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Nayab Kanwal, Achyut Adhikari, Abdul Hameed, Rahman M Hafizur, Syed Ghulam Musharraf
Seven previously undescribed, sulfated triterpenoid glycosides, named nayabin A-G along with a known triterpenoid glycoside were isolated from the whole plant of Fagonia indica. Their structures were elucidated through spectral studies including 1D- ((1)H and (13)C), 2D-NMR spectroscopy (HSQC, HMBC, COSY and NOESY), and mass spectrometry (ESI-MS/MS). β-D-Glucopyranosyl 3β-hydroxy-23-O-β-D-glucopyranosyloxy-taraxast-20-en-28-oate, a known compound exerts glucose-dependent insulin secretory activity, which seems to exhibit a decreased risk of drug-induced hypoglycemia and may offer distinct advantages as anti-diabetic agent...
August 13, 2017: Phytochemistry
Yui Harauchi, Tadashi Kajimoto, Emi Ohta, Hiroyuki Kawachi, Aya Imamura-Jinda, Shinji Ohta
Three previously undescribed isoguanine glycosides with an N(3)-prenyl group, designated locustoside B, saikachinoside B, and saikachinoside C, have been isolated from the seed of Gleditsia japonica Miquel (Fabaceae) along with two known compounds, locustoside A and saikachinoside A. Their structures were determined from spectroscopic data and X-ray crystallographic analysis. The inhibitory activity against acid phosphatase was evaluated.
August 13, 2017: Phytochemistry
Paola S Colombo, Guido Flamini, Graziella Rodondi, Claudia Giuliani, Laura Santagostini, Gelsomina Fico
The genus Primula is the largest among the Primulaceae and is widespread mainly in the cold and temperate regions of the Northern Hemisphere. Since the beginning of the Twentieth century, several studies on the phytochemical composition of different species of Primula have been carried out. The main constituents examined were tissue and epicuticular flavonoids and saponins, which are of therapeutic significance. Only in recent years studies of the volatiles emitted by leaves and flowers have been carried out as well, but they are restricted to a small number of species...
August 11, 2017: Phytochemistry
Andreas Berger, Elias Tanuhadi, Lothar Brecker, Johann Schinnerl, Karin Valant-Vetschera
We report 14 harmala and tryptamine-iridoid alkaloids with various tri-, tetra- and pentacyclic cores from leaves and stem bark of six species of the large and complex neotropical genus Palicourea. Among them is the previously undescribed compound deoxostrictosamide which is related to strictosamide, a key intermediate in camptothecin biosynthesis. In addition, we describe the occurrence of 1,2,3,4-tetrahydronorharman-1-one for the first time within Rubiaceae and ophiorine A and B, two alkaloids with an unusual core bearing a betaine function and a zwitterion as new for the genus...
August 11, 2017: Phytochemistry
Praphatsorn Saetang, Vatcharin Rukachaisirikul, Souwalak Phongpaichit, Sita Preedanon, Jariya Sakayaroj, Suparerk Borwornpinyo, Sawinee Seemakhan, Chatchai Muanprasat
Nine previously undescribed depsidones (simplicildones A-I) and one previously undescribed α-pyrone (simplicilopyrone) were isolated from the endophytic fungus Simplicillium sp. PSU-H41 along with 11 known compounds. Their structures were established by extensive spectroscopic analysis. Simplicildone A and known botryorhodine C displayed weak antibacterial against Staphylococcus aureus with equal MIC values of 32 μg/mL. Additionally, botryorhodine C was active against methicillin-resistant S. aureus with the same MIC value...
August 9, 2017: Phytochemistry
Hahk-Soo Kang, So-Ae Ji, So-Hyun Park, Jong-Pyung Kim
Three new chlorinated sesquiterpenes, named lepistatins A-C, were isolated from the culture broth of Basidiomycete Lepista sordida. The structures were determined by the analysis of spectroscopic data including HREIMS and 1D and 2D NMR. The absolute configuration of lepistatin B was determined by comparing the specific rotation and circular dichroism spectrum with those of known structurally related compounds bearing the same chiral carbon. The structures of lepistatins A-C feature the indanone core structure, but differ from other indanone-containing sesquiterpenes of fungal origin by the alkyl substitution pattern...
August 9, 2017: Phytochemistry
Zeynep Tohtahon, Jingjing Xue, Jianxin Han, Yushuang Liu, Huiming Hua, Tao Yuan
Chemical investigation of a bioactive methanolic extract of the fruiting bodies of Piptoporus betulinus led to the isolation of five previously undescribed lanostane triterpenoids named piptolinic acids A-E, as well as five known lanostane triterpenoids. Their structures were elucidated on the basis of 1D and 2D NMR spectroscopic and HRESIMS analysis. Piptolinic acid A with an unusual moiety (3-hydroxy-4-methoxycarbonyl-3-methylbutyryloxy) at C-3 exhibited comparable cytotoxic activity against human promyelocytic leukemia cell line HL-60 (IC50 = 1...
August 8, 2017: Phytochemistry
Sheng-Zhuo Huang, Qing-Yun Ma, Fan-Dong Kong, Zhi-Kai Guo, Cai-Hong Cai, Li-Li Hu, Li-Man Zhou, Qi Wang, Hao-Fu Dai, Wen-Li Mei, You-Xing Zhao
To search for active anti-cancer constituents in the fruiting body of Ganoderma calidophilum, we have successfully isolated four previously undescribed spiro-lactone lanostane triterpenoids (spiroganocalitones A-D), two previously undescribed lanostanoids (ganodecalones A and B) together with twenty-three known ones. The structures of the six previously undescribed compounds were elucidated based on 1D, 2D-NMR, and HRMS analyses. Ganoderone A showed moderate cytotoxic activity against K562, BEL7402, and SGC790 cell lines with IC50 values of 7...
August 8, 2017: Phytochemistry
Pieter Wytynck, Pierre Rougé, Els J M Van Damme
Ribosome-inactivating proteins (RIPs) are cytotoxic enzymes capable of halting protein synthesis by irreversible modification of ribosomes. Although RIPs are widespread they are not ubiquitous in the plant kingdom. The physiological importance of RIPs is not fully elucidated, but evidence suggests a role in the protection of the plant against biotic and abiotic stresses. Searches in the rice genome revealed a large and highly complex family of proteins with a RIP domain. A comparative analysis retrieved 38 RIP sequences from the genome sequence of Oryza sativa subspecies japonica and 34 sequences from the subspecies indica...
August 7, 2017: Phytochemistry
Wenjie Huang, Xiaomin Yi, Jianying Feng, Yihai Wang, Xiangjiu He
Six previously undescribed piperidine alkaloids were isolated from the rhizomes of Alocasia macrorrhiza (L.) Schott. Their structures were elucidated based on 1D and 2D NMR, IR, HR-ESI-MS spectroscopic analysis and the application of a modified Mosher method. All isolated alkaloids were evaluated for cytotoxicity against five human cancer cell lines (CNE-1, Detroit 562, Fadu, MGC-803, and MCF-7) using the MTT method. Only one compound exhibited cytotoxic effects against Detroit 562, Fadu, and MCF-7 cell lines with IC50 values less than 10 μM...
August 3, 2017: Phytochemistry
Ashish Kumar Choudhary, P Sunojkumar, Girish Mishra
Genus Leucas with about 41 species found in India, is an Asian genus with separation from its close relatives in Africa based on phylogenetic evidence. Present study represents the only comprehensive phytochemical investigation on this genus. We have analyzed the seed fatty acid compositions of 26 species and five varieties of Leucas for nutritional, pharmaceutical and chemotaxonomic perspectives. The fatty acids and their composition in seeds of Leucas species, collected from different geographical regions in India, were analyzed by gas chromatography and mass spectrometry...
August 1, 2017: Phytochemistry
Xiu-Ren Hu, Gui-Xin Chou, Cheng-Gang Zhang
Three flavonoids, cropalliflavones A-C, including two homoisoflavonoids with rare skeletons; three previously undescribed alkaloids, usaramine-N-oxide and cropallins A-B; and sixteen known compounds, were isolated from the seeds of Crotalaria pallida Ait. The absolute configurations of cropalliflavone A and usaramine-N-oxide were established by an ECD calculation and X-ray crystallography, respectively. Additionally, cropalliflavone B showed anti-proliferative activity against the MCF-7 cell line with an IC50 value of 6...
August 1, 2017: Phytochemistry
Joanna Kolodziejczyk-Czepas, Justyna Krzyżanowska-Kowalczyk, Malgorzata Sieradzka, Pawel Nowak, Anna Stochmal
This in vitro study provides a new insight into the phytochemical, antioxidant, antiplatelet and cytotoxic profiles of commercial trans-clovamide and clovamide-rich extracts, isolated from aerial parts of three Trifolium species (i.e. T. clypeatum L., T. obscurum Savi and T. squarrosum L.). Under inorganic experimental conditions, the EC50 for the investigated substances varied between 4.87 (clovamide) and 7.91 μg/ml (T. clypeatum) according to the DPPH(•) assay. The most effective 1 mM ONOO(-) scavenger was clovamide (IC50 = 19...
August 1, 2017: Phytochemistry
Vincent P Sica, Evan R Rees, Huzefa A Raja, José Rivera-Chávez, Joanna E Burdette, Cedric J Pearce, Nicholas H Oberlies
Peptaibols are an intriguing class of fungal metabolites due both to their wide range of reported bioactivities and to the structural variability that can be generated by the exchange of variable amino acid building blocks. In an effort to streamline the discovery of structurally diverse peptaibols, a mass spectrometry surface sampling technique was applied to screen the chemistry of fungal cultures in situ. Four previously undescribed peptaibols, all containing a rare threonine residue, were identified from a fungal culture (MSX53554), which was identified as Nectriopsis Maire (Bionectriaceae, Hypocreales, Ascomycota)...
July 31, 2017: Phytochemistry
Jutatip Boonsombat, Chulabhorn Mahidol, Pornsuda Chawengrum, Nanthawan Reuk-Ngam, Nitirat Chimnoi, Supanna Techasakul, Somsak Ruchirawat, Sanit Thongnest
Eight previously undescribed ditepenoids, including four oxygenated abietanes (roscotanes A-D) and four oxygenated pimaranes (roscoranes A-D), along with twelve known diterpenoids were isolated from the whole plants of Kaempferia roscoeana. Their structures were elucidated by extensive spectroscopic analysis, and the structure of roscotane A was further confirmed by single crystal X-ray diffraction analysis. Most isolated compounds were evaluated for their antimicrobial and antimalarial activities.
July 28, 2017: Phytochemistry
Vítor Spínola, Paula C Castilho
The study was performed to assess, for the first time, the in vitro anti-diabetic potential of ten Asteraceae plant extracts to inhibit the activity of digestive enzymes (α-amylase, α-, β-glucosidases and lipase) responsible for hydrolysis/digestion of sugar and lipids. Prevention of advanced glycation end-products (AGEs) formation was evaluated in bovine serum albumin/ribose glycation reaction model. The phytochemical profiles and caffeoylquinic acids (CQAs) contents were determined for the methanolic extract of each plant...
July 26, 2017: Phytochemistry
Geoffrey C Kite, Wilbert L A Hetterscheid
The chemical composition of inflorescence odours of 80 species of Amorphophallus (Araceae) were determined by headspace-thermal desorption GC-MS. When compared to published molecular phylogenies of the genus, the data reveal evidence both of phylogenetic constraint and plasticity of odours. Dimethyl oligosulphides were found as common constituents of Amorphophallus odours and were the most abundant components in almost half of the species studied. Odours composed mainly of dimethyl oligosulphides, and perceived as being 'gaseous', were only found among Asian species, and some of these species clustered in certain clades in molecular phylogenies; e...
July 24, 2017: Phytochemistry
Rebecca Mackelprang, Rachel A Okrent, Mary C Wildermuth
The GH3 family of adenylating enzymes conjugate acyl substrates such as the growth hormone indole-3-acetic acid (IAA) to amino acids via a two-step reaction of acyl substrate adenylation followed by amino acid conjugation. Arabidopsis thaliana GH3.5 was previously shown to be unusual in that it could adenylate both IAA and the defense hormone salicylic acid (SA, 2-hydroxybenzoate). Our detailed studies of the kinetics of GH3.5 on a variety of auxin and benzoate substrates provides insight into the acyl preference and reaction mechanism of GH3...
July 22, 2017: Phytochemistry
Serdar Demir, Canan Karaalp, Erdal Bedir
The genus Centaurea L. (Asteraceae) is represented by 200 taxa in the flora of Turkey and several Centaurea species are used as herbal remedies against different conditions. Previous phytochemical investigations on this genus generally revealed the isolation of sesquiterpene lactones and flavonoid derivatives. In our continuous search on Centaurea genus, a phytochemical study was performed on Centaurea polyclada DC., an endemic of West Anatolia. Previously undescribed two sesquiterpene-amino acid conjugates, an elemane and an eudesmane derivative were isolated from the aerial parts of Centaurea polyclada, together with eight known compounds; two elemane derivatives, three flavonoids, a lignan, a phenolic glucoside and a phenylpropanoid glucoside...
July 21, 2017: Phytochemistry
Yu Tang, Juan Xiong, Yike Zou, Wei Wang, Chao Huang, Hai-Yan Zhang, Jin-Feng Hu
Seven lycopodine-type (annotinolide F and lycoannotines A-F), two lycodine-type (lycoannotines G and H), and one fawcettimine-type (lycoannotine I) previously undescribed naturally occurring Lycopodium alkaloids together with thirteen known ones were isolated from the whole plant of Lycopodium annotinum. Their structures and absolute configurations were determined by extensive spectroscopic methods, single-crystal X-ray diffraction, chemical transformation, and electronic circular dichroism (ECD) calculations...
July 21, 2017: Phytochemistry
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