Four new koumine metabolites in rat liver microsomes.

Abstract:

:Four new metabolites M-1 [1,2,18,19-tetradehydro-4-demethyl-3,17-epoxy-7,20(2H,19H)-cyclovobasan], M-2 [1,2,4,21,18,19-hexadehydro-4-demethyl-3,17-epoxy-7,20(2H,19H)-cyclovobasan], M-3 [1,2,18,19-tetradehydro-4-demethyl-4-formaldehyde-3,17-epoxy-7,20(2H,19H)-cyclovobasan], and M-4 [1,2,4,21,18,19-hexadehydro-4-demethyl-4-oxy-3,17-epoxy-7,20(2H,19H)-cyclovobasan] were isolated from the chloroform extract of koumine incubated with phenobarbital-treated rat liver microsomes. The structures of M-1, M-2, M-3, and M-4 were elucidated by spectroscopic methods including ESI-TOF-MS, 1D, and 2D NMR experiments. The metabolic pathway of koumine was proposed. The cytotoxic activities between koumine and its metabolites were also compared in the A549 cell line.

journal_name

J Asian Nat Prod Res

authors

Zhang L,Du L,Lv WW,Zhao QC,Hua W,An Y,Guo T,Wu LJ

doi

10.1080/10286020.2012.742511

subject

Has Abstract

pub_date

2013-01-01 00:00:00

pages

46-52

issue

1

eissn

1028-6020

issn

1477-2213

journal_volume

15

pub_type

杂志文章
  • 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

  • Novel ursane-type triterpene from the fresh leaves of Carissa carandas and evaluation of cytotoxicity.

    abstract::One novel ursolic acid derivative sabiracin 1 (11,25-epoxy-3β-hydroxy-urs-12-en-28-oic acid) was isolated from the leaves of Carissa carandas, together with five known compounds para hydroxy benzaldehyde (2), ursolic acid (3), carissin (4), 22α-hydroxyursolic acid (5) and β-sitosterol-3-O-β-D-glucopyranoside (6). Comp...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2020.1791098

    authors: Bano Z,Begum S,Ali SS,Kiran Z,Siddiqui BS,Khawaja S,Ahmed A

    更新日期:2020-07-10 00:00:00

  • New anthraquinones from Gladiolus gandavensis.

    abstract::Two new anthraquinones, methyl 8-hydroxy-3-methoxy-6,7-methylenedioxy-1-methylanthraquinone-2-carboxylate (gandavensin A, 1) and methyl 8-hydroxy-3,6,7-trimethoxy-1-methylanthraquinone-2-carboxylate (gandavensin B, 2), have been isolated from the light petroleum extract of the subterranean corm of Gladiolus gandavensi...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/1028602031000111950

    authors: Wang DY,Ye Q,Zhang GL,Li BG

    更新日期:2003-12-01 00:00:00

  • Four lanostane-type triterpenes from the fruiting bodies of mushroom Laetiporus sulphureus var. miniatus.

    abstract::Two new 3,4-seco-lanostane-type triterpenes, named as 15α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid (1), 5α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid 3-methyl ester (2), and one new lanostane triterpene 15α-acetoxylhydroxytrametenolic acid (3) together with a known one versisponic aci...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2015.1027694

    authors: Yin X,Li ZH,Li Y,Feng T,Liu JK

    更新日期:2015-01-01 00:00:00

  • Labdane-type diterpenes as new cell cycle inhibitors and apoptosis inducers from Vitex trifolia L.

    abstract::Five labdane-type diterpenes, vitexilactone (1), (rel 5S,6R,8R,9R,10S)-6-acetoxy-9-hydroxy-13(14)-labden-16,15-olide (2), rotundifuran (3), vitetrifolin D (4), and vitetrifolin E (5), have been isolated from Vitex trifolia L., a Chinese folk medicine used to treat cancers, as new cell cycle inhibitors and apoptosis in...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020310001617165

    authors: Li WX,Cui CB,Cai B,Yao XS

    更新日期:2005-04-01 00:00:00

  • A pair of 24-hydroperoxyl epimeric dammarane saponins from flower-buds of Panax ginseng.

    abstract::Further investigation on the saponins of the flower-buds of Panax ginseng C. A. Meyer has resulted in the isolation and structural elucidation of a pair of new 24-epimers of dammarane type saponins named ginsenoside I and II. The structures of the epimers were characterized on the basis of chemical and spectral eviden...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020108041396

    authors: Qiu F,Ma ZZ,Xu SX,Yao XS,Che CT,Chen YJ

    更新日期:2001-01-01 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

  • Three new decenynol glucosides from Artemisia scoparia (Asteraceae).

    abstract::Three new decenynol glucosides were isolated from the aerial parts of Artemisia scoparia. Their structures were determined to be 6E,8Z-decadien-4-yn-ol 1-O-β-d-glucopyranoside, 6E,8E-decadien-4-yn-ol 1-O-β-d-glucopyranoside, and 6E-decen-4-yn-ol 1-O-β-d-glucopyranoside based on extensive spectroscopic (NMR and MS) ana...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2019.1646729

    authors: Cho JY,Park KH,Hwang DY,Lee SY,Moon JH,Ju Lee Y,Park KD,Ham KS

    更新日期:2020-09-01 00:00:00

  • A new biologically active flavone glycoside from the seeds of Cassia fistula (Linn.).

    abstract::A new bioactive flavone glycoside 1 [mp 252-254 degrees C, C28H32O16, [M]+ 624 (EIMS)] was isolated from the acetone soluble fraction of the defatted seeds of Cassia fistula (Linn.). It was characterized as a new bioactive flavone glycoside 5,3',4'-tri-hydroxy-6-methoxy-7-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-beta-D-g...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/1028602031000080478

    authors: Yadava RN,Verma V

    更新日期:2003-03-01 00:00:00

  • Isolation of two new C-glucofuranosyl isoflavones from Pueraria lobata (Wild.) Ohwi with HPLC-MS guiding analysis.

    abstract::A profiling analysis of the total isoflavone extract of the root of Pueraria lobata (Wild.) Ohwi was performed using HPLC coupled with ESI-ion trap mass spectrometry. A total of seven isoflavones were identified according to their retention times, UV, MS data, and comparing with the literature data. Among them, two pr...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286021003745445

    authors: Zhang HJ,Yang XP,Wang KW

    更新日期:2010-04-01 00:00:00

  • Two new sesquiterpene derivatives from Chinese eaglewood.

    abstract::Two new sesquiterpene derivatives, (+)-8β-hydroxy-longicamphenylone (1) and 11β-hydroxy-13-isopropyl-dihydrodehydrocostus lactone (2), were isolated from Chinese eaglewood. Their structures were elucidated on the basis of spectroscopic analyses including HR-ESI-MS, (1)H and (13)C NMR, DEPT, (1)H-(1)H COSY, HSQC, HMBC,...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2012.704910

    authors: Yang L,Qiao LR,Zhang JJ,Dai JG,Guo SX

    更新日期:2012-01-01 00:00:00

  • New cycloartanes and new iridoids from Dolichandrone spathacea collected in the mangrove forest of Soc Trang province, Vietnam.

    abstract::Two new cycloartanes, named dolichandrone A (1) and dolichandrone B (2), as well as two new iridoids, named [6-O-[(E)-4-methoxycinnamoyl]-1β-hydroxy-dihydrocatalpolgenin (3) and 6-O-[(E)-4-methoxycinnamoyl]-1α-hydroxy-dihydrocatalpolgenin (4), together with four known iridoids (5-8), were isolated from the leaves and ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2017.1406927

    authors: Nguyen VT,Do LQ,Nguyen TA,Nguyen TT,Tran VL,Ho NA,Tran VC,Tran VS,Tran TPT

    更新日期:2018-09-01 00:00:00

  • Four new triterpenoid saponins from Ardisia gigantifolia Stapf. and their cytotoxic activity.

    abstract::Four new oleanane-type triterpenoid saponins, cyclamiretin A 3beta-O-alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-xylopyranosyl-(1 --> 2)]-beta-D-glucopyranosyl-(1 --> 4)-[beta-D-glucopyranosyl-(1 --> 2)]-alpha-L-arabinopyranoside (1), cyclamiretin A 3beta-O-alpha-L-rhamnopyranosyl-(1 --> 3)-[beta-D-glucopyranosyl-(1 -->...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020802144719

    authors: Wen P,Zhang XM,Yang Z,Wang NL,Yao XS

    更新日期:2008-09-01 00:00:00

  • Three new alkaloids from the seeds of Nigella glandulifera.

    abstract::Three new alkaloids namely 8-(4-hydroxyphenyl)-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one (1), 4-aminonigellidine (2), and N-[(4-hydroxy-2-isopropyl-5-methyl)]phenylurea (3), along with six known ones (4-9), were isolated from the seeds of Nigella glandulifera. The structures of 1-3 were determined through spectroscop...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2016.1184654

    authors: Guo WH,Li XM,Huang SS,Yang MH,Kong LY

    更新日期:2017-01-01 00:00:00

  • One new dihydrobenzofuran lignan from Vitex trifolia.

    abstract::A new benzofuran-type lignan, vitrifol A (1), was isolated from the fruits of Vitex trifolia, along with three known compounds 2-4. Their structures were elucidated mainly on the basis of 1D, 2D NMR and MS spectral data. Compound 1 was first isolated as a dimer of dihydrobenzofuran-type lignan. ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020801967359

    authors: Gu Q,Zhang XM,Zhou J,Qiu SX,Chen JJ

    更新日期:2008-05-01 00:00:00

  • A new bioactive coumestan from the seeds of Psoralea corylifolia.

    abstract::A new coumestan named bavacoumestan D (1), together with five known compounds (2-6), was isolated from EtOAc-soluble extract of seeds of Psoralea corylifolia. Their structures were elucidated on the basis of spectroscopic and physico-chemical analyses. All compounds were evaluated for in vitro inhibitory activity agai...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2018.1563073

    authors: Chai MY

    更新日期:2020-03-01 00:00:00

  • Three new ursane-type triterpenoids from the aerial parts of Isodon excisoides.

    abstract::Three new ursane-type triterpenoids, 2α,3β-dihydroxy-11α,12α-epoxy-urs-28,13β-olide (1), 2α,3β,24-trihydroxy-11α,12α-epoxy-urs-28,13β-olide (2), and 2α,3α,24-trihydroxy-11,20(30)-dien-urs-28,13β-olide (6), together with six known ursane-type triterpenoids (3-5, 7-9), were isolated from the EtOAc extract of the aerial ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2013.837458

    authors: Jiao K,Li HY,Zhang P,Pi HF,Ruan HL,Wu JZ

    更新日期:2013-09-01 00:00:00

  • Irritant and co-carcinogenic diterpene esters from the latex of Euphorbia cauducifolia L.

    abstract::Ten (1-10) irritant and mild co-carcinogenic diterpene esters were isolated from the latex of Euphorbia cauducifolia L. using bioassay-guided countercurrent distribution and other chromatographic techniques. The isolated compounds were characterized on the basis of spectroscopic results and mass measurements. As an ou...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2010.489039

    authors: Baloch IB,Baloch MK

    更新日期:2010-07-01 00:00:00

  • Isoflavonoid glycosides from the flowers of Pueraria lobata.

    abstract::Pueraria lobata flower is a medicinal herb for treating intoxication, hepatic, and gastrointestinal tract lesions induced by alcohol. This study aims to investigate the isoflavonoid glycosides in P. lobata flowers. Two new isoflavone compounds were isolated from the extract of P. lobata flowers. Their structures were ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2011.554404

    authors: Yu YL,Liao YT,Li X,Ye Y,Ke CQ,Li XQ,Yang XZ,Yao MC

    更新日期:2011-04-01 00:00:00

  • Two new caffeoyl conjugation from Erigeron breviscapus.

    abstract::Two new constituents with a novel basic skeleton were isolated from Erigeron breviscapus. On the basis of chemical and spectroscopic evidences, the structures of the new compounds were elucidated as 1R,3R-dihydroxy-4S,5R-dicaffeoyloxy cyclohexane carboxylic acid methyl ester (V), 1,4-dihydroxy-3R,5R-dicaffeoyloxy cycl...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020008041367

    authors: Zhang WD,Tam HT,Chen WS,Kong DY,Li HT,Wang YH,Fouraste I

    更新日期:2000-01-01 00:00:00

  • Two new acylgluconic acids from the nearly ripe fruits of Evodia rutaecarpa.

    abstract::Two new acylgluconic acids, trans-feruloylgluconic acid (1) and trans-caffeoylgluconic acid (2), together with three known compounds, myo-inositol (3), phthalic acid dibutyl ester (4), and wuzhuyuamide-I (5), were isolated from the water soluble part of the dried nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth. ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020802031080

    authors: Zhao MY,Yang XW

    更新日期:2008-07-01 00:00:00

  • New alkylated benzoquinones from mangrove plant Aegiceras corniculatum with anticancer activity.

    abstract::Three new alkylated benzoquinones, 2-hydroxy-5-ethoxy-3-nonyl-1,4-benzoquinone (1), 5-O-butyl-embelin (2), and 2,5-dihydroxy-6-methyl-3-pentadecyl-1,4-benzoquinone (3), together with seven known analogues (4-10), were isolated from the stems and twigs of mangrove plant, Aegiceras corniculatum. Their structural elucida...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2018.1540604

    authors: Li Y,Dong C,Xu MJ,Lin WH

    更新日期:2020-02-01 00:00:00

  • Chemical constituents of the red alga Laurencia tristicha.

    abstract::Six new sesquiterpenes, 10-hydroxy-epiaplysin (1), 10-hydroxy-aplysin (2), 10-hydroxy-debromoepiaplysin (3), aplysin-9-ene (4), epiaplysinol (5) and debromoepiaplysinol (6), together with 13 known compounds (7-19), have been isolated from the red alga Laurencia tristicha. The structures of 1-6 were determined by spect...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020601103338

    authors: Sun J,Shi DY,Li S,Wang SJ,Han LJ,Fan X,Yang YC,Shi JG

    更新日期:2007-09-01 00:00:00

  • Xanthone glycosides from herbs of Polygala hongkongensis Hemsl and their antioxidant activities.

    abstract::Two new xanthone O-glycosides, polyhongkongenosides A (1) and B (2), together with four known xanthone glycosides, were isolated from the herbs of Polygala hongkongensis Hemsl. Their structures were elucidated on the basis of UV, IR, NMR, and MS spectral data. The antioxidant in vitro activities of 1-6 were determined...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020801967201

    authors: Wu JF,Chen SB,Gao JC,Song HL,Wu LJ,Chen SL,Tu PF

    更新日期:2008-07-01 00:00:00

  • Synthesis of novel tetrandrine derivatives and their inhibition against NSCLC A549 cells.

    abstract::A series of novel tetrandrine (Tet) derivatives were synthesized through Suzuki -Miyaura reaction and evaluated for their cytotoxicity against human non-small cell lung carcinoma (NSCLC) A549 cells. Interestingly, most of derivatives showed similar cytotoxicity to Tet against NSCLC A549 cells, and particularly, compou...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2018.1478817

    authors: Yang QH,Jiang CS,Jin T,Xu JF,Qu TL,Guo YW,Zhao ZB

    更新日期:2018-11-01 00:00:00

  • One-pot synthesis of a 3,6-branched hexaarabinogalactan using galactopyranosyl thioglycoside diol as a key glycosylating agent.

    abstract::We present in this paper the efficient four-component one-pot synthesis of a fully protected hexaarabinogalactan 2 with di-branched structure by using D-thiogalactopyranoside 3,6-diol 3 as the central glycosylating agent. After global deprotection, 2 was converted into the 3-aminopropyl linker-containing free oligosac...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2014.917084

    authors: Huang H,Han L,Lan YM,Zhang LL

    更新日期:2014-01-01 00:00:00

  • Effect of proliferation, cell cycle, and Bcl-2s of MCF-7 cells by resveratrol.

    abstract::Our goals were to examine the dual-directional regulation effects of resveratrol (1) in vitro by using MCF-7 cells (estradiol receptor-positive cells), study its mechanism of action, and give a systematical analysis of the regulatory networks of each related factor. An MTT test and growth curve showed that the prolife...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020902772096

    authors: Wang YZ,Cao B,Li SX,Zang ZH,Zhang JZ,Chen H

    更新日期:2009-01-01 00:00:00

  • New cytotoxic steroids from the fruits of Syzygium siamense.

    abstract::A new sterol, stigmast-5-ene-3beta,17alpha-diol (1), together with six known compounds, stigmast-5-ene-3beta-yl formate (2), stigmast-5-ene-3beta,7alpha-diol (3), stigmast-5-ene-7alpha-methoxy-3beta-ol (4), stigmast-5-ene-3-one (5), 3beta-sitostanol (6), and 3beta-sitosterol (7), was isolated from the fruits of Syzygi...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286021003762028

    authors: Chumkaew P,Kato S,Chantrapromma K

    更新日期:2010-05-01 00:00:00

  • Chemical constituents from Eupatorium chinense.

    abstract::Two new monoterpenoid glycosides, α-(E)-acaridiol 8-O-β-d-glucopyranoside (1) and α-(E)-acaridiol 9-O-β-d-glucopyranoside (2), as well as a new thiophen, 2-acetyl-3-hydroxy-5-(prop-1-ynyl)thiophen 3-O-β-d-glucopyranoside (3), were isolated from the roots of Eupatorium chinense. Their structures were determined on the ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2011.598149

    authors: Wang WJ,Wang Y,Zhang QW,Zhang XQ,Yang TT,Dai Y,Wang L,Zhang LH,Ye WC

    更新日期:2011-09-01 00:00:00

  • Phenylpropanoids from the leaves of Acanthopanax koreanum and their antioxidant activity.

    abstract::By various chromatographic methods, one new phenylpropanoid, acanthopanic acid (1), and three known compounds, 1,2-O-dicaffeoylcyclopenta-3-ol (2), (4S)-α-terpineol 8-O-β-D-glucopyranoside (3), and rutin (4), were isolated from the methanol extract of the Acanthopanax koreanum leaves. Their structures were elucidated ...

    journal_title:Journal of Asian natural products research

    pub_type: 杂志文章

    doi:10.1080/10286020.2010.525743

    authors: Nhiem NX,Kim KC,Kim AD,Hyun JW,Kang HK,Van Kiem P,Van Minh C,Thu VK,Tai BH,Kim JA,Kim YH

    更新日期:2011-01-01 00:00:00