Isolation of Three New Diterpenes from Dodonaea viscosa.

Abstract:

:An investigation into the methanol extracts obtained from the stems of Dodonaea viscosa led to the isolation of one nor-clerodane diterpene (1) and two labdane diterpenes (2, 3), as well as 17 known compounds (4-20). The structures of these compounds were elucidated based on chemical and spectral evidence. The stereochemical structure of the nor-clerodane diterpene was confirmed via its circular dichroism spectrum and calculated electronic circular dichroism spectrum. Isolated compounds were evaluated for their inhibitory effects on collagenase and tyrosinase. Since 5,7,4'-trihydroxy-3'-(4-hydroxy-3-methylbutyl)-5'-(3-methylbut-2-enyl)-3,6-dimethoxyflavone (9) showed collagenase inhibitory activity and scopoletin (12) had significant tyrosinase inhibitory activity, they were considered to be good candidates for cosmetic agents.

authors

Sagara T,Sugimoto S,Yamano Y,Nehira T,Masuda K,Otsuka H,Matsunami K

doi

10.1248/cpb.c20-00327

subject

Has Abstract

pub_date

2021-01-01 00:00:00

pages

40-47

issue

1

eissn

0009-2363

issn

1347-5223

journal_volume

69

pub_type

杂志文章
  • Development and validation of LC-MS/MS method for the quantification of oxcarbazepine in human plasma using an experimental design.

    abstract::A rapid tandem mass spectrometric (MS-MS) method for the quantification of Oxcarbazepine (OXB) in human plasma using imipramine as an internal standard (IS) has been developed and validated. Chromatographic separation was achieved isocratically on a C18 reversed-phase column within 3.0 min, using a mobile phase of ace...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.28

    authors: Srinubabu G,Ratnam BV,Rao AA,Rao MN

    更新日期:2008-01-01 00:00:00

  • Spectrophotometric and atomic absorption determination of ramipril, enalapril maleate and fosinopril through ternary complex formation with molybdenum (V)-thiocyanate (Mo(V)-SCN).

    abstract::Three different sensitive and accurate spectroscopic procedures were developed for the determination of three angiotensin-converting enzyme inhibitors, namely, ramipril, enalapril maleate and fosinopril. The first two spectrophotometric (extractive and non-extractive) procedures were based on ternary complex formation...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1521

    authors: Baraka MM,El-Sadek M,Moussa EM,Abd-Alaty NM

    更新日期:2008-11-01 00:00:00

  • Molecular state of chlorpheniramine in resinates.

    abstract::Chlorpheniramine (CPM) maleate was prepared as a series of resinates by the batch method. The several resinates were investigated by differential scanning calorimetry (DSC), X-ray powder diffraction (XRPD) and infrared (IR) spectrometry. The results from DSC and XRPD showed that the molecular state of the entrapped dr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.231

    authors: Akkaramongkolporn P,Yonemochi E,Terada K

    更新日期:2000-02-01 00:00:00

  • Formal Aerobic Oxidative Cross-Coupling of Benzofuranones with Azo Compounds Using Pd-μ-hydroxo Complex.

    abstract::We have developed a catalytic aerobic oxidative dimerization reaction of benzofuranones using a Pd(II)-µ-hydroxo complex. Radical-radical cross-coupling of the resulting dimers with azo compounds enabled the one-pot synthesis of structurally congested benzofuranones having two distinct vicinal all-carbon quaternary ce...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c20-00359

    authors: Ohnishi R,Sugawara M,Ezawa T,Sohtome Y,Sodeoka M

    更新日期:2020-01-01 00:00:00

  • Nitric oxide (NO) production inhibitory constituents of Tabebuia avellanedae from Brazil.

    abstract::From the water extract of Brazilian Tabebuia avellanedae, two new iridoids (1, 2) and a new phenylethanoid glycoside (3) have been isolated together with twelve known compounds (4-15). Their structures were determined based on the spectroscopic data. The isolated compounds inhibited nitric oxide (NO) production in lip...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.710

    authors: Awale S,Kawakami T,Tezuka Y,Ueda JY,Tanaka K,Kadota S

    更新日期:2005-06-01 00:00:00

  • Magnolin Inhibits Proliferation and Invasion of Breast Cancer MDA-MB-231 Cells by Targeting the ERK1/2 Signaling Pathway.

    abstract::The aim of this study was to evaluate the effects of Magnolin (MGL) on inhibition of human breast cancer cells, and explore the underlying molecular mechanisms. The viability of the treated cells was assessed with the Cell Counting Kit-8 (CCK-8) assay, and the proliferation was analyzed in terms of EdU uptake, colony ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c19-00820

    authors: Wang J,Zhang S,Huang K,Shi L,Zhang Q

    更新日期:2020-01-01 00:00:00

  • A novel cytotoxic C-methylated biflavone, taiwanhomoflavone-B from the twigs of Cephalotaxus wilsoniana.

    abstract::A novel C-methylated biflavone, taiwanhomoflavone-B (1), together with known compounds, 7,4',7"-tri-O-methylamentoflavone, 6-C-methylnaringenin and apigenin-7-O-beta-glucoside were isolated from an ethanolic extract of Cephalotaxus wilsoniana. The structure of 1 was elucidated on the basis of spectroscopic analysis. T...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.1607

    authors: Kuo YH,Hwang SY,Yang Kuo LM,Lee YL,Li SY,Shen YC

    更新日期:2002-12-01 00:00:00

  • Stereoselective synthesis of tetrasubstituted (Z)-alkenes from aryl alkyl ketones utilizing the Horner-Wadsworth-Emmons reaction.

    abstract::Tetrasubstituted (Z)-alkenes were readily prepared through the Horner-Wadsworth-Emmons reactions of methyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate with aryl alkyl ketones by employing Sn(OSO(2)CF(3))(2) and N-ethylpiperidine. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.1300

    authors: Sano S,Takehisa T,Ogawa S,Yokoyama K,Nagao Y

    更新日期:2002-09-01 00:00:00

  • Preparation of S-acetylthioglycoloyl insulins based on separation by anion-exchange high-performance liquid chromatography.

    abstract::A method for the preparation of insulin derivatives having protected sulfhydryl group(s) on definite site(s) on the molecule which uses anion-exchange high performance liquid chromatography on a TSKgel DEAE-2SW column for separation is described. Porcine insulin reacts with N-succinimidyl S-acetylthioacetate to afford...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.957

    authors: Nanami M,Zaitsu K,Ohkura Y

    更新日期:1992-04-01 00:00:00

  • Importance of Proton-Coupled Electron Transfer from Natural Phenolic Compounds in Superoxide Scavenging.

    abstract::The superoxide O2(·-) scavenging reaction of (+)-catechin (Cat), quercetin (Que), rutin, and α-tocopherol (α-TOH) as natural phenolic compounds is investigated on the basis of electrochemical and ESR spectral measurements with the aid of density functional theory (DFT) calculations. Reversibility of the O2/O2(·-) redo...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00447

    authors: Nakayama T,Uno B

    更新日期:2015-01-01 00:00:00

  • In-die evaluation of capping tendency of pharmaceutical tablets using force-displacement curve and stress relaxation parameter.

    abstract::A novel in-die evaluation method of tablet capping tendency was proposed based on a force-displacement curve and stress relaxation parameter in a tableting process. In our previous study (Chem. Pharm. Bull., 59, 2011, Nakamura et al.), the phase diagram consisting of elastic recovery energy (E(e)) and plastic deformat...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.60.772

    authors: Nakamura H,Sugino Y,Watano S

    更新日期:2012-01-01 00:00:00

  • Iridoid glycosides from Globularia davisiana.

    abstract::From the ethanolic extract of the aerial parts of Globularia davisiana, a new iridoid glycoside, davisioside (1), was isolated. Davisioside (1) comprises a rare iridoid aglycone structure with a saturated double bond between C-3 and C-4. Nine known iridoid glycosides, asperuloside (2), alpinoside (3), geniposide (4), ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.678

    authors: Caliş I,Kirmizibekmez H,Taşdemir D,Ireland CM

    更新日期:2002-05-01 00:00:00

  • Effect of compression on interaction between 1,4-dihydropyridine compounds and lactose monohydrate.

    abstract::Manidipine dihydrochloride or benidipine hydrochloride will change to hydrate form in part, when differential scanning calorimetric (DSC) measurement is carried out together with lactose monohydrate. This interaction was accelerated by compressing their mixture. It can be suggested that the interaction may cause by th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.503

    authors: Hosaka S,Sato M,Ozawa Y,Hamada C,Takahashi Y,Kitamori N

    更新日期:2005-05-01 00:00:00

  • Electrochemical oxidation of anti-tumor agent, etoposide.

    abstract::As part of a search for new potent derivatives, electrochemical oxidation of etoposide (1) was carried out under controlled potential (500 mV) to yield 1,2-dehydroetoposide (4), 4'-O-demethyl-1,2,3,4-tetradehydro-4-dehydroxy-podophyllotox in (5) and 1,2,3,4-tetradehydroetoposide (6). They showed no cytotoxicity agains...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1846

    authors: Obata R,Ohnuma T

    更新日期:1993-10-01 00:00:00

  • Synthesis of heterocyclic compounds via nucleophilic aroylation catalyzed by imidazolidenyl carbene.

    abstract::Xanthones and acridones were synthesized from 3,4-difluoronitrobenzene and 2-fluorobenzaldehydes in two or three steps. The key step was nucleophilic aroylation catalyzed by imidazolidenyl carbene. The nucleophilic aroylation of 3,4-difluoronitrobenzene afforded 2,2'-difluoro-4-nitrobenzophenones. The cyclization of t...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1653

    authors: Suzuki Y,Toyota T,Miyashita A,Sato M

    更新日期:2006-12-01 00:00:00

  • Amino acids and peptides. XXIX. Synthesis of peptide fragments related to active center of eglin c and studies on the relationship between their structure and their inhibitory activity against cathepsin G and alpha-chymotrypsin.

    abstract::H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe, corresponding to the sequence 41-49 of eglin c, inhibited human leukocyte cathepsin G and alpha-chymotrypsin. In order to gain further insight into the relationship between the structure and the inhibitory activity against cathepsin G and alpha-chymotrypsin, peptide fragments...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.3249

    authors: Nakabayashi K,Tsuboi S,Fujimoto T,Okada Y,Nagamatsu Y,Yamamoto J

    更新日期:1990-12-01 00:00:00

  • Oleanene-type triterpene glycosides from puerariae radix. IV. Six new saponins from Pueraria lobata.

    abstract::From Puerariae Radix, the root of Pueraria lobata (Leguminosae), six new oleanene-type triterpene glycosides, called kudzusaponins A1 (1), A2 (2), Ar (3), SA4 (5), and SB1 (6) were isolated together with kudzusaponin A3 (7), soyasaponins SA3 (8), and I (9). The structures of 1-6 were determined to be 3-O-alpha-L-rhamn...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.362

    authors: Arao T,Kinjo J,Nohara T,Isobe R

    更新日期:1997-02-01 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

  • structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentus fungi: (2). Spectral analysis of the sugar-inositol portion by 2D-NMR.

    abstract::The sugar-inositol portion of the novel glycosylinositol-phosphoceramides, ZGL1 and ZGL2, from the filamentus fungi, Acremonium sp., were elucidated by a combination of NMR techniques including (1)H-(1)H (COSY and HOHAHA) and (1)H-(13)C (HMQC and HMBC) spectroscopy. Further, examination of the (1)H-(31)P HMQC spectrum...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.473

    authors: Yamada-Hada J,Hada N,Aoki K,Yamamoto K,Takeda T

    更新日期:2004-04-01 00:00:00

  • Fern constituents: dryocrassy formate, sitostanyl formate and 12alpha-hydroxyfern-9(11)-ene from Cyathea podophylla.

    abstract::Dryocrassyl formate, sitostanyl formate, and 12alpha-hydroxyfern-9(11)-ene were isolated from the fresh fronds of Cyathea podophylla. Their structures were elucidated by spectroscopic techniques and synthesis. Ten known triterpenoids, three derivatives of phytol, a stanol, and beta-tocopherol were also identified from...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.1311

    authors: Arai Y,Hattori T,Hamaguchi N,Masuda K,Takano A,Shiojima K

    更新日期:2003-11-01 00:00:00

  • Evaluation of mitochondrial function by measuring the heat production in state 3 and state 4 respiration.

    abstract::Using a microcalorimetric method, we have measured the heat production in states 3 and 4 respiration of a mitochondrial preparation from rat heart ventricle. Adenosine triphosphate production in state 3 respiration was also determined for the same preparation after heat production was measured. In Tris-buffered soluti...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.3033

    authors: Tamura K,Hayatsu H,Watanabe I,Nakano T,Sugawara Y,Nishii Y

    更新日期:1989-11-01 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

  • Development of Supramolecular Saccharide Sensors Based on Cyclodextrin Complexes and Self-assembling Systems.

    abstract::Cyclodextrins (CDs) are water-soluble host compounds having nano-size hydrophobic cavities that enable them to incorporate organic molecules in water. Optically inert CDs can be efficiently combined with various types of chromoionophores and fluoroionophores. In this study, using diverse combinations of phenylboronic ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c16-00963

    authors: Tsuchido Y,Fujiwara S,Hashimoto T,Hayashita T

    更新日期:2017-01-01 00:00:00

  • Indonesian medicinal plants. IX. Chemical structures of gongganosides A, B, and C, three new quinovic acid glycosides from the bark of Bhesa paniculata (Celastraceae).

    abstract::Three new quinovic acid glycosides, named gongganosides A (1), B (2), and C (3), were isolated from the bark of Bhesa paniculata (Celastraceae), an Indonesian medicinal plant collected in Sumatra Island. The chemical structures have been elucidated on the basis of chemical and physicochemical evidence as quinovic acid...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1596

    authors: Ohashi K,Kojima H,Tanikawa T,Okumura Y,Kawazoe K,Tatara N,Shibuya H,Kitagawa I

    更新日期:1994-08-01 00:00:00

  • New neplanocin analogues. VIII. Synthesis and biological activity of 6'-C-ethyl, -ethenyl, and -ethynyl derivatives of neplanocin A.

    abstract::This report describes the synthesis and antiviral effects of (6'R)-6'-C-ethynyl, -ethenyl, and -ethyl derivatives of neplanocin A (7a, 8a, and 9a, respectively) and the corresponding 6'S-diastereomers (7b, 8b, and 9b, respectively), as examples of 6'-C-substituted analogues of neplanocin A. Grignard reaction of the 6'...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.1163

    authors: Shuto S,Obara T,Saito Y,Yamashita K,Tanaka M,Sasaki T,Andrei G,Snoeck R,Neyts J,Padalko E,Balzarini J,De Clercq E,Matsuda A

    更新日期:1997-07-01 00:00:00

  • Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. V. Thienopyridazinone derivatives.

    abstract::Synthesis and pharmacological evaluation of novel thienopyridazinones and related compounds are described. A thiophene ring was found to be able to replace the benzene ring of a phthalazinone without loss of biological activities. This observation supports our hypothesis that the benzene ring plays an important role i...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.236

    authors: Yamaguchi M,Maruyama N,Koga T,Kamei K,Akima M,Kuroki T,Hamana M,Ohi N

    更新日期:1995-02-01 00:00:00

  • Method for optical resolution of racemic homochlorcyclizine and comparison of optical isomers in antihistamine activity and pharmacokinetics.

    abstract::A method was developed for semi-preparative scale enantioseparation of racemic homochlorcyclizine (HCZ) by high performance liquid chromatography (HPLC) on Chiralcel OD column. The best resolution was achieved using an eluent composed of n-hexane plus 0.2 M isopropylamine. By this method, about 5.0 mg of racemic HCZ c...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.1341

    authors: Nishikata M,Nakai A,Fushida H,Miyake K,Arita T,Kitagawa S,Kunitomo M,Iseki K,Miyazaki K

    更新日期:1992-05-01 00:00:00

  • Isolation and characterization of 1,3-dicapryloyl-2-linoleoylglycerol: a novel triglyceride from berries of Hippophae rhamnoides.

    abstract::1,3-Dicapryloyl-2-linoleoylglycerol (1), a novel triglyceride, was isolated from berries of Hippophae rhamnoides. The structure was elucidated on the basis of MS, 1D and 2D NMR experiments including HMQC and HMBC. The metal chelating, free radical scavenging, and lipid peroxidation inhibiting properties of the compoun...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1021

    authors: Swaroop A,Sinha AK,Chawla R,Arora R,Sharma RK,Kumar JK

    更新日期:2005-08-01 00:00:00

  • Synthesis and platelet-activating factor (PAF)-antagonistic activities of trisubstituted piperazine derivatives.

    abstract::2- or 3-Substituted 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8- ylcarbonyl)-4-(3,4,5-trimethoxybenzoyl)- and 4-(3,4,5-trimethoxybenzyl)piperazines (2a-s, 3a, b) were prepared and evaluated for antagonistic activities against platelet-activating factor (PAF)-induced platelet aggregation and blood pressure reduc...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.551

    authors: Fukushi H,Mabuchi H,Terashita Z,Nishikawa K,Sugihara H

    更新日期:1994-03-01 00:00:00

  • Product analyses of ozone mediated nitration of benzimidazole derivatives with nitrogen dioxide: formation of 1-nitrobenzimidazoles and conversion to benzotriazoles.

    abstract::Several benzimidazole derivatives having electron-withdrawing or -donating substituent(s) at the benzene moiety were used as models of the imidazole moiety of purine bases and their nitration with nitrogen dioxide and ozone (so-called Kyodai nitration) were examined. Products were extracted from the reaction mixture w...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.570

    authors: Kaiya T,Nakamura K,Tanaka M,Miyata N,Kohda K

    更新日期:2004-05-01 00:00:00