Phytochemistry Vol. 89

Contents

PROTEIN BIOCHEMISTRY AND PROTEOMICS

Functional characterization of three Coffea arabica L. monoterpene synthases: Insights intothe enzymatic machinery of coffee aroma

pp 6–14

Lorenzo Del Terra*, Valentina Lonzarich, Elisa Asquini, Luciano Navarini, Giorgio Graziosi,Furio Suggi Liverani, Alberto Pallavicini

A limonene synthase and two linalool/myrcene synthases have been isolated from Coffea arabica and functionallycharacterized in vitro after recombinant protein expression and purification.

MOLECULAR GENETICS AND GENOMICS

Purification, cDNA cloning and recombinant protein expression of a phloem lectin-likeanti-insect defense protein BPLP from the phloem exudate of the wax gourd, Benincasahispida

pp 15–25

Eiji Ota, Wataru Tsuchiya, Toshimasa Yamazaki, Masatoshi Nakamura, Chikara Hirayama,Kotaro Konno*

A 35 kDa anti-insect defense protein designated BPLP (Benincasa hispida phloem Lectin-like protein) was purifiedfrom the phloem exudate of the wax gourd, Benincasa hispida, and the encoding gene was cloned.

METABOLISM

Biosynthesis of steroidal alkaloids in Solanaceae plants: Involvement of an aldehydeintermediate during C-26 amination

pp 26–31

Kiyoshi Ohyama*, Akiko Okawa, Yuka Moriuchi, Yoshinori Fujimoto*

Elimination of two hydrogen atoms from C-26 of cholesterol during the biosynthesis of tomatine, solanine,chaconine and solasonine suggest a transamination mechanism for the C-26 amination.

Phytochemistry 89 (2013) 1–5

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Phytochemistry

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

Spatio-temporal variation of the diterpene steviol in Stevia rebaudiana grown underdifferent photoperiods

pp 32–38

Stijn Ceunen, Jan M.C. Geuns*

In Stevia rebaudiana, the spatio-temporal variations in steviol content were strongly influenced by photoperiodand genotype, yet in most conditions, a significant decline was seen after flower opening.

Microbiological transformation of two 15a-hydroxy-ent-kaur-9(11),16-diene derivatives bythe fungus Fusarium fujikuroi

pp 39–46

Braulio M. Fraga*, Victoria González-Vallejo, Ricardo Guillermo, Juan M. Amaro-Luis

CO2H4

OHIncubation of 15a-hydroxy-grandiflorenic acid (4) with Fusarium fujikuroi gave its 3b,6b-dihydroxy-,3b-hydroxy-6b,7b-epoxy- and 3b-hydroxy-6-oxo-derivatives, together with a 19-nor compound and a3a-hydroxy-19,6a-lactone. In addition, the biotransformation of 15a,18-dihydroxy-ent-kaur-9(11),16-diene ledto the isolation of its 3b-, 6b-, 7a- and 12b-hydroxy-derivatives.

Modulation of the phenylacetic acid metabolic complex by quinic acid alters the disease-causing activity of Rhizoctonia solani on tomato

pp 47–52

Faith E. Bartz*, Norman J. Glassbrook, David A. Danehower, Marc A. Cubeta

Metabolic control of plant growth regulator production in the plant pathogenic fungus Rhizoctonia solani by quinicacid leads to increased survival of inoculated tomato plants.

CHEMOTAXONOMY

Fatty acids as biomarkers of microalgae pp 53–58

Abhishek Sahu, Imran Pancha, Deepti Jain, Chetan Paliwal, Tonmoy Ghosh, Shailesh Patidar,Sourish Bhattacharya, Sandhya Mishra*

C16:0 (A) and C18:1n9c (B) are the most abundant fatty acids in microalgae. PCA and AHC study ofthe 12 microalgal strains, segregated into 2 different phyla belonging to 8 distinct taxonomic orders.

2 Contents / Phytochemistry 89 (2013) 1–5

BIOACTIVE PRODUCTS

Limonoids from the fruits of Melia azedarach and their cytotoxic activities pp 59–70

Toshihiro Akihisa*, Xin Pan, Yasuhiro Nakamura, Takashi Kikuchi, Nami Takahashi,Masahiro Matsumoto, Eri Ogihara, Makoto Fukatsu, Kazuo Koike, Harukuni Tokuda

β-Actin (45 kDa)

Procaspase-9 (47 kDa)

Procaspase-3 (32 kDa)

Procaspase-8 (57 kDa)

0 8 24 (h) 26

HO H

O

OO

O

H

O

MeOOO

Limonoids, meliarachin C and 3-O-deacetyl-40-demethyl-28-oxosalannin, were isolated from fruits ofMelia azedarach. They induced caspase-dependent apoptotic cell death in HL60 human leukemia cells.

Leishmanicidal activity of Cecropia pachystachya flavonoids: Arginase inhibition andaltered mitochondrial DNA arrangement

pp 71–77

Ebenézer de Mello Cruz, Edson Roberto da Silva*, Claudia do Carmo Maquiaveli,Eliomara Sousa Sobral Alves, João Francisco Lucon Jr., Matheus Balduino Gonçalves dos Reis,Cleyton Eduardo Mendes de Toledo, Frederico Guaré Cruz,Marcos André Vannier-Santos

Inhibition of arginase blocks the first step of the synthesis of polyamines that are essential for the multiplicationand maintenance of the antioxidant mechanism through synthesis of trypanothione.

Prenylated flavonoids from Artocarpus altilis: Antioxidant activities and inhibitory effectson melanin production

pp 78–88

Wen-Chun Lan, Cheng-Wei Tzeng, Chun-Ching Lin, Feng-Lin Yen, Horng-Huey Ko*

O

OH

MeOHO OH

OO

OOH

HO

OH

HO OH

OH

O

OOH

O

OH

HO OH

OH

O

OO

OH

HO OH

O

O

OO

O

OH

OH

O

HO

1 2 3 54

Compounds 1–5, together with 12 known compounds, were isolated from the heartwood and cortex ofArtocarpus altilis. Several of these showed free radical scavenging activity, and some reduced melaninproduction without affecting cell viability. These compounds could be considered as cosmetic agents in the future.

Rearranged abietane diterpenoids from the roots of Clerodendrum trichotomum and theircytotoxicities against human tumor cells

pp 89–95

Wen-Xuan Wang, Juan Xiong, Yu Tang, Jing-Jing Zhu, Ming Li, Yun Zhao, Guo-Xun Yang,Gang Xia, Jin-Feng Hu*

Rearranged abietane diterpenoids (1–6) were isolated from the roots of Clerodendrum trichotomum. The absoluteconfiguration of compound 1 was completely deduced. Compounds 4, 6, 9, 10, 12, and 14, each possessing acommon 17(15 fi 16),18(4 fi 3)-diabeoabietane framework, exhibited remarkable cytotoxic effects against a smallpanel of human cancer cell lines.

Contents / Phytochemistry 89 (2013) 1–5 3

Phytotoxic dioxolanone-type secondary metabolites from Guignardia bidwellii pp 96–103

Iris Buckel, Daniel Molitor, Johannes C. Liermann, Louis P. Sandjo,Beate Berkelmann-Löhnertz, Till Opatz, Eckhard Thines*

Optimisation of cultivation conditions of G. bidwellii led to the identification of seven secondary metabolites,structurally related to guignardic acid, a known secondary metabolite from Guignardia species containing adioxolanone moiety.

Minor C-geranylated flavanones from Paulownia tomentosa fruits with MRSA antibacterialactivity

pp 104–113

Alice Navrátilová, Kristyna Schneiderová, Daniela Veselá, Zuzana Hanáková, Anna Fontana,Stefano Dall’Acqua*, Josef Cvacka, Gabbriella Innocenti, Jana Novotná, Marie Urbanová,Jerry Pelletier, Alois Cízek, Helena Zemlicková, Karel Šmejkal*

Paulownia tomentosa (Thunb). Steud. (Paulowniaceae) fruits analysis has led to discovery of 10 C-6 geranylatedflavanones tomentodiplacone C–I and mimulone C–E.

CHEMISTRY

Comparative metabolite profiling and chemical study of Ramalina siliquosa complexusing LC–ESI-MS/MS approach

pp 114–124

Delphine Parrot, Saleem Jan, Nicolas Baert, Sylvain Guyot, Sophie Tomasi*

LC–ESI-MSn led to the MS-fragmentation study of 10 major compounds and the detection of 22 minor compoundsfrom eight chemotypes of Ramalina siliquosa complex.

Ent-pimarane and ent-trachylobane diterpenoids from Mitrephora alba and theircytotoxicity against three human cancer cell lines

pp 125–130

Kanok-on Rayanil*, Suphaluck Limpanawisut, Pittaya Tuntiwachwuttikul

Phytochemical study of Mitrephora alba led to the isolation of two ent-pimaranes and three ent-trachylobanes,as well as five known related diterpenoids.

4 Contents / Phytochemistry 89 (2013) 1–5

OTHER CONTENTS

Announcement for the Phytochemical Society of North America (PSNA) p I

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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 89 (2013) 1–5 5