Cryptic and free skin irritants of the daphnane and tigliane types in latex of Excoecaria agallocha.

Abstract:

:In the extremely skin irritant and caustic latex of Excoecaria agallocha the major part of the polyfunctional diterpene esters (DTE) (group I) are aliphatic polyunsaturated 9,13,14-orthoesters of the daphnane-type parent alcohol 5 beta-hydroxyresiniferonol-6 alpha, 7 alpha-epoxide, esterified simultaneously in their 20-positions with aliphatic saturated homologous n-carboxylic acids (even numbered, C22-C30). The minor part of DTE is composed of analogous structures of 5 beta, 12 beta-dihydroxyresiniferonol-6 alpha, 7 alpha-epoxide (group II) and of aliphatic 13-polyunsaturated, 20-saturated diesters of the tigliane-type parent alcohol 12-deoxyphorbol (group III). All three groups of DTE exhibit practically no irritant activity on the mouse ear. By alkaline transesterification of groups I-III, the corresponding highly irritant multicomponent mixtures of Excoecaria factors A (OH-20 deacylated) are released. They comprise a mixture of the known Excoecaria factors A1/A2/A3 and three mixtures of hitherto unknown Excoecaria factors A4/A5, A6/A7 and A8/A9. The groups I-III are typical structures of "cryptic irritants". By an alternative, extremely mild separation procedure the highly irritant mixture A1/A2/A3 was obtained directly. It represents the "free" Excoecaria factors, the natural constituents of the latex responsible for its bioactivity.

journal_name

Planta Med

journal_title

Planta medica

authors

Karalai C,Wiriyachitra P,Opferkuch HJ,Hecker E

doi

10.1055/s-2006-959499

subject

Has Abstract

pub_date

1994-08-01 00:00:00

pages

351-5

issue

4

eissn

0032-0943

issn

1439-0221

journal_volume

60

pub_type

杂志文章
  • Volatile Components of Cleistopholis patens.

    abstract::Volatile oils of the leaves, fruits and stem-bark of CLEISTOPHOLIS PATENTS Engl. et Diels. (Annonacae) were analysed by means of gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of sixty-one components were identified; qualitative and quantitative differences in the oil composition wer...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-962450

    authors: Ekundayo O,Laakso I,Oguntimein B,Hiltunen R

    更新日期:1988-08-01 00:00:00

  • [New cardioactive drugs II, detection and isolation of cardiotonic amines with ionpair-HPLC].

    abstract::An ionpair-HPLC-technic using a reversed-phase column was developed to screen plant extracts for cardiotonic amines and to isolate them in a preparative scale for direct MS and pharmacological investigations. By this method the positive inotropic tyramine could be isolated from Selenicereus grandiflorus (L.) Britt et ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-971397

    authors: Wagner H,Grevel J

    更新日期:1982-01-01 00:00:00

  • Determination of naphthazarin derivatives in endemic Turkish Alkanna species by reversed phase high performance liquid chromatography.

    abstract::The quantification of free and total alkannins in 13 endemic Anatolian Alkanna species is described for the first time. Extraction of the samples was performed by sonication with hexane, followed by hydrolysis in 1 N NaOH. For analysis, a new HPLC method, utilizing reversed phase material (Synergi Max RP), was develop...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-967110

    authors: Pekin G,Ganzera M,Senol S,Bedir E,Korkmaz KS,Stuppner H

    更新日期:2007-03-01 00:00:00

  • The alkaloid 4-methylaaptamine isolated from the sponge Aaptos aaptos impairs Herpes simplex virus type 1 penetration and immediate-early protein synthesis.

    abstract::We describe in this paper that the alkaloid 4-methylaaptamine, isolated from the marine sponge Aaptos aaptos, inhibited HSV-1 infection. We initially observed that 4-methylaaptamine inhibited HSV-1 replication in Vero cells in a dose-dependent manner with an EC50 value of 2.4 microM. Moreover, the concentration requir...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-967109

    authors: Souza TM,Abrantes JL,de A Epifanio R,Leite Fontes CF,Frugulhetti IC

    更新日期:2007-03-01 00:00:00

  • Cyclopentanoid cyanohydrin glucosides and amides of Lindackeria dentata.

    abstract::A mixture of cyanogenic glucosides epivolkenin and taraktophyllin, 1,4-dihydroxy-2-cyclopentenecarboxamide, and uridine were isolated from leaves of Lindackeria dentata (Flacourtiaceae). Another cyclopentanoid amide, (1 R,4 S,5 R)-1,4,5-trihydroxy-2-cyclopentenecarboxamide, was synthesized in two steps from gynocardin...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2004-832628

    authors: Jaroszewski JW,Ekpe P,Witt M

    更新日期:2004-10-01 00:00:00

  • Extracellular polysaccharides produced by suspension-cultured cells from Digitalis lanata.

    abstract::Extracellular polysaccharides (ECP) were isolated in yields of up to 4 mg/ml from the culture media of suspension-cultured cells from Digitalis lanata Ehrh. ECP content was increasing continuously over the first ten days of cultivation and then stayed constant until day 20. ECP were fractionated by ion-exchange chroma...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957730

    authors: Hensel A,Schmidgall J,Kreis W

    更新日期:1997-10-01 00:00:00

  • New acylated clionasterol glycosides from Valeriana officinalis.

    abstract::The chloroform extract of Valeriana officinalis led to the isolation of clionasterol-3-O-beta-D-glucopyranoside and a mixture of 6'-O-acyl-beta-D-glucosyl-clionasterols. The acyl moieties were identified as hexadecanoyl, 8 E,11 E-octadecadienoyl and 14-methylpentadecanoyl by alkaline hydrolysis followed by GC-MS analy...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2005-864179

    authors: Pullela SV,Choi YW,Khan SI,Khan IA

    更新日期:2005-10-01 00:00:00

  • Effect of astilbin on experimental diabetic nephropathy in vivo and in vitro.

    abstract::Astilbin, a flavonoid compound, was isolated from the rhizome of Smilax glabra Roxb. This study was conducted to investigate the efficacy of astilbin on experimental diabetic nephropathy (DN) in vivo and in vitro and its possible mechanisms. Astilbin was added in high glucose stimulated HK-2 cells, streptozotocin-indu...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0029-1185802

    authors: Li GS,Jiang WL,Yue XD,Qu GW,Tian JW,Wu J,Fu FH

    更新日期:2009-11-01 00:00:00

  • Glutathione adducts of helenalin and 11 alpha,13-dihydrohelenalin acetate inhibit glutathione S-transferase from horse liver.

    abstract::The 2-mono- and 2,13-bis-glutathionyl adducts of helenalin and the 2-monoglutathionyl adduct of 11 alpha,13-dihydrohelenalin acetate were previously shown to be formed by spontaneous Michael addition at physiological pH. In living cells, glutathione (GSH) conjugation of many types of electrophilic agents is catalysed ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2000-11123

    authors: Schmidt TJ

    更新日期:2000-03-01 00:00:00

  • Endothelium-dependent vasodilator effect of extract prepared from the roots of Paeonia lactiflora on isolated rat aorta.

    abstract::Paeoniae Radix (the roots of Paeonia lactiflora Pallas) is a crude drug that is used in Asia and Europe to improve blood flow. We studied its vasodilator effect and mechanisms of action in vitro. The extract from Paeoniae Radix (PRE) relaxed prostaglandin F2a-precontracted aortic ring preparations of isolated rat aort...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957934

    authors: Goto H,Shimada Y,Akechi Y,Kohta K,Hattori M,Terasawa K

    更新日期:1996-10-01 00:00:00

  • Identification of New Diterpenes as Putative Marker Compounds Distinguishing Agnus Castus Fruit (Chaste Tree) from Shrub Chaste Tree Fruit (Viticis Fructus).

    abstract::Agnus Castus Fruit is defined in the European Pharmacopoeia as the dried ripe fruit of Vitex agnus-castus. In Europe it is used as a medicine targeting premenstrual syndrome and climacteric disorder. In Japan, Agnus Castus Fruit is becoming popular as a raw material for over-the-counter drugs and health food products,...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0035-1558089

    authors: Oshima N,Masada S,Suzuki R,Yagi K,Matsufuji H,Suenaga E,Takahashi Y,Yahagi T,Watanabe M,Yahara S,Iida O,Kawahara N,Maruyama T,Goda Y,Hakamatsuka T

    更新日期:2016-01-01 00:00:00

  • Protein tyrosine phosphatase 1B (PTP1B)-inhibiting constituents from the leaves of Syzygium polyanthum.

    abstract::A methanol extract of the leaves of Syzygium polyanthum (Wight) Walp. afforded four new acylbenzene derivatives (1-4) together with seven known compounds (5-11). The structures of 1-11 were elucidated by extensive spectroscopic methods and comparison with the literature data. The new compounds 1-3 and a known compound...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0032-1315000

    authors: Saifudin A,Tanaka K,Kadota S,Tezuka Y

    更新日期:2012-08-01 00:00:00

  • New Flavonoids from Boldoa purpurascens Cav.

    abstract::Phytochemical analysis of the leaves of BOLDOA PURPURASCENS Cav. led to isolation of four flavone glycosides, three of which are new compounds. Their structures have been determined by mass spectrometry and by 1 D and 2 D NMR analysis, i. e., 4',5-dihydroxy-6,7-methylenedioxyflavonol 3- O-alpha- L-rhamnopyranosyl-(1--...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2008-1081332

    authors: Mosquera DM,Kilonda A,Toppet S,Compernolle F,Dehaen W,François IE,Cammue BP,Apers S,Pieters L,Cuéllar AC

    更新日期:2008-10-01 00:00:00

  • Arctigenin Attenuates Learning and Memory Deficits through PI3k/Akt/GSK-3β Pathway Reducing Tau Hyperphosphorylation in Aβ-Induced AD Mice.

    abstract::Arctigenin is a phenylpropanoid dibenzylbutyrolactone lignan compound possessing antitumor, anti-inflammatory, anti-influenza, antioxidant, antibacterial, and hypoglycaemic activities. Our previous study demonstrated that arctigenin exerts neuroprotective effects both in vitro and in vivo in a Parkinson's disease mode...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0042-107471

    authors: Qi Y,Dou DQ,Jiang H,Zhang BB,Qin WY,Kang K,Zhang N,Jia D

    更新日期:2017-01-01 00:00:00

  • Antifungal sesquiterpenes from Cedrus deodara.

    abstract::Two new sesquiterpenes, (E)-(2S,3S,6R)-atlantone-2,3-diol (1) and (E)-(2S,3S,6S)-atlantone-2,3,6-triol (2), along with two known sesquiterpenes, atlantolone (3) and (E)-α-atlantone (4), were isolated from Cedrus deodara Loud. The structures of the new compounds were elucidated on the basis of UV, IR, NMR, HR‑ESI-QTOF‑...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-0031-1280264

    authors: Chaudhary A,Sood S,Kaur P,Kumar N,Thakur A,Gulati A,Singh B

    更新日期:2012-01-01 00:00:00

  • Stimulatory effects of ingenols from Euphorbia kansui on the expression of macrophage Fc receptor.

    abstract::Immune complex binding to macrophages was enhanced by treatment with an E. kansui extract. Systematic fractionation of the extract led to the characterization of 3-O-(2'E,4'Z-decadienoyl)- and 3-O-(2,3-dimethylbutyryl)-13- O-n-dodecanoyl-13-hydroxyingenol as the active principles. Immune complex binding to macrophages...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-961447

    authors: Matsumoto T,Cyong JC,Yamada H

    更新日期:1992-06-01 00:00:00

  • Isolation and Structure of Neriucoumaric and Isoneriucoumaric Acids from the Leaves of Nerium oleander.

    abstract::Two new coumaryloxy triterpenoids, neriucoumaric and isoneriucoumaric acids, have been isolated from fresh, undried and uncrushed leaves of NERIUM OLEANDER and their structures established as 3beta-hydroxy-2alpha-cis- P-coumaryloxy-urs-12-en-28-oic acid and 3beta-hydroxy-2alpha- TRANS- P-coumaryloxy-urs-12-en-28-oic a...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-962763

    authors: Siddiqui S,Siddiqui BS,Hafeez F,Begum S

    更新日期:1987-10-01 00:00:00

  • Flavonol glycoside gallate and ferulate esters from Persicaria lapathifolia as inhibitors of superoxide production in human monocytes stimulated by unopsonized zymosan.

    abstract::Aerial parts of Persicaria lapathifolia S.F. Gray (Polygonaceae) exhibited an inhibitory effect on superoxide production in unopsonized zymosan-stimulated human monocytes. Two known compounds, quercetin 3-O-beta-(2"-galloyl)-glucopyranoside and quercetin 3-O-beta-(2"-galloyl)-rhamnopyranoside, and a new compound, quer...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-0029-1243112

    authors: Kim Y,Jang DS,Park SH,Yun J,Min BK,Min KR,Lee HK

    更新日期:2000-02-01 00:00:00

  • Stimulatory effect of puerarin on alpha1A-adrenoceptor to increase glucose uptake into cultured C2C12 cells of mice.

    abstract::Effects of puerarin, an active principle contained in the roots of Pueraria lobata (Leguminosae), on the regulation of glucose metabolism in an insulin deficient state were investigated in cultured myoblast C 2 C 12 cells using glucose uptake as indicator. Puerarin enhanced the uptake of radioactive glucose into C 2 C...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2002-35656

    authors: Hsu HH,Chang CK,Su HC,Liu IM,Cheng JT

    更新日期:2002-11-01 00:00:00

  • Effects of Sideritis scardica Extract on Glucose Tolerance, Triglyceride Levels and Markers of Oxidative Stress in Ovariectomized Rats.

    abstract::Menopause is characterized by deep metabolic disturbances, including decreased insulin sensitivity, adiposity, and changes in lipid profiles. Estrogen replacement therapy can partially reverse these changes, and while it is safe in most healthy postmenopausal women, there are still existing concerns regarding an incre...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/a-0835-6622

    authors: Jeremic I,Petricevic S,Tadic V,Petrovic D,Tosic J,Stanojevic Z,Petronijevic M,Vidicevic S,Trajkovic V,Isakovic A

    更新日期:2019-04-01 00:00:00

  • Cytotoxic alkaloids from the roots of Tylophora atrofolliculata.

    abstract::Four new phenanthroindolizidine alkaloids, tylophoridicines C-F, together with three known ones, R-(+)-deoxytylophorinidine, tylophorinine and tylophorinidine, were isolated from the roots of Tylophora atrofolliculata. The structures were determined on the basis of spectral evidence. These alkaloids exhibited cytotoxi...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2004-818973

    authors: Huang X,Gao S,Fan L,Yu S,Liang X

    更新日期:2004-05-01 00:00:00

  • Anti-asthmatic effects of Perilla seed oil in the guinea pig in vitro and in vivo.

    abstract::The aim of this study was to investigate the anti-asthmatic effects of Perilla seed oil in vitro and in vivo in sensitized guinea pigs. Aerosolized antigen caused an immediate bronchoconstriction. Perilla seed oil per os inhibited the increase in lung resistance and the decrease in dynamic lung compliance in a dose-de...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957062

    authors: Deng YM,Xie QM,Zhang SJ,Yao HY,Zhang H

    更新日期:2007-01-01 00:00:00

  • Cytotoxic cyclopenta[b]benzofuran derivatives from the stem bark of Aglaia formosana.

    abstract::A new cytotoxic cyclopenta[b]benzofuran derivative, aglaiformosanin (1) and three known cyclopenta[b]benzofuran derivatives (2 - 4) were isolated from the stem bark of Aglaia formosana. Compounds 1 - 4 exhibited potent cytotoxicity against the P-388, KB, HT-29, HL-60, and A549 cell lines. The structure of compound 1 w...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-2001-16471

    authors: Wang SK,Duh CY

    更新日期:2001-08-01 00:00:00

  • High frequency plant regeneration from leaf derived callus of high Δ9-tetrahydrocannabinol yielding Cannabis sativa L.

    abstract::An efficient in vitro propagation protocol for rapidly producing Cannabis sativa plantlets from young leaf tissue was developed. Using gas chromatography-flame ionization detection (GC-FID), high THC yielding elite female clone of a drug-type CANNABIS variety (MX) was screened and its vegetatively propagated clones we...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0030-1249773

    authors: Lata H,Chandra S,Khan IA,Elsohly MA

    更新日期:2010-10-01 00:00:00

  • Composition of the Essential Oil of Cymbopogon travancorensis.

    abstract::The chemical composition of the essential oil of CYMBOPOGON TRAVANCORENSIS Bor. (Poaceae) was investigated by capillary GC and GC-MS. Thirty-five compounds were identified. The oil contains mono- and sesquiterpene hydrocarbons (39.60%), oxygenated terpenes (30.45%), and phenyl propanoids (22.04%). The main constituent...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-961434

    authors: Mallavarapu GR,Ramesh S,Kulkarni RN,Syamasundar KV

    更新日期:1992-04-01 00:00:00

  • Isolation of two triterpenoids and a biflavanone with anti-Inflammatory activity from Schinus molle fruits.

    abstract::Three compounds with anti-inflammatory activity were isolated from Schinus molle fruits. Two of the compounds were identified as 3- epi-isomasticadienolalic acid ( 1), isomasticadienonalic acid ( 2) and chamaejasmin ( 3). Triterpenes 1 and 2, and biflavanone 3 were tested on two models of mice paw inflammation: one of...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2003-45096

    authors: Yueqin Z,Recio MC,Máñez S,Giner RM,Cerdá-Nicolás M,Ríos JL

    更新日期:2003-10-01 00:00:00

  • Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection.

    abstract::Many compounds of plant origin have been identified that inhibit different stages in the replication cycle of human immunodeficiency virus (HIV): 1) virus adsorption: chromone alkaloids (schumannificine), isoquinoline alkaloids (michellamines), sulphated polysaccharides and polyphenolics, flavonoids, coumarins (glycoc...

    journal_title:Planta medica

    pub_type: 杂志文章,评审

    doi:10.1055/s-2006-957384

    authors: Vlietinck AJ,De Bruyne T,Apers S,Pieters LA

    更新日期:1998-03-01 00:00:00

  • Essential oil from Myrcia ovata: chemical composition, antinociceptive and anti-inflammatory properties in mice.

    abstract::The leaves of Myrcia ovata, popularly known as "laranjinha do mato", are frequently used as an infusion in folk medicine. The essential oil obtained from these leaves is rich in citral, a mixture of neral and geranial isomers, known for its analgesic effect. Male Swiss mice (20-22 g) were tested in models of acute pai...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0034-1383120

    authors: Dos Santos GC,Gomes GA,Gonçalves GM,de Sousa LM,Santiago GM,de Carvalho MG,Marinho BG

    更新日期:2014-11-01 00:00:00

  • [Iridoid Glucosides from Euphrasia rostkoviana].

    abstract::Eight iridoid glucosides have been isolated from Euphrasia rostkoviana by the combination of open column- and high performance liquid chromatography. The structure of a new compound, named eurostoside, and the identity of the others have been established by chemical transformations and spectral evidence of the compoun...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-969960

    authors: Salama O,Sticher O

    更新日期:1983-02-01 00:00:00

  • Antineoplastic agents. II. Four furostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca.

    abstract::During activity-guided fractionations to screen for antineoplastic agents, further studies by means of preparative HPLC led to the isolation of four known furostanol saponins: protoneodioscin, protodioscin, protoneogracillin, protogracillin, along with their corresponding artifacts: methyl protoneodioscin, methyl prot...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957636

    authors: Hu K,Dong A,Yao X,Kobayashi H,Iwasaki S

    更新日期:1997-04-01 00:00:00