub_type

杂志文章
  • Three new lignan glycosides from the fruits of Forsythia suspense.

    abstract::Two new lignan glycosides forsythiayanoside A (1) and forsythiayanoside B (2), one new stereoisomer of lignan glycoside (+)-8-hydroxyepipinoresinol-4-O-β-D-glucopyranoside (3), together with seven known compounds (4-10), were isolated from the fruits of Forsythia suspense (Thunb.) Vahl. Compounds 4 and 10 were isolate...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2014.917631

    authors: Yan XJ,Peng Y,Liu ZX,Wen J,Liu QB,Li LZ,Song SJ

    更新日期:2014-01-01 00:00:00

  • New abietane diterpenoid glucosides from underground parts of Isodon taliensis.

    abstract::Two new abietane diterpenoid glucosides, talienosides A and B (1 and 2), along with four known compounds (3 - 6), were isolated from the ethyl acetate soluble portion of 70% acetone extract of the underground parts of Isodon taliensis. Their structures were elucidated based on the analyses of extensive spectroscopic d...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2018.1518321

    authors: Xiang P,Xiao CJ,Xu W,Shan H,Qiu L,Li Y,Dong X,Jiang B

    更新日期:2019-12-01 00:00:00

  • A new prenylated xanthone from the branches of Calophyllum inophyllum.

    abstract::The investigation of chemical constituents from the branches of Calophyllum inophyllum Linn led to the isolation of a new prenylated xanthone, named caloxanthone Q (1), together with three known compounds, 2-deprenylrheediaxanthone B (2), jacareubin (3), and 6-deoxyjacareubin (4). Their structures were completely eluc...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2010.550884

    authors: Wei DJ,Mei WL,Zhong HM,Zeng YB,Wu XD,Dai HF

    更新日期:2011-03-01 00:00:00

  • Three 11,12-seco-tanshinone derivatives from the rhizomes of Salvia miltiorrhiza.

    abstract::Three new compounds named tanshinoic acid A (1), tanshinoic acid B (2), and tanshinoic acid C (3) were isolated from the rhizomes of Salvia miltiorrhiza, together with two known compounds methyl salvianolate A (4) and methyl salvianolate C (5). Their structures were determined on the basis of spectroscopic data (UV, I...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2020.1799988

    authors: Gu QC,Yin ZK,Feng ZM,Jiang JS,Zhang X,Zhang PC,Yang YN

    更新日期:2020-10-01 00:00:00

  • Two novel lignans from Gaultheria yunnanensis.

    abstract::Two new lignans, 9-salicyl-(+)-isolariciresinol (1) and gaultheroside G (2), together with seven known compounds, were isolated from the ethanolic extract of the whole plant of Gaultheria yunnanensis. Their structures were determined by extensive NMR and MS analyses. Gaultheroside G (2) was found to have an unusual et...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2014.898634

    authors: Gao YP,Shen YH,Xu XK,Tian JM,Zeng HW,Lin S,Liu CM,Zhang WD

    更新日期:2014-01-01 00:00:00

  • Cytotoxic lanostanoid triterpenes from Ganoderma lucidum.

    abstract::Two new lanostanoid triterpenes, 23S-hydroxy-3,7,11,15-tetraoxo-lanost-8,24E-diene-26-oic acid (1), and 12beta-acetoxy-3beta-hydroxy-7,11,15,23-tetraoxo-lanost-8,20E-diene-26-oic acid (16), together with 17 known compounds, were isolated from the fruit bodies of Ganoderma lucidum. Their structures were established by ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020802016297

    authors: Guan SH,Xia JM,Yang M,Wang XM,Liu X,Guo DA

    更新日期:2008-07-01 00:00:00

  • The sesquiterpenes from the roots of Cacalia roborowskii.

    abstract::A new sesquiterpene cacaroborin (1) was isolated from the roots of Cacalia roborowskii, together with three known ones, cinalbicol (2), isopetasin (3), and 3alpha-angeloyloxylactone (4). The structure of compound 1 was elucidated as 1beta,10alpha-dihydroxy-8alpha-methoxyeremophil-7(11)-en-8beta,12-olide on the basis o...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020903264093

    authors: Zhang ZX,Fei DQ

    更新日期:2009-11-01 00:00:00

  • Chalcone-derived Diels-Alder adducts as NF-κB inhibitors from Morus alba.

    abstract::A bioassay-guided phytochemical fractionation of the methanol extract of the Morus alba root barks led to the isolation of two chalcone-derived Diels-Alder adducts (1 and 2). Their structures were elucidated as kuwanon J 2,4,10″-trimethyl ether (1) and kuwanon R (2) by means of spectroscopic methods. Both compounds st...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2012.670221

    authors: Phung TX,Tran TH,Dan TT,Chau VM,Hoang TH,Nguyen TD

    更新日期:2012-01-01 00:00:00

  • Glycosidic constituents from Carpesium cernuum L.

    abstract::Carpesides A (1) and B (2), two new 8-O-4'-neolignan glucosides, and eupatriol 9-O-beta-d-apiofuranosyl-(1 --> 6)-beta-d-glucopyranoside (3), one new monoterpenoid diglycoside, together with 10 known glycosidic compounds, were isolated from the aerial part of Carpesium cernuum L. The structures of the new glycosides a...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020801966724

    authors: Ma JP,Tan CH,Zhu DY

    更新日期:2008-05-01 00:00:00

  • Paniculacin, a new coumarin derivative from Murraya paniculata.

    abstract::Paniculacin (1), a new coumarin derivative, has been isolated from the ethyl acetate soluble fraction of the ethanolic extract of Murraya paniculata along with umbelliferone, scopoletin, 4-hydroxybenzoic acid, trans-cinnamic acid, and β-sitosterol. Their structures were elucidated on the basis of spectral data. ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2011.586343

    authors: Saeed S,Shah S,Mehmood R,Malik A

    更新日期:2011-08-01 00:00:00

  • Two new components from Gnetum pendulum.

    abstract::Two new compounds, 3-O-(13-hydroxy-9Z,11E,15E-octadecatrienoyl) cycloeucalenol (1) and 24'-hydroxy-tetracosyl ferulate (2), together with one known compound, tetracosyl ferulate (3), were isolated from the dried stems of Gnetum pendulum. The two new compounds were structurally elucidated by spectroscopic and chemical ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020802318958

    authors: Xiang WS,Wang JD,Wang XJ,Zhang J

    更新日期:2008-11-01 00:00:00

  • Two new selaginellin derivatives from Selaginella tamariscina (Beauv.) Spring.

    abstract::Two new selaginellin derivatives, selaginellins K (1) and L (2), were isolated from Selaginella tamariscina (Beauv.) Spring and characterized as 2-formyl-4,4'-dihydroxy-3-[(4-hydroxyphenyl)ethynyl]biphene and 4,4'-dihydroxy-2-methyl-3-[(4-hydroxyphenyl)ethynyl]biphene on the basis of their spectroscopic data including...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2011.558840

    authors: Xu KP,Zou H,Li FS,Xiang HL,Zou ZX,Long HP,Li J,Luo YJ,Li YJ,Tan GS

    更新日期:2011-04-01 00:00:00

  • Chemical constituents of the leaves of Diospyros kaki and their cytotoxic effects.

    abstract::Isolation and structure elucidation of two new compounds, kakispyrone (1) and kakisaponin A (2), together with 11 known compounds, from the leaves of Diospyros kaki L. are described. Their cytotoxic effects against several cancer cell lines (A549, HepG2 and HT29) are also reported. ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020600727731

    authors: Chen G,Xue J,Xu SX,Zhang RQ

    更新日期:2007-04-01 00:00:00

  • Water-soluble constituents of the root barks of Fraxinus rhynchophylla (Chinese drug Qinpi).

    abstract::Chemical studies on the roots of Fraxinus rhynchophylla led to the isolation of fraxisecoside (1), a novel coumarin-secoiridoid hybrid glycoside, namely, fraxetin-8-O-[11'-methyl-oleosidyl-(7'-->6'')]-beta-D-glucopyranoside and 14 known compounds. Their structures were elucidated based on chemical evidence and spectro...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020701394514

    authors: Xiao K,Song QH,Zhang SW,Xuan LJ

    更新日期:2008-01-01 00:00:00

  • C19-Diterpenoid alkaloids from Delphinium umbrosum.

    abstract::Three new C(19)-diterpenoid alkaloids, umbrosumines A-C (1-3), and 11 known compounds (4-14) were isolated from the roots of Delphinium umbrosum. Their structures were elucidated on the basis of the spectroscopic data interpretation. ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2010.489827

    authors: Chen FZ,Chen QH,Wang FP

    更新日期:2010-06-01 00:00:00

  • Phenol esters and other constituents from the stem barks of Stereospermum acuminatissimum.

    abstract::A new ester, 2-(4'-hydroxyphenyl)ethyl dotriacontanoate (1), and a new inseparable mixture of octacosan-1,28-dioldiferulate and triacontan-1,30-dioldiferulate (2) were isolated from the stem barks of Stereospermum acuminatissimum, along with 24 known compounds including 4 triterpenoids, 11 anthraquinones, 2 lignans, 3...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2011.619182

    authors: Sob SV,Wabo HK,Tang CP,Tane P,Ngadjui BT,Ye Y

    更新日期:2011-12-01 00:00:00

  • Indole alkaloid glucosides from the roots of Isatis indigotica.

    abstract::Five new indole alkaloid glucosides named isatindigotindolosides A-E (1-5), along with three known analogs (6-8), were isolated from an aqueous extract of the Isatis indigotica roots. Their structures including the absolute configurations were determined based on comprehensive spectroscopic data analysis, combined wit...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2015.1117452

    authors: Liu YF,Chen MH,Lin S,Li YH,Zhang D,Jiang JD,Shi JG

    更新日期:2016-01-01 00:00:00

  • Two new diterpenoid dimers, fritillebinide D and E, from bulbs of Fritillaria ebeiensis.

    abstract::Two new ent-kaurane diterpenoid dimers, fritillebinide D (1) and fritillebinide E (2), were isolated from bulbs of Fritillaria ebeiensis G.D. Yu et G.Q. Ji. Their structures have been determined to be ent-3beta-acetoxy-kauran-16beta, 17-acetal ent-3beta-acetoxy-16beta-kauran-17(R)-aldehyde (1) and ent-3beta-acetoxy-ka...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/1028602021000049113

    authors: Ruan HL,Zhang YH,Wu JZ,Sun HD,Fujita T

    更新日期:2002-12-01 00:00:00

  • Two new furostanol glycosides from the fibrous root of Ophiopogon japonicus (Thunb.) Ker-Gawl.

    abstract::Two new furostanol glycosides, ophiopogonins H (1) and I (2), were isolated from the fibrous root of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-[(O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside and (25R)-26-[(...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2010.495332

    authors: Duan CL,Ma XF,Jiang Y,Liu JX,Tu PF

    更新日期:2010-09-01 00:00:00

  • Three new triterpenoid saponins from Albizia julibrissin.

    abstract::Three new triterpenoid saponins, julibrosides A5-A7 (1-3), together with five known saponins (4-8), were isolated from the stem bark of Albizia julibrissin. Their structures were elucidated on the basis of extensive spectroscopic data analysis of MS, 1D and 2D NMR, and chemical methods. Compounds 7 and 8 were isolated...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2018.1473385

    authors: Wang XD,Han QH,Zhang J,Zhang QY,Tu PF,Liang H

    更新日期:2019-06-01 00:00:00

  • Two new compounds from rhizomes of Musa basjoo.

    abstract::Two new benzo[de]isoquinoline derivatives, 4-phenyl-benzo[de]isoquinoline-1,3-dione (1) and 4-(4-hydroxyphenyl)-benzo[de]isoquinoline-1,3-dione (2), were isolated from 70% ethanol extract of the rhizomes of Musa basjoo. Their chemical structures were elucidated by HRESIMS, 1 D and 2 D spectra. ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2021.1871604

    authors: Ma X,Jiang L,Zhu MH,Liu CH,Wang GC,Li YT,Liu T,Li YJ

    更新日期:2021-01-19 00:00:00

  • Two new triterpenes from the roots of Pfaffia glomerata.

    abstract::Pfaffia paniculata is a commercialized dietary supplement used as the substitute for the Asian ginseng in Brazil. We conducted the systematic isolation of the EtOAc fraction with anti-inflammatory effect and two new triterpenoids, along with 26 known compounds were characterized by means of MS and NMR analysis. Intere...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2018.1446949

    authors: Lian L,Feng Y,Li YW,Bei B,Tang YT,Wang H,Feng QM,Chen G

    更新日期:2019-05-01 00:00:00

  • Further polyoxypregnane glycosides from Marsdenia tenacissima.

    abstract::Three new polyoxypregnane glycosides, tenacigenosides F-H (1-3), were isolated from the stems of Marsdenia tenacissima. The structures of these new compounds were elucidated from 1D and 2D NMR spectra, as well as from HR-MS and acid hydrolysis. ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2010.495330

    authors: Wang XL,Peng SL,Ding LS

    更新日期:2010-08-01 00:00:00

  • Two new indole alkaloids from Nauclea officinalis.

    abstract::Two new indole alkaloids, naucleactonin A and B, along with two known compounds, naucleficine and nauclefidine, were isolated from the bark and wood of Naucleaofficinalis, which has been used as an anti-inflammatory and anti-bacterial agent in folk medicine. Their chemical structures were elucidated by the spectral da...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020500246741

    authors: Xuan WD,Chen HS,Du JL,Liang S,Li TZ,Cai DG

    更新日期:2006-12-01 00:00:00

  • Chemical constituents of Nouelia insignis Franch.

    abstract::Two new diterpenes and ent-15alpha-hydroxykaur-16-en-19-oic acid 11,12-acetonide (3), together with 23 known compounds were isolated from the dried aerial parts of Nouelia insignis Franch. The structures of new compounds were determined to be ent-14beta,15alpha-dihydroxykaur-16-en-19-oic acid (1), ent-14beta-hydroxy-1...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020701189500

    authors: Hu XY,Luo YG,Chen XZ,Zhou L,Zhang GL

    更新日期:2008-01-01 00:00:00

  • Two eudesmane sesquiterpenes from Laggera pterodonta.

    abstract::The phytochemical study of the aerial parts of Laggera pterodonta afforded two new eudesmane sesquiterpenes, 3alpha,4beta,11-trihydroxyenantioeudesmane (pterodontriol E) (1) and 4beta,8beta,11-trihydroxyenantioeudesmane (pterodontriol F) (2), along with seven known compounds. Their structures were elucidated on the ba...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020500034964

    authors: Liu YB,Jia W,Gao WY,Zhao AH,Zhang YW,Takaishi Y,Duan HQ

    更新日期:2006-06-01 00:00:00

  • Synthesis and antibacterial activity of 11,12-carbamate-3-O-acyl erythromycin derivatives.

    abstract::A novel series of acylide derivatives have been synthesized which exhibit in vitro potency against key respiratory pathogens. Modification of position 3 was accomplished by replacing different 3-O-substituted acyl groups in the macrolide core via a facile procedure. Compounds 7a-7i were eventually yielded by the conju...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020903176461

    authors: Xu P,Liu L,He W,Li Y,Liu J,Lei PS

    更新日期:2009-10-01 00:00:00

  • Differential expressed analysis of Tripterygium wilfordii unigenes involved in terpenoid backbone biosynthesis.

    abstract::Tripterygium wilfordii Hook. f. is the traditional medicinal plants in China. Triptolide, wilforgine, and wilforine are the bioactive compounds in T. wilfordii. In this study, the contents of three metabolites and transcription levels of 21 genes involved in three metabolites biosynthesis in T. wilfordii were examined...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2016.1232713

    authors: Zhang J,Huo YB,Liu Y,Feng JT,Ma ZQ,Zhu CS,Zhang X

    更新日期:2017-08-01 00:00:00

  • Polyketides from the fungus Penicillium decumbens.

    abstract::Two new polyketides, 3,11-dihydroxy-6,8-dimethyldodecanoic acid (1) and trichopyrone B (2), together with two known polyketides, sorbicillin (3) and penicillone A (4), have been isolated from the cultures broth of the fungus Penicillium decumbens. Their structures were elucidated by extensive spectroscopic analysis. A...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2018.1424139

    authors: Lin S,Wu YZ,Chen KY,Ye J,Yang XW,Zhang WD

    更新日期:2018-05-01 00:00:00

  • Structural features of a polysaccharide from Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao.

    abstract::A polysaccharide Astragalus polysaccharide (APS) was obtained from the boiling water extract of Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao. The results of gas chromatography (GC) indicated that APS consisted of l-rhamnose (l-Rha), d-xylose (d-Xyl), d-glucose (d-Glc), and d-galactose (d-Gal) in...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2013.778832

    authors: Fu J,Huang L,Zhang H,Yang S,Chen S

    更新日期:2013-01-01 00:00:00