21beta-Hydroxy-oleanane-type triterpenes from Hippocratea excelsa.

Abstract:

:Stem bark of Hippocratea excelsa afforded six pentacyclic triterpenes, five oleanane and one ursane types. They were identified as 11beta,21beta-dihydroxy-olean-12-ene-3-one (2), 3alpha,11alpha,21beta-trihydroxy-olean-12-ene (3), 3alpha,21beta-dihydroxy-11alpha-methoxy-olean-12-ene (4), 3alpha,21beta-dihydroxy-olean-9(11),12-diene (5), 3alpha,21beta-dihydroxy-olean-12-ene (6) and 3alpha,21beta-dihydroxy-11alpha-methoxy-urs-12-ene, isolated as its diacetate derivative (7), as well as 3alpha,21beta-dihydroxy-olean-12-ene (1) previously isolated from the root bark. The known alpha- and beta-amyrin, oleanoic and ursolic acids, trans-polyisoprene, and the ubiquitous beta-sitosterol were also isolated. Structures were elucidated on the basis of spectroscopic analyses, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC and HMBC) and comparison with literature data. The antigiardial activity of compounds 2-5 was not significant.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Cáceres-Castillo D,Mena-Rejón GJ,Cedillo-Rivera R,Quijano L

doi

10.1016/j.phytochem.2007.10.016

subject

Has Abstract

pub_date

2008-02-01 00:00:00

pages

1057-64

issue

4

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(07)00635-8

journal_volume

69

pub_type

杂志文章
  • Carotene derivatives in sexual communication of zygomycete fungi.

    abstract::Recognition between mating partners, early sexual morphogenesis and development are regulated by a family of beta-carotene derived signal compounds, the trisporoids, in zygomycete fungi. Mating type-specific precursors are released from the hyphae and exert their physiological effects upon compatible mating partners. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2009.07.014

    authors: Schimek C,Wöstemeyer J

    更新日期:2009-10-01 00:00:00

  • Partial purification and characterization of three ginsenoside-metabolizing beta-glucosidases from Pythium irregulare.

    abstract::The ginseng pathogen Pythium irregulare is able to selectively metabolize the 20(S) protopanaxadiol ginsenosides Rb1, Rb2, Rc, Rd, and gypenoside XVII via extracellular glycosidases, leading to the formation and partial assimilation of ginsenoside F2. Herein we have partially purified three ginsenoside-deglycosylating...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.09.007

    authors: Andreea Neculai M,Ivanov D,Bernards MA

    更新日期:2009-12-01 00:00:00

  • Bridelionosides A-F: Megastigmane glucosides from Bridelia glauca f. balansae.

    abstract::The chemical investigation of leaves of Bridelia glauca f. balansae afforded six megastigmane glucosides, named bridelionosides A-F, along with seven known megastigmane glucosides. Their structures were determined by a combination of spectroscopic analyses and by application of the modified Mosher's method. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.09.007

    authors: Sueyoshi E,Liu H,Matsunami K,Otsuka H,Shinzato T,Aramoto M,Takeda Y

    更新日期:2006-11-01 00:00:00

  • Benzoxazinoid biosynthesis, a model for evolution of secondary metabolic pathways in plants.

    abstract::Benzoxazinoids are secondary metabolites that are effective in defence and allelopathy. They are synthesised in two subfamilies of the Poaceae and sporadically found in single species of the dicots. The biosynthesis is fully elucidated in maize; here the genes encoding the enzymes of the pathway are in physical proxim...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2009.05.012

    authors: Frey M,Schullehner K,Dick R,Fiesselmann A,Gierl A

    更新日期:2009-10-01 00:00:00

  • Biochemical characterization of two differentially expressed polyphenol oxidases from hybrid poplar.

    abstract::Two polyphenol oxidase isoforms with distinct expression patterns were identified in hybrid poplar (Populus trichocarpaxP. deltoides). PPO-1, corresponding to the previously cloned PtdPPO (Constabel et al., Plant Physiol. 124: 285-295) was primarily leaf tissue-specific and detected only after wounding. PPO-2 was expr...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00159-6

    authors: Wang J,Constabel CP

    更新日期:2003-09-01 00:00:00

  • Stereoselectivity of the demethylation of nicotine piperidine homologues by Nicotiana plumbaginifolia cell suspension cultures.

    abstract::The metabolism of (R,S)-N-methylanabasine and (R,S)-N-methylanatabine has been studied in a cell suspension culture of Nicotiana plumbaginifolia. Both substrates are effectively demethylated, anabasine or anatabine, respectively, accumulating in the medium. Similarly, there is strong stereoselectivity for the (R)-isom...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.07.012

    authors: Bartholomeusz TA,Molinié R,Roscher A,Felpin FX,Gillet F,Lebreton J,Mesnard F,Robins RJ

    更新日期:2005-08-01 00:00:00

  • A potent bidirectional promoter from the monocot cereal Eleusine coracana.

    abstract::Ragi bifunctional α-amylase-trypsin inhibitor (RBI) of Eleusine coracana (L.) Gaertn. (finger millet) simultaneously inhibits α-amylase and trypsin. In continuation of previous work on the cloning, expression and characterization of RBI, a bidirectional promoter from finger millet was explored on the basis of experime...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.07.009

    authors: Sen S,Dutta SK

    更新日期:2016-09-01 00:00:00

  • Conversions of deoxyradicinin to radicinin and of radicinin to 3-epi-radicinin in the phytopathogenic fungus Bipolaris coicis.

    abstract::Radicinin is a phytotoxic and antibiotic metabolite produced by some phytopathogenic fungi. Precursor administration and cell-free experiments with deoxyradicinin and radicinin were carried out in Bipolaris coicis H13-3. When deoxyradicinin was administered to the fungus, radicinin and 3-epi-radicinin formed. When rad...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.11.010

    authors: Suzuki M,Sakuno E,Ishihara A,Tamura J,Nakajima H

    更新日期:2012-03-01 00:00:00

  • ent-Labdane glycosides from the aquatic plant Potamogeton lucens and analytical evaluation of the lipophilic extract constituents of various Potamogeton species.

    abstract::Two new ent-labdane glycosides, one known furano-ent-labdane and a new hydroxylated fatty acid were isolated from the dichloromethane extract of the freshwater aquatic plant Potamogeton lucens. The new compounds were assigned the structures of beta-d-glucopyranosyl-8(17),13-ent-labdadien-16,15-olid-18-oate, 18-beta-d-...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.01.018

    authors: Waridel P,Wolfender JL,Lachavanne JB,Hostettmann K

    更新日期:2004-04-01 00:00:00

  • Thiol redox-sensitive seed proteome in dormant and non-dormant hybrid genotypes of wheat.

    abstract::The thiol redox-sensitive and the total proteome in harvest-ripe grains of closely related genotypes of wheat (Triticum aestivum L.), with either a dormant or a non-dormant phenotype, were investigated using hybrid lines of spring wheat double haploid population segregating transgressively, to gain further insight int...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.12.021

    authors: Bykova NV,Hoehn B,Rampitsch C,Hu J,Stebbing JA,Knox R

    更新日期:2011-07-01 00:00:00

  • Secondary products in mycorrhizal roots of tobacco and tomato.

    abstract::Colonization of the roots of various tobacco species and cultivars (Nicotiana glauca Grah., N. longiflora Cav., N. rustica L., N. tabacum L., N. tabacum L. cv. Samsun NN, N. sanderae hort. Sander ex Wats.) as well as tomato plants (Lycopersicon esculentum L. cv. Moneymaker) by the arbuscular mycorrhizal fungus Glomus ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00047-9

    authors: Maier W,Schmidt J,Nimtz M,Wray V,Strack D

    更新日期:2000-06-01 00:00:00

  • Characterization of bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase from aspen.

    abstract::Bispecific O-methyltransferase (OMT, EC 2.1.1.68) which catalyses the meta-specific methylation of caffeic acid and 5-hydroxyferulic acid was purified to homogeneity from the developing secondary xylem of aspen (Populus tremuloides). The enzyme was purified by conventional techniques and affinity chromatography on S-a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(92)83093-e

    authors: Bugos RC,Chiang VL,Campbell WH

    更新日期:1992-05-01 00:00:00

  • Anti-inflammatory and cytotoxic carbazole alkaloids from Murraya kwangsiensis.

    abstract::Chemical investigation of the traditional Chinese medicine, Murraya kwangsiensis, led to the isolation of 16 undescribed biscarbazole alkaloids, kwangsines A-M, two undescribed natural products, (+/-)-bispyrayafoline C, and 19 known monomeric analogues. (±)-Bispyrayafoline C and (±)-kwangsines A-C are four pairs of bi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2019.112186

    authors: Chen Y,Cao N,Lv H,Zeng K,Yuan J,Guo X,Zhao M,Tu P,Jiang Y

    更新日期:2020-02-01 00:00:00

  • Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana.

    abstract::The glucosinolate content of various organs of the model plant Arabidopsis thaliana (L.) Heynh., Columbia (Col-0) ecotype, was analyzed at different stages during its life cycle. Significant differences were noted among organs in both glucosinolate concentration and composition. Dormant and germinating seeds had the h...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00549-6

    authors: Brown PD,Tokuhisa JG,Reichelt M,Gershenzon J

    更新日期:2003-02-01 00:00:00

  • A-type proanthocyanidin antioxidant from Dioclea lasiophylla.

    abstract::The A-type proanthocyanidin, epigallocatechin-(2beta-->7,4beta-->8)-epicatechin, together with the known epicatechin, luteolin 3'beta-D-glucopyranoside, chrysoeriol 7beta-D-glucopyranoside and 2-methylpentan-2,4-diol, were isolated from leaves of Dioclea lasiophilla. The structures were established on the basis of the...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00297-1

    authors: Barreiros AL,David JP,de Queiroz LP,David JM

    更新日期:2000-12-01 00:00:00

  • Ambiguanine A-G, hexahydrobenzophenanthridine alkaloids from Corydalis ambigua var. amurensis.

    abstract::Seven hexahydrobenzophenanthridine-type alkaloids, Ambiguanine A-G, along with eight known alkaloids, were isolated from tubers of Corydalis ambigua var. amurensis. Their structures were elucidated based on extensive spectroscopic analyses, with absolute configurations determined by CD experiments. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.05.013

    authors: Yang ZY,Jiang BH,Teng FK,Han N,Liu ZH,Zhou JJ,Wang Y,Guo DA,Yin J

    更新日期:2014-09-01 00:00:00

  • Tropane alkaloids from the stem bark of Erythroxylum bezerrae.

    abstract::Six previously undescribed tropane alkaloids, designated as erythrobezerrines A-F, were isolated from the EtOH extract from the stem bark of Erythroxylum bezerrae Plowman. Their structures were elucidated based on the interpretation of the NMR and MS data and in some instances, confirmed by X-ray diffraction analysis....

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112458

    authors: Brito LSO,Pinto FDCL,de Filho MOM,Rocha DD,Mendoza MFM,Ayala AP,Bezerra BP,Loiola MIB,Canuto KM,Silveira ER,Pessoa ODL

    更新日期:2020-10-01 00:00:00

  • Phytotoxic steroidal saponins from Agave offoyana leaves.

    abstract::A bioassay-guided fractionation of Agave offoyana leaves led to the isolation of five steroidal saponins (1-5) along with six known saponins (6-11). The compounds were identified as (25R)-spirost-5-en-2α,3β-diol-12-one 3-O-{α-l-rhamnopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyr...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.05.014

    authors: Pérez AJ,Simonet AM,Calle JM,Pecio Ł,Guerra JO,Stochmal A,Macías FA

    更新日期:2014-09-01 00:00:00

  • nor-Lignans from the leaves of Styrax ferrugineus (Styracaceae) with antibacterial and antifungal activity.

    abstract::Chemical examination of the leaves of Styrax ferrugineus yielded 5-[3''-(beta-D-glucopyranosyloxy)propyl]-7-methoxy-2-(3',4'-dimethoxyphenyl) benzofuran, along with the known nor-lignans 5-(3''-hydroxypropyl)-7-methoxy-2-(3',4'-methylenedioxyphenyl) benzofuran, 5-(3''-hydroxypropyl)-7-methoxy-2-(3',4'-dimethoxyphenyl)...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00225-9

    authors: Pauletti PM,Araújo AR,Young MC,Giesbrecht AM,Bolzani VD

    更新日期:2000-11-01 00:00:00

  • Hemicellulosic polysaccharides from bamboo shoot cell-walls.

    abstract::Cell-wall polysaccharides of bamboo shoots were extracted with chelating reagent (CDTA, trans-1,2-cyclohexanediamine-N,N,N',N'-tetraacetic acid), Na(2)CO(3) and KOH solutions. Glycosyl composition and glycosyl linkage analyses showed that the hemicellulose was composed of arabinoxylan, (1-->3, 1-->4)-beta-D-glucan, xy...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00237-4

    authors: Edashige Y,Ishii T

    更新日期:1998-11-20 00:00:00

  • Glucosinolate diversity within a phylogenetic framework of the tribe Cardamineae (Brassicaceae) unraveled with HPLC-MS/MS and NMR-based analytical distinction of 70 desulfoglucosinolates.

    abstract::As a basis for future investigations of evolutionary trajectories and biosynthetic mechanisms underlying variations in glucosinolate structures, we screened members of the crucifer tribe Cardamineae by HPLC-MS/MS, isolated and identified glucosinolates by NMR, searched the literature for previous data for the tribe, a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.09.013

    authors: Olsen CE,Huang XC,Hansen CIC,Cipollini D,Ørgaard M,Matthes A,Geu-Flores F,Koch MA,Agerbirk N

    更新日期:2016-12-01 00:00:00

  • Cytotoxic xanthones from the roots of Mesua ferrea L.

    abstract::Five undescribed xanthones, 4-methoxypyranojacareubin, 4-hydroxy-3-prenylpyranoxanthone, 1-hydroxy-5,7-dimethoxyxanthone, 5-hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone, together with thirty-three known xanthones were isolated from the roots of Mesua ferrea L. The structures of all isolated xan...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.10.008

    authors: Chukaew A,Saithong S,Chusri S,Limsuwan S,Watanapokasin R,Voravuthikunchai SP,Chakthong S

    更新日期:2019-01-01 00:00:00

  • Acylated pregnane glycosides from Caralluma sinaica.

    abstract::Caralluma sinaica is sold on local markets of Saudi Arabia for various health benefits however no phytochemical study has specifically been performed on this species. NMR and UHPLC-ESI-TOF-MS profilings of the ethanolic extract of the whole plant reveal a very complex phytochemical composition dominated by pregnanes. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.04.003

    authors: Al-Massarani SM,Bertrand S,Nievergelt A,El-Shafae AM,Al-Howiriny TA,Al-Musayeib NM,Cuendet M,Wolfender JL

    更新日期:2012-07-01 00:00:00

  • Abietane diterpenoids and triterpenoic acids from Salvia cilicica and their antileishmanial activities.

    abstract::Bioguided-fractionation of an acetone extract of the roots of Salvia cilicica (Lamiaceae) led to isolation of two new diterpenes, 7-hydroxy-12-methoxy-20-nor-abieta-1,5(10),7,9,12-pentaen-6,14-dione and abieta-8,12-dien-11,14-dione (12-deoxy-royleanone), together with oleanolic acid, ursolic acid, ferruginol, inuroyol...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00361-8

    authors: Tan N,Kaloga M,Radtke OA,Kiderlen AF,Oksüz S,Ulubelen A,Kolodziej H

    更新日期:2002-12-01 00:00:00

  • Cadinane sesquiterpenoids from the basidiomycete Stereum cf. sanguinolentum BCC 22926.

    abstract::Stereumins Q-U, together with known stereumins A, B, K, L, and N, as well as ent-strobilols E and G were isolated from the culture of Stereum cf. sanguinolentum BCC 22926. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of stereumins A and Q, as well as ent-strobilol E...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.06.006

    authors: Bunyapaiboonsri T,Yoiprommarat S,Nopgason R,Komwijit S,Veeranondha S,Puyngain P,Boonpratuang T

    更新日期:2014-09-01 00:00:00

  • Guaiane sesquiterpenes and isopimarane diterpenes from an endophytic fungus Xylaria sp.

    abstract::Nine oxygenated guaiane-type sesquiterpenes and three isopimarane diterpenes were isolated from the culture broth of an endophytic fungus, Xylaria sp. YM 311647, obtained from Azadirachta indica. The structures of these compounds were elucidated by interpretation of spectroscopic data. The absolute configurations of t...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.04.016

    authors: Wu SH,He J,Li XN,Huang R,Song F,Chen YW,Miao CP

    更新日期:2014-09-01 00:00:00

  • The defensive functions of plant inhibitors are not restricted to insect enzyme inhibition.

    abstract::Three plant proteinase inhibitors BbKI (kallikrein inhibitor) and BbCI (cruzipain inhibitor) from Bauhinia bauhinioides, and a BrTI (trypsin inhibitor) from B. rufa, were examined for other effects in Callosobruchus maculatus development; of these only BrTI affected bruchid emergence. BrTI and BbKI share 81% identitie...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.10.009

    authors: Sumikawa JT,Brito MV,Macedo ML,Uchoa AF,Miranda A,Araujo AP,Silva-Lucca RA,Sampaio MU,Oliva ML

    更新日期:2010-02-01 00:00:00

  • Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii.

    abstract::From the water soluble fraction of the dried fruits of Alangium lamrckii, four tetrahydroisoquinoline-monoterpene glycosides, 6-O-methyl-N-deacetylisoipecosidic acid, 7-O-methyl-N-deacetylisoipecosidic acid, 6,7-di-O-methyl-N-deacetylisoipecosidic acid and 6"-O-alpha-D-glucopyranosyl-6-O-methyl-N-deacetylisoipecosidic...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00417-9

    authors: Itoh A,Tanahashi T,Tabata M,Shikata M,Kakite M,Nagai M,Nagakura N

    更新日期:2001-03-01 00:00:00

  • Bioactive polyketides and 8,14-seco-ergosterol from fruiting bodies of the ascomycete Daldinia childiae.

    abstract::Seven previously undescribed polyketides, namely childinins A-G, and one previously undescribed 8,14-seco-ergosterol, namely childinasterone A, were obtained from the fruiting bodies of Daldinia childiae. Their structures and absolute configurations were established via extensive spectroscopic analyses, single-crystal...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.06.020

    authors: Zhao ZZ,Chen HP,Huang Y,Zhang SB,Li ZH,Feng T,Liu JK

    更新日期:2017-10-01 00:00:00

  • Pregnane glycosides from fruits of Balanites aegyptiaca.

    abstract::From the mesocarp of Balanites aegyptiaca fruits, two pregnane glycosides were isolated. One is new and identified as pregn-5-ene-3 beta,16 beta,20(R)-triol 3-O-(2,6-di-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside (balagyptin), while the other is known and assigned as pregn-5-ene-3 beta,16 beta,20(R)-triol 3-O-be...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00551-h

    authors: Kamel MS,Koskinen A

    更新日期:1995-12-01 00:00:00