Phytochemistry Vol. 88

Contents

PROTEIN BIOCHEMISTRY AND PROTEOMICS

A heterotetrameric alpha-amylase inhibitor from emmer (Triticum dicoccon Schrank) seeds pp 6–14

A. Capocchi, V. Muccilli, V. Cunsolo, R. Saletti, S. Foti, D. Fontanini*

A heterotetrameric a-amylase inhibitor (ETI) resulting from the aggregation of three CM proteins, was isolated fromemmer wheat seeds. Inhibition kinetics of heterologous a-amylases by the heterotetramer as well as the subunitsbinary assemblies were studied. Based on MS sequence analyses, possible homology models for both the singlesubunits and the heterotetrameric aggregate were proposed.

METABOLISM

In vitro formation of the anthranoid scaffold by cell-free extracts fromyeast-extract-treated Cassia bicapsularis cell cultures

pp 15–24

Iman A.M. Abdel-Rahman, Till Beuerle, Ludger Ernst, Afaf M. Abdel-Baky,Ezz El-Din K. Desoky, Amany S. Ahmed, Ludger Beerhues*

acetyl-CoA malonyl-CoA

SCoAH3C

O

COOHSCoA

O

OH O OH

CH3HO

emodin anthrone

+ 7

OH OH O

CH3CH3O

OH

torosachrysone

Incubation of cell-free extracts with acetyl-CoA and [2-14C]malonyl-CoA or [U-13C3]malonyl-CoA resulted inbiosynthesis of torosachrysone (tetrahydroanthracene) and emodin anthrone.

ECOLOGICAL BIOCHEMISTRY

Is the C:N ratio a reliable indicator of C allocation to primary and defence-relatedmetabolisms in tomato?

pp 25–33

Mathilde Royer, Romain Larbat, Jacques Le Bot, Stéphane Adamowicz, Christophe Robin*

Defence-related compounds concentrations (phenolics and glycoalkaloids) and starch were positively correlated toC:N ratios (total and resource), whatever the organ considered.

Phytochemistry 88 (2013) 1–5

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Phytochemistry

journal homepage: www.elsevier .com/locate /phytochem

CHEMOTAXONOMY

LC–MS/APCI identification of glucoside esters and diesters of astaxanthin from the snowalga Chlamydomonas nivalis including their optical stereoisomers

pp 34–42

Tomáš Rezanka*, Linda Nedbalová, Irena Kolouchová, Karel Sigler

HPLC methods (LC–MS/APCI and chiral HPLC) were used for the identification of astaxanthin derivatives from thered snow alga Chlamydomonas nivalis collected in Austrian Alps, Slovak High Tatra Mountains and Bulgarian Pirin.We observed a striking difference in the composition of astaxanthin optical isomers in C. nivalis collected ingeographically distinct regions. Furthermore, algae from the Pirin Mountains differed in the dominance ofastaxanthin diglucoside diesters, suggesting an alternative strategy to enhance cell viability at low temperatures.

BIOACTIVE PRODUCTS

Seasonal accumulation of major alkaloids in organs of pharmaceutical cropNarcissus Carlton

pp 43–53

Andrea Lubbe*, Henk Gude, Robert Verpoorte, Young Hae Choi

Seasonal variations in the alkaloids and metabolic profiles of Narcissus pseudonarcissus bulbs,leaves and roots were investigated using 1H NMR spectrometry and multivariate data analysis.

Acylated pregnane glycosides from Caralluma quadrangula pp 54–60

Hossam M. Abdallah, Abdel-Moneim M. Osman, Hussein Almehdar, Essam Abdel-Sattar*

OH

OBz OBz

RO

OOOH3C

OH3C

OHO

OCH3

H3CHO

OH

CymaroseCanaroseDigitoxose

B

1

3

56

7

9

1911

1218

17

20

21

15OH

OBz OBz

R-O

1

3

56

7

9

1911

1218

17

20

21

15

OH

OOOH3C

OH3C

OHO

OCH3

H3C

O

OH

CymaroseCanaroseDigitoxose

OHOHO

OH

OH

Glucose

OOOH3C

OH3C

OHO

OCH3

H3CHO

OCH3

CymaroseCanaroseCymarose

COBz

A

4

Compound R

1 A2 B3 C4 C

1-3

RR

Four acylated pregnane glycosides were isolated from Caralluma quadrangula. The isolated compounds were testedfor their cytotoxicity against breast cancer (MCF7) cell line.

Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum pp 61–66

Gaoussou Timité, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto,Chiaki Tanaka, Jean-François Mirjolet, Olivier Duchamp, Marie-Aleth Lacaille-Dubois*

A phytochemical analysis of the whole plant ofAllium schoenoprasum, has led to the isolation offour new spirostane-type glycosides (1-4), andfour known steroidal saponins. Their structureswere elucidated mainly by 2D NMR spectroscopicanalysis and mass spectrometry. Four of theisolated compounds were tested for cytotoxicactivity against the HCT 116 and HT-29 humancolon cancer cell lines.

2 Contents / Phytochemistry 88 (2013) 1–5

1,5-Diphenylpent-3-en-1-ynes and methyl naphthalene carboxylates fromLawsonia inermis and their anti-inflammatory activity

pp 67–73

Jing-Ru Liou, Mohamed El-Shazly, Ying-Chi Du, Chao-Neng Tseng, Tsong-Long Hwang,Yueh-Lin Chuang, Yu-Ming Hsu, Pei-Wen Hsieh, Chin-Chun Wu, Shu-Li Chen, Ming-Feng Hou,Fang-Rong Chang*, Yang-Chang Wu*

Three 1,5-diphenylpent-3-en-1-ynes and three methyl naphthalene carboxylates, along with 25 knowncompounds, were isolated from the stems and leaves of Lawsonia inermis.

CHEMISTRY

Clausenawallines G–K, carbazole alkaloids from Clausena wallichii twigs pp 74–78

Wisanu Maneerat, Wong Phakhodee, Sarot Cheenpracha, Thunwadee Ritthiwigrom,Suwana Deachathai, Surat Laphookhieo*

NH

HO CHO

OH

NH

O CO2Me

OH NH

O CHO

OH

OH

OH

5

NH

HO CO2Me

OH

NH

O CHO

1 2

34

Five carbazole alkaloids (1–5) along with 12 known alkaloids were isolated from the twigs of Clausena wallichii.Their structures were established using spectroscopic methods. Compounds 1–5 had weak antibacterial activity.

Benzene, coumarin and quinolinone derivatives from roots of Citrus hystrix pp 79–84

Kanda Panthong*, Yuranan Srisud, Vatcharin Rukachaisirikul, Nongporn Hutadilok-Towatana,Supayang Piyawan Voravuthikunchai, Supinya Tewtrakul

OO O

OH

O

OO

O

O1

O OMeO

O

2

O

3

4

N

O

Me

OHOH

Hystrixarin (1), (+)-hopeyhopin (2), hystroxene-I (3) and hystrolinone (4), together with 33 known compounds,were isolated from roots of Citrus hystrix.

Highly glycosylated flavonols with an O-linked branched pentasaccharidefrom Iberis saxatilis (Brassicaceae)

pp 85–91

Thomas A.K. Prescott, Geoffrey C. Kite, Elaine A. Porter, Nigel C. Veitch*

Leafy shoot extracts of Iberis saxatilis (Brassicaceae) afforded four isorhamnetin glycosidesincluding three characterised by the branched pentasaccharide, b-DD-Glcp-(1 fi 3)-a-LL-Rhap-(1 fi 2)[b-DD-Glcp-(1 fi 2)-a-LL-Rhap-(1 fi 6)]-b-DD-Glcp.

Contents / Phytochemistry 88 (2013) 1–5 3

Circular dichroism of anthocyanidin 3-glucoside self-aggregates pp 92–98

Raquel Gavara, Vesselin Petrov, Alexandre Quintas*, Fernando Pina*

The circular dichroism spectra of the six most common anthocyanidin 3-glucoside show the formation of lefthanded aggregates compatible with dimers. The absorption bands of the monomer split by increasing concentrationaccording to the formation of H and J aggregates. The angle and distance between the transition moments of the twomonomers in the dimer was calculated from the splitting of the 0–0 absorption band. While the angle is similar forthe series the distance changes dramatically. The intensity of the CD signal is proportional to the inverse of thesquare of the distance.

Microbial transformation of cycloastragenol pp 99–104

Melis Kuban, Gaye Öngen, Ikhlas A. Khan, Erdal Bedir*

The microbial transformation of cycloastragenol by the fungi Cunninghamella blakesleeanaNRRL 1369 and Glomerella fusarioides ATCC 9552, and the bacterium Mycobacterium sp.NRRL 3805 provided hydroxylated metabolites together with products formed bycyclization, dehydrogenation, oxidation and ring cleavage.

Cardenolide glycosides from root of Streptocaulon juventas pp 105–111

Rui Xue, Na Han, Chun Ye, Hai-bo Wang, Jun Yin* O

OH

R3R2O

H

H

O

R1 R4Six cardenolide glycosides, together with 18 known ones, were isolated and identified from the anti-tumor activefraction of the aqueous ethanol extract of Streptocaulon juventas. Most of them showed significant antiproliferationactivity on A549 cell lines.

Sesquiterpenoids from Chloranthus multistachys pp 112–118

Hai-Yang Liu*, Xin-Hui Ran, Ning-Bo Gong, Wei Ni, Xu-Jie Qin, Yan-Yan Hou, Yang Lü,Chang-Xiang Chen

O O

O

HOO

H

O O

OH

OO

O

1

CO2Me

O2 4

Chemical investigation of whole plant tissues of Chloranthus multistachys resulted in isolation of one8,9-seco-lindenane disesquiterpenoid (1), four eudesmane sesquiterpenoids (e.g. 2 and 4), and four guaianesesquiterpenoids, along with 14 known compounds. Except for the 8,9-seco-lindenane disesquiterpenoid, theabsolute configuration of compounds were characterized by single-crystal X-ray experiments and CD spectra.

4 Contents / Phytochemistry 88 (2013) 1–5

OTHER CONTENTS

Phytochemical Society of Europe pp I–II

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Abstracted/indexed in: Current Awareness in Biological Sciences (CABS), Curr Cont ASCA. Chem. Abstr. BIOSIS Data, PASCAL-CNRS Data,CAB Inter, Cam Sci Abstr, Curr Cont/Agri Bio Env Sci, Curr Cont/Life Sci, Curr Cont Sci Cit Ind, Curr Cont SCISEARCH Data, Bio Agri Ind. Alsocovered in the abstract and citation database SciVerse Scopus�. Full text available on SciVerse ScienceDirect�.

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Contents / Phytochemistry 88 (2013) 1–5 5