Cytotoxic phenolic constituents from Hypericum japonicum.

Abstract:

:Nine undescribed compounds, including five xanthone derivatives, two flavonoids, one 2-pyrone derivative, and one undescribed naturally occurring compound, along with 30 known phenolic compounds, were isolated from Hypericum japonicum. In addition, hyperjaponols A and B were identified as racemates. The structures and absolute configurations of the undescribed compounds were determined by comprehensive MS, NMR spectroscopy, and electronic circular dichroism (ECD) calculations. The cytotoxic effects of the isolated compounds on two human tumour cell lines (HEL and MDA-MB-231) were evaluated by the MTT assay. Eighteen compounds showed good inhibitory activities against the HEL cell line, with IC50 values of 3.53-18.7 μM, while nine compounds exhibited moderate cytotoxicity against the MDA-MB-231 cancer cell line, with IC50 values ranging from 4.92 to 10.75 μM. Their preliminary structure-activity relationship of the isolated compounds was also discussed.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Zhu W,Qiu J,Zeng YR,Yi P,Lou HY,Jian JY,Zuo MX,Duan L,Gu W,Huang LJ,Li YM,Yuan CM,Hao XJ

doi

10.1016/j.phytochem.2019.04.012

subject

Has Abstract

pub_date

2019-08-01 00:00:00

pages

33-40

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(19)30038-X

journal_volume

164

pub_type

杂志文章
  • The C-terminal zinc finger domain of Arabidopsis cold shock domain proteins is important for RNA chaperone activity during cold adaptation.

    abstract::Among the four cold shock domain proteins (CSDPs) identified in Arabidopsis thaliana, it has recently been shown that CSDP1 harboring seven CCHC-type zinc fingers, but not CSDP2 harboring two CCHC-type zinc fingers, function as a RNA chaperone during cold adaptation. However, the structural features relevant to this d...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.12.006

    authors: Park SJ,Kwak KJ,Jung HJ,Lee HJ,Kang H

    更新日期:2010-04-01 00:00:00

  • Isolation and identification of 4-α-rhamnosyloxy benzyl glucosinolate in Noccaea caerulescens showing intraspecific variation.

    abstract::Glucosinolates are secondary plant compounds typically found in members of the Brassicaceae and a few other plant families. Usually each plant species contains a specific subset of the ∼ 130 different glucosinolates identified to date. However, intraspecific variation in glucosinolate profiles is commonly found. Sinal...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.11.016

    authors: de Graaf RM,Krosse S,Swolfs AE,te Brinke E,Prill N,Leimu R,van Galen PM,Wang Y,Aarts MG,van Dam NM

    更新日期:2015-02-01 00:00:00

  • Kinetics of glucosylated and non-glucosylated aryltetralin lignans in Linum hairy root cultures.

    abstract::Due to their pronounced cytotoxic activity, a number of aryltetralin lignans (ATLs), such as podophyllotoxin (PTOX), are used as antitumor compounds. The production of such molecules from entire plants or plant cell-tissue-organ cultures is thus of interest to the pharmaceutical industry. Hairy root cultures constitut...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.01.001

    authors: Cong LH,Dauwe R,Lequart M,Vinchon S,Renouard S,Fliniaux O,Colas C,Corbin C,Doussot J,Hano C,Lamblin F,Molinié R,Pilard S,Jullian N,Boitel M,Gontier E,Mesnard F,Laberche JC

    更新日期:2015-07-01 00:00:00

  • Microbiological transformation of two 15α-hydroxy-ent-kaur-9(11),16-diene derivatives by the fungus Fusarium fujikuroi.

    abstract::The incubation of 15α-hydroxy-ent-kaur-9(11),16-dien-19-oic acid (15α-hydroxy-grandiflorenic acid) with the fungus Fusarium fujikuroi gave as main metabolite its 3β,6β-dihydroxy derivative, which by an oxidative decarboxylation afforded a 19-nor compound with a 4,18-double bond. Other substances obtained were a 3α-hyd...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.01.006

    authors: Fraga BM,González-Vallejo V,Guillermo R,Amaro-Luis JM

    更新日期:2013-05-01 00:00:00

  • An unusual dimeric guaianolide with antiprotozoal activity and further sesquiterpene lactones from Eupatoriumperfoliatum.

    abstract::The CH(2)Cl(2) extract of aerial parts of Eupatorium perfoliatum L. exhibits antiprotozoal activity under in vitro conditions, especially against Plasmodium falciparum (IC(50)=2.7μg/ml). The search for active compounds yielded seven sesquiterpene lactones: Four structurally similar guaianolides, one dimeric guaianolid...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.01.025

    authors: Maas M,Hensel A,Costa FB,Brun R,Kaiser M,Schmidt TJ

    更新日期:2011-05-01 00:00:00

  • Functional characterisation of a tropine-forming reductase gene from Brugmansia arborea, a woody plant species producing tropane alkaloids.

    abstract::Brugmansia arborea is a woody plant species that produces tropane alkaloids (TAs). The gene encoding tropine-forming reductase or tropinone reductase I (BaTRI) in this plant species was functionally characterised. The full-length cDNA of BaTRI encoded a 272-amino-acid polypeptide that was highly similar to tropinone r...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.03.008

    authors: Qiang W,Xia K,Zhang Q,Zeng J,Huang Y,Yang C,Chen M,Liu X,Lan X,Liao Z

    更新日期:2016-07-01 00:00:00

  • Polyoxygenated cyclohexene derivatives from Ellipeiopsis cherrevensis.

    abstract::Aerial parts of Ellipeiopsis cherrevensis contained the polyoxygenated cyclohexenes zeylenol, ferrudiol and three analogs, ellipeiopsols A, B and C. The C-1 stereochemistry of ferrudiol has been revised. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00465-4

    authors: Kijjoa A,Bessa J,Pinto MM,Anatachoke C,Silva AM,Eaton G,Herz W

    更新日期:2002-03-01 00:00:00

  • Differential inhibition of Helicoverpa armigera gut proteinases by proteinase inhibitors of pigeonpea (Cajanus cajan) and its wild relatives.

    abstract::The seeds of 36 pigeonpea [Cajanus cajan (L) Millsp.] cultivars, resistant and susceptible to pests and pathogens and 17 of its wild relatives were analysed for inhibitors of trypsin, chymotrypsin, and insect gut proteinases to identify potential inhibitors of insect (Helicoverpa armigera) gut enzymes. Proteinase inhi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00375-3

    authors: Chougule NP,Hivrale VK,Chhabda PJ,Giri AP,Kachole MS

    更新日期:2003-10-01 00:00:00

  • The biosynthetic origin of oxygen functions in phenylphenalenones of Anigozanthos preissii inferred from NMR- and HRMS-based isotopologue analysis.

    abstract::The biosynthetic origin of 9-phenylphenalenones and the sequence according to which their oxygen functionalities are introduced were studied using nuclear magnetic resonance (NMR) spectroscopy and high-resolution electrospray ionization mass spectrometry (HRESIMS). (13)C-labelled precursors were administered to root c...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.10.007

    authors: Munde T,Maddula RK,Svatos A,Schneider B

    更新日期:2011-01-01 00:00:00

  • Hepatoprotective pyranocoumarins from the stems of Clausena emarginata.

    abstract::Seven pyranocoumarins, clauemarmarins A-G, along with 6 known analogues were isolated from the stems of Clausena emarginata. Their structures were elucidated by extensive spectroscopic analyses, and the absolute stereochemistries at C-6″ of clauemarmarin B, C and D and the absolute configurations of clauemarmarin E, F...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.05.010

    authors: Xia HM,Li CJ,Yang JZ,Ma J,Li Y,Li L,Zhang DM

    更新日期:2016-10-01 00:00:00

  • Profile and quantification of glucosinolates in Pentadiplandra brazzeana Baillon.

    abstract::Glucosinolates (GLs) present in root, seed, and leaf extracts of Pentadiplandra brazzeana Baillon were characterized and quantified according to the ISO 9167-1 method based on the HPLC analysis of desulfo-GLs. The analyses were complemented by GC-MS analyses of the isothiocyanates (ITCs) generated from GL degradation ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.09.006

    authors: De Nicola GR,Nyegue M,Montaut S,Iori R,Menut C,Tatibouët A,Rollin P,Ndoyé C,Zollo PH

    更新日期:2012-01-01 00:00:00

  • Flavonoids from Ochna integerrima.

    abstract::Two biflavonoids namely, 2",3"-dihydroochnaflavone and 2",3"-dihydroochnaflavone 7"-O-methyl ether, and a flavonoid glycoside, 6-gamma,gamma-dimethylallyltaxifolin 7-O-beta-D-glucoside were isolated from the leaves of Ochna integerrima. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00409-x

    authors: Likhitwitayawuid K,Rungserichai R,Ruangrungsi N,Phadungcharoen T

    更新日期:2001-02-01 00:00:00

  • Aporphine Alkaloids from Illigera aromatica from Guangxi Province, China.

    abstract::Three undescribed aporphine alkaloids laurodionine B (1), illigerine A (2), and N-formyl-laurolitsine (3) were isolated from the methanolic extracts of the Chinese medicinal plant, Illigera aromatica, together with three known analogues (4-6). The chemical structures of 1-6 were identified by spectroscopic methods inc...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.06.017

    authors: Ge YC,Zhang HJ,Wang KW,Fan XF

    更新日期:2018-10-01 00:00:00

  • Differing mechanisms of simple nitrile formation on glucosinolate degradation in Lepidium sativum and Nasturtium officinale seeds.

    abstract::Glucosinolates are sulphur-containing glycosides found in brassicaceous plants that can be hydrolysed enzymatically by plant myrosinase or non-enzymatically to form primarily isothiocyanates and/or simple nitriles. From a human health perspective, isothiocyanates are quite important because they are major inducers of ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.07.035

    authors: Williams DJ,Critchley C,Pun S,Chaliha M,O'Hare TJ

    更新日期:2009-07-01 00:00:00

  • Cardenolide glycosides from root of Streptocaulon juventas.

    abstract::Six cardenolides were isolated from the anti-tumor active fraction of the 75% ethanol extract of Streptocaulon juventas (Asclepiadaceae), mainly found in southwest of China. These were named 1α, 14β-dihydroxy-5β-card-20 (22)-enolide 3-O-[O-β-D-glucopyranosyl-(1→2)-β-D-digitalopyranoside] (1), acovenosigenin A 3-O-[O-β...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.12.004

    authors: Xue R,Han N,Ye C,Wang HB,Yin J

    更新日期:2013-04-01 00:00:00

  • Neolignan and flavonoid glycosides in Juniperus communis var. depressa.

    abstract::Two neolignan glycosides (junipercomnosides A and B) were isolated from aerial parts of Juniperus communis var. depressa along with two known neolignan glycosides and seven flavonoid glycosides. The structures of the isolated compounds were determined by spectral analysis, in particular by 2D-NMR analysis. The signifi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2003.10.025

    authors: Nakanishi T,Iida N,Inatomi Y,Murata H,Inada A,Murata J,Lang FA,Iinuma M,Tanaka T

    更新日期:2004-01-01 00:00:00

  • Tropane alkaloid production by shoot culture of Duboisia myoporoides R. Br.

    abstract::This work demonstrates the presence of hyoscyamine and scopolamine at different stages of shoot regeneration from non-organogenic and organogenic calli. The 11-week-old non-organogenic calli contained 0.41+/-0.03 and 0.23+/-0.02 microg g(-1) dry wt hyoscyamine and scopolamine respectively. However, no root meristem wa...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00342-3

    authors: Khanam N,Khoo C,Close R,Khan AG

    更新日期:2001-01-01 00:00:00

  • Anti-HIV-1 and anti-HIV-1-protease substances from Ganoderma lucidum.

    abstract::A new highly oxygenated triterpene named ganoderic acid alpha has been isolated from a methanol extract of the fruiting bodies of Ganoderma lucidum together with twelve known compounds. The structures of the isolated compounds were determined by spectroscopic means including 2D-NMR. Ganoderiol F and ganodermanontriol ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00254-4

    authors: el-Mekkawy S,Meselhy MR,Nakamura N,Tezuka Y,Hattori M,Kakiuchi N,Shimotohno K,Kawahata T,Otake T

    更新日期:1998-11-01 00:00:00

  • Polyketide synthases of bacterial symbionts in sponges--evolution-based applications in natural products research.

    abstract::Marine sponges are an unusually rich source of bioactive natural products with clinical potential. They also often harbor rich communities of symbiotic bacteria that have often been suspected as the true producers of sponge-derived compounds. To date, these bacteria can in most cases not be cultivated, but culture-ind...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2009.04.010

    authors: Hochmuth T,Piel J

    更新日期:2009-10-01 00:00:00

  • Anti-neuroinflammatory polyoxygenated lanostanoids from Chaga mushroom Inonotus obliquus.

    abstract::Chaga mushroom, Inonotus obliquus, was used as food and nutrient food and traditional herbs in Russia, China and Japan, with anti-inflammatory and anticancer activities. Chemical investigations of the fruiting bodies of Chaga were carried to uncover the bioactive metabolites. As a result, seven undescribed lanostane-t...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112647

    authors: Kou RW,Han R,Gao YQ,Li D,Yin X,Gao JM

    更新日期:2021-01-09 00:00:00

  • Biologically active compounds and pharmacological activities of species of the genus Crocus: A review.

    abstract::The present article is the first comprehensive review on the chemical composition and pharmacological activities of the raw materials of Crocus species. In the present review, data on chemical constituents and pharmacological profile of Crocus sativus stigmas, as well as of other plant parts (perianth, stamens, leaves...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2019.02.004

    authors: Mykhailenko O,Kovalyov V,Goryacha O,Ivanauskas L,Georgiyants V

    更新日期:2019-06-01 00:00:00

  • Volatile constituents of Capillipedium parviflorum.

    abstract::The essential oil of aerial parts of Capillipedium parviflorum (family Poaceae) was obtained by hydrodistillation in 0.4% yield on dry weight basis. The oil was analysed by capillary GC and GC-MS techniques. Two new compounds from plant source 4-nonanol 51.7% and 4-undecanone 23.5% predominated in the essential oil an...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.04.003

    authors: Mahmood U,Kaul VK,Acharya R

    更新日期:2004-07-01 00:00:00

  • Tuber borchii fruit body: 2-dimensional profile and protein identification.

    abstract::The formation of the fruit body represents the final phase of the ectomycorrhizal fungus T. borchii life cycle. Very little is known concerning the molecular and biochemical processes involved in the fructification phase. 2-DE maps of unripe and ripe ascocarps revealed different protein expression levels and the compa...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.02.012

    authors: Pierleoni R,Buffalini M,Vallorani L,Guidi C,Zeppa S,Sacconi C,Pucci P,Amoresano A,Casbarra A,Stocchi V

    更新日期:2004-04-01 00:00:00

  • Glutathione reductase activity and isoforms in leaves and roots of wheat plants subjected to cadmium stress.

    abstract::The behavior of glutathione reductase (GR, EC 1.6.4.2) activity and isoforms were analyzed in wheat (Triticum aestivum L.) leaves and roots exposed to a chronic treatment with a toxic cadmium (Cd) concentration. A significant growth inhibition (up to 55%) was found in leaves at 7, 14 and 21 days, whereas roots were af...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.11.016

    authors: Yannarelli GG,Fernández-Alvarez AJ,Santa-Cruz DM,Tomaro ML

    更新日期:2007-02-01 00:00:00

  • Phylogeny, structural diversity and genome-wide expression analysis of fibrillin family genes in rice.

    abstract::Fibrillins (FBNs) constitute a plastid-lipid-associated protein family that plays a role in chloroplast development, lipids metabolism and stress responses in plants. Until now, FBNs have been functionally characterized in stability of thylakoid and responses to the different stress stimuli. Consequently, phylogeny, d...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112377

    authors: Li J,Li X,Khatab AA,Xie G

    更新日期:2020-07-01 00:00:00

  • Rapid isolation and identification of minor natural products by LC-MS, LC-SPE-NMR and ECD: isoflavanones, biflavanones and bisdihydrocoumarins from Ormocarpum kirkii.

    abstract::The combination of the hyphenated techniques LC-MS and LC-SPE-NMR constitutes a powerful platform for the rapid isolation and identification of minor components from natural sources. Electronic circular dichroism (ECD) is a useful tool to determine the absolute configuration of small quantities of chiral molecules. In...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.04.004

    authors: Xu YJ,Foubert K,Dhooghe L,Lemière F,Maregesi S,Coleman CM,Zou Y,Ferreira D,Apers S,Pieters L

    更新日期:2012-07-01 00:00:00

  • Production of phenylacetic acid derivatives and 4-epiradicinol in culture by Curvularia lunata.

    abstract::Phenylacetic acid derivatives, methyl 2-acetyl-3,5-dihydroxyphenylacetate (1) and methyl 2-acetyl-5-hydroxy-3-methoxyphenylacetate (3); curvulin or ethyl 2-acetyl-3,5-dihydroxyphenylacetate (4), a known metabolite of Curvularia siddiqui, and 4-epiradicinol (5) have been isolated from the culture mycelia of Curvularia ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.05.032

    authors: Varma GB,Fatope MO,Marwah RG,Deadman ME,Al-Rawahi FK

    更新日期:2006-09-01 00:00:00

  • Uniconazole, a cytochrome P450 inhibitor, inhibits trans-zeatin biosynthesis in Arabidopsis.

    abstract::Cytokinin (CK) is a plant hormone that plays important regulatory roles in many aspects of plant growth and development. Although functions of CK and its biosynthesis pathway have been studied extensively, there is still no efficient biosynthesis inhibitor, which would be useful for studying CK from a chemical genetic...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.11.023

    authors: Sasaki E,Ogura T,Takei K,Kojima M,Kitahata N,Sakakibara H,Asami T,Shimada Y

    更新日期:2013-03-01 00:00:00

  • Iridoids from Caryopteris x clandonensis.

    abstract::In continuation of our phytochemical studies on Caryopteris x clandonensis (Lamiaceae), three further iridoids were isolated from the methanolic extract of the stems. Their structures were established by 1D and 2D NMR and MS analysis as a C-6 epimer of 8-O-acetylharpagide (6-epi-8-O-acetylharpagide), a derivative of h...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00069-8

    authors: Hannedouche S,Stanislas E,Moulis C,Fourasté I

    更新日期:2000-08-01 00:00:00

  • Diterpene constituents of leaves from Juniperus brevifolia.

    abstract::The dichloromethane extract from leaves of Juniperus brevifolia, through chromatographic fractionations yield six compounds: 3beta-hydroxy-abieta-8,11,13-trien-7-one, 18-hydroxy-sandaracopimara-8(14),15-dien-7-one, sandaracopimara-8(14),15-dien-18-yl formate; and the first examples of sandaracopimaranes and abieta-8,1...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.07.026

    authors: Seca AM,Silva AM,Bazzocchi IL,Jimenez IA

    更新日期:2008-01-01 00:00:00