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Taewoong Rho, Kee Dong Yoon
In this study, the chloroform-soluble extract of C. auralis was separated successfully using off-line two-dimensional high-performance countercurrent chromatography, yielding a γ-pyrone, two alkaloids, a flavonoid and four lignans. The first-dimensional countercurrent separation using a methylene chloride/methanol/water (11:6:5, v/v/v) system yielded three sub-fractions (fractions I-III). The second-dimensional countercurrent separations, conducted on fractions I-III using n-hexane/ethyl and acetate/methanol/acetic acid (5:5:5:5:0, 3:7:3:7:0 and 1:9:1:9:0...
February 16, 2018: Journal of Separation Science
Bo Liu, Shou-Zhen Du, Fang Kuang, Ying Liu, Xing-Jun Tian, Ye-Gao Chen, Rui Zhan
Two new dibenzylbutyrolactol lignans and three known dibenzylbutyrolactone lignans were isolated from the twigs and leaves of Horsfieldia kingii. Their structures were elucidated by spectroscopic analysis. Cytotoxicity evaluation of these compounds against five human tumour lines showed no inhibitory effects.
February 15, 2018: Natural Product Research
Shekhar Kc, Prakash Basnet, Surendra Thapa, Bijay Shrestha, Ramesh Giri
We disclose a (terpy)NiBr2-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with tethered alkyl halides and arylzinc reagents. The reaction shows excellent functional group tolerance (such as ketones, esters, nitriles and halides) and moderate to good level of diastereoselectivity. The current cyclization/cross-coupling also tolerates molecules containing base-sensitive racemizable stereocenters, which are preserved without racemization during reaction. This cyclization/cross-coupling provides rapid access to (arylmethyl)carbo- and heterocyclic scaffolds, which occur widely as structural cores in various natural products and bioactive molecules...
February 15, 2018: Journal of Organic Chemistry
Hee Rae Kang, Hyung Sik Yun, Tae Kyoung Lee, Seulah Lee, Seon-Hee Kim, Eunjung Moon, Ki-Moon Park, Ki Hyun Kim
Oryza sativa L. is consumed globally as a staple food and its roots have been used as a Korean and Chinese medical supplement for protection of the stomach and lungs and for amelioration of vomiting and fever. In our continuing search for biologically effective metabolites from Korean natural materials, we found that an EtOH extract of O. sativa root reciprocally regulated adipocyte and osteoblast differentiation. Chemical analysis of the EtOH extract using a bioassay-guided fractionation protocol led to the isolation and determination of two novel lignans, oryzativols A and B, responsible for these regulatory activities...
February 14, 2018: Journal of Agricultural and Food Chemistry
Thressi Maxwell, Kyu Shik Lee, Soyoung Kim, Kyung-Soo Nam
Arctigenin, a member of the Asteraceae family, is a biologically active lignan that is consumed worldwide due to its several health benefits. However, its use may pose a problem for patients with estrogen receptor (ER)α-positive breast cancer, since studies have shown that arctigenin is a phytoestrogen that exerts a proliferative effect by binding to the ER. Thus, in this study, we examined the effect of arctigenin on ERα-positive MCF-7 human breast cancer cells to determine whether the consumption of arctigenin is safe for patients with breast cancer...
February 9, 2018: International Journal of Oncology
Regiane Godoy de Lima, Maria Teresa Barros, Rosangela da Silva Laurentiz
Lignans are a large class of natural products that have been isolated from many plants. They reveal diverse biological activities, especially antiviral and antitumor properties. From Piper cubeba , lignans of several classes can be isolated from the roots, rhizomes, stems, leaves, seeds, and fruits. Among its various chemical constituents, (-)-cubebin and (-)-hinokinin are found in significant quantities. Although they have been known for some time, during the last few decades their biological properties have been studied by several research groups...
February 2018: ChemistryOpen
Hemavathy Harikrishnan, Ibrahim Jantan, Md Areeful Haque, Endang Kumolosasi
Hypophyllanthin (HYP) and niranthin (NIR) are major lignans in Phyllanthus spp. and have been shown to possess strong anti-inflammatory activity. In this study, we investigated the anti-inflammatory effects and the underlying molecular mechanisms of HYP and NIR in in vitro cellular model of LPS-induced U937 macrophages. The effects of HYP and NIR on the production of prostaglandin E2 (PGE2), cyclooxygenase-2 (COX-2), tumor necrosis factor-α (TNF-α), and interleukin-1β (IL-1β) were measured by using ELISA, Western blot, and qRT-PCR...
February 9, 2018: Inflammation
Juan-Juan Li, Ling Cheng, Gang Shen, Ling Qiu, Cheng-Ying Shen, Juan Zheng, Rong Xu, Hai-Long Yuan
The present study was designed to improve storage stability and oral bioavailability of Ganneng dropping pills (GNDP) by transforming lignans of Herpetospermum caudigerum (HL) composed of herpetrione (HPE) and herpetin (HPN) into nanosuspension (HL-NS), the main active ingredient of GNDP, HL-NS was prepared by high pressure homogenization and lyophilized to transform into solid nanoparticles (HL nanoparticles), and then the formulated HL nanoparticles were perfused into matrix to obtain NS-GNDP by melting method...
January 2018: Chinese Journal of Natural Medicines
Justyna Godos, Sonia Bergante, Angela Satriano, Francesca Romana Pluchinotta, Marina Marranzano
BACKGROUND: Dietary polyphenols, including phytoestrogens are abundantly present in a balanced diet. Evidence for their role in preventing non-communicable diseases is emerging. METHODS: We examined the association between estimated habitual intakes of dietary phytoestrogens and hypertension in a cohort study. The baseline data included 1936 men and women aged 18 years and older. Intakes of total phytoestrogens, isoflavones, and lignans were calculated from validated food frequency questionnaire...
February 9, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Byoung Hoon You, Eun Chae Gong, Young Hee Choi
Herb-drug interaction (HDI) limits clinical application of herbs and drugs, and inhibition of herbs towards uridine diphosphate (UDP)-glucuronosyltransferases (UGTs) has gained attention as one of the important reasons to cause HDIs. Sauchinone, an active lignan isolated from aerial parts of Saururus chinensis (Saururacease), possesses anti-oxidant, anti-inflammatory, and anti-viral activities. In pharmacokinetics of sauchinone, sauchinone is highly distributed to the liver, forming extensive metabolites of sauchinone via UGTs in the liver...
February 9, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Jian Xiao, Xiao-Wei Cong, Gui-Zhen Yang, Ya-Wen Wang, Yu Peng
A Ni-catalyzed reductive cascade to a diastereocontrolled construction of THN[2,3-c]furan, is developed. The mild reaction conditions led to the tolerance of broad functional groups that can be placed in almost every position of this skeleton with good yields. The conformational control for the observed trans- or cis-fused selectivity during this tandem cyclization-coupling is also proposed.
February 7, 2018: Chemical Communications: Chem Comm
Gang Liao, Qi-Jun Yao, Zhuo-Zhuo Zhang, Yong-Jie Wu, Dan-Ying Huang, Bing-Feng Shi
Dibenzocyclooctadiene lignans are an interesting class of molecules for their unique structure of axially chiral biaryls as well as their significant biological activities. Herein, a Pd-catalyzed atroposelective C-H alkynylation was developed for the gram-scale, stereocontrolled formal syntheses of (+)-isoschizandrin and (+)-steganone. tert-Leucine was identified as an efficient, catalytic transient chiral auxiliary. The scope of this reaction is also presented and a wide range of enantioenriched biaryls were prepared in good yields (up to 99%) with excellent enantioselectivities (up to >99% ee)...
February 1, 2018: Angewandte Chemie
Jishou Piao, Lu Liu, Wang Sihong, Yingjin Kang, Yafeng Jin, Ninghai Quan, Donghao Li
Despite the strong antihepatotoxic, antioxidant, and antitumor properties of lignans in Schisandra chinensis, their applications in new drug development, bioscience and functional foods etc. are limited because of their low abundance and complex co-extractions. In this study, a magnetic separation method has been developed based on the polyethylenimine modified magnetic nanoparticles to rapidly and effectively separate and purify the lignans from Schisandra chinensis crude extracts through cation-π interaction and electrostatic adsorption...
January 31, 2018: Journal of Separation Science
Slava Rom, Viviana Zuluaga-Ramirez, Nancy L Reichenbach, Michelle A Erickson, Malika Winfield, Sachin Gajghate, Melpo Christofidou-Solomidou, Kelly L Jordan-Sciutto, Yuri Persidsky
BACKGROUND: Secoisolariciresinol diglucoside (SDG), the main lignan in flaxseed, is known for its beneficial effects in inflammation, oxidative stress, heart disease, tumor progression, atherosclerosis, and diabetes. SDG might be an attractive natural compound that protects against neuroinflammation. Yet, there are no comprehensive studies to date investigating the effects of SDG on brain endothelium using relevant in vivo and in vitro models. METHODS: We evaluated the effects of orally administered SDG on neuroinflammatory responses using in vivo imaging of the brain microvasculature during systemic inflammation and aseptic encephalitis...
January 27, 2018: Journal of Neuroinflammation
Bo Liu, Yanfang Yang, Hongbin Liu, Zhoutao Xie, Qun Li, Meng Deng, Fangping Li, Jingling Peng, Hezhen Wu
BACKGROUND: The Acanthaceae family is an important source of therapeutic drugs and ethno medicines. There are many famous medicinal plants from this family, such as Andrographis paniculata, Baphicacanthus cusia, and Dicliptera chinensis. Justicia procumbens (J. procumbens) is widely distributed in tropical and sub-tropical of the world. It has long been used in traditional Chinese medicine for cancer. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay showed the ethyl acetate extract of J...
January 25, 2018: Chemistry Central Journal
Xu Zhang, Bing Han, Zi-Ming Feng, Ya-Nan Yang, Jian-Shuang Jiang, Pei-Cheng Zhang
Four new ferulic acid derivatives ligusticumacid A-C (1-3) and ligusticumaldehyde A (4), one new dimer ligusticumacid D (5), and two novel 8-8' lignans ligusticumacid E-F (6-7) were isolated from the rhizome of Ligusticum chuanxiong Hort. In particular, compounds 1-2, 5 were rarely phenylpropanoid phenolic acid dimers through different polymerization action in natural products. Their structures were established using UV, IR, HRESIMS, NMR data. The absolute configurations of 3 was determined by quantum ECD calculation and 4, 6-7 were determined by the ECD exciton chirality method...
January 19, 2018: Fitoterapia
Yanjun Gao, Hongyu Zhao, Yang Li
Sauchinone is one of the active lignan isolated from Saururus chinensis, which has been considered to possess various pharmacological activities, such as antitumor, hepatoprotective, antioxidant, and anti-inflammatory effects. However, the functional roles of sauchinone in interleukin-1 beta (IL-1β)-stimulated human osteoarthritis (OA) chondrocytes are still unknown. Thus, in this study, we investigated the anti-inflammatory effects of sauchinone in IL-1β-stimulated chondrocytes. Our results demonstrated that sauchinone significantly attenuated NO and PGE2 production, as well as inhibited iNOS and COX-2 expression in IL-1β-stimulated OA chondrocytes...
January 22, 2018: Journal of Biochemical and Molecular Toxicology
Kijun Lee, Ji-Hye Ahn, Kyung-Tae Lee, Dae Sik Jang, Jung-Hye Choi
Deoxyschizandrin, a major lignan of Schisandra berries, has been demonstrated to have various biological activities such as antioxidant, hepatoprotective, and antidiabetic effects. However, the anti-cancer effects of deoxyschizandrin are poorly characterized. In the present study, we investigated the anti-cancer effect of deoxyschizandrin on human ovarian cancer cell lines and tumour-associated macrophages (TAMs). Deoxyschizandrin induced G₀/G₁ phase cell cycle arrest and inhibited cyclin E expression in human ovarian cancer cells...
January 15, 2018: Nutrients
Diana I Saavedra, Benjamin D Rencher, Doo-Hyun Kwon, Stacey J Smith, Daniel H Ess, Merritt B Andrus
Deoxypodophyllotoxin is a secondary metabolite lignan possessing potent anticancer activity with potential as a precursor for known anticancer drugs, but its use is limited by scarcity from natural sources. We here report the total synthesis of racemic deoxypodophyllotoxin (DPT) in seven steps using an intramolecular styryl Diels-Alder reaction (ISDA) strategy uniquely suited to assemble the deoxypodophyllotoxin core. Computational studies are also reported for this reaction that demonstrate the ability to overcome the limitations of slow reactivity and electronic mismatch of the diene and dieneophile...
January 17, 2018: Journal of Organic Chemistry
Shweta Sharma, Puneet Parashar, Subhasini Sharma, Kanta Prasad Sharma
Plant species rich in antioxidants (vitamins, flavonoids, lignans, and carotenoids) have been explored for complementary therapy of chronic diseases (cancers, coronary heart disease) and mitigation of pollutant toxicity. This article investigates their ameliorative role on selective hematological and serum biochemical parameters in fluoride-exposed (190 mg/kg body weight) Swiss albino mice pretreated with the antioxidant-rich diet supplements tomato puree (with and without peels), spirulina (cyanobacteria), and lycopene (present in tomato) for 45 days prior to entry into experimental protocol...
January 16, 2018: Journal of Dietary Supplements
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