Chemical constituents from the fruit of Gardenia jasminoides and their inhibitory effects on nitric oxide production.

Abstract:

:Three new iridoid glycosides, 6"-O-trans-caffeoylgenipin gentiobioside (1), genipin 1-O-β-D-apiofuranosyl (1→6)-β-D-glucopyranoside (2), genipin 1-O-α-D-xylopyranosyl (1→6)-β-D-glucopyranoside (3), three new monocyclic monoterpenoids, jasminoside R (4), jasminoside S (5), jasminoside T (6), together with nine known iridoid glycosides (7-15) and three crocetin glycosides (16-18), were isolated from the fruit of Gardenia jasminoides. Their chemical structures were established mainly by 1D and 2D NMR techniques and mass spectrometry. Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated. Compounds 8 and 18 showed strong inhibitory activity on NO production with IC(50) values of 11.14±0.67 and 5.99±0.54 μM, respectively.

journal_name

Bioorg Med Chem Lett

authors

Peng K,Yang L,Zhao S,Chen L,Zhao F,Qiu F

doi

10.1016/j.bmcl.2012.11.099

subject

Has Abstract

pub_date

2013-02-15 00:00:00

pages

1127-31

issue

4

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(12)01551-X

journal_volume

23

pub_type

杂志文章
  • Design and regioselective synthesis of a new generation of targeted chemotherapeutics. Part II: Folic acid conjugates of tubulysins and their hydrazides.

    abstract::Efficient syntheses of folate conjugates of tubulysins and their hydrazides 1a-d are described. These water soluble folate receptor (FR) targeted conjugates are derivatives of folic acid and the potent cytotoxic agents: tubulysin A, B, or their respective hydrazides, connected in regioselective manner via a hydrophili...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.07.041

    authors: Vlahov IR,Wang Y,Kleindl PJ,Leamon CP

    更新日期:2008-08-15 00:00:00

  • N-4-Substituted-benzyl-N'-tert-butylbenzyl thioureas as vanilloid receptor ligands: investigation on the role of methanesulfonamido group in antagonistic activity.

    abstract::A series of N-4-substituted-benzyl-N'-tert-butylbenzyl thioureas were prepared for the study of their agonistic/antagonistic activities to the vanilloid receptor in rat DRG neurons. Their structure-activity relationship reveals that not only the two oxygens and amide hydrogen of sulfonamido group, but also the optimal...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.11.019

    authors: Park HG,Choi JY,Choi SH,Park MK,Lee J,Suh YG,Cho H,Oh U,Lee J,Kang SU,Lee J,Kim HD,Park YH,Su Jeong Y,Kyu Choi J,Jew SS

    更新日期:2004-02-09 00:00:00

  • Diphenyl ethers as androgen receptor antagonists for the topical suppression of sebum production.

    abstract::A series of diphenyl ethers was prepared and evaluated for androgen receptor antagonist activity in human androgen receptor binding and cellular functional assays. Analogs with potent in vitro activities were evaluated for topical in vivo efficacy in the Golden Syrian Hamster ear model. Several compounds showed reduct...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.02.104

    authors: Mitchell LH,Hu LY,Nguyen M,Fakhoury S,Smith Y,Iula D,Kostlan C,Carroll M,Dettling D,Du D,Pocalyko D,Wade K,Lefker B

    更新日期:2009-04-15 00:00:00

  • Mesoionic pyrido[1,2-a]pyrimidinones: A novel class of insecticides inhibiting nicotinic acetylcholine receptors.

    abstract::A novel class of mesoionic pyrido[1,2-a]pyrimidinones has been discovered with exceptional insecticidal activity controlling a number of insect species, particularly hemiptera and lepidoptera. Mode-of-action studies showed that they act on nicotinic acetylcholine receptors (nAChRs) primarily as inhibitors. Here we rep...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.10.031

    authors: Zhang W,Holyoke CW Jr,Barry J,Leighty RM,Cordova D,Vincent DR,Hughes KA,Tong MT,McCann SF,Xu M,Briddell TA,Pahutski TF,Lahm GP

    更新日期:2016-11-15 00:00:00

  • The development of monocyclic pyrazolone based cytokine synthesis inhibitors.

    abstract::4-Aryl-5-pyrimidyl based cytokine synthesis inhibitors that contain a novel monocyclic, pyrazolone heterocyclic core are described. Many of these inhibitors showed low nanomolar activity against LPS-induced TNF-alpha production. One of the compounds (6e) was found to be efficacious in the rat iodoacetate (RIA) in vivo...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.03.007

    authors: Golebiowski A,Townes JA,Laufersweiler MJ,Brugel TA,Clark MP,Clark CM,Djung JF,Laughlin SK,Sabat MP,Bookland RG,VanRens JC,De B,Hsieh LC,Janusz MJ,Walter RL,Webster ME,Mekel MJ

    更新日期:2005-05-02 00:00:00

  • Structure-based design of ketone-containing, tripeptidyl human rhinovirus 3C protease inhibitors.

    abstract::Tripeptide-derived molecules incorporating C-terminal ketone electrophiles were evaluated as reversible inhibitors of the cysteine-containing human rhinovirus 3C protease (3CP). An optimized example of such compounds displayed potent 3CP inhibition activity (K = 0.0045 microM) and in vitro antiviral properties (EC50=0...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00587-9

    authors: Dragovich PS,Zhou R,Webber SE,Prins TJ,Kwok AK,Okano K,Fuhrman SA,Zalman LS,Maldonado FC,Brown EL,Meador JW 3rd,Patick AK,Ford CE,Brothers MA,Binford SL,Matthews DA,Ferre RA,Worland ST

    更新日期:2000-01-03 00:00:00

  • Estrogen receptor ligands. Part 10: Chromanes: old scaffolds for new SERAMs.

    abstract::The discovery, synthesis, and SAR of chromanes as ER alpha subtype selective ligands are described. X-ray studies revealed that the origin of the ER alpha-selectivity resulted from a C-4 trans methyl substitution to the cis-2,3-diphenyl-chromane platform. Selected compounds from this class demonstrated very potent in ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.01.046

    authors: Tan Q,Blizzard TA,Morgan JD 2nd,Birzin ET,Chan W,Yang YT,Pai LY,Hayes EC,DaSilva CA,Warrier S,Yudkovitz J,Wilkinson HA,Sharma N,Fitzgerald PM,Li S,Colwell L,Fisher JE,Adamski S,Reszka AA,Kimmel D,DiNinno F,Rohre

    更新日期:2005-03-15 00:00:00

  • Optimization of diarylazines as anti-HIV agents with dramatically enhanced solubility.

    abstract::Non-nucleoside inhibitors of HIV-1 reverse transcriptase are reported that have ca. 100-fold greater solubility than the structurally related drugs etravirine and rilpivirine, while retaining high anti-viral activity. The solubility enhancements come from strategic placement of a morpholinylalkoxy substituent in the e...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.06.091

    authors: Bollini M,Cisneros JA,Spasov KA,Anderson KS,Jorgensen WL

    更新日期:2013-09-15 00:00:00

  • 2,2-Dimethyl-4,5-diaryl-3(2H)furanone derivatives as selective cyclo-oxygenase-2 inhibitors.

    abstract::A series of 2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]-4-phenyl-3(2H)furanones was prepared and evaluated for their ability to inhibit cyclo-oxygenase-2 (COX-2). ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00634-x

    authors: Shin SS,Noh MS,Byun YJ,Choi JK,Kim JY,Lim KM,Ha JY,Kim JK,Lee CH,Chung S

    更新日期:2001-01-22 00:00:00

  • The synthesis and SAR of 2-arylsulfanyl-phenyl piperazinyl acetic acids as glyT-1 inhibitors.

    abstract::Elevation of glycine levels and activation of the NMDA receptor by inhibition of the glycine transporter 1 (GlyT-1) is a potential strategy for the treatment of schizophrenia. A novel series of GlyT-1 inhibitors have been identified containing the 2-arylsulfanyl-phenylpiperazine motif. The most prominent member of thi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.05.043

    authors: Smith G,Ruhland T,Mikkelsen G,Andersen K,Christoffersen CT,Alifrangis LH,Mørk A,Wren SP,Harris N,Wyman BM,Brandt G

    更新日期:2004-08-02 00:00:00

  • Synthesis, biological evaluation of prenylflavonoids as vasorelaxant and neuroprotective agents.

    abstract::A series of prenylflavonoids with multiple hydroxyl groups were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pre-contracted by phenylephrine (PE), as well as their neuroprotective effects against OGD induced PC12 cell injury. The results indicated that the prenyl group at A-ring ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.04.120

    authors: Dong X,Qi L,Jiang C,Chen J,Wei E,Hu Y

    更新日期:2009-06-15 00:00:00

  • Discovery of highly potent and efficacious MC4R agonists with spiroindane N-Me-1,2,4-triazole privileged structures for the treatment of obesity.

    abstract::We report an SAR study of MC4R analogs containing spiroindane heterocyclic privileged structures. Compound 26 with N-Me-1,2,4-triazole moiety possesses exceptional potency at MC4R and potent anti-obesity efficacy in a mouse model. However, the efficacy is not completely mediated through MC4R. Additional SAR studies le...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.09.049

    authors: He S,Ye Z,Dobbelaar PH,Bakshi RK,Hong Q,Dellureficio JP,Sebhat IK,Guo L,Liu J,Jian T,Lai Y,Franklin CL,Reibarkh M,Holmes MA,Weinberg DH,MacNeil T,Tang R,Tamvakopoulos C,Peng Q,Miller RR,Stearns RA,Chen HY,Chen

    更新日期:2010-11-15 00:00:00

  • Vialinin A and thelephantin G, potent inhibitors of tumor necrosis factor-α production, inhibit sentrin/SUMO-specific protease 1 enzymatic activity.

    abstract::Several p-terphenyl compounds have been isolated from the edible Chinese mushroom Thelephora vialis. Vialinin A, a p-terphenyl compound, strongly inhibits tumor necrosis factor-α production and release. Vialinin A inhibits the enzymatic activity of ubiquitin-specific peptidase 5, one of the target molecules in RBL-2H3...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.07.051

    authors: Yoshioka Y,Namiki D,Makiuchi M,Sugaya K,Onose J,Ashida H,Abe N

    更新日期:2016-09-01 00:00:00

  • Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities.

    abstract::Eight monosaccharide analogs of the potent antitumor OSW saponins (2-9) were synthesized. One analog, 2-O-acetyl-alpha-l-arabinopyranoside 3, showed antiproliferative activity against the Jurkat cells (IC(50)=0.078microM) comparable to that of the disaccharide derivative (1). ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.11.032

    authors: Tang P,Mamdani F,Hu X,Liu JO,Yu B

    更新日期:2007-02-15 00:00:00

  • Nociceptin/Orphanin FQ(1-13)NH2 analogues modified in the Phe1-Gly2 peptide bond.

    abstract::The synthesis and pharmacological activity of novel nociceptin/orphanin FQ (N/OFQ) analogues modified in the Phe(1)-Gly(2) peptide bond are reported. The aim of the present work was to elucidate the importance of this peptide bond for the N/OFQ receptor (NOP) interaction. Our study indicates that the first peptide bon...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)01004-1

    authors: Guerrini R,Rizzi D,Zucchini M,Tomatis R,Regoli D,Calo' G,Salvadori S

    更新日期:2003-02-10 00:00:00

  • Diaryl-dialkyl-substituted pyrazoles: regioselective synthesis and binding affinity for the estrogen receptor.

    abstract::We have developed two novel series of tetrasubstituted pyrazoles, embodying 1,3-diaryl-4,5-dialkyl or 3,5-diaryl-1,4-dialkyl substitution patterns. The scope of a regioselective method, developed by us earlier, was expanded to allow the synthesis of the first series of these tetrasubstituted pyrazoles directly from al...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00057-4

    authors: Nishiguchi GA,Rodriguez AL,Katzenellenbogen JA

    更新日期:2002-03-25 00:00:00

  • Selective alpha1a adrenergic receptor antagonists based on 4-aryl-3,4-dihydropyridine-2-ones.

    abstract::A series of alpha1a receptor antagonists derived from a 4-aryl-3,4-dihydropyridine-2-one heterocycle is disclosed. Potency in the low nanomolar to picomolar range along with high selectivity was obtained. In vivo efficacy in a prostate contraction model in rats was observed with a few derivatives. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00696-4

    authors: Nantermet PG,Barrow JC,Selnick HG,Homnick CF,Freidinger RM,Chang RS,O'Malley SS,Reiss DR,Broten TP,Ransom RW,Pettibone DJ,Olah T,Forray C

    更新日期:2000-08-07 00:00:00

  • New arylalkanones from Horsfieldia macrobotrys, effective antidiabetic agents concomitantly inhibiting α-glucosidase and free radicals.

    abstract::In search of effective antidiabetic agents having therapeutic effect by inhibiting α-glucosidase and preventive effect by scavenging free radicals, Horsfieldia macrobotrys showed promising bioactivity required for the proposed criteria. Bioassay-guided isolation of the stem bark extract resulted in two new arylalkanon...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.08.069

    authors: Ramadhan R,Phuwapraisirisan P

    更新日期:2015-10-15 00:00:00

  • Inhibition of human neuraminidase 3 (NEU3) by C9-triazole derivatives of 2,3-didehydro-N-acetyl-neuraminic acid.

    abstract::We report the synthesis of a series of C9 and N5Ac modified analogs of 2,3-didehydro-N-acetyl-neuraminic acid (DANA) and their inhibitory potency for the human neuraminidase 3 (NEU3) enzyme. We were able to generate a small library of compounds through the synthesis of azide derivatives of DANA, followed by Cu-catalyz...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.09.111

    authors: Zou Y,Albohy A,Sandbhor M,Cairo CW

    更新日期:2010-12-15 00:00:00

  • P4 and P1' optimization of bicycloproline P2 bearing tetrapeptidyl alpha-ketoamides as HCV protease inhibitors.

    abstract::With the aim of improving HCV protease inhibitors reported in our previous manuscripts, we synthesized and evaluated a series of 1a-based tetrapeptidyl alpha-ketoamides with additional P4 modification. The promising analog discovered through this SAR, 5a, was further derivatized at P1' or P1 position. As a result of t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.07.007

    authors: Yip Y,Victor F,Lamar J,Johnson R,Wang QM,Glass JI,Yumibe N,Wakulchik M,Munroe J,Chen SH

    更新日期:2004-10-04 00:00:00

  • Novel BACE1 inhibitors possessing a 5-nitroisophthalic scaffold at the P2 position.

    abstract::Recently, we reported substrate-based pentapeptidic BACE1 inhibitors possessing a hydroxymethylcarbonyl isostere as a substrate transition-state mimic. These inhibitors showed potent inhibitory activities in enzymatic and cell assays. We also designed and synthesized non-peptidic and small-sized inhibitors possessing ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.05.089

    authors: Hamada Y,Nakanishi T,Suzuki K,Yamaguchi R,Hamada T,Hidaka K,Ishiura S,Kiso Y

    更新日期:2012-07-15 00:00:00

  • Discovery of a novel 2,3-dimethylimidazo[1,2-a]pyrazine-6-carboxamide M4 positive allosteric modulator (PAM) chemotype.

    abstract::This Letter details our efforts to discover structurally unique M4 PAMs containing 5,6-heteroaryl ring systems. In an attempt to improve the DMPK profiles of the 2,3-dimethyl-2H-indazole-5-carboxamide and 1-methyl-1H-benzo[d][1,2,3]triazole-6-carboxamide cores, we investigated a plethora of core replacements. This exe...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.126812

    authors: Temple KJ,Engers JL,Long MF,Watson KJ,Chang S,Luscombe VB,Jenkins MT,Rodriguez AL,Niswender CM,Bridges TM,Conn PJ,Engers DW,Lindsley CW

    更新日期:2020-02-01 00:00:00

  • Synthesis and biological evaluation of oxazole derivatives as T-type calcium channel blockers.

    abstract::T-type calcium channel is one of therapeutic targets for the treatment of cardiovascular diseases and neuropathic pain. In this study, as a part of our ongoing efforts to develop potent T-type calcium channel blockers, we designed oxazole derivatives substituted with arylpiperazinylalkylamines. The oxazoles were synth...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.05.030

    authors: Lee JE,Koh HY,Seo SH,Baek YY,Rhim H,Cho YS,Choo H,Pae AN

    更新日期:2010-07-15 00:00:00

  • Synthesis and biological activity of pyridopyridazin-6-one p38α MAP kinase inhibitors. Part 2.

    abstract::This manuscript concludes the Structure Activity Relationship (SAR) on the pyridazinone scaffold and identifies a compound with subnanomolar p38α activity and 24h coverage in the rat arthritis efficacy model. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.07.035

    authors: Tynebor RM,Chen MH,Natarajan SR,O'Neill EA,Thompson JE,Fitzgerald CE,O'Keefe SJ,Doherty JB

    更新日期:2012-09-15 00:00:00

  • Muscarinic acetylcholine receptor binding affinities of pethidine analogs.

    abstract::A series of pethidine analogs were synthesized and their affinities for the [(3)H]N-methyl-scopolamine (NMS) binding site on muscarinic acetylcholine receptors (mAChRs) were determined using M1, M3 or M5 human mAChRs expressed by Chinese hamster ovary (CHO) cell membranes. Compound 6b showed the highest binding affini...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.10.029

    authors: Lee NR,Zhang X,Darna M,Dwoskin LP,Zheng G

    更新日期:2015-11-15 00:00:00

  • Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.

    abstract::Two natural piperamides (piperlonguminine and refrofractamide A) and their derivatives were synthesized and evaluated for inhibitory activity against histone deacetylases, as well as the HCT-116 human colon cancer cell line. The preliminary structure activity relationship was discussed. Compounds featuring a hydroxami...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.06.046

    authors: Luo Y,Liu HM,Su MB,Sheng L,Zhou YB,Li J,Lu W

    更新日期:2011-08-15 00:00:00

  • Synthesis and antitumor activity of leinamycin derivatives: modifications of C-8 hydroxy and C-9 keto groups.

    abstract::A series of leinamycin derivatives were synthesized and evaluated for antitumor activity. Modifications at C-8 and C-9 positions revealed a broad structure-activity relationship in vitro and some derivatives showed potent antiproliferative activity against HeLa S3 cells. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00133-4

    authors: Kanda Y,Ashizawa T,Saitoh Y,Saito H,Gomi K,Okabe M

    更新日期:1998-04-21 00:00:00

  • Novel, potent, and orally bioavailable phosphinic acid inhibitors of the hepatitis C virus NS3 protease.

    abstract::A potent and novel class of product-like inhibitors of the HCV NS3 protease was discovered by employing a phosphinic acid as a carboxylate isostere. The replicon activity and pharmacokinetic profile of this series of compounds was optimized by exploring the substitution of the phosphinic acid, as well as conformationa...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.04.125

    authors: Clarke MO,Chen X,Cho A,Delaney WE 4th,Doerffler E,Fardis M,Ji M,Mertzman M,Pakdaman R,Pyun HJ,Rowe T,Yang CY,Sheng XC,Kim CU

    更新日期:2011-06-15 00:00:00

  • Recent progress in human telomere RNA structure and function.

    abstract::Human telomeric DNA is transcribed into telomeric RNA in cells. Telomeric RNA performs the fundamental biological functions such as regulation and protection of chromosome ends. This digest highlights the human telomere RNA G-quadruplex structures, telomere RNA functions, G-quadruplex-binding small molecules, and futu...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmcl.2018.06.021

    authors: Xu Y

    更新日期:2018-08-15 00:00:00

  • Synthesis and antitumor activities of 5-methyl-1- and 2-[[2-dimethylaminoethyl]amino]-aza-thiopyranoindazoles.

    abstract::The synthesis of 1- and 2-substituted aza-benzothiopyranoindazoles has been accomplished. The comparisons of the in vitro antitumor activities of the 2-substituted analogues with the benzothiopyranoindazole chemotypes indicate that the positioning of the nitrogen atom at C-9 (9-aza analogue 4d) leads to a substrate wi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00689-7

    authors: Krapcho AP,Haydar SN,Truong-Chiott S,Hacker MP,Menta E,Beggiolin G

    更新日期:2000-02-07 00:00:00