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plant lignans

Ricarda Höhner, Joaquim V Marques, Tetsuro Ito, Yoshiaki Amakura, Alan D Budgeon, Karl Weitz, Kim K Hixson, Laurence B Davin, Helmut Kirchhoff, Norman G Lewis
Arogenate dehydratase (ADT) catalyzes the final step of phenylalanine (Phe) biosynthesis. Previous work showed that ADT-deficient Arabidopsis thaliana mutants had significantly reduced lignin contents, with stronger reductions in lines that had deficiencies in more ADT isoforms. Here, by analyzing Arabidopsis ADT mutants using our phenomics facility and UPLC-MS based metabolomics, we describe the effects of modulation of ADT on photosynthetic parameters and secondary metabolism. Our data indicate that a reduced carbon flux into Phe biosynthesis in ADT mutants impairs the consumption of photosynthetically produced ATP leading to an increased ATP/ADP ratio, the over-accumulation of transitory starch, and lower electron transport rates...
March 9, 2018: Plant Physiology
Wenjuan Zhang, Yang Wang, Zhufeng Geng, Shanshan Guo, Juqin Cao, Zhe Zhang, Xue Pang, Zhenyang Chen, Shushan Du, Zhiwei Deng
The speciation of a methanolic extract of Zanthoxylum armatum stem bark has enabled the isolation and characterization of 11 known lignans. Among them, five compounds ( 6 , 8 - 11 ) are reported in this plant for the first time. All of the chemical structures were elucidated on the basis of NMR spectral analysis. Additionally, their antifeedant activities against Tribolium castaneum were evaluated scientifically. Among them, asarinin ( 1 ), with an EC50 of 25.64 ppm, exhibited a much stronger antifeedant activity than the positive control, toosendanin (EC50 = 71...
March 9, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Ahmed Ramadan El-Rokh, Amr Negm, Maha El-Shamy, Mohamed El-Gindy, Mamdouh Abdel-Mogib
Four previously undescribed sucrose diester of aryldihydronaphthalene-type lignans, named echiumins A-D, were isolated from the butanol fraction of Echium angustifolium Mill, in addition to a known compound, trigonotin A, which is reported for the first time from the title plant. The structures of isolated compounds were elucidated using spectroscopic methods such as HRESIMS and 1D and 2D NMR spectroscopy. The isolated compounds displayed strong to weak antitumor activity against HepG2 and MCF7 cancer cell lines, with echiumins A and D showed the most potent activity...
March 5, 2018: Phytochemistry
Mana Sampei, Midori A Arai, Masami Ishibashi
Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca by monitoring antioxidative activity using the 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Starting from a tandem Michael-aldol reaction, the lignan skeleton was synthesized in 6 steps, including a cyclization step. To determine the stereochemistry of 1, we synthesized the natural product (±)-isolariciresinol (18) from alcohol 17...
March 5, 2018: Journal of Natural Medicines
Pooja Vyas, Dinesh Kumar Yadav, Poonam Khandelwal
Tectona grandis Linn (Teak), is locally known as Sagwan, belongs to Lamiaceae family. It is one of the most valuable timber in the world, due to its beautiful surface and its resistance to termite and fungal damage. The main active ingredient compounds that are responsible for these action are tectoquinone, lapachol and deoxylapachol. Naphthoquinones, anthraquinones and isoprenoid quinones are abundant metabolites in teak. In addition to these, teak contains several other phytochemicals such as triterpenoids, steroids, lignans, fatty esters and phenolic compounds...
March 6, 2018: Natural Product Research
Shi-Man Gao, Jiu-Shi Liu, Min Wang, Ting-Ting Cao, Yao-Dong Qi, Ben-Gang Zhang, Xiao-Bo Sun, Hai-Tao Liu, Pei-Gen Xiao
ETHNOPHARMACOLOGICAL RELEVANCE: Species of the genus Codonopsis are perennial herbs mainly distributed throughout East, Southeast and Central Asia. As recorded, they have been used as traditional Chinese medicines since the Qing Dynasty, where they were claimed for strengthening the spleen and tonifying the lung, as well as nourishing blood and engendering liquid. Some species are also used as food materials in southern China and Southeast Asia, such as tea, wine, soup, plaster, and porridge...
February 28, 2018: Journal of Ethnopharmacology
Padam Kumar, Kapil Dev, Khushbu Sharma, Mahendra Sahai, Rakesh Maurya
Phytochemical investigation of Cissus quadrangularis stems led to the isolation of one new phenolic glycoside (1) and two new lignan glycosides (7 & 8) along with twelve known compounds (2-6 & 9-15). Their chemical structures were determined on the basis of extensive spectroscopic analysis using 1D, 2D NMR, and mass spectrometric analysis. Among the known compounds, 4-6, 9 and 12 were isolated for the first time from the genus Cissus whereas compounds 10, 11 and 13 for the first time from this plant...
February 28, 2018: Natural Product Research
David Picking, Bentley Chambers, James Barker, Iltaf Shah, Roy Porter, Declan P Naughton, Rupika Delgoda
Understanding the potential for adverse drug reactions (ADRs), from herb-drug interactions, is a key aspect of medicinal plant safety, with particular relevance for public health in countries where medicinal plant use is highly prevalent. We undertook an in-depth assessment of extracts of Hyptis verticillata Jacq., via its impact on activities of key cytochrome P450 (CYP) enzymes (CYPs 1A1, 1A2, 1B1, 3A4 and 2D6), its antioxidant properties (determined by DPPH assays) and chemical characterisation (using LC-MS)...
February 15, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
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
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
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
Ya-Li Wang, Lin Zhang, Meng-Yan Li, Li-Wei Wang, Chao-Mei Ma
Two lignans including a new one, five flavonoids and five coumarins were isolated from the whole plant of Viola philippica (synonymised as Viola yedoensis Makino). The new compound was structurally determined as (7R,8S,8'S) -3,3'-dimethoxy- 4,4',9-trihydroxy- 7,9'-epoxy-8,8'-lignan 9-O-rutinoside by analysis of its NMR, MS and CD spectroscopic data. The known compounds were characterised by comparing their NMR and MS data with those reported. Among the known compounds, 5-hydroxy-4'-methoxyflavone-7-O- rutinoside, 6,7-di-O-β-D- glucopyranosylesculetin, and 7R,8S-dihydrodehydrodiconiferyl alcohol 4-O-β-D- glucopyranoside were isolated and identified from this genus for the first time...
January 15, 2018: Natural Product Research
Iqra Sarfraz, Azhar Rasul, Farhat Jabeen, Tahira Younis, Muhammad Kashif Zahoor, Muhammad Arshad, Muhammad Ali
Fraxinus, a member of the Oleaceae family, commonly known as ash tree is found in northeast Asia, north America, east and western France, China, northern areas of Pakistan, India, and Afghanistan. Chemical constituents of Fraxinus plant include various secoiridoids, phenylethanoids, flavonoids, coumarins, and lignans; therefore, it is considered as a plant with versatile biological and pharmacological activities. Its tremendous range of pharmacotherapeutic properties has been well documented including anticancer, anti-inflammatory, antioxidant, antimicrobial, and neuroprotective...
2017: Evidence-based Complementary and Alternative Medicine: ECAM
Ta-Chin Lin, Kai-Hung Wang, An-Pei Kao, Kuo-Hsiang Chuang, Tsung-Cheng Kuo
OBJECTIVE: The notion that the human endometrium may contain a population of stem cells has recently been proposed. The mesenchymal stem cells (MSCs) in the endometrium are believed to be responsible for the remarkable regenerative ability of endometrial cells. Estrogens influence the physiological and pathological processes of several hormone-dependent tissues, such as the endometrium. Pueraria mirifica (PM) is a herbal plant that contains several phytoestrogens, including isoflavones, lignans, and coumestans, and is known to exert an estrogenic effect on animal models...
December 2017: Taiwanese Journal of Obstetrics & Gynecology
Young Seon Cho, Woo Seok Song, Sang Ho Yoon, Kyeong-Yeol Park, Myoung-Hwan Kim
Many neuromodulating drugs acting on the nervous system originate from botanical sources. These plant-derived substances modulate the activity of receptors, ion channels, or transporters in neurons. Their properties make the substances useful for medicine and research. Here, we show that the plant lignan (+)-syringaresinol (SYR) suppresses excitatory synaptic transmission via presynaptic modulation. Bath application of SYR rapidly reduced the slopes of the field excitatory postsynaptic potentials (fEPSPs) at the hippocampal Schaffer collateral (SC)-CA1 synapse in a dose-dependent manner...
March 15, 2018: Neuropharmacology
Yuan Zhao, Hong-Xia Zheng, Ying Xu, Na Lin
Phytoestrogens are plant-derived compounds, which have a similarity in structure with human endogenous estrogen 17-β-estradiol. Structural likeness enables phytoestrogens to interact with estrogen receptors, not simply mimicking the effects of human steroidal estrogen but also exhibiting similar and divergent actions. The global literature relating to phytoestrogen in recent years was systematically summarized in this paper. Chemical compositions of phytoestrogens were mainly flavonoids, coumarins, lignans, terpenoids, steroids, etc...
September 2017: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
Naoki Mori
Lignans are a large class of naturally occurring secondary metabolites which are widely spread within the plant kingdom. Their diverse structures and variety of biological activities have fascinated organic chemists. For synthesizing optically active lignans, we have developed the novel asymmetric dimerization of cinnamic acid derivatives, and applied it to the enantioselective syntheses of furofuran lignans (yangambin, sesamin, eudesmin, caruilignan A) and diarylbutane lignans (sauriols A and B). This review summarizes the methodology of our asymmetric dimerization of cinnamic acid derivatives, and efficient total syntheses of furofuran and diarylbutane lignans reported by our and other groups...
January 2018: Bioscience, Biotechnology, and Biochemistry
Yusuke Baba, Zenpei Shigemi, Naoko Hara, Misato Moriguchi, Marina Ikeda, Tadashi Watanabe, Masahiro Fujimuro
Kaposi's sarcoma-associated herpesvirus (KSHV) is the causative agent of primary effusion lymphoma (PEL) and Kaposi's sarcoma. PEL is a type of non-Hodgkin's B-cell lymphoma, affecting immunosuppressed individuals, such as post-transplant or AIDS patients. However, since PEL is resistant to chemotherapeutic regimens, new effective treatment strategies are required. Arctigenin, a natural lignan compound found in the plant Arctium lappa, has been widely investigated as a potential anticancer agent in the clinical setting...
February 2018: International Journal of Oncology
Md Abdul Muhit, Kaoru Umehara, Hiroshi Noguchi
EtOAc extract from the leaves of Terminalia citrina collected in Bangladesh were separated, and seven previously undescribed α-keto tetrahydrofuran lignan glucosides (terminalosides Q to W) were isolated and characterized. NOESY analysis of (1)H NMR spectra and ECD spectroscopic data analysis revealed the absolute stereochemistry of the tetrahydrofuran ring of the isolated constituents as being a (7S,8R,8'S)- configuration in terminalosides Q to U and a (7R,8R,8'S)- configuration in terminalosides V and W...
November 14, 2017: Phytochemistry
Da Hye Kwon, Hee-Jae Cha, Eun Ok Choi, Sun-Hee Leem, Gi-Young Kim, Sung-Kwon Moon, Young-Chae Chang, Seok-Joong Yun, Hye Jin Hwang, Byung Woo Kim, Wun-Jae Kim, Yung Hyun Choi
Schisandrin A is a bioactive lignan occurring in the fruits of plants of the Schisandra genus that have traditionally been used in Korea for treating various inflammatory diseases. Although the anti-inflammatory and antioxidant effects of lignan analogues similar to schisandrin A have been reported, the underlying molecular mechanisms have remained elusive. In the present study, schisandrin A significantly suppressed the lipopolysaccharide (LPS)-induced production of the key pro-inflammatory mediators nitric oxide (NO) and prostaglandin E2 by suppressing the expression of inducible NO synthase and cyclooxygenase-2 at the mRNA and protein levels in RAW 264...
October 25, 2017: International Journal of Molecular Medicine
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