Synthesis and anti-hepatocellular carcinoma activity of novel O2-vinyl diazeniumdiolate-based nitric oxide-releasing derivatives of oleanolic acid.

Abstract:

:Considering that high levels of nitric oxide (NO) exert anti-cancer effect and the derivatives of oleanolic acid (OA) have shown potent anti-cancer activity, new O2-vinyl diazeniumdiolate-based NO releasing derivatives (5a-l, 11a-l) of OA were designed, synthesized, and biologically evaluated in the present study. These derivatives could release different amounts of NO in liver cells. Among them, 5d, 5i, 5j, 11g, 11h, and 11j released more NO in SMMC-7721 cells and displayed stronger proliferative inhibition against SMMC-7721 and HepG2 cells than OA and other tested compounds. The most active compound 5j showed almost 20-fold better solubility than OA in aqueous solution, released larger amounts of NO in liver cancer cells than that in normal ones, and exhibited potent anti-hepatocellular carcinoma activity but little effect on the normal liver cells. The inhibitory activity against the cancer cells was significantly diminished upon addition of an NO scavenger, suggesting that NO may contribute, at least in part, to the activity of 5j.

journal_name

Chin J Nat Med

authors

Zou Y,Yan C,Liu JC,Huang ZJ,Xu JY,Zhou JP,Zhang HB,Zhang YH

doi

10.1016/S1875-5364(18)30009-8

subject

Has Abstract

pub_date

2017-12-01 00:00:00

pages

928-937

issue

12

eissn

2095-6975

issn

1875-5364

pii

S1875-5364(18)30009-8

journal_volume

15

pub_type

杂志文章
  • Triterpenes from the stem bark of Mitragyna diversifolia and their cytotoxic activity.

    abstract:AIM:To study the chemical constituents and bioactivity of the stem bark of Mitragyna diversifolia. METHOD:Compounds were isolated by various chromatographic methods. Their structures were elucidated on the basis of spectroscopic techniques (IR, UV, MS, and NMR), and they were evaluated for their cytotoxic activities b...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(14)60096-0

    authors: Cao XF,Wang JS,Wang PR,Kong LY

    更新日期:2014-08-01 00:00:00

  • Discovery of novel limonin derivatives as potent anti-inflammatory and analgesic agents.

    abstract::Novel series of limonin derivatives (V-A-1-V-A-8, V-B-1-V-B-8) were synthesized by adding various tertiary amines onto the C (7)-position of limonin. The synthesized compounds possessed favorable physicochemical property, and the intrinsic solubility of the novel compounds were significantly improved, compared with li...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(18)30052-9

    authors: Wang SC,Yang Y,Liu J,Jiang AD,Chu ZX,Chen SY,Gong GQ,He GW,Xu YG,Zhu QH

    更新日期:2018-03-01 00:00:00

  • Difficulties in research of Chinese medicine polysaccharides.

    abstract::Polysaccharides from Chinese medicines are attracting increasing attention to their wide range of valuable biological activities. As these polysaccharides are mostly from edible materials, their safety can be greatly ensured. Therefore, the Chinese medicine polysaccharides have been the focus of research and developme...

    journal_title:Chinese journal of natural medicines

    pub_type: 社论

    doi:10.1016/S1875-5364(19)30107-4

    authors: Li LF,Wong TL,Han QB

    更新日期:2019-12-01 00:00:00

  • Effect of Ipomea carnea Jacq. flowers on hematological changes in toluene diisocyanate-induced inflammation in Wistar rats.

    abstract:AIM:To investigate the active chloroform fraction of the ethanol extract of Ipomoea carnea flowers on hematological changes in toluene diisocyanate-induced inflammation in Wistar rats. METHOD:Except for the control group, all of the rats were sensitized with intranasal application of 5 μL of 10% toluene diisocyanate (...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(14)60027-3

    authors: Smita J,Patil UK

    更新日期:2014-03-01 00:00:00

  • Total synthesis of D-glycero-D-mannno-heptose 1β, 7-bisphosphate with 3-O-amyl amine linker and its monophosphate derivative.

    abstract::D-Glycero-D-mannno-heptose 1β, 7-bisphosphate (HBPβ) is an important intermediate for constructing the core structure of Gram-negative bacterial lipopolysaccharides and was reported as a pathogen-associated molecular pattern (PAMP) that regulates immune responses. HBPβ with 3-O-amyl amine linker and its monophosphate ...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(20)30075-3

    authors: Zou XP,Qin CJ,Hu J,Fu JJ,Tian GZ,Moscovitz O,Seeberger PH,Yin J

    更新日期:2020-08-01 00:00:00

  • A review of isolation methods, structure features and bioactivities of polysaccharides from Dendrobium species.

    abstract::Dendrobium, orchid, is a traditional Chinese herb medicine applied extensively as tonic and precious food for thou-sands of years recorded in ancient Chinese medical book "Shen Nong's Materia Medica". It's well known that bioactivities are usually related to the ingredients' basis. Based on the previous research, Dend...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章,评审

    doi:10.1016/S1875-5364(20)30001-7

    authors: Yue H,Zeng H,Ding K

    更新日期:2020-01-01 00:00:00

  • Cytotoxic constituents from the leaves of Broussonetia papyrifera.

    abstract:AIM:To investigate the chemical constituents from the leaves of Broussonetia papyrifera. METHODS:The chemical constituents were isolated and purified by macroporous adsorptive resin D101, silica gel, and ODS column chromatography and preparative HPLC. Their structures were elucidated on the basis of 1D and 2D NMR anal...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(13)60027-8

    authors: Ran XK,Wang XT,Liu PP,Chi YX,Wang BJ,Dou DQ,Kang TG,Xiong W

    更新日期:2013-05-01 00:00:00

  • Saposhnikoviae divaricata: a phytochemical, pharmacological, and pharmacokinetic review.

    abstract::Saposhnikoviae divaricata (Turcz.) Schischk (SD) is a traditional Chinese herb commonly used to treat clinical conditions such as rheumatism and allergic rhinitis. This review article evaluates a collection of works on in vitro and biochemical studies of SD. The discourse on the diverse class of chromones and coumarin...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章,评审

    doi:10.1016/S1875-5364(17)30042-0

    authors: Kreiner J,Pang E,Lenon GB,Yang AWH

    更新日期:2017-04-01 00:00:00

  • A new sesquiterpene lactone from the fruits of Illicium henryi.

    abstract:AIM:To study the chemical constituents of the fruits of Illicium henryi. METHOD:Chromatographic separations on silica gel, Sephadex LH-20 gel and MCI gel were used to isolate the compounds. The structures were elucidated based on extensive spectroscopic data analyses. RESULTS:Seven compounds were obtained and their s...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(14)60074-1

    authors: Liu JF,Li HJ,Zhang JM,Wang LX,Wang YF,Liu MQ,Bi YF,Zhang YB

    更新日期:2014-06-01 00:00:00

  • Oral JS-38, a metabolite from Xenorhabdus sp., has both anti-tumor activity and the ability to elevate peripheral neutrophils.

    abstract:AIM:JS-38 (mitothiolore), a synthetic version of a metabolite isolated from Xenorhabdus sp., was evaluated for its anti-tumor and white blood cell (WBC) elevating activities. METHOD:These anti-proliferative activities were assessed in vitro using a panel of ten cell lines. The anti-tumor activities were tested in vivo...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(14)60117-5

    authors: Liu MY,Xiao L,Chen GH,Wang YX,Xiong WX,Li F,Liu Y,Huang XL,Deng YF,Zhang Z,Sun HY,Liu QH,Yin M

    更新日期:2014-10-01 00:00:00

  • Quantification of Panax notoginseng saponins metabolites in rat plasma with in vivo gut microbiota-mediated biotransformation by HPLC-MS/MS.

    abstract::Panax notoginseng saponins (PNS) are the major components of Panax notoginseng, with multiple pharmacological activities but poor oral bioavailability. PNS could be metabolized by gut microbiota in vitro, while the exact role of gut microbiota of PNS metabolism in vivo remains poorly understood. In this study, pseudo ...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(19)30026-3

    authors: Guo YP,Chen MY,Shao L,Zhang W,Rao T,Zhou HH,Huang WH

    更新日期:2019-03-01 00:00:00

  • Chemical constituents of flowers and fruits of Rabdosia excisa.

    abstract:AIM:To study the chemical constituents in the flowers and fruits of Rabdosia excisa. METHODS:The compounds were isolated and purified by silica gel column chromatography and their structures were identified by spectroscopic methods. RESULTS:Sixteen compounds isolated from the flowers and fruits of this plant were ide...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(12)60010-7

    authors: Wu YX,Zhang W,Li JC,Liu N

    更新日期:2012-01-01 00:00:00

  • Guidelines and strategy of the International Conference of Harmonization (ICH) and its member states to overcome existing impurity control problems for antibiotics in China.

    abstract::In the present report, we review the technical guidelines and principles on impurity research and control for antibiotics established by various agencies, including the International Conference of Harmonization (ICH), the US Food and Drug Administration (FDA), the European Medicines Agency (EMA) and the China Food and...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(15)30044-3

    authors: Jiang Y,Xia JP,Yang JH,Zhang ZF,Hu CQ,Zhang ZR

    更新日期:2015-07-01 00:00:00

  • Combination of LC/MS and GC/MS based metabolomics to study the hepatotoxic effect of realgar nanoparticles in rats.

    abstract::Realgar nanoparticles (NPs) are increasingly used as therapeutic agents for their enhanced anti-proliferation effect and cytotoxicity on cancer cells. However, the alteration of particle size may enhance biological reactivity as well as toxicity. A LC/MS and GC/MS based metabolomics approach was employed to explore th...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(17)30098-5

    authors: Zhang MH,Chen JQ,Guo HM,Li RT,Gao YQ,Tian Y,Zhang ZJ,Huang Y

    更新日期:2017-09-01 00:00:00

  • Novel natural product therapeutics targeting both inflammation and cancer.

    abstract::Inflammation is recently recognized as one of the hallmarks of human cancer. Chronic inflammatory response plays a critical role in cancer development, progression, metastasis, and resistance to chemotherapy. Conversely, the oncogenic aberrations also generate an inflammatory microenvironment, enabling the development...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章,评审

    doi:10.1016/S1875-5364(17)30062-6

    authors: Qin J,Wang W,Zhang R

    更新日期:2017-06-01 00:00:00

  • Network pharmacology-based analysis of Chinese herbal Naodesheng formula for application to Alzheimer's disease.

    abstract::Naodesheng (NDS) formula, which consists of Rhizoma Chuanxiong, Lobed Kudzuvine, Carthamus tinctorius, Radix Notoginseng, and Crataegus pinnatifida, is widely applied for the treatment of cardio/cerebrovascular ischemic diseases, ischemic stroke, and sequelae of cerebral hemorrhage, etc. At present, the studies on NDS...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(18)30029-3

    authors: Pang XC,Kang,Fang JS,Zhao Y,Xu LJ,Lian WW,Liu AL,DU GH

    更新日期:2018-01-01 00:00:00

  • A new megastigmane glycoside from the aerial parts of Cirsium setosum.

    abstract:AIM:To study the chemical constituents of the aerial parts of Cirsium setosum (Willd.) MB.. METHODS:The chemical constituents were isolated and purified by various chromatographic techniques. Their structures were determined on the basis of physical properties and spectroscopic data. RESULTS:A new megastigmane glycos...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(13)60097-7

    authors: Jiang H,Meng YH,Yang L,Wang QH,Yang BY,Liu C,Kuang HX

    更新日期:2013-09-01 00:00:00

  • Phytochemical progress made in investigations of Angelica sinensis (Oliv.) Diels.

    abstract::The phytochemical progress on Angelica sinensis (Oliv.) Diels over the past decades is summarized. Since 1970s, 165 chemical constituents, including phthalides, phenylpropanoids, terpenoids and essential oils, aromatic compounds, alkaloids, alkynes, sterols, fatty acids, and polysaccharides have been isolated or detec...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章,评审

    doi:10.1016/S1875-5364(15)30010-8

    authors: Ma JP,Guo ZB,Jin L,Li YD

    更新日期:2015-04-01 00:00:00

  • Anti-colorectal cancer effects of tripolinolate A from Tripolium vulgare.

    abstract::Tripolinolate A (TLA) is recently identified as a new compound from a halophyte plant Tripolium vulgare and has been shown to have significant in vitro activity against the proliferation of colorectal cancer and glioma cells. This study was designed to further investigate the effects of TLA on the proliferation of hum...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(17)30085-7

    authors: Chen L,Wang WL,Song TF,Xie X,Ye XW,Liang Y,Huang HC,Yan SL,Lian XY,Zhang ZZ

    更新日期:2017-08-01 00:00:00

  • An in vitro study on interaction of anisodine and monocrotaline with organic cation transporters of the SLC22 and SLC47 families.

    abstract::Current study systematically investigated the interaction of two alkaloids, anisodine and monocrotaline, with organic cation transporter OCT1, 2, 3, MATE1 and MATE2-K by using in vitro stably transfected HEK293 cells. Both anisodine and monocrotaline inhibited the OCTs and MATE transporters. The lowest IC50 was 12.9 µ...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(19)30070-6

    authors: Chen JY,Brockmöller J,Tzvetkov MV,Wang LJ,Chen XJ

    更新日期:2019-07-01 00:00:00

  • Effects of six compounds with different chemical structures on melanogenesis.

    abstract::Several chemical compounds can restore pigmentation in vitiligo through mechanisms that vary according to disease etiology. In the present study, we investigated the melanogenic activity of six structurally distinct compounds, namely, scopoletin, kaempferol, chrysin, vitamin D3, piperine, and 6-benzylaminopurine. We d...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(18)30116-X

    authors: Heriniaina RM,Dong J,Kalavagunta PK,Wu HL,Yan DS,Shang J

    更新日期:2018-10-01 00:00:00

  • Ginsenoside Rk1 suppresses pro-inflammatory responses in lipopolysaccharide-stimulated RAW264.7 cells by inhibiting the Jak2/Stat3 pathway.

    abstract::The saponin ginsenoside Rk1 is a major compound isolated from ginseng. Ginsenoside Rk1 has been reported to have anti-inflammatory and anti-tumor properties and to be involved in the regulation of metabolism. However, the effect and mechanism of anti-inflammatory action of ginsenoside Rk1 has not been fully clarified....

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(17)30106-1

    authors: Yu Q,Zeng KW,Ma XL,Jiang Y,Tu PF,Wang XM

    更新日期:2017-10-01 00:00:00

  • Four new steroids from the marine soft coral-derived fungus Penicillium sp. SCSIO41201.

    abstract::Penicildiones A-D (1-4), four new steroids derivatives together with three known compounds including 16α-methylpregna-17α,19-dihydroxy-(9,11)-epoxy-4-ene-3,18-dione-20-acetoxy (5), stachybotrylactone B (6) and stachybotrin (7) were isolated from the soft coral-derived fungus Penicillium sp. SCSIO41201, cultured in the...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(20)30030-3

    authors: Long JY,Wang JF,Liao SR,Lin XP,Zhou XF,Li YQ,Yang B,Liu YH

    更新日期:2020-04-01 00:00:00

  • Impact of parameter fluctuations on the performance of ethanol precipitation in production of Re Du Ning Injections, based on HPLC fingerprints and principal component analysis.

    abstract::The present study was designed to determine the relationships between the performance of ethanol precipitation and seven process parameters in the ethanol precipitation process of Re Du Ning Injections, including concentrate density, concentrate temperature, ethanol content, flow rate and stir rate in the addition of ...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.3724/SP.J.1009.2015.00073

    authors: Sun LQ,Wang SY,Li YJ,Wang YX,Wang ZZ,Huang WZ,Wang YS,Bi YA,Ding G,Xiao W

    更新日期:2016-01-01 00:00:00

  • Effects of feeding tyrosine and phenylalanine on the accumulation of phenylethanoid glycosides to Cistanche deserticola cell suspension culture.

    abstract:AIM:To investigate the effects of feeding phenylalanine (Phe) and tyrosine (Tyr) on the accumulation of total phenolic compounds and four phenylethanoid glycosides (PeGs) to a cell suspension culture of the parasitic plant Cistanche deserticola. METHOD:A cell suspension culture of C. deserticola was established and pr...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(14)60045-5

    authors: Hu GS,Jia JM,Kim DH

    更新日期:2014-05-01 00:00:00

  • A new ursane-type triterpenoid saponin from the aerial parts of Clematoclethra scandens subsp. actinidioides.

    abstract::A new ursane-type triterpenoid saponin, 2α,3α,24-trihydroxyurs-12,20(30)-dien-28-oic acid β-D-glucopyranosyl ester (1), together with six known triterpenoid saponins, was isolated and characterized from the aerial parts of Clematoclethra scandens subsp. actinidioides. ...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(15)60008-5

    authors: Xiao SJ,Chen F,Ding LS,Zhou Y

    更新日期:2015-01-01 00:00:00

  • YGS40, an active fraction of Yi-Gan San, reduces hydrogen peroxide-induced apoptosis in PC12 cells.

    abstract::In our previous study, we have elucidated the chemical profile of YGS40, a fraction of Yi-Gan San (YGS), used for the treatment of Alzheimer's disease (AD). Oxidative stress-induced apoptosis is implicated in neurodegenerative disorders such as AD. The aim of the present study was to explore the protective effects of ...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(15)30037-6

    authors: Zhao YR,Qu W,Liu WY,Hong H,Feng F,Chen H,Xie N

    更新日期:2015-06-01 00:00:00

  • Improved anti-tumor activity and safety profile of a paclitaxel-loaded glycyrrhetinic acid-graft-hyaluronic acid conjugate as a synergistically targeted drug delivery system.

    abstract::The present study was designed to develop and evaluate glycyrrhetinic acid-graft-hyaluronic acid (HGA) conjugate for intravenous paclitaxel (PTX) delivery. Lyophilized PTX-loaded self-assembled HGA nanoparticles (PTX/HGAs) were prepared and characterized by dynamic light scattering measurements. Hemolysis test, intrav...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(15)30097-2

    authors: Zhang L,Zhou JP,Yao J

    更新日期:2015-12-01 00:00:00

  • Synthesis and evaluation of 2-cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide as a potent anti-inflammatory agent for intervention of LPS-induced acute lung injury.

    abstract::The present study was designed to synthesize 2-Cyano-3, 12-dioxooleana-1, 9(11)-en-28-oate-13β, 28-olide (1), a lactone derivative of oleanolic acid (OA) and evaluate its anti-inflammatory activity. Compound 1 significantly diminished nitric oxide (NO) production and down-regulated the mRNA expression of iNOS, COX-2, ...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(17)30055-9

    authors: Mou Y,Jian YL,Chen T,Huang ZJ,Qiao YX,Peng SX,Zhang DY,Ji H,Zhang YH

    更新日期:2017-05-01 00:00:00

  • Engineering CrtW and CrtZ for improving biosynthesis of astaxanthin in Escherichia coli.

    abstract::This study engineered β-carotene ketolase CrtW and β-carotene hydroxylase CrtZ to improve biosynthesis of astaxanthin in Escherichia coli. Firstly, crtW was randomly mutated to increase CrtW activities on conversion from β-carotene to astaxanthin. A crtW* mutant with A6T, T105A and L239M mutations has improved 5.35-fo...

    journal_title:Chinese journal of natural medicines

    pub_type: 杂志文章

    doi:10.1016/S1875-5364(20)60005-X

    authors: Li D,Li Y,Xu JY,Li QY,Tang JL,Jia SR,Bi CH,Dai ZB,Zhu XN,Zhang XL

    更新日期:2020-09-01 00:00:00