A novel cyclopentene derivative and a polyhydroxylated steroid from a South China Sea gorgonian Menella sp.

Abstract:

:A chemical investigation on a South China Sea gorgonian, Menella sp. resulted in the isolation and elucidation of menellin A (1), a highly oxygenated racemate with C(8) skeleton, and a polyhydroxylated steroid, menellsteroid C (2), along with eight known compounds (3-10). The structures of the new compounds were elucidated by means of MS, 1D and 2D NMR spectra, and the relative stereochemistry of 1 was determined by X-ray single-crystal diffraction analysis. In addition, compound 7 was isolated as a new natural product. Compounds 1-3 and 7 were selected to test the anti-inflammatory inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages. 1 and 3 exhibited modest inhibitory effects with IC(50) of 71.3, 33.9 µM, respectively, compared to the positive control aminoguanidine (IC(50) 25.0 µM).

authors

Chai XY,Sun JF,Tang LY,Yang XW,Li YQ,Huang H,Zhou XF,Yang B,Liu Y

doi

10.1248/cpb.58.1391

subject

Has Abstract

pub_date

2010-10-01 00:00:00

pages

1391-4

issue

10

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/58.1391

journal_volume

58

pub_type

杂志文章
  • Synthetic study on selenocystine-containing peptides.

    abstract::N-9-Fluorenylmethoxycarbonyl-Se-4-methoxybenzylselenocysteine++ + [Fmoc-Sec(MBzl)-OH] was synthesized from selenocystine and successfully applied to Fmoc-based solid-phase peptide synthesis. The stability and the deprotection conditions of the Se-MBzl group were examined. The diselenide bond of a peptide was directly ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.502

    authors: Koide T,Itoh H,Otaka A,Yasui H,Kuroda M,Esaki N,Soda K,Fujii N

    更新日期:1993-03-01 00:00:00

  • Development of a novel granular detergent with an interspersion particle comprising an anionic surfactant and a polymeric polycarboxalate.

    abstract::This paper discusses a process for making a novel granular detergent with an interspersion particle comprising an anionic surfactant and a polymeric polycarboxalate. This process contains three steps to develop the interspersion particles with anionic surfactant and polymeric ploycarboxalate. The first step was to for...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.743

    authors: Ebihara F,Watano S

    更新日期:2003-06-01 00:00:00

  • Amino acids and peptides. XIII. Synthetic studies on N-terminal tripeptide amide analogs of fibrin alpha-chain.

    abstract::N-Terminal tripeptide analogs of fibrin alpha-chain were synthesized and their inhibitory effect on fibrinogen/thrombin clotting was examined. A new water-soluble active ester, 3-pyridinium ester, was used for the synthesis. Among the synthetic peptides, H-Gly-Pro-Arg-hexamethyleneimine exhibited the highest inhibitor...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.584

    authors: Kawasaki K,Tsuji T,Hirase K,Miyano M,Imoto Y,Iwamoto M

    更新日期:1991-03-01 00:00:00

  • Inhibition of adenosine 3',5'-cyclic monophosphate phosphodiesterase by flavonoids from licorice roots and 4-arylcoumarins.

    abstract::Isoliquiritigenin, glabridin, licoarylcoumarin and licoricidin were identified as strong inhibitors of adenosine 3',5'-cyclic monophosphate (cAMP) phosphodiesterase in waste materials which were obtained during the industrial extraction of glycyrrhizin from licorice roots. The structure-activity relationships of 12 fl...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.930

    authors: Kusano A,Nikaido T,Kuge T,Ohmoto T,Delle Monache G,Botta B,Botta M,Saitoh T

    更新日期:1991-04-01 00:00:00

  • Preparation and evaluation of highly drug-loaded fine globular granules using a multi-functional rotor processor.

    abstract::The manufacture of highly drug-loaded fine globular granules eventually applied for orally disintegrating tablets has been investigated using a unique multi-functional rotor processor with acetaminophen, which was used as a model drug substance. Experimental design and statistical analysis were used to evaluate potent...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c14-00687

    authors: Iwao Y,Kimura S,Ishida M,Mise R,Yamada M,Namiki N,Noguchi S,Itai S

    更新日期:2015-01-01 00:00:00

  • Antiallergic agent from natural sources. Structures and inhibitory effect of histamine release of naphthopyrone glycosides from seeds of Cassia obtusifolia L.

    abstract::Two new naphthopyrones, cassiasides B2 (1) and C2 (2), were isolated from the seeds (Cassiae Semen) of Cassia obtusifolia L. The structures of the two new compounds 1 and 2 were established as rubrofusarin 6-O-beta-D- glucopyranosyl-(1-->6)-O-beta-D-glucopyranosyl-(1-->3)-O-beta-D- glucopyranosyl-(1-->6)-O-beta-D-gluc...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.1650

    authors: Kitanaka S,Nakayama T,Shibano T,Ohkoshi E,Takido M

    更新日期:1998-10-01 00:00:00

  • Simultaneous determination of triterpene saponins in ginseng drugs by high-performance liquid chromatography.

    abstract::A HPLC method for the simultaneous determination of 11 triterpene saponins with four-type aglycones (protopanaxadiol, protopanaxatriol, ocotillol and oleanolic acid types) in Ginseng drugs was developed and validated. Using a gradient of acetonitrile and 10 mM K-phosphate buffer (pH 5.80) as the mobile phase and UV de...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.995

    authors: Zhu S,Zou K,Cai S,Meselhy MR,Komatsu K

    更新日期:2004-08-01 00:00:00

  • Synthesis and antibacterial activity of some imidazo[1,2-a]pyrimidine derivatives.

    abstract::A series of 75 imidazo[1,2-a]pyrimidine derivatives were synthesized. The "in vitro" antibacterial activity of these compounds and their corresponding alpha-bromoketones against a variety of gram (+), gram (-) bacteria and Mycobacterium species is reported. Some of the prepared derivatives exhibited potent antimicrobi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1170

    authors: Rival Y,Grassy G,Michel G

    更新日期:1992-05-01 00:00:00

  • Highly sensitive spectrophotometric determination of human serum albumin with 3',4',5',6'-tetrachlorogallein-molybdenum(VI) complex.

    abstract::A highly sensitive spectrophotometric determination of human serum albumin (HSA) with 3',4',5',6'-tetrachlorogallein (T.Cl.Gall)-Mo(VI) complex in a Triton X-100 + polyvinyl alcohol micellar medium is proposed. This method can be used to determine up to ca. 150 micrograms/10 ml of HSA from the optical absorbance at 64...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.2452

    authors: Fujita Y,Mori I,Ikuta K,Nakahashi Y,Kato K,Nakanishi T

    更新日期:1989-09-01 00:00:00

  • Lobophytones H-N, Biscembranoids from the Chinese soft coral Lobophytum pauciflorum.

    abstract::Chemical examination of a Chinese soft coral Lobophytum pauciflorum resulted in the isolation of seven new biscembranoids, named lobophytones H-N (1-7). Their structures were determined by interpretation of 1D- and 2D-NMR (correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear mu...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.1591

    authors: Yan P,Deng Z,van Ofwegen L,Proksch P,Lin W

    更新日期:2010-12-01 00:00:00

  • Intercalation compound of diclofenac sodium with layered inorganic compounds as a new drug material.

    abstract::The intercalation reaction of diclofenac sodium (DFS) with layered inorganic compounds, gamma-titanium phosphate (gamma-TiP), proton type titanium oxide (H-TiO2) and sodium type synthetic mica (Na-TSM), was examined on. The direct reaction of DFS in ethanol-water mixed solvent resulted in the large amount accommodatio...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1396

    authors: Tajima T,Suzuki N,Watanabe Y,Kanzaki Y

    更新日期:2005-11-01 00:00:00

  • The screening of Chinese crude drugs for Ca2+ antagonist activity: identification of active principles from the aerial part of Pogostemon cablin and the fruits of Prunus mume.

    abstract::Hot aqueous extracts of 134 Chinese crude drugs were subjected to screening for inhibitory activity on K+ contracture of guinea pig taenia coli, and significant activity was observed in 17 crude drugs. Chemical investigations of two crude drugs, Kakko and Ubai, which originate from Pogostemon cablin and Prunus mume, r...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.345

    authors: Ichikawa K,Kinoshita T,Sankawa U

    更新日期:1989-02-01 00:00:00

  • Studies on novel bone resorption inhibitors. I. Synthesis and pharmacological activities of aminomethylenebisphosphonate derivatives.

    abstract::A series of aminomethylenebisphosphonate derivatives was synthesized and evaluated for their antiresorptive activities using a parathyroid hormone (PTH)-induced hypercalcemia model in rats (PIH model). Among these compounds, (cycloheptylamino)methylenebis(phosphonic acid) (3j) was finally selected for further investig...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.688

    authors: Takeuchi M,Sakamoto S,Yoshida M,Abe T,Isomura Y

    更新日期:1993-04-01 00:00:00

  • Chiral Calcium-Catalyzed Asymmetric Epoxidation Reactions Using Hydrogen Peroxide as the Terminal Oxidant.

    abstract::Asymmetric epoxidation reactions of chalcone derivatives catalyzed by chiral calcium complexes using hydrogen peroxide were developed. The epoxidation reactions proceeded smoothly to afford the desired products in good yields with good enantioselectivities. This is the first example of chiral calcium-catalyzed asymmet...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00485

    authors: Yamashita Y,Macor JA,Fushimi S,Tsubogo T,Kobayashi S

    更新日期:2018-01-01 00:00:00

  • A cytotoxic and apoptosis-inducing sesquiterpenoid isolated from the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk).

    abstract::Repeated silica gel and octadecyl silica gel (ODS) column chromatography of the aerial parts of Artemisia princeps PAMPANINI (Sajabalssuk) led to the isolation of a new sesquiterpenoid, 3-((S)-2-methylbutyryloxy)-costu-1(10),4(5)-dien-12,6 alpha-olide (2), along with two previously reported sesquiterpenoids: 8 alpha-a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1168

    authors: Bang MH,Han MW,Song MC,Cho JG,Chung HG,Jeong TS,Lee KT,Choi MS,Kim SY,Baek NI

    更新日期:2008-08-01 00:00:00

  • Practical approach for measuring heat capacity of pharmaceutical crystals/glasses by modulated-temperature differential scanning calorimetry.

    abstract::A practical protocol to obtain accurate heat capacity values of pharmaceutical compounds using modulated-temperature differential scanning calorimetry was established. Three pharmaceutical compounds, acetaminophen, indomethacin, and tri-O-methyl-β-cyclodextrin were used as model compounds. Powder samples did not produ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00928

    authors: Harada T,Kawakami K,Yoshihashi Y,Yonemochi E,Terada K,Moriyama H

    更新日期:2013-01-01 00:00:00

  • N-Arylpiperazine-1-carboxamide derivatives: a novel series of orally active nonsteroidal androgen receptor antagonists.

    abstract::A novel series of N-arylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic properties were evaluated. Reporter assays indicated that trans-2,5-dimethylpiperazine derivatives are potent AR antagonists, and in this series trans-N-4-[4-cy...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.402

    authors: Kinoyama I,Taniguchi N,Kawaminami E,Nozawa E,Koutoku H,Furutani T,Kudoh M,Okada M

    更新日期:2005-04-01 00:00:00

  • Relationship between effects of phenolic compounds on the generation of free radicals from lactoperoxidase-catalyzed oxidation of NAD(P)H or GSH and their DPPH scavenging ability.

    abstract::The influence of various phenolic compounds on the lactoperoxidase (LPO)/hydrogen peroxide (H2O2)-catalyzed oxidation of biochemical reductants such as reduced beta-nicotinamide adenine dinucleotide (NADH), reduced beta-nicotinamide adenine dinucleotide phosphate (NADPH) or reduced glutathione (GSH) was investigated b...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.299

    authors: Ueda J,Tsuchiya Y,Ozawa T

    更新日期:2001-03-01 00:00:00

  • Synthesis and SAR Study of the Novel Thiadiazole-Imidazole Derivatives as a New Anticancer Agents.

    abstract::In the present study, a novel series of 2-(2-(3-aryl-5-substituted-1,3,4-thiadiazol-2(3H)-ylidene)hydrazinyl)-4,4-diphenyl-1H-imidazol-5(4H)-one derivatives were designed and prepared via the reaction of the most versatile, hitherto unreported 2-(5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-N-phenylhydrazinecarbot...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00344

    authors: Gomha SM,Abdel-Aziz HM,Khalil KD

    更新日期:2016-01-01 00:00:00

  • An effective synthesis of 5,4'-disubstituted flavones via a cesium enolate assisted intramolecular ipso-substitution reaction.

    abstract::A variety of 5,4'-disubstituted flavones, which are anticipated to be androgen receptor antagonists to treat diseases mediated by the androgen receptor, were synthesized. It was found that an intramolecular ipso-substitution reaction via cesium enolate using 2-fluoro-6-hydroxyacetophenone and various benzoyl chlorides...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.1107

    authors: Matsugi M,Takeda M,Takahashi A,Tazaki T,Tamura H,Shioiri T

    更新日期:2010-08-01 00:00:00

  • Prolyl endopeptidase inhibitory activity of fourteen Kampo formulas and inhibitory constituents of Tokaku-joki-to.

    abstract::Prolyl endopeptidase (PEP, EC 3.4.21.26) is an enzyme playing a role in the metabolism of proline-containing neuropeptides which have been suggested to be involved in learning and memory processes. In screening for PEP inhibitors from fourteen traditional Kampo formulas, we found that Tokaku-joki-to shows a significan...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1055

    authors: Fan W,Tezuka Y,Kadota S

    更新日期:2000-07-01 00:00:00

  • Two new acyclic diterpene glycosides from fruits of Habanero, Capsicum chinense.

    abstract::Four acyclic diterpene glycosides were extracted from Habanero, the fruits of Capsicum chinense JACQ., which is known as one of the hottest peppers in existence. Two of these glycosides were identified as capsianoside XIII and capsianoside XV. The other two were new ones and were characterized as 3-O-beta-D-glucopyran...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.730

    authors: Lee JH,El-Aasr M,Ikeda T,Oda K,Miyashita H,Yoshimitsu H,Okawa M,Kinjo J,Nohara T

    更新日期:2009-07-01 00:00:00

  • In Vitro Transformation of Chlorinated Parabens by the Liver S9 Fraction: Kinetics, Metabolite Identification, and Aryl Hydrocarbon Receptor Agonist Activity.

    abstract::We investigated the kinetics of in vitro transformation of a dichlorinated propyl paraben (2-propyl 3,5-dichloro-4-hydroxybenzoate; Cl2PP) by the rat liver S9 fraction and assessed the aryl hydrocarbon receptor (AhR) agonist activity of the metabolite products identified in HPLC and GC/MS analysis and by metabolite sy...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00977

    authors: Terasaki M,Wada T,Nagashima S,Makino M,Yasukawa H

    更新日期:2016-01-01 00:00:00

  • Synthesis and absolute configurations of the cytotoxic polyacetylenes isolated from the callus of Panax ginseng.

    abstract::Panaxacol (1) and dihydropanaxacol (2), cytotoxic polyacetylenes isolated from the callus of Panax ginseng, were synthesized starting from D-(-)-diethyl tartrate. The absolute configuration of 1 was determined to be 9R, 10R and the absolute configuration at C-3 of 2 was tentatively assigned as 3S by the application of...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.1447

    authors: Fujimoto Y,Satoh M,Takeuchi N,Kirisawa M

    更新日期:1990-06-01 00:00:00

  • Synthesis and antimicrobial activity of pyridines bearing thiazoline and thiazolidinone moieties.

    abstract::Two series of new pyridines bearing thiazoline (3a--n) and thiazolidinone (5a--e) moieties were prepared via the cyclization of the corresponding substituted pyridyl thiourea (2a--g) with an appropriately substituted phenacyl bromide or chloroacetic acid, respectively. The antimicrobial activity was determined for rep...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.863

    authors: Hassan HY,el-Koussi NA,Farghaly ZS

    更新日期:1998-05-01 00:00:00

  • Phospholipid dependency of hepatic uridine diphosphate-glucuronyltransferase in the developing fetus of the rat.

    abstract::The developmental change of uridine diphosphate-glucuronyltransferase (UDPGT) was studied using hepatic microsomes of rat fetuses on days 18 and 21 of gestation. Total phospholipid content was higher on day 21 than on day 18, although no significant difference in the composition between the two stages was observed. Li...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.2454

    authors: Nanbo T

    更新日期:1991-09-01 00:00:00

  • Potential of Enzymomics Methodologies to Characterize Disease-Related Protein Functions.

    abstract::Enzymatic functions are often altered during disease onset and progression, and therefore chemical-biological studies, which utilize chemical knowledge to discover novel protein functions, are often employed to find proteins with functions closely related to disease phenotypes. Such studies are known as forward chemic...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c17-00144

    authors: Komatsu T

    更新日期:2017-01-01 00:00:00

  • Different Degradation Mechanisms of Inhibitor of Apoptosis Proteins (IAPs) by the Specific and Nongenetic IAP-Dependent Protein Eraser (SNIPER).

    abstract::Targeted protein degradation by small molecules is an emerging modality with significant potential for drug discovery. We previously developed chimeric molecules, termed specific and non-genetic inhibitor of apoptosis protein (IAP)-dependent protein erasers (SNIPERs), which induce the ubiquitylation and proteasomal de...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00567

    authors: Ohoka N,Ujikawa O,Shimokawa K,Sameshima T,Shibata N,Hattori T,Nara H,Cho N,Naito M

    更新日期:2019-03-01 00:00:00

  • 2-Acyl-3-carboxyl-tetrahydroisoquinoline Derivatives: Mixed-Type PTP1B Inhibitors without PPARγ Activation.

    abstract::A novel series of 2-acyl-3-carboxyl-tetrahydroisoquinoline derivatives were synthesized and biologically evaluated. Among them, (S)-2-{(E)-3-furan-2-ylacryloyl}-7-[(2E,4E)-5-(2,4,6-trifluorophenyl)penta-2,4-dienyloxy]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (compound 17u) was identified as a potent protein ty...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00571

    authors: Morishita K,Shoji Y,Fukui M,Ito Y,Kitao T,Ozawa SI,Hirono S,Shirahase H

    更新日期:2018-01-01 00:00:00

  • Three New Polyphenolic Acids from the Leaves of Eucalyptus citriodora with Antivirus Activity.

    abstract::Six polyphenolic acids (1-6), including the three new compounds citriodolic acids A, B, and C (1-3), were isolated from the leaves of Eucalyptus citriodora. Their structures were elucidated by spectroscopic methods including one dimensional (1D)- and 2D-NMR, high-resolution electrospray ionization (HR-ESI)-MS, and cir...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00362

    authors: Lin SQ,Zhou ZL,Yin WQ

    更新日期:2016-11-01 00:00:00