Pyranonaphthoquinone and anthraquinone derivatives from Ventilago harmandiana and their potent anti-inflammatory activity.

Abstract:

:The chemical study on the heartwoods extract of Ventilago harmandiana (Rhamnaceae) resulted in the isolation of ten previously undescribed pyranonaphthoquinones (ventilanones A-J), an undescribed anthraquinone (ventilanone K), together with eight known anthraquinone derivatives. Their structures were elucidated by extensive analysis of their spectroscopic data. The absolute configuration of ventilanone A was established from single crystal X-ray crystallographic analysis of its p-bromobenzenesulfonate ester derivative using Cu Kα radiation. The absolute configurations of the other related compounds were identified by comparison of their ECD data with those of ventilanone A and related known compounds. Cytotoxic and anti-inflammatory activities of some of the isolated compounds were evaluated. Ventilanone A and ventilanone C exhibited moderate cytotoxicity against P-388 cell line. Ventilanone D exhibited significant anti-inflammatory activity while ventilanone A and ventilanone C showed moderate activity.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Panthong K,Hongthong S,Kuhakarn C,Piyachaturawat P,Suksen K,Panthong A,Chiranthanut N,Kongsaeree P,Prabpai S,Nuntasaen N,Reutrakul V

doi

10.1016/j.phytochem.2019.112182

subject

Has Abstract

pub_date

2020-01-01 00:00:00

pages

112182

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(19)30659-4

journal_volume

169

pub_type

杂志文章
  • Heterogeneity of carrageenans from Chondrus crispus.

    abstract::Carrageenans extracted from gametophytic and sporophytic Chondrus crispus were analysed by hydrolysis, KCl fractionation and 1H NMR spectroscopy. The carrageenan from gametophytic plants is composed predominantly of two KCl insoluble fractions which contain kappa-carrageenan as the major component with 1-carrageenan a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(92)90032-l

    authors: Matsuhiro B,Urzua CC

    更新日期:1992-02-01 00:00:00

  • Metabolic profiling for studying chemotype variations in Withania somnifera (L.) Dunal fruits using GC-MS and NMR spectroscopy.

    abstract::Withania somnifera (L.) Dunal (Solanaceae), commonly known as Ashwagandha, is one of the most valued Indian medicinal plant with several pharmaceutical and nutraceutical applications. Metabolic profiling was performed by GC-MS and NMR spectroscopy on the fruits obtained from four chemotypes of W. somnifera. A combinat...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.03.013

    authors: Bhatia A,Bharti SK,Tewari SK,Sidhu OP,Roy R

    更新日期:2013-09-01 00:00:00

  • Distribution of morphinan and benzo[c]phenanthridine alkaloid gene transcript accumulation in Papaver somninferum.

    abstract::The opium poppy Papaver somniferum L. produces the antimicrobial benzo[c]phenanthridine alkaloid sanguinarine and the narcotic analgesic morphinan alkaloid morphine. Transcripts of three genes of alkaloid biosynthesis in P. somniferum in developing seedlings, mature plants and plant cell suspension culture were monito...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00600-7

    authors: Huang FC,Kutchan TM

    更新日期:2000-03-01 00:00:00

  • (+/-)-Dievodialetins A-G: Seven pairs of enantiomeric coumarin dimers with anti-acetylcholinesterase activity from the roots of Evodia lepta Merr.

    abstract::Seven pairs of undescribed enantiomeric bis-coumarins, (±)-dievodialetins A-G, were separated from the roots of Evodia lepta Merr. Two coumarin nuclei were linked via a 1,4-dimethyl4-vinylcyclohexene moiety in (±)-dievodialetins C-G. The structures of the undescribed compounds, including their absolute configurations ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112597

    authors: Huang GY,Cui H,Lu XY,Zhang LD,Ding XY,Wu JJ,Duan LX,Zhang SJ,Liu Z,Zhang RR

    更新日期:2021-02-01 00:00:00

  • Biosynthesis of the dimethylallyl moiety of glabrol in Glycyrrhiza glabra hairy root cultures via a non-mevalonate pathway.

    abstract::Incorporation of [1-13C]glucose indicates that the biosynthesis of the hemiterpene moiety of glabrol, the main prenylated flavanone in the hairy root cultures of Glycyrrhiza glabra, proceeds via a glyceraldehyde/pyruvate non-mevalonate pathway. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00327-7

    authors: Asada Y,Li W,Yoshikawa T

    更新日期:2000-10-01 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

  • Mangiterpenes A-C and 2',3'-seco-manginoid C, four sesquiterpene/monoterpene-shikimate-conjugated spirocyclic meroterpenoids from Guignardia mangiferae.

    abstract::Mangiterpenes A-C and 2',3'-seco-manginoid C, four undescribed sesquiterpene/monoterpene-shikimate-conjugated meroterpenoids with spiro ring systems, were isolated from Guignardia mangiferae. The structures and absolute configurations of these compounds were established by comprehensive spectroscopic analyses and elec...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2019.05.018

    authors: Chen K,Chen C,Guo J,Sun W,Liu J,Yang J,Liu X,Wang J,Luo Z,Zhu H,Zhang Y

    更新日期:2019-08-01 00:00:00

  • Two cationic peroxidases from cell walls of Araucaria araucana seeds.

    abstract::We have previously reported the purification and partial characterization of two cationic peroxidases from the cell walls of seeds and seedlings of the South American conifer, Araucaria araucana. In this work, we have studied the amino acid composition and NH2-terminal sequences of both enzymes. We also compare the da...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(94)00665-g

    authors: Riquelme A,Cardemil L

    更新日期:1995-05-01 00:00:00

  • Antitumor sterols from the mycelia of Cordyceps sinensis.

    abstract::Activity guided fractionations led to the isolation of two antitumor compounds 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3 beta-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-beta-D-g...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00128-4

    authors: Bok JW,Lermer L,Chilton J,Klingeman HG,Towers GH

    更新日期:1999-08-01 00:00:00

  • Photo-induced synthesis of tomatidenol-based glycoalkaloids in Solanum phureja tubers.

    abstract::The effect of light exposure on the steroidal glycoalkaloid content of Solanum phureja tubers has been investigated and compared with that in domesticated potato (Solanum tuberosum) tubers. The results indicated that the increase in the concentration of solanidine-based glycoalkaloids, alpha-solanine and alpha-chaconi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00023-6

    authors: Griffiths DW,Bain H,Deighton N,Robertson GW,Finlay M,Dale B

    更新日期:2000-04-01 00:00:00

  • Structure and stereochemistry of dimeric proteracacinidins possessing the rare C-4(C) --> C-5(D) interflavanyl linkage.

    abstract::The rare series of (4-->5)-linked proteracacinidins is extended by identification of oritin-(4alpha-->5)-epioritin-4beta-ol, ent-epioritin-(4alpha-->5)-epioritin-4beta-ol, epioritin-(4beta-->5)-epioritin-4alpha-ol and ent-oritin-(4beta-->5)-epioritin-4alpha-ol from the heartwoods of Acacia galpinii and Acacia caffra. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00010-9

    authors: Bennie L,Coetzee J,Malan E,Ferreira D

    更新日期:2002-03-01 00:00:00

  • Characterization of native and yeast-expressed tomato fruit fructokinase enzymes.

    abstract::Three fructokinase isozymes (FKI, FKII, FKIII) were separated from both immature and ripe tomato fruit pericarp. All three isozymes were specific for fructose with undetectable activity towards glucose or mannose. The three isozymes could be distinguished from one another with respect to response to fructose, Mg and n...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00331-4

    authors: Petreikov M,Dai N,Granot D,Schaffer AA

    更新日期:2001-11-01 00:00:00

  • Malate. Jack of all trades or master of a few?

    abstract::The dicarboxylic acid malate has long been thought to play important roles in plant physiology. In addition to being a major photosynthate in C4 and CAM plants and an intermediate of the tricarboxylic acid cycle it has been proposed to play essential roles in pH regulation and important roles in pathogen response, as ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.04.023

    authors: Fernie AR,Martinoia E

    更新日期:2009-05-01 00:00:00

  • Hydroperoxide lyase cascade in pea seedlings: Non-volatile oxylipins and their age and stress dependent alterations.

    abstract::The profiles of non-volatile oxylipins of pea (Pisum sativum) seedlings were examined by gas chromatography-mass spectrometry after invitro incubation with α-linolenic acid. The 13-lipoxygenase/hydroperoxide lyase (HPL) products were predominant in the leaves, while the roots possess both 13- and 9-HPL products. Allen...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.01.013

    authors: Mukhtarova LS,Mukhitova FK,Gogolev YV,Grechkin AN

    更新日期:2011-04-01 00:00:00

  • Chemical interactions between plants in Mediterranean vegetation: the influence of selected plant extracts on Aegilops geniculata metabolome.

    abstract::Allelopathy is the chemical mediated communication among plants. While on one hand there is growing interest in the field, on the other hand it is still debated as doubts exist at different levels. A number of compounds have been reported for their ability to influence plant growth, but the existence of this phenomeno...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.07.006

    authors: Scognamiglio M,Fiumano V,D'Abrosca B,Esposito A,Choi YH,Verpoorte R,Fiorentino A

    更新日期:2014-10-01 00:00:00

  • Phragmalin limonoids from Chukrasia tabularis.

    abstract::Six phragmalin limonoids, named tabulalin and tabulalides A-E, were isolated from the root bark of Chukrasia tabularis (Meliaceae). Their structures were determined by spectroscopic methods, and their antifeedant properties evaluated. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.08.010

    authors: Nakatani M,Abdelgaleil SA,Saad MM,Huang RC,Doe M,Iwagawa T

    更新日期:2004-10-01 00:00:00

  • Phytochemistry and medicinal plants.

    abstract::A truncated history of the contribution of plants to medicine is given with reference to some of the less well known ancestors of the Harborne family. Six of the top 20 prescriptions dispensed in 1996 were natural products and the clinical use of drugs such as artemisinin, etoposide and taxol has once more focussed at...

    journal_title:Phytochemistry

    pub_type: 历史文章,杂志文章

    doi:10.1016/s0031-9422(00)00456-8

    authors: Phillipson JD

    更新日期:2001-02-01 00:00:00

  • Antioxidant flavonoids from leaves of Polygonum hydropiper L.

    abstract::Ten flavonoid compounds were isolated from the dried leaves of Polygonum hydropiper L. (Laksa leaves), and identified as 3-O-alpha-L-rhamnopyranosyloxy-3',4',5,7-tetrahydroxyflavone; 3-O-beta-D-glucopyranosyloxy-4',5,7-trihydroxyflavone; 6-hydroxyapigenin; 6"-O-(3,4,5-trihydroxybenzoyl) 3-O-beta-D-glucopyranosyloxy-3'...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00504-6

    authors: Peng ZF,Strack D,Baumert A,Subramaniam R,Goh NK,Chia TF,Tan SN,Chia LS

    更新日期:2003-01-01 00:00:00

  • Seco-dammarane triterpenoids from the leaves of Cyclocarya paliurus.

    abstract::The leaves of Cyclocarya paliurus with sweet taste are often used as herbal tea in People's Republic of China. In this study eight previously undescribed seco-dammarane type triterpenoids, cyclocariols A-H along with seven known compounds were isolated and characterized from its leaves. A possible biogenetic pathway f...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.10.013

    authors: Chen YJ,Na L,Fan J,Zhao J,Hussain N,Jian YQ,Yuan H,Li B,Liu B,Choudhary MI,Khan I,Wang W

    更新日期:2018-01-01 00:00:00

  • Cytotoxic benzil and coumestan derivatives from Tephrosia calophylla.

    abstract::A benzil, calophione A, 1-(6'-Hydroxy-1',3'-benzodioxol-5'-yl)-2-(6''-hydroxy-2''-isopropenyl-2'',3''-dihydro-benzofuran-5''-yl)-ethane-1,2-dione and three coumestan derivatives, tephcalostan B, C and D were isolated from the roots of Tephrosia calophylla. Their structures were deduced from spectroscopic data, includi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.10.009

    authors: Ganapaty S,Srilakshmi GV,Pannakal ST,Rahman H,Laatsch H,Brun R

    更新日期:2009-01-01 00:00:00

  • Triterpenoid glycosides from the stems of Gordonia kwangsiensis.

    abstract::Eleven oleanane-type triterpenoid glycosides, named gordonsaponins A-K, were isolated from the stems of Gordonia kwangsiensis. Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of all eleven were evaluated against five human tumor cell lines (HCT-8, Bel-7402, BGC-823, A54...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.08.019

    authors: Fu HZ,Li CJ,Yang JZ,Chen XG,Zhang DM

    更新日期:2013-01-01 00:00:00

  • Identification of fermented tea (Camellia sinensis) polyphenols and their inhibitory activities against amyloid-beta aggregation.

    abstract::Thirty-three phenolic compounds were identified from the extract of fermented tea (Camellia sinensis L.), including three undescribed flavonoids, namely quamoreokchaside I-II and kamoreokchaside I, along with thirty known compounds. All isolates were tested to evaluate their inhibitory effects against amyloid-beta (Aβ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.12.013

    authors: Rho T,Choi MS,Jung M,Kil HW,Hong YD,Yoon KD

    更新日期:2019-04-01 00:00:00

  • Flavonoids from two Lonchocarpus species of the Yucatan Peninsula.

    abstract::Leaves, stem bark and root of Lonchocarpus xuul and Lonchocarpus yucatanensis were studied separately. A chalcone, 2',4-dimethoxy-6'-hydroxylonchocarpin (), and the flavones 5,4'-dihydroxy-3'-methoxy-(6:7)-2,2-dimethylpyranoflavone (2) and 5,4'-dimethoxy-(6:7)-2,2-dimethylpyrano-flavone (3), together with the known ca...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00131-0

    authors: Borges-Argáez R,Peña-Rodríguez LM,Waterman PG

    更新日期:2002-07-01 00:00:00

  • Triterpene saponins from Eryngium kotschyi.

    abstract::Four new oleanane-type saponins 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyl-22-O-β,β-dimethylacryloylA1-barrigenol (1), 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyl-22-O-angeloylA1-barrigenol (2), 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-21,22,28-O-triacetyl-(...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.11.017

    authors: Aslan Erdem S,Mitaine-Offer AC,Miyamoto T,Kartal M,Lacaille-Dubois MA

    更新日期:2015-02-01 00:00:00

  • Caudatan A, an undescribed human kidney-type glutaminase inhibitor with tetracyclic flavan from Ohwia caudata.

    abstract::Human kidney-type glutaminase (KGA) is an important target that is often over expressed in many cancer cells but very few effective inhibitors of this enzyme have yet reached clinical trials. Caudatan A and caudatan B, two undescribed tetracyclic flavans with an unusual ether bond between the C-4 and C-2' were isolate...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.04.013

    authors: Sun Y,Feng X,Liu X,Qian C,Che X,Cao F,Jin S,Meng D

    更新日期:2018-08-01 00:00:00

  • Uptake and modification of umbelliferone by various seedlings.

    abstract::Inspired by the recently discovered phenomenon of "horizontal natural product transfer" we investigated the putative uptake of phenolic specialized metabolites. Umbelliferone was chosen for this case study, since this coumarin as well as its derivatives can easily be determined by HPLC analyses. Barley (Hordeum vulgar...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.10.032

    authors: Hijazin T,Radwan A,Abouzeid S,Dräger G,Selmar D

    更新日期:2019-01-01 00:00:00

  • Cytotoxic cycloartanes from Aglaia argentea.

    abstract::Aglaia argentea leaves yielded three new cycloartanes: argenteanones A and B, and argenteanol. The first two possess cytotoxic activity against KB cells (IC50 7.5 micrograms ml-1 and 6.5 micrograms ml-1 respectively). Structural elucidation was done by two-dimensional NMR spectroscopy. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00745-8

    authors: Omobuwajo OR,Martin MT,Perromat G,Sevenet T,Awang K,Païs M

    更新日期:1996-03-01 00:00:00

  • Glucosinolates, flea beetle resistance, and leaf pubescence as taxonomic characters in the genus Barbarea (Brassicaceae).

    abstract::Glucosinolate content of leaves and roots, diversity in leaf pubescence, and resistance to two near-isogenic lines of the flea beetle Phyllotreta nemorum with or without an R-gene, were determined for 27 accessions of 7 Barbarea taxa, i.e. B. stricta, B. orthoceras, B. intermedia, B. verna, B. vulgaris var. vulgaris, ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00750-1

    authors: Agerbirk N,Ørgaard M,Nielsen JK

    更新日期:2003-05-01 00:00:00

  • An extensive study on the chemical diversity of lipophilic extractives from Eucalyptus globulus wood.

    abstract::Three mature Eucalyptus globulus trees with 40 years of age were studied at three height levels (0%, 35%, and 60% of total tree height) and at three radial regions (sapwood, inner and outer heartwood). The composition of lipophilic extracts was evaluated and an extensive list of 202 compounds was reported for the firs...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112520

    authors: Gominho J,Lourenço A,Marques AV,Pereira H

    更新日期:2020-12-01 00:00:00

  • Monoterpenoid accumulation in 1,8-cineole, terpinolene and terpinen-4-ol chemotypes of Melaleuca alternifolia seedlings.

    abstract::Individual leaves of the three most common chemotypes of Melaleuca alternifolia were examined both quantitatively and qualitatively for volatile constituents from the emergence of the first true leaves, through to 6-week-old tenth leaf set material. The 1,8-cineole and terpinolene chemotypes were investigated and comp...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00607-6

    authors: Russell MF,Southwell IA

    更新日期:2003-03-01 00:00:00