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De-Huai Zhang, Na Li, Xuya Yu, Peng Zhao, Tao Li, Jun-Wei Xu
Ganoderic acids (GAs) in Ganoderma lingzhi exhibit anticancer and antimetastatic activities. GA yields can be potentially improved by manipulating G. lingzhi through genetic engineering. In this study, a putative lanosterol synthase (LS) gene was cloned and overexpressed in G. lingzhi. Results showed that its overexpression (OE) increased the ganoderic acid (GA) content and the accumulation of lanosterol and ergosterol in a submerged G. lingzhi culture. The maximum contents of GA-O, GA-Mk, GA-T, GA-S, GA-Mf, and GA-Me in transgenic strains were 46...
November 25, 2016: Phytochemistry
Colin C Duke, Van H Tran, Rujee K Duke, Abdallah Abu-Mellal, George T Plunkett, Douglas I King, Kaiser Hamid, Karen L Wilson, Russell L Barrett, Jeremy J Bruhl
Propolis samples from Kangaroo Island, South Australia, were investigated for chemical constituents using high-field nuclear magnetic resonance spectral profiling. A type of propolis was found containing a high proportion of prenylated hydroxystilbenes. Subsequently, the botanical origin of this type of propolis was identified using a beehive propolis depletion method and analysis of flora. Ligurian honey bees, Apis mellifera ligustica Spinola, were found to produce propolis from resin exuded by the Australian native sedge plant Lepidosperma sp...
November 24, 2016: Phytochemistry
Sanit Thongnest, Jutatip Boonsombat, Hunsa Prawat, Chulabhorn Mahidol, Somsak Ruchirawat
Bioactivity-guided chemical investigation of the CH2Cl2 and CH2Cl2MeOH extracts of the stem and stem bark material of Ailanthus tryphysa (Simaroubaceae) led to the isolation of five cycloapotirucallanes, ailanthusins A-E, two malabaricanes, ailanthusins F-G, and one nor-lupane triterpenoid, 29-nor-lup-1-ene-3,20-dione along with twenty known compounds. Their structures were elucidated through the application of extensive spectroscopic methods, and the structure of ailanthusin A was further confirmed by single crystal X-ray analysis...
November 24, 2016: Phytochemistry
Yumi Fujiwara, Michiho Ito
Perilla produces the cyclohexanoid monoterpene perillaldehyde as a major constituent of an essential oil that is accumulated in its glandular trichomes. Perillaldehyde is a marker compound for quality control of soyo and has biological activities such as antibacterial, sedative, or vasodilatory effects. The predicted perillaldehyde formation involves the cyclization of geranyl diphosphate, hydroxylation, and oxidation, and cytochrome P450 plays a crucial role in perillaldehyde biosynthesis. In this study, a cytochrome P450-type enzyme with perillyl alcohol and perillaldehyde synthase activities was isolated by analyzing an expressed sequence tag library from several oil types of pure lines of perilla...
November 24, 2016: Phytochemistry
Zhenxing Zou, Pingsheng Xu, Guogang Zhang, Fei Cheng, Kai Chen, Jing Li, Weixing Zhu, Dongsheng Cao, Kangping Xu, Guishan Tan
Eight triflavonoids, selagintriflavonoids A-H, were isolated from whole herbs of Selaginella doederleinii. The structures of compounds selagintriflavonoids A-C consisted of three naringenin units, whereas those of selagintriflavonoids D-H consisted of apigenin and two naringenin moieties. The structures and absolute configurations of the compounds were determined based on NMR, HRESIMS, and experimental and calculated electronic circular dichroism (ECD) data. The ability of the compounds to inhibit β-secretase (BACE1) was also evaluated...
November 23, 2016: Phytochemistry
Carla W Sabandar, Juriyati Jalil, Norizan Ahmat, Nor-Ashila Aladdin
The genus Dillenia is comprised of about 100 species of evergreen and deciduous trees or shrubs of disjunct distribution in the seasonal tropics of Madagascar through South and South East Asia, Malaysia, North Australia, and Fiji. Species from this genus have been widely used in medicinal folklore to treat cancers, wounds, jaundice, fever, cough, diabetes mellitus, and diarrhea as well as hair tonics. The plants of the genus also produce edible fruits and are cultivated as ornamental plants. Flavonoids, triterpenoids, and miscellaneous compounds have been identified in the genus...
November 23, 2016: Phytochemistry
Hector H F Koolen, Elizabeth M F Pral, Silvia C Alfieri, Jane V N Marinho, Alessandra F Serain, Alvaro J Hernández-Tasco, Nathalia L Andreazza, Marcos J Salvador
Five alkaloids, in addition to hydroxytyrosol and uridine, were isolated from aerial parts of Alternanthera littoralis P. Beauv. Among the isolated compounds, alternamide A was an unusual tricyclic alkaloid with a bridged benzoazepine core. All isolated alkaloids have a catechol moiety, indicating a possible common biosynthetic route. Their structures were established by 1D and 2D NMR spectroscopy in combination with extensive tandem MS experiments by collisional induced dissociation (CID). The antiprotozoal activity of the isolated compounds was assayed against trypomastigote forms of Trypanosoma cruzi and amastigotes of Leishmania amazonensis...
November 23, 2016: Phytochemistry
Kazuya Koyama, Hiroshi Kamigakiuchi, Kazuhiro Iwashita, Ryosuke Mochioka, Nami Goto-Yamamoto
Grapes (Vitis spp.) produce diverse polyphenolic compounds, which are phytochemicals that contribute to human health. In this study, the polyphenolic profiles of the red-purple berries of two wild grape species native to Japan, Vitis ficifolia and V. coignetiae, and their interspecific hybrid cultivars were investigated and compared with the profiles of V. vinifera and V. × labruscana cultivars. Proanthocyanidins (PAs) were present at lower concentrations in both skins and seeds of wild grape species and their hybrid cultivars than those in V...
November 22, 2016: Phytochemistry
Juha Kontturi, Raisa Osama, Xianbao Deng, Hany Bashandy, Victor A Albert, Teemu H Teeri
The chalcone synthase superfamily consists of type III polyketidesynthases (PKSs), enzymes responsible for producing plant secondary metabolites with various biological and pharmacological activities. Anther-specific chalcone synthase-like enzymes (ASCLs) represent an ancient group of type III PKSs involved in the biosynthesis of sporopollenin, the main component of the exine layer of moss spores and mature pollen grains of seed plants. In the latter, ASCL proteins are localized in the tapetal cells of the anther where they participate in sporopollenin biosynthesis and exine formation within the locule...
November 21, 2016: Phytochemistry
Nicolas Baert, Jorma Kim, Maarit Karonen, Juha-Pekka Salminen
Rosebay willowherb (Epilobium angustifolium) contains large amounts of polyphenolic compounds, including tellimagrandin I-based oligomeric ellagitannins (ETs). The aim of this study was to assess the interpopulational and inter-organ variability of the polyphenol fingerprint of E. angustifolium. Seven ETs, 11 flavonol glycosides and neochlorogenic acid were quantified by UHPLC-DAD-ESI-QqQ-MS in the leaves, flowers and stem parts of plants from 10 populations. Total polyphenol content of leaves and flowers ranged from 150 to 200 mg/g dry wt, of which 90% was constituted by dimeric to heptameric ETs...
November 17, 2016: Phytochemistry
Diane Patricia Apie Gossan, Abdulmagid Alabdul Magid, Philomène Akoua Yao-Kouassi, Antoine Ahibo Coffy, Jérome Josse, Sophie C Gangloff, Hamid Morjani, Laurence Voutquenne-Nazabadioko
Six previously undescribed triterpenoid saponins, gouaniaside I-VI, were isolated from the aerial parts of Gouania longipetala Hemsl. (Rhamnaceae), in addition to four known triterpenes. The structure elucidation of these compounds was based on analyses of spectroscopic data including 1D- and 2D-NMR and HR-ESI-MS techniques. The inhibitory activity of isolated compounds against promyelocytic leukemia HL60 and human erythromyeloblastoid leukemia K562 cell lines was evaluated and jujuboside I exhibited moderate cytotoxicity, with IC50 values of 13...
November 16, 2016: Phytochemistry
Sławomir Dresler, Ewelina Rutkowska, Wiesław Bednarek, Grzegorz Stanisławski, Tomasz Kubrak, Anna Bogucka-Kocka, Małgorzata Wójcik
The aim of this study was to evaluate the effect of severe environmental conditions prevailing on metalliferous waste heaps and heavy metal-contaminated growth substrates on accumulation of selected secondary metabolites, antioxidant capacity, and heavy metal concentration in two metallicolous (MC, MZ) and one nonmetallicolous (NM) populations of Echium vulgare L. The shoots and the roots of the three studied populations were collected from their natural habitats. Additionally, the plants were cultivated on different growth substrates, i...
November 14, 2016: Phytochemistry
Dirk Hölscher, Antje Vollrath, Marco Kai, Suganthaguntalam Dhakshinamoorthy, Riya C Menezes, Aleš Svatoš, Ulrich S Schubert, Andreas Buerkert, Bernd Schneider
The interaction of two Sternorrhyncha species, the banana aphid (Pentalonia nigronervosa Coquerel (Hemiptera: Aphididae, Aphidinae)), vector of the banana bunchy top virus (BBTV), and the latania scale (Hemiberlesia lataniae Signoret (Hemiptera: Diaspididae, Diaspidinae)) with Musa acuminata × balbisiana Colla (ABB Group) 'Bluggoe' (Musaceae) was investigated by a combination of conventional and spatially resolved analytical techniques, (1)H NMR, UHPLC-MS, and matrix-free UV-laser desorption/ionization MS imaging...
November 10, 2016: Phytochemistry
F Sezer Senol, Sylwester Ślusarczyk, Adam Matkowski, Alfonso Pérez-Garrido, Francisco Girón-Rodríguez, José P Cerón-Carrasco, Helena den-Haan, Jorge Peña-García, Horacio Pérez-Sánchez, Krzysztof Domaradzki, Ilkay Erdogan Orhan
Cholinesterase inhibition is one of the most treatment strategies against Alzheimer's disease (AD) where metal accumulation is also strongly associated with pathology of the disease. In the current study, we assessed inhibitory effect against acetyl- (AChE) and butyrylcholinesterase (BChE) and metal-chelating capacity of twelve diterpenes: arucadiol, miltirone, tanshinone IIa, 1-oxomiltirone, cryptotanshinone, 1,2-didehydromiltirone, 1,2-didehydrotanshinone IIa, 1β-hydroxycryptotanshinone, 15,16-dihydrotanshinone, tanshinone I, isotanshinone II, 1(S)-hydroxytanshinone IIa, and rosmarinic acid, isolated from Perovskia atriplicifolia and Salvia glutinosa...
November 3, 2016: Phytochemistry
Yu Chen, Christian Paetz, Riya C Menezes, Bernd Schneider
Phytochemical investigation of root cultures of Xiphidium caeruleum (Haemodoraceae) resulted in the structure elucidation of five previously undescribed phenylphenalenone-type compounds, structure revision of a phenylphenalenone glucoside, and identification of nine additional constituents previously reported from other Haemodoraceae and Musaceae plants. The observed extractant-dependent metabolic profiles indicated that phenylphenalenones had been converted hydrolytically and oxidatively. Stable isotope labeling experiments extended the understanding of the phenylphenalenone pathway in plants and provided evidence for a network of biosynthetic and spontaneous conversions linking phenylphenalenones and their derivatives detected in extracts of cultured roots of this plant...
November 2, 2016: Phytochemistry
Nguyen Quoc Tuan, Joonseok Oh, Hyun Bong Park, Daneel Ferreira, Sanggil Choe, Juseon Lee, MinKyun Na
A growing body of evidence points to the useful roles of computational approaches in the structural characterization of natural products. Rhododendron brachycarpum has been traditionally used for the control of diabetes, hepatitis, hypertension, and rheumatoid arthritis and classified as an endangered species in Korea. A grayanotox-9(11)-ene derivative along with five known diterpenoids, were isolated from the MeOH extract of R. brachycarpum. Extensive 1D and 2D NMR experiments were conducted to establish the 2D structure and relative configuration of the grayanotox-9(11)-ene derivative...
November 2, 2016: Phytochemistry
Dennis Lindqvist, Elin Dahlgren, Lillemor Asplund
Hydroxylated polybrominated diphenyl ethers (OH-PBDEs) have been identified in a variety of marine organisms from different trophic levels indicating a large spread in the environment. There is much evidence pointing towards natural production as the major source of these compounds in nature. However, much is still not known about the natural production of these compounds. Seasonal trend studies have shown large fluctuations in the levels of OH-PBDEs in Ceramium tenuicorne from the Baltic Sea. Yet, even though indications of stimuli that can induce the production of these compounds have been observed, none, neither internal nor external, has been assigned to be responsible for the recorded fluctuations...
October 29, 2016: Phytochemistry
Jing Qu, Shidong Deng, Li Li, Yunbao Liu, Yong Li, Shuanggang Ma, Xiaoguang Chen, Shishan Yu
Nine dimeric xanthanolides, pungiolides F-N, and five known analogues, pungiolides A-E, were isolated from fruits of Xanthium chinense. Their structures were elucidated through spectroscopic and electronic circular dichroism (ECD) analyses. Pungiolide F is a xanthanolide dimer with an acyclic linkage. Five of the dimers, pungiolides H, L, A, C and E, exhibited moderate cytotoxicities with IC50 values in the range of 0.90-6.84 μM using taxol as the positive control, which had, by comparison, IC50 values in the range of 0...
October 20, 2016: Phytochemistry
Brent Wiens, Vincenzo De Luca
The monoterpenoid indole alkaloids, reserpine and rescinnamine contain 3, 4, 5-trimethoxybenzoate or 3, 4, 5-trimethoxycinnamate, respectively, within their structures and they accumulate in different plant organs and particularly within roots of Rauwolfia serpentina. This plant also accumulates acylated sugars substituted with 3, 4, 5-trimethoxybenzoate and 3, 4, 5-trimethoxycinnamate. In the present study, transcriptome and metabolome analyses of R. serpentina roots allowed the identification of 7 candidate O-methytransferase (OMT) genes that might be associated with the formation of 3, 4, 5-trimethoxybenzoate and 3, 4, 5-trimethoxycinnamate and led to the molecular cloning of 4 genes for functional expression and analysis...
October 19, 2016: Phytochemistry
Seiichi Shinomiya, Arihiro Iwasaki, Osamu Ohno, Kiyotake Suenaga
In 2014, the γ-pyrone-containing polyketide, yoshinone A, was isolated from the marine cyanobacterium Leptolyngbya sp. and its structure was determined. Yoshinone A inhibited differentiation of 3T3-L1 cells into adipocytes, with an EC50 value of 420 nM without any cytotoxicity, and therefore is expected to be a lead compound for obesity drugs. To establish its absolute configuration, and to provide sufficient amounts for further research, the total synthesis of yoshinone A was achieved through synthesis of its two possible diastereomers...
October 17, 2016: Phytochemistry
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