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Callistiviminenes A-O, fifteen adducts of β-triketone with sesqui- or monoterpene, along with a known compound, were isolated from the fruits of Callistemon viminalis . Callistiviminenes A and B are β-triketone-coupled (−)-bicyclosequiphellandrene contained an oxaspiro[5.5]undecene unit, and callistiviminenes C-E are rare adducts of β-triketone and bicyclogermacrene. Their structures and absolute configurations were elucidated by spectroscopic and computational methods, as well as by single-crystal X-ray diffraction experiment. A plausible biosynthetic pathway to these compounds involves a hetero-Diels–Alder reaction. Callistiviminenes C and D exhibited inhibition against lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages with IC 50 value of 20.3 μ M and 32.5 μ M, respectively. [ABSTRACT FROM AUTHOR]

Abstract: Melaleuca quinquenervia (Cav) S.T. Blake (broadleaf paperbark) is an Australian tree that has become a serious weed in many places around the world. Two insects Oxyops vitiosa (the melaleuca weevil), and Boreioglycaspis melaleucae (the melaleuca psyllid), which were introduced to Florida as part of a biological control programme, have been very effective in reducing survival and reproduction of this weed. There are two terpene chemotypes of M.quinquenervia; one rich in the sesquiterpene E-nerolidol whereas the other is rich in viridiflorol. Viridiflorol is a strong feeding deterrent for the melaleuca weevil and retards larval development. The larvae therefore avoid the viridiflorol-rich chemotype, in contrast, female melaleuca psyllids prefer to oviposit on these leaves. To identify the molecular basis of these preferences, we isolated and characterised two terpene synthases from the viridiflorol-rich chemotype, both of which utilise farnesyl pyrophosphate and have the same product profile. Chemotypic variation in terpenes in M. quinquenervia is under strong genetic control and the reproductive potential of each chemotype is limited by a different insect. These insects could, therefore, be selective agents for the maintenance of chemotypic variation in M. quinquenervia. [Copyright &y& Elsevier]

Abstract: Myrtaceae is one of the chemically most variable and most significant essential oil yielding plant families. Despite an abundance of chemical information, very little work has focussed on the biochemistry of terpene production in these plants. We describe 70 unique partial terpene synthase transcripts and eight full-length cDNA clones from 21 myrtaceous species, and compare phylogenetic relationships and leaf oil composition to reveal clades defined by common function. We provide further support for the correlation between function and phylogenetic relationships by the first functional characterisation of terpene synthases from Myrtaceae: a 1,8-cineole synthase from Eucalyptus sideroxylon and a caryophyllene synthase from Eucalyptus dives. [Copyright &y& Elsevier]

Phytochemical investigation of Callistemon citrinus (Curtis) Skeels (syn. Callistemon lanceolatus (Sm.) Sweet and Melaleuca citrina (Curtis) Dum.Cours.) leaves resulted in the isolation of five undescribed compounds, including one acylphloroglucinol derivative and four monoterpene galloylglucosides, in addition to 29 known diverse secondary metabolites. Interestingly, this study reports chemosystematically significant isolation of the monoterpene galloylglucosides from the genus for the first time. Furthermore, exploration of the isolated compounds as inhibitors of inflammation-related molecular targets, molecular docking studies targeting human adipocyte lipid-binding protein FABP4 (3P6H) and human nitric oxide synthase (3E7G) were carried out in order with the in vitro evaluation of the isolated compounds for their anti-microbial and inhibitory of inducible nitric oxide synthase (iNOS) activities. Molecular docking studies revealed that eighteen compounds showed lower docking scores than ibuprofen, the native ligand in the crystal structure 3P6H, and nine compounds showed lower docking scores than AR-C95791, the native ligand in the binding site of 3E7G. Additionally, in vitro studies revealed that seven compounds showed moderate iNOS inhibitory activity. They also were moderately cytotoxic to HepG2, LLC-PK 1 and Vero cells. Pulverulentone A showed moderate antibacterial activity against MRSA (IC 50 22.2 μM) and antifungal activity against C. neoformans, while corosolic acid showed strong antibacterial activity against VRE (IC 50 15.9 μM).Thus, the in silico and in vitro studies indicated that some isolated compounds hold potentials as inhibitors of iNOS activity and anti-microbial agents. [Display omitted] • Isolation of five undescribed compounds, one acylphloroglucinol and four monoterpenegalloylglucosides from C. citrinus leaves • In addition to the isolation of 29 known compounds. • This is the first report for the occurrence of the monoterpene galloylglucosides in the genus Callistemon. • Molecular docking of the isolated compounds to study their potential as inhibitors for FABP4 protein and iNOS. • Some of the isolated compounds were tested for their antimicrobial and inhibitory of iNOS activities. [ABSTRACT FROM AUTHOR]