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Triterpenoids

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https://www.readbyqxmd.com/read/29218010/calenduloside-e-analogues-protecting-h9c2-cardiomyocytes-against-h2o2-induced-apoptosis-design-synthesis-and-biological-evaluation
#1
Yu Tian, Yu-Yang Du, Hai Shang, Min Wang, Zhong-Hao Sun, Bao-Qi Wang, Di Deng, Shan Wang, Xu-Dong Xu, Gui-Bo Sun, Xiao-Bo Sun
Modulation of apoptosis is therapeutically effective in cardiomyocytes damage. Calenduloside E (CE), a naturally occurring triterpenoid saponin, is a potent anti-apoptotic agent. However, little is known about its synthetic analogues on the protective effects in apoptosis of cardiomyocytes. The present research was performed to investigate the potential protective effect of CE analogues against H2O2-induced apoptosis in H9c2 cardiomyocytes and the underlying mechanisms. Sixteen novel CE anologues have been designed, synthesized and biological evaluation...
2017: Frontiers in Pharmacology
https://www.readbyqxmd.com/read/29216402/soyasaponins-a-new-class-of-root-exudates-in-soybean-glycine-max
#2
Yuhei Tsuno, Teruhisa Fujimatsu, Keiji Endo, Akifumi Sugiyama, Kazufumi Yazaki
Root exudates are plant metabolites secreted from the roots into the soil. These exudates are involved in many important biological processes, including acquisition of nutrients, defense, and signaling to rhizosphere bacteria, such as isoflavones of soybean crucial for the symbiosis with rhizobium. Less is known, however, about other types of root exudates. This study shows that soybean roots secrete large amounts of soyasaponins (triterpenoid glycosides) as root exudates. The soyasaponins are classified into four groups, with group A being the most secreted of these compounds, whereas DDMP soyasaponins being the group showing greatest accumulation in root tissues, suggesting a selection system for secreted compounds...
December 4, 2017: Plant & Cell Physiology
https://www.readbyqxmd.com/read/29215673/extraction-of-triterpenoids-and-phenolic-compounds-from-ganoderma-lucidum-optimization-study-using-the-response-surface-methodology
#3
Taofiq Oludemi, Lillian Barros, M A Prieto, Sandrina A Heleno, Maria F Barreiro, Isabel C F R Ferreira
The extraction of triterpenoids and phenolic compounds from Ganoderma lucidum was optimized by using the response surface methodology (RSM), using heat and ultrasound assisted extraction techniques (HAE and UAE). The obtained results were compared with that of the standard Soxhlet procedure. RSM was applied using a circumscribed central composite design with three variables (time, ethanol content, and temperature or ultrasonic power) and five levels. The conditions that maximize the responses (extraction yield, triterpenoids and total phenolics) were: 78...
December 7, 2017: Food & Function
https://www.readbyqxmd.com/read/29212369/chemical-characterisation-of-the-constituents-of-eugenia-protenta-mcvaugh-and-leishmanicidal-activity-of-dimethylxanthoxylin
#4
Flávio N Sarges, Márcia M Cascaes, Lienne S Moraes, Giselle M S P Guilhon, Edilene O Silva, Maria das Graças B Zoghbi, Eloisa H A Andrade, Ana Paula D Rodrigues, Brenda F Costa, Rayssa N M Figueiredo
The chemical study of Eugenia protenta McVaugh extracts performed by classical and high-performance liquid chromatography techniques and spectral methods has led to the identification of known triterpenoids, flavonoids and an acetophenone derivative (dimethylxanthoxylin). The effect of dimethylxanthoxylin on Leishmania (Leishmania) amazonensis was evaluated against the promastigotes forms after 96 h of treatment. Dimethylxanthoxylin reduced 57 and 59% of the promastigotes growth when treated with 50 and 100 μg/mL solutions, respectively (IC50 117...
December 6, 2017: Natural Product Research
https://www.readbyqxmd.com/read/29205603/selective-profiling-of-saponins-from-gypsophila-trichotoma-wend-by-hilic-separation-and-hrms-detection
#5
Reneta Gevrenova, Ventzislav Bardarov, Krum Bardarov, Laurence Voutquenne-Nazabadioko, Max Henry
INTRODUCTION: Roots of Gypsophila trichotoma Wend. (Caryophyllaceae) are rich sources of glucuronide oleanane-type triterpenoid carboxylic acid 3,28-O-bidesmosides (GOTCABs). These saponins have been reported to possess synergistic cytotoxicity in combination with type I ribosome-inactivating protein saporin. OBJECTIVE: To develop ultra high-performance liquid chromatography - electrospray ionisation/high resolution mass spectrometry (UHPLC-ESI/HRMS) acquisition strategy for the recognition of Gypsophila GOTCAB saponins...
December 4, 2017: Phytochemical Analysis: PCA
https://www.readbyqxmd.com/read/29204767/heterologous-biosynthesis-of-triterpenoid-ambrein-in-engineered-escherichia-coli
#6
Di Ke, Qinggele Caiyin, Fanglong Zhao, Ting Liu, Wenyu Lu
OBJECTIVES: To genetically engineer Escherichia coli for the heterologous biosynthesis of triterpenoid, ambrein, the main bioactive component of ambergris, by constituting a novel squalene-derived ambrein biosynthetic pathway in E. coli. RESULTS: The ScERG9 gene encoding the squalene synthase (SS) was integrated into the E. coli genome to generate a squalene-producing strain that supplied the central precursor squalene for the formation of cyclic triterpenoids. The mutated squalene-hopene synthase (D377C SHC) and the tetraprenyl-β-curcumene cyclase (BmeTC) were co-expressed with SS to construct a novel ambrein biosynthetic pathway in E...
December 4, 2017: Biotechnology Letters
https://www.readbyqxmd.com/read/29204150/rhizobium-impacts-on-seed-productivity-quality-and-protection-of-pisum-sativum-upon-disease-stress-caused-by-didymella-pinodes-phenotypic-proteomic-and-metabolomic-traits
#7
Nima Ranjbar Sistani, Hans-Peter Kaul, Getinet Desalegn, Stefanie Wienkoop
In field peas, ascochyta blight is one of the most common fungal diseases caused by Didymella pinodes. Despite the high diversity of pea cultivars, only little resistance has been developed until to date, still leading to significant losses in grain yield. Rhizobia as plant growth promoting endosymbionts are the main partners for establishment of symbiosis with pea plants. The key role of Rhizobium as an effective nitrogen source for legumes seed quality and quantity improvement is in line with sustainable agriculture and food security programs...
2017: Frontiers in Plant Science
https://www.readbyqxmd.com/read/29203557/a-single-oxidosqualene-cyclase-produces-the-seco-triterpenoid-%C3%AE-onocerin
#8
Aldo Almeida, Lemeng Dong, Bekzod Khakimov, Jean-Etienne André Bassard, Tessa Moses, Frederic Lota, Alain Goossens, Giovanni Appendino, Soren Bak
8,14-seco-triterpenoids are characterized by their unusual open C-ring. Their distribution in nature is rare and scattered in taxonomically unrelated plants. The 8,14-seco-triterpenoid α-onocerin is only known from the evolutionarily distant clubmoss genus Lycopodium and leguminous genus Ononis, which makes the biosynthesis of this seco-triterpenoid intriguing from an evolutionary standpoint. In our experiments with Ononis spinosa, α-onocerin was detected only in the roots. Through transcriptome analysis of the roots, an oxidosqualene cyclase, OsONS1, was identified that produces α-onocerin from squalene-2,3;22,23-dioxide, when transiently expressed in Nicotiana bethaminana...
December 4, 2017: Plant Physiology
https://www.readbyqxmd.com/read/29203373/betulinic-oleanolic-and-ursolic-acids-inhibit-the-enzymatic-and-biological-effects-induced-by-a-p-i-snake-venom-metalloproteinase
#9
Lina María Preciado, Paola Rey-Suárez, Isabel Cristina Henao, Jaime Andrés Pereañez
Betulinic acid (BA), Oleanolic acid (OA) and Ursolic acid (UA), are pentacyclic triterpenoids with widespread occurrence throughout the plant kingdom, these compounds are widely recognized by their pharmacological and biological properties, such as, anti-tumoral, anti-inflammatory, anti-microbial and hepatoprotective activity. In this work we determined the inhibitory ability of these compounds on the enzymatic, hemorrhagic, myotoxic and edema-inducing activities of Batx-I, a P-I metalloproteinase isolated from Bothrops atrox venom...
December 1, 2017: Chemico-biological Interactions
https://www.readbyqxmd.com/read/29202513/new-pharmacological-opportunities-for-betulinic-acid
#10
José Luis Ríos, Salvador Máñez
Betulinic acid is a naturally occurring pentacyclic lupane-type triterpenoid usually isolated from birch trees, but present in many other botanical sources. It is found in different plant organs, both as a free aglycon and as glycosyl derivatives. A wide range of pharmacological activities has been described for this triterpenoid, including antiviral and antitumor effects. In addition, several other interesting properties have been identified in the fields of immunity and metabolism, namely antidiabetic, antihyperlipidemic, and anti-inflammatory activities...
December 4, 2017: Planta Medica
https://www.readbyqxmd.com/read/29202408/synthesis-and-antimycobacterial-activity-of-triterpeni%C3%A2-a-ring-azepanes
#11
Natalya I Medvedeva, Oxana B Kazakova, Tatyana V Lopatina, Irina E Smirnova, Gul'nara V Giniyatullina, Irina P Baikova, Vladimir E Kataev
A series of A-ring azepanones and azepanes derived from betulonic, oleanonic and ursonic acids was synthesized and evaluated for their in vitro antimycobacterial activities against M. tuberculosis (MTB) H37Rv and SDR-TB in the National Institute of Allergy and Infectious Diseases. Triterpenic A-azepano-28-hydroxy-derivatives were synthesized by the reduction with LiAlH4 of triterpenic azepanones available from the Beckmann rearrangement of the corresponding C3-oximes. Modification of azepanes at NH-group and atoms С12, C20, C28 and C29 of triterpenic core led to the derivatives with oxo, epoxy, aminopropyl, oximino and acyl substituents...
November 21, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29200903/ardipusilloside-i-stimulates-gastrointestinal-motility-and-phosphorylation-of-smooth-muscle-myosin-by-myosin-light-chain-kinase
#12
Zhili Xu, Hanye Liang, Mingbo Zhang, Xiaojun Tao, Deqiang Dou, Liping Hu, Tingguo Kang
Ardipusilloside-I is a natural triterpenoid saponin, which was isolated from Ardisia pusilla A. DC. The aim of the study was to evaluate the stimulation of ardipusilloside-I on gastrointestinal motility in vitro and in vivo. The experiment of smooth muscle contraction directly monitored the contractions of the isolated jejunal segment (IJS) in different contractile states, and the effects of ardipusilloside-I on myosin were measured in the presence of Ca2+-calmodulin using the activities of 20 kDa myosin light chain (MLC20) phosphorylation and myosin Mg2+-ATPase...
November 2017: Korean Journal of Physiology & Pharmacology
https://www.readbyqxmd.com/read/29200718/%C3%AE-glucosidase-inhibitory-activity-from-ethyl-acetate-extract-of-antidesma-bunius-l-spreng-stem-bark-containing-triterpenoids
#13
Marista Gilang Mauldina, Rani Sauriasari, Berna Elya
Background: Buni (Antidesma bunius [L.] Spreng) has been used as a traditional antidiabetic agent in Asia. Objective: The mechanism of antidiabetic properties was studied in this study by determine its α-glucosidase inhibitory activity. Method: Inhibition of α-glucosidase was performed in all fraction of Buni stem bark with acarbose and miglitol as standards. The half maximal inhibitory concentration (IC50) value of acarbose and miglitol was 5...
October 2017: Pharmacognosy Magazine
https://www.readbyqxmd.com/read/29197730/platanic-acid-a-new-scaffold-for-the-synthesis-of-cytotoxic-agents
#14
Michael Kahnt, Lucie Heller, Patricia Grabandt, Ahmed Al-Harrasi, René Csuk
Thirty-seven different derivatives (2-38) have been prepared from platanic acid, a natural occurring triterpenoid. Main emphasis was the introduction of several N-containing functional groups such as amines, amides and oximes and their screening for cytotoxic activity employing several human tumor cell lines using SRB assays. In these SRB assays, nearly all compounds showed good cytotoxicity for these human tumor cell lines. Two compounds (17 and 38), however, were submitted to extended biological testing and investigated with respect to their mode of action using fluorescence microscopy and FACS analysis...
November 21, 2017: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29197540/miscellaneous-lanostane-triterpenoids-with-cytotoxicities-from-fruiting-bodies-of-the-basidiomycete-stereum-sp
#15
Jian-Neng Yao, Lin Chen, He-Ping Chen, Zhen-Zhu Zhao, Shuai-Bing Zhang, Ying Huang, Yang Tang, Masahiko Isaka, Zheng-Hui Li, Tao Feng, Ji-Kai Liu
Ten new highly oxygenated lanostane triterpenoids, stereinones A-J (1-10), were isolated from the fruiting bodies of the basidiomycete Stereum sp. Compounds 3 and 4 are structurally characterized as intact lanostane-type triterpenoids containing unusual 1,2-diketone functionality at C-11 and C-12, while compound 10 is a 24-methylene-lanostane. The structures of these new compounds were established based on detailed 1D and 2D NMR spectroscopic analyses, along with quantum chemical NMR calculations. All isolates were evaluated for their in vitro cytotoxicities against five human tumor cell lines (including HL-60, A-549, SMMC-7721, MCF-7, and SW480 cell lines)...
November 29, 2017: Fitoterapia
https://www.readbyqxmd.com/read/29196123/boosting-11-oxo-%C3%AE-amyrin-and-glycyrrhetinic-acid-synthesis-in-saccharomyces-cerevisiae-via-pairing-novel-oxidation-and-reduction-system-from-legume-plants
#16
Ming Zhu, Caixia Wang, Wentao Sun, Anqi Zhou, Ying Wang, Genlin Zhang, Xiaohong Zhou, Yixin Huo, Chun Li
Glycyrrhetinic acid (GA) and its precursor, 11-oxo-β-amyrin, are typical triterpenoids found in the roots of licorice, a traditional Chinese medicinal herb that exhibits diverse functions and physiological effects. In this study, we developed a novel and highly efficient pathway for the synthesis of GA and 11-oxo-β-amyrin in Saccharomyces cerevisiae by introducing efficient cytochrome P450s (CYP450s: Uni25647 and CYP72A63) and pairing their reduction systems from legume plants through transcriptome and genome-wide screening and identification...
November 28, 2017: Metabolic Engineering
https://www.readbyqxmd.com/read/29194373/anti-proliferative-activity-of-triterpenoids-and-sterols-isolated-from-alstonia-scholaris-against-non-small-cell-lung-carcinoma-cells
#17
Chao-Min Wang, Kuei-Lin Yeh, Shang-Jie Tsai, Yun-Lian Jhan, Chang-Hung Chou
(1) Background: In China and South Asia, Alstonia scholaris (Apocynaceae) is an important medicinal plant that has been historically used in traditional ethnopharmacy to treat infectious diseases. Although various pharmacological activities have been reported, the anti-lung cancer components of A. scholaris have not yet been identified. The objective of this study is to evaluate the active components of the leaf extract of A. scholaris, and assess the anti-proliferation effects of isolated compounds against non-small-cell lung carcinoma cells; (2) Methods: NMR was used to identify the chemical constitutes isolated from the leaf extract of A...
December 1, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/29192448/-simultaneous-determination-of-six-triterpenoid-acids-from-guizhi-fuling-capsules-by-uplc-ms-ms
#18
Ying Ma, Jia-Chun Li, Wen-Zhe Huang, Zhen-Zhong Wang, Wei Xiao, Ya-Ling Song, Yong-Wen Zhang
To establish a UPLC-MS/MS method for simultaneous determination of six triterpenoid constituents (pachymic acid, dehydropachymic acid, dehydrotumulosic acid, polyporenic acid C, dehydroeburicoic acid and dehydrotra metenolic acid) in Guizhi Fuling capsules (GFC). Chromatographic analysis was conducted on Agilent Porosheell 120 SB-C₁₈ column (4.6 mm×150 mm, 2.7 μm), with 0.1% formic acid aqueous solution-methanol as the mobile phase for gradient elution at a flow rate of 0.4 mL•min-1. The column temperature was 30 ℃ and the sample size was 5 μL...
September 2017: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/29192442/-study-of-heterologous-efficient-synthesis-of-cucurbitadienol
#19
Shou-Lian Li, Dong Wang, Yi Liu, Ting-Ting Lin, Jin-Lei Tang, Er-Bing Hua, Xue-Li Zhang, Zhu-Bo Dai, Lu-Qi Huang
Cucurbitadienol has anti-inflammation, anti-cancer activities, and acts as a precursor of traditional Chinese medicine active ingredients mogroside and cucurbitacine. For construction of a Sacchromyces cerevisiae cell factory for production of cucurbitadienol, we firstly cloned a cucurbitadienol synthase (CBS) gene from Siraitia grosvenorii. Then, through heterologous expression of CBS in the triterpenoid chassis strain WD-2091, the engineered strain could produced 27.44 mg•L ⁻¹ cucurbitadienol, which was determined by GC-MS...
September 2017: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/29191092/plant-derived-isoprenoid-sweeteners-recent-progress-in-biosynthetic-gene-discovery-and-perspectives-on-microbial-production
#20
Hikaru Seki, Keita Tamura, Toshiya Muranaka
Increased public awareness of negative health effects associated with excess sugar consumption has triggered increasing interest in plant-derived natural sweeteners. Steviol glycosides are a group of highly sweet diterpene glycosides contained in the leaves of stevia (Stevia rebaudiana). Mogrosides, extracted from monk fruit (Siraitia grosvenorii), are a group of cucurbitane-type triterpenoid glycosides. Glycyrrhizin is an oleanane-type triterpenoid glycoside derived from the underground parts of Glycyrrhiza plants (licorice)...
December 1, 2017: Bioscience, Biotechnology, and Biochemistry
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