Phytochemistry (v.65, #4)

Graphical Abstracts (371-376).

Quivisianthone, an evodulone limonoid from the Madagascan Meliaceae Quivisia papinae by Philip H. Coombes; Dulcie A. Mulholland; Milijaona Randrianarivelojosia (377-380).
An investigation of the seeds of the Madagascan Meliaceae Quivisia papinae has yielded quivisianthone, a novel evodulone group limonoid, together with the known azadiradione and two novel derivatives: 6α-hydroxyazadiradione and 7-deacetyl-7-angeloyl-6α-hydroxyazadiradione. Quivisianthone is the first reported evodulone group limonoid possessing both a ring A lactone and an azadiradione-type ring D.The seeds of the Madagascan Meliaceae Quivisia papinae have yielded quivisianthone, a novel evodulone group limonoid, together with the known azadiradione and two novel derivatives: 6α-hydroxyazadiradione and 7-deacetyl-7-angeloyl-6α-hydroxyazadiradione. Quivisianthone is the first reported evodulone group limonoid possessing both a ring A lactone and an azadiradione-type ring D.
Keywords: Quivisia papinae; Meliaceae; Madagascar; Seeds; Isolation; Limonoids; Azadiradone; 6α-Hydroxyazadiradione; 7-Deacetyl-7-angeloyl-6α-hydroxyazadiradione; Evodulone; Quivisianthone;

Four illudane sesquiterpenes from Coprinopsis episcopalis by Matı́as Reina; Juan C Orihuela; Azucena González-Coloma; Concepción de Inés; Mercedes de la Cruz; Antonio González del Val; José R Torno; Braulio M Fraga (381-385).
Four new illudane derivatives with antibiotic and cytotoxic properties, illudins I (1), I2 (2), J (3) and J2 (4), have been isolated from the fungus Coprinopsis episcopalis (syn. Coprinus episcopalis). These sesquiterpenes are stereoisomers, and their relative structures have been determined taking into consideration 2D NMR data.Four new illudane derivatives, illudins I (1), I2 (2), J (3) and J2 (4), have been isolated from the fungus Coprinopsis episcopalis.
Keywords: Coprinopsis episcopalis; Basidiomycetes; Sesquiterpenes; Illudins;

Neo-clerodane diterpenes from Teucrium fruticans by Josep Coll; Yudelsy Tandrón (387-392).
In addition to three out of the four previously reported neo-clerodanes already found in Teucrium fruticans (fruticolone, isofruticolone and 8β-hydroxyfruticolone), and 6-acetylteucjaponin B (isolated from T. scordium and T. grisebachii), four new neo-clerodanes, namely 7β-hydroxyfruticolone, 11-hydroxyfruticolone, deacetylfruticolone and 6-acetyl-10-hydroxyteucjaponin B were also isolated. The structures were unambiguously elucidated based on extensive NMR spectral studies (one- and two-dimensional experiments). Semi-prep-HPLC proved to be a convenient purification procedure, occasionally being followed by TLC. The new compounds were assayed against Spodoptera littoralis and two of them were shown to have potent antifeedant activity.Four new neo-clerodane diterpenes were isolated from aerial parts of T. fruticans, together with four known compounds. Antifeedant activity against Spodoptera littoralis was determined.
Keywords: Teucrium fruticans; Labiatae; Structure elucidation; NMR; Neo-clerodane diterpenes; Antifeedant activity;

Lanostanes and friedolanostanes from the bark of Garcinia speciosa by Luis M.M. Vieira; Anake Kijjoa; Artur M.S. Silva; Ing-On Mondranondra; Surapong Kengthong; Luis Gales; Ana Margarida Damas; Werner Herz (393-398).
The CHCl3 extract of the bark of Garcinia speciosa contained four 17,14-friedolanostanes and five lanostanes as well as friedelin and common plant constituents. The friedolanostanes were the previously known methyl ester of (24E)-3α,23α-dihydroxy-17,14-friedolanostan-8,14,24-trien-26-oic acid and the methyl esters of three hitherto unknown acids, 3α-hydroxy-16α,23α-epoxy-17,14-friedolanostan-8,14,24-trien-26-oic acid, 3α,23α-dihydroxy-8α,9α-epoxy-17,14-friedolanostan-15-oxo-24-en-26-oic acid and 3α,23α-dihydroxy-17,14-friedolanostan-15-oxo-8(14),24-dien-26-oic acid. New lanostanes were 3β,9α-dihydroxylanost-24-en-26-al and the methyl ester of 3β-hydroxy-23-oxo-9,16-lanostadien-26-oic acid. Structures were established by analysis of spectroscopic data. In the case of the lanostanes the previously unassigned C-25 stereochemistry was shown to be 25R by X-ray analysis of 3β-hydroxy-23-oxo-9,16-lanostadien-26-oic acid. In the case of the friedolanostanes the configuration at C-23 was established as 23R, identical with the absolute configuration at C-23 of mariesiic acids A and B.Five 17,14-friedolanostanes and five lanostanes were isolated from the bark of Garcinia speciosa. Structures of new compounds were established by spectroscopic methods.
Keywords: Garcinia speciosa; Guttiferae; 17,14-Friedolanostanes; Lanostanes;

(±)-Schefflone: a trimeric monoterpenoid from the root bark of Uvaria scheffleri by Mayunga H.H. Nkunya; Stephan A. Jonker; René de Gelder; Sabina W. Wachira; Charles Kihampa (399-404).
The trimeric monoterpene and mildly mosquito larvicidal agent, (±)-schefflone, that is an apparent derivative of the antiparasitic aromatic monoterpene espintanol, was isolated from the antimalarial extracts of the root bark of Uvaria scheffleri, together with espintanol. Structural determination of (±)-schefflone was achieved from spectroscopic data and confirmed by single-crystal X-ray diffraction analysis. (±)-Schefflone can be considered a product of a non-enzymatic Diels–Alder-type cycloaddition reaction of the quinonemethide derivative of espintanol as the diene and dienophile.The trimeric monoterpene and mild mosquito larvicide (±)-schefflone (3), and the antiprotozoal and presumed monoterpene precursor espintanol (4) were isolated from the root bark of Uvaria scheffleri. Structure 3 was determined from spectral and single-crystal X-ray data.
Keywords: Uvaria scheffleri; Annonaceae; Trimeric monoterpene; (±)-Schefflone; Espintanol; Mosquitocides;

Anthocyanin from strawberry (Fragaria ananassa) with the novel aglycone, 5-carboxypyranopelargonidin by Øyvind M Andersen; Torgils Fossen; Kjell Torskangerpoll; Arve Fossen; Unni Hauge (405-410).
An anthocyanin, 1, with the novel 4-substituted aglycone, 5-carboxypyranopelargonidin, was isolated in small amounts from the acidified, methanolic extract of strawberries, Fragaria ananassa Duch., by preparative HPLC after purification by partition against ethyl acetate, Amberlite XAD-7 and Sephadex LH-20 column chromatography. It was identified mainly by 2D NMR spectroscopy and electrospray LC-MS as the 3-O-β-glucopyranoside of 5-carboxy-2-(4-hydroxyphenyl)-3,8-dihydroxy-pyrano[4,3,2-de]-1-benzopyrylium, an anthocyanidin which is homologous to 5-carboxypyranomalvidin (vitisidin A) reported in red wines and 5-carboxypyranocyanidin recently isolated from red onions. By comparison of UV–Vis absorption spectra, 1 showed in contrast to 2, pelargonidin 3-O-β-glucopyranoside, a local absorption peak around 360 nm, a hypsochromic shift (8 nm) of the visible absorption maximum, and lack of a distinct UV absorption peak around 280 nm. The similarities between the absorption spectra of 1 in various acidic and neutral buffer solutions implied restricted formation of the instable colourless equilibrium forms, which are typical for most anthocyanins in weakly acidic solutions. The molar absorptivity (ϵ) of 1 varied little with pH contrary to similar values of for instance the major anthocyanin in strawberry, 2. However, 2 revealed higher ϵ-values than 1 at all pH values except 5.1. At pH 5.1, the ϵ-value of 1 (6250) was nearly four times the corresponding value of 2 (1720), which showed the potential of 5-carboxypyranopelargonidin derivatives as colorants in solutions with pH around 5. The colours of 1 and 2 in buffered solutions with pH 1.1 and pH 6.9 have been described by the CIELAB coordinates h ab (hue angle), C* (chroma), and L* (lightness).The minor anthocyanin 5-carboxypryanopelargonidin 3-O-β-glucopyranoside, 1, has been isolated from acidified, methanolic extracts of strawberries. Its UV–Vis absorption spectra and CIELAB parameter have been recorded at various pH values.
Keywords: Strawberries; Fragaria ananassa; Anthocyanin; 5-Carboxypyranopelargonidin 3-O-β-glucopyranoside; UV–Vis spectrum; Colours; CIELAB; 2D NMR;

Detection of hypericins in the “red glands” of Hypericum elodes by ESI–MS/MS by Anna Piovan; Raffaella Filippini; Rosy Caniato; Anna Borsarini; Laura Bini Maleci; Elsa Mariella Cappelletti (411-414).
The biologically active naphthodianthrones hypericin and pseudohypericin were detected by electrospray ionization mass spectrometry (ESI-MS/MS) in microsamples from the sepals of Hypericum elodes (Hypericaceae) containing the so-called “red glands”, i.e. stipitate glands with red-coloured heads. The occurrence of hypericins in the red glands of H. elodes supports the taxonomic position of the section Elodes within the genus Hypericum and provides evidence that the ability of carrying out the biosynthetic pathway leading to the naphthodianthrone compounds, rather than the absolute amounts produced, should be regarded as a chemical marker of the phylogenetically more advanced sections of genus Hypericum. The biologically active phloroglucinol derivatives hyperforin and adhyperforin, so far found only in H. perforatum, were also detected and evidence for their localization in the sepal secretory canals with large lumen, is given.The biologically active naphthodianthrones hypericin and pseudohypericin were detected by electrospray ionization mass spectrometry (ESI–MS/MS) in microsamples from the sepals of Hypericum elodes (Hypericaceae) containing the so-called “red glands”.
Keywords: Hypericum elodes; Hypericaceae; Red glands; ESI–MS/MS; Naphthodianthrones; Hypericin; Phloroglucinols; Hyperforin;

Structural investigations on betacyanin pigments by LC NMR and 2D NMR spectroscopy by Florian C Stintzing; Jürgen Conrad; Iris Klaiber; Uwe Beifuss; Reinhold Carle (415-422).
Four betacyanin pigments were analysed by LC NMR and subjected to extensive NMR characterisation after isolation. Previously, low pH values were applied for NMR investigations of betalains resulting in rapid degradation of the purified substances thus preventing extensive NMR studies. Consequently, up to now only one single 13C NMR spectrum of a betalain pigment, namely that of neobetanin (=14,15-dehydrobetanin), was available. Because of its sufficient stability under highly acidic conditions otherwise detrimental for betacyanins, this pigment remained an exemption. Since betalains are most stable in the pH range of 5–7, a new solvent system has been developed allowing improved data acquisition through improved pigment stability at near neutral pH. Thus, not only 1H, but for the first time also partial 13C data of betanin, isobetanin, phyllocactin and hylocerenin isolated from red-purple pitaya [Hylocereus polyrhizus (Weber) Britton & Rose, Cactaceae] could be indirectly obtained by gHSQC– and gHMQC–NMR experiments.Four betacyanin pigments hitherto characterised by mass spectrometric and proton nuclear magnetic resonance (NMR) analyses were subjected to extensive NMR characterisation. A new solvent system considering the pH stability characteristics of betalain pigments was developed. For the first time, 13C NMR data of betanin, isobetanin, phyllocactin and hylocerenin could thus be obtained.
Keywords: Betalains; Betacyanin; Betanin; Isobetanin; Phyllocactin; Hylocerenin; Pitaya; Hylocereus polyrhizus; NMR spectroscopy; LC NMR spectroscopy;

l-O-Caffeoylhomoserine from Matteuccia struthiopteris by Toshiyuki Kimura; Masahiro Suzuki; Makiko Takenaka; Kenji Yamagishi; Hiroshi Shinmoto (423-426).
A caffeic acid derivative was isolated from Matteuccia struthiopteris (ostrich fern) as a major radical scavenger. The compound consisted of caffeic acid and l-homoserine. NMR and MS analysis revealed the structure as l-O-caffeoylhomoserine.A caffeic acid derivative was isolated from Matteuccia struthiopteris (ostrich fern) as a major radical scavenger. The compound consists of caffeic acid and l-homoserine.
Keywords: Matteuccia struthiopteris; Dryopteridaceae; Ostrich fern; l-O-Caffeoylhomoserine; Radical scavenger;

Diprenylated chalcones and other constituents from the twigs of Dorstenia barteri var. subtriangularis by Barthelemy Ngameni; Bonaventure T. Ngadjui; Gabriel N. Folefoc; Jean Watchueng; Berhanu M. Abegaz (427-432).
The twigs of Dorstenia barteri var. subtriangularis yielded three diprenylated chalcones: (−)-3-(3,3-dimethylallyl)-5′-(2-hydroxy-3-methylbut-3-enyl)-4,2′,4′-trihydroxychalcone, (+)-3-(3,3-dimethylallyl)-4′,5′-[2‴-(1-hydroxy-1-methylethyl)-dihydrofurano]-4,2′-dihydroxychalcone and 3,4-(6″,6″-dimethyldihydropyrano)-4′,5′-[2‴,-(1-hydroxy-1-methylethyl)-dihydrofurano]-2′-hydroxychalcone for which the names bartericins A, B and C, respectively, are proposed. Stipulin, β-sitosterol and its 3-β-D-glucopyranosyl derivative were also isolated. The structures of these secondary metabolites were determined on the basis of spectroscopic analysis, especially, NMR spectra in conjunction with 2D experiments, COSY, HMQC and HMBC. The structural relationship of bartericins B and C was further established by the chemical cyclization of one to the other.The twigs of Dorstenia barteri var. subtriangularis yielded three new diprenylated chalcones, named: bartericins A (3), B (4) and C (5).
Keywords: Dorstenia barteri var. subtriangularis; Moraceae; Twigs; Isolation; Prenylated chalcones; Bartericins A, B and C;

Cyclobutanes from Combretum albopunctatum by David R Katerere; Alexander I Gray; Alan R Kennedy; Robert J Nash; Roger D Waigh (433-438).
A dichloromethane extract of the aerial parts of Combretum albopunctatum Suesseng afforded five phenolic compounds—three known flavonoids and two novel cyclobutane chalcone dimers. The chemical structures were determined by standard spectroscopic techniques and the structure and relative stereochemistry of one chalcone dimer, rel-(1α,2β)-di-(2,6-dimethoxy-4-hydroxy)-benzoyl-rel-(3α,4β)-diphenylcyclobutane, were confirmed by single crystal X-ray diffraction.Two new cyclobutane chalcone dimers have been isolated from the aerial parts of C. albopunctatum.
Keywords: Combretum albopunctatum; Combretaceae; Flavonoids; Chalcones; Flavanones Chalcone dimer;

Furanoflavonoids from Pongamia pinnata fruits by Prem P Yadav; Ghufran Ahmad; Rakesh Maurya (439-443).
Fruits of Pongamia pinnata afforded four new furanoflavonoids, pongapinnol A–D (14), and a new coumestan, pongacoumestan (5) along with thirteen known compounds 618. Compounds 16 and 17 are isolated for the first time from this plant. The structures of isolated compounds were elucidated on the basis of spectroscopic data interpretation.Fruits of Pongamia pinnata afforded four new furanoflavonoids, pongapinnol A–D (14), and a new coumestan, pongacoumestan (5), along with 13 known compounds 618. Compounds 16 and 17 are isolated for the first time from this plant.
Keywords: Pongamia pinnata; Leguminosae; Furanoflavones; Furanoflavonols; Coumestan;

Flavonoids from Cleistocalyx operculatus by Chun-Lin Ye; Yan-Hua Lu; Dong-Zhi Wei (445-447).
Two flavonoids 3′-formyl-4′,6′-dihydroxy-2′-methoxy-5′-methylchalcone and (2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone together with five known compounds, were isolated from the dried buds of Cleistocalyx operculatus. Their structures were determined on the basis of spectroscopic analyses (UV, IR, EIMS, 1H, 13C NMR and HMBC).Two flavonoids and five known compounds were isolated from the buds of Cleistocalyx operculatus. The structures were elucidated by spectroscopic methods, including analysis by 2D NMR spectroscopy.
Keywords: Cleistocalyx operculatus; Myrtaceae; Flavonoids; Chalcones; Flavanones;

N,β-d-Glucopyranosyl vincosamide, a light regulated indole alkaloid from the shoots of Psychotria leiocarpa by Amélia T. Henriques; Sı́lvia O. Lopes; Juçara T. Paranhos; Tatiana S. Gregianini; Arthur G. Fett-Neto; Jan Schripsema; Gilsane Lino Von Poser (449-454).
From leaves of Psychotria leiocarpa, an indole alkaloid was isolated to which the structure N,β-d-glucopyranosyl vincosamide (1) was assigned. This represents the first report of an N-glycosylated monoterpenoid indole alkaloid. In field-grown plants highest amounts of 1 were found in the leaves (2.5% of dry wt) and fruit pulp (1.5% dry wt). Lower amounts were found in the stems (0.2% dry wt) and the seeds (0.1% of dry wt), whereas the alkaloid was not detected in the roots. The accumulation of 1 in aseptic seedlings was also restricted to the shoots and increased with plant age and light exposure, independent of the supply of sucrose in the culture medium.The first N-glycosylated monoterpenoid indole alkaloid, N,β-d-glucopyranosyl vincosamide was isolated from leaves of Psychotria leiocarpa. It was restricted to shoots (2.5% dry wt in leaves) and its accumulation was promoted by light and age.
Keywords: Psychotria leiocarpa; Rubiaceae; Light regulation; Organ distribution; Indole alkaloid; N,β-d-glucopyranosyl vincosamide;

Enteridinines A and B from slime mold Enteridium lycoperdon by Tomáš Řezanka; Radmila Dvořáková; Lumı́r O. Hanuš; Valery M. Dembitsky (455-462).
Two novel deoxysugar esters, named enteridinines A and B, were isolated from the slime mold Enteridium lycoperdon. Their structures, including the absolute configurations of the hydroxyl and methyl groups, were determined by means of extensive spectroscopic data such as UV, IR, MS, 1D and 2D NMR spectra. Enteridinines A and B have unique structures containing 1,7-dioxaspiro[5.5]undecanes with an O-β-d-mycarosyl-(1→4)-β-d-olivosyl and an O-β-l-olivomycosyl-(1→4)-β-d-amicetosyl-(1→4)-β-l-digitoxosyl unit, respectively, and showed growth inhibitory activities against Gram positive bacteria.Two novel deoxysugar esters, named enteridinines A and B, were isolated from the slime mold Enteridium lycoperdon. They have structures containing 1,7-dioxaspiro[5.5]undecanes with deoxysugars and showed growth inhibitory activities against Gram positive bacteria.
Keywords: Enteridium lycoperdon; Myxomycetes; Deoxysugar esters; Spiro[5.5]undecane derivatives; Slime mold;

C,O-Bisglycosylapigenins from the leaves of Rhamnella inaequilatera by Yoshio Takeda; Yoshihiro Okada; Toshiya Masuda; Eiji Hirata; Takakazu Shinzato; Hideaki Otsuka (463-468).
From the leaves of Rhamnella inaequilatera, three flavone C,O-bisglycosides, rhamnellaflavosides A, B and C, were isolated and their structures were elucidated based on their spectral data and chemical evidence.From the leaves of Rhamnella inaequilatera, three flavone C,O-bisglycosides were isolated and the structures were elucidated.
Keywords: Rhamnella inaequilatera; Rhamnaceae; Rhamnellaflavosides A, B and C; Apigenin; Oliose; Boivinose;

Cyclic azaphilones daldinins E and F from the ascomycete fungus Hypoxylon fuscum (Xylariaceae) by Dang Ngoc Quang; Toshihiro Hashimoto; Masami Tanaka; Marc Stadler; Yoshinori Asakawa (469-473).
Phytochemical examination of the methanolic extract of fruit bodies of the Xylariaceous ascomycete fungus Hypoxylon fuscum led to the isolation of two azaphilone derivatives named daldinins E and F together with two known compounds daldinin C and 4,5,4′,5′-tetrahydroxy-1:1′-binaphthyl using a combination of reversed phase HPLC and high performance gel permeation chromatography. Their structures were determined by 2D NMR, MS, IR, UV, and CD spectroscopy. Their antioxidative activities were also estimated by an indication of a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging effect. The chemosystematics of Hypoxylon is discussed.Two azaphilones named daldinins E (1) and F (2) together with two known compounds daldinin C and tetrahydroxybinaphthyl were isolated from the xylariaceous ascomycete Hypoxylon fuscum. Their structures were determined by a combination of 2D NMR, IR, UV, CD and MS.
Keywords: Daldinin; Hypoxylon; Xylariaceae; Fungus; Azaphilone; Chemosystematics;

Ascosonchine, the enol tautomer of 4-pyridylpyruvic acid with herbicidal activity produced by Ascochyta sonchi by Antonio Evidente; Anna Andolfi; Mohamed A Abouzeid; Maurizio Vurro; Maria Chiara Zonno; Andrea Motta (475-480).
A new phytotoxic enol tautomer of 4-pyridylpyruvic acid, named ascosonchine, was isolated from the culture filtrate of Ascochyta sonchi. Such a leaf pathogen is a potential biocontrol agent of Sonchus arvensis, a perennial herbaceous weed occurring throughout the temperate regions of the world. Ascosonchine, characterised as (Z)-2-hydroxy-3-(4-pyridyl)-2-propenoic acid by spectroscopic methods, showed selective herbicidal properties, that are not associated with antibacterial, antifungal or zootoxic activities.We report the isolation and the chemical and biological characterisation of ascosonchine (1), the (Z)-2-hydroxy-3-(4-pyridyl)-2-propenoic acid produced by Ascochyta sonchi, and showing interesting selective herbicidal properties, not associated to antibacterial, antifungal or zootoxic activities.
Keywords: Ascosonchine; Sonchus arvensis; Ascochyta sonchi; Mycoherbicide; Phytotoxins; 4-Pyridylpyruvic acid; Weed biocontrol;

Maltol glucosides from the tuber of Smilax bockii by Hongzhu Guo; Kazuo Koike; Wei Li; Dean Guo; Tamotsu Nikaido (481-484).
Two maltol glucosides, bockiosides A and B, along with 10 known compounds, were isolated from the tuber of Smilax bockii (Liliaceae), and their structures were elucidated by spectral experiments, chemical analysis and comparison with literature data.Two maltol glucosides, bockiosides A (1) and B (2), along with ten known compounds were isolated from the tuber of Smilax bockii. Their structures were elucidated by spectral and chemical analysis.
Keywords: Smilax bockii; Liliaceae; Bockioside A; Bockioside B; Maltol glucoside;

Lasianthionosides A–C, megastigmane glucosides from leaves of Lasianthus fordii by Yoshio Takeda; Hideko Shimizu; Toshiya Masuda; Eiji Hirata; Takakazu Shinzato; Masahiko Bando; Hideaki Otsuka (485-489).
From the leaves of Lasianthus fordii, three megastigmane glucosides, lasianthionosides A, B and C, were isolated together with the known iridoid glucoside, asperuloside, deacetylasperuloside and methyl deacetyl-asperulosidate, and a megastigmane glucoside, citroside A. The structures have been elucidated based on spectroscopic analyses and/or X-ray crystallographic analysis.From the leaves of Lasianthus fordii, three megastigmane glucosides were isolated and the structures were elucidated by means of spectroscopic analyses and X-ray analysis.
Keywords: Lasianthus fordii; Rubiaceae; Lasianthionosides A, B and C; Megastigmane glucoside;

Fascicularones A and B from a mycelial culture of Naematoloma fasciculare by Yoshihito Shiono; Ryutarou Matsuzaka; Hiroko Wakamatsu; Kimiko Muneta; Tetsuya Murayama; Michimasa Ikeda (491-496).
Two sesquiterpenoids, fascicularones A and B, have been isolated from the culture broth of a poisonous mushroom, Naematoloma fasciculare. Their structures were determined using spectroscopic methods.Two sesquiterpenoids, fascicularones A and B, were isolated from the mycelia of a poisonous mushroom, Naematoloma fasciculare in a shaken culture. The structures of compounds were established on the basis of spectroscopic techniques.
Keywords: Naematoloma fasciculare; Nigakuritake; Poisonous mushroom; Fascicularones A and B; Sesquiterpenoids;

Structure elucidation and phytotoxicity of C13 nor-isoprenoids from Cestrum parqui by Brigida D'Abrosca; Marina DellaGreca; Antonio Fiorentino; Pietro Monaco; Palma Oriano; Fabio Temussi (497-505).
Twelve C13 nor-isoprenoids have been isolated from the leaves of Cestrum parqui (Solanaceae). The structure (2R,6R,9R)-2,9-dihydroxy-4-megastigmen-3-one has been assigned to the new compound. All the structures have been determined by spectroscopic means and chemical correlations. The compounds showed phytotoxic effect on the germination and growth of Lactuca sativa L.Twelve C13 nor-isoprenoids have been isolated from the leaves of Cestrum parqui. All the structures have been determined by spectroscopic means and chemical correlations. The compounds showed phytotoxic effect on the germination and growth of Lactuca sativa.
Keywords: Cestrum parqui; Solanaceae; Spectroscopic analysis; Phytotoxicity; C13-Nor-isoprenoids;

Cytotoxic cardenolide glycoside from the seeds of Cerbera odollam by Surat Laphookhieo; Sarot Cheenpracha; Chatchanok Karalai; Suchada Chantrapromma; Yanisa Rat-a-pa; Chanita Ponglimanont; Kan Chantrapromma (507-510).
A cardenolide glycoside, 3β-O-(2′-O-acetyl-l- thevetosyl)-15(14→8)-abeo-5β-(8R)-14-oxo-card-20(22)-enolide (2′-O-acetyl cerleaside A), was isolated from a methylene chloride extract of the seeds of Cerbera odollam, together with four known compounds: cerleaside A, 17α-neriifolin, 17β- neriifolin and cerberin. Their structures were elucidated by spectroscopic methods. All compounds except cerleaside A exhibited cytotoxic activities against oral human epidermoid carcinoma (KB), human breast cancer cell (BC) and human small cell lung cancer (NCI-H187).Cardenolide glycoside, 3β-O-(2′-O-acetyl-l- thevetosyl)-15(14→8)-abeo-5β-(8R)-14-oxo-card-20(22)-enolide (2′-O-acetyl cerleaside A), was isolated from methylene chloride extract from the seeds of Cerbera odollam.
Keywords: Cerbera odollam; Apocynaceae; Cardenolide; Cytotoxicity;