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1. Antibacterial neolignans from the leaves of Melaleuca bracteata

Author:
Can Li; Hongxin Liu; Liyun Zhao; Weimin Zhang; Shengxiang Qiu; Xiaoyun Yang; Haibo Tan
Source:
Fitoterapia 2017 v.120 pp. 171-176
ISSN:
0367-326X
Subject:
Melaleuca; aldehydes; antibiotic resistance; antimicrobial properties; biochemical pathways; biomimetics; leaves; lignans; methicillin; methicillin-resistant Staphylococcus aureus; odors; spectral analysis
Abstract:
... Phytochemical study on the leaves of Melaleuca bracteata resulted in the isolation of ten compounds including three new neolignans, named melaleucins A–C (1–3). Among them, melaleucin B shares a rarely occurring nor-neolignan skeleton, and both melaleucins B and C bear a novel aldehyde moiety, which might also be response for the delicate fragrance of M. bracteata. Their structures were extensivel ...
DOI:
10.1016/j.fitote.2017.06.015

2. Antioxidant and cytotoxic lignans from the roots of Bupleurum chinense

Author:
Dan-Qi Li; Di Wang; Le Zhou; Ling-Zhi Li; Qing-Bo Liu; Ying-Ying Wu; Jing-Yu Yang; Shao-Jiang Song; Chun-Fu Wu
Source:
Journal of Asian natural products research 2017 v.19 no.5 pp. 519-527
ISSN:
1477-2213
Subject:
2,2-diphenyl-1-picrylhydrazyl; Bupleurum chinense; antioxidant activity; bioactive compounds; cytotoxicity; ethanol; fluorouracil; free radical scavengers; glucosides; inhibitory concentration 50; lignans; neoplasm cells; nuclear magnetic resonance spectroscopy; roots; spectral analysis
Abstract:
... In the search for biologically active compounds from the roots of Bupleurum chinense D C., phytochemical investigation of its ethanol extract led to the isolation and identification of a new 8- O -4′ neolignan glucoside, saikolignanoside A (1), along with eight known lignans (2–9). Their structures were determined on the basis of IR, UV, HRESIMS, and NMR spectroscopic analyses. The antioxidant and ...
DOI:
10.1080/10286020.2016.1234456

3. Antiplasmodial Securinega alkaloids from Phyllanthus fraternus: Discovery of natural (+)-allonorsecurinine

Author:
Gustav Komlaga; Grégory Genta-Jouve; Sandrine Cojean; Rita A. Dickson; Merlin L.K. Mensah; Philippe M. Loiseau; Pierre Champy; Mehdi A. Beniddir
Source:
Tetrahedron letters 2017 pp. -
ISSN:
0040-4039
Subject:
Phyllanthus fraternus; Plasmodium falciparum; Securinega; alkaloids; antimalarials; antiparasitic properties; chemical reactions; chemical structure; inhibitory concentration 50; lignans; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:
... The chemical investigation of the antimalarial plant Phyllanthus fraternus G. L. Webster (Phyllanthaceae) resulted in the discovery of the Securinega alkaloid (+)-allonorsecurinine (1), previously reported as a synthetic compound, together with the known ent-norsecurinine (2), nirurine (3), bubbialine (4), epibubbialine (5) and the lignan phyllanthin (6). The structure and absolute configuration o ...
DOI:
10.1016/j.tetlet.2017.08.045

4. Bioactive Asarone-Derived Phenylpropanoids from the Rhizome of Acorus tatarinowii Schott

Author:
Gao En; Zhou Zheng-Qun; Zou Jian; Yu Yang; Feng Xiao-Lin; Chen Guo-Dong; He Rong-Rong; Yao Xin-Sheng; Gao Hao
Source:
Journal of natural products 2017 v.80 no.11 pp. 2923-2929
ISSN:
1520-6025
Subject:
2,2-diphenyl-1-picrylhydrazyl; Acorus gramineus; acarbose; acetylcholinesterase; alpha-glucosidase; antioxidant activity; antioxidants; benzene; drugs; enantiomers; enzyme inhibition; high performance liquid chromatography; inhibitory concentration 50; lignans; phenylpropanoids; rhizomes; spectral analysis
Abstract:
... Eight new (1a/1b, 2a, 3a, 4a/4b, and 5a/5b) and seven known (2b, 3b, and 6–10) asarone-derived phenylpropanoids, a known asarone-derived lignan (12), and four known lignan analogues (11 and 13–15) were isolated from the rhizome of Acorus tatarinowii Schott. The structures were elucidated via comprehensive spectroscopic analyses, modified Mosher’s method, and quantum chemical calculations. Compound ...
DOI:
10.1021/acs.jnatprod.7b00457

5. Cytotoxic neolignans from the traditional Chinese medicine Daphniphyllum macropodum Miq.

Author:
Xinhua Ma; Jie Yang; Christopher L. Brown; Chao Wang; Shihao Deng; Ruifang Ke; Shicheng Xu; Mi Huang; Xinzhou Yang; Yunjiang Feng
Source:
RSC advances 2017 v.7 no.83 pp. 52970-52976
ISSN:
2046-2069
Subject:
Daphniphyllum; Oriental traditional medicine; apoptosis; benzaldehyde; caspase-3; caspase-9; cell growth; cell lines; circular dichroism spectroscopy; cytotoxicity; dose response; humans; lignans; mitochondria; neoplasm cells; neoplasms; nuclear magnetic resonance spectroscopy; seeds; spectral analysis
Abstract:
... Four new neolignans, (E)-3-(hydroxymethyl)-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-6-ol (1), methyl (E)-6-hydroxy-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-3-carboxylate (2), (R)-4-hydroxy-3-(1-(4-hydroxyphenyl)propan-2-yl)benzaldehyde (3) and methyl (E,R)-3-(4-hydroxy-3-(1-(4-hydroxyphenyl)propan-2-yl)phenyl)acrylate (4) were isolated from the seeds of Daphniphyllum macropodum Miq ...
DOI:
10.1039/c7ra09569d

6. Diarylpropanes and lignans from Horsfieldia tetratepala

Author:
Shou-Zhen Du; Zhi-Chong Wang; Ying Liu; Rui Zhan; Ye-Gao Chen
Source:
Phytochemistry letters 2017 v.19 pp. 98-100
ISSN:
1874-3900
Subject:
acetone; branches; cytotoxicity; lignans; neoplasms; spectral analysis
Abstract:
... Two new diarylpropanes (1–2), four known compounds, and a new artifact, were isolated from 70% aqueous acetone extract of the twigs of Horsfieldia tetratepala. Their structures were elucidated by spectroscopic analysis. Cytotoxicity evaluation against five cancer cell lines showed that none of these compounds was cytotoxic. ...
DOI:
10.1016/j.phytol.2016.12.018

7. Enantiomeric 8-O-4′ type neolignans from red raspberry as potential inhibitors of β-amyloid aggregation

Author:
Le Zhou; Li-Li Lou; Wei Wang; Bin Lin; Jun-Ning Chen; Xiao-Bo Wang; Xiao-Xiao Huang; Shao-Jiang Song
Source:
Journal of functional foods 2017 v.37 pp. 322-329
ISSN:
1756-4646
Subject:
Alzheimer disease; Rubus idaeus; chemical composition; chemical structure; functional foods; lignans; neuroprotective effect; spectral analysis; stereochemistry
Abstract:
... Red raspberry (Rubus idaeus L.) is an edible fruit-producing species belonging to the Rosaceae family. In our search for potential agents for treating Alzheimer’s disease in this functional food, we decided to investigate the chemical constituents of red raspberry. Four pairs of enantiomeric 8-O-4′-type neolignans (1a/1b–4a/4b), including three new compounds (1a/1b and 2a), were identified from th ...
DOI:
10.1016/j.jff.2017.08.007

8. Flavonol glycosides and lignans from the leaves of Opilia amentacea

Author:
Abdulmagid Alabdul Magid; Anaëlle Abdellah; Virginie Pecher; Laure Pasquier; Dominique Harakat; Laurence Voutquenne-Nazabadioko
Source:
Phytochemistry letters 2017 v.21 pp. 84-89
ISSN:
1874-3900
Subject:
2,2-diphenyl-1-picrylhydrazyl; Opiliaceae; antioxidant activity; flavonols; glycosides; inhibitory concentration 50; leaves; lignans; mushrooms; spectral analysis
Abstract:
... Two previously undescribed flavonol tetraglycosides, isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (1) and isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside (2), along with nine known compounds including seven flavonoids and two lignans, were isolated from the l ...
DOI:
10.1016/j.phytol.2017.05.023

9. Furofuran lignan glucosides from the leaves of Vitex negundo var. cannabifolia

Author:
Yue-Ting Li; Man-Man Li; Jing Sun; Zhi-Xiang Zhu; Yue-Lin Song; Dao-Ran Pang; Jiao Zheng; Yun-Fang Zhao; Peng-Fei Tu; Jun Li
Source:
Natural product research 2017 v.31 no.8 pp. 918-924
ISSN:
1478-6427
Subject:
Vitex negundo; glucosides; inhibitory concentration 50; leaves; lignans; nitric oxide; spectral analysis; spectroscopy
Abstract:
... Two new furofuran lignan glucosides, cannabilignin (1) and isocannabilignin (2), together with four known compounds (3 – 6), were isolated from the leaves of Vitex negundo var. cannabifolia . The structures of the isolates were elucidated by analysis of spectroscopic data. Compound 3 exhibited weak inhibition of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells with IC ...
DOI:
10.1080/14786419.2016.1255887

10. Lignan glycosides from the Rhizomes of Smilax trinervula and their Biological activities

Author:
Jicheng Shu; Fang Liang; Genhua Zhu; Xing Liu; Jiangli Yu; Huilian Huang
Source:
Phytochemistry letters 2017 v.20 pp. 1-8
ISSN:
1874-3900
Subject:
Smilax; cytotoxicity; electrospray ionization mass spectrometry; glycosides; humans; inhibitory concentration 50; lignans; neoplasm cells; nuclear magnetic resonance spectroscopy; rhizomes; spectral analysis
Abstract:
... Phytochemical investigation of the rhizomes of Smilax trinervula led to isolation and structure elucidation of eight lignan glycosides, including five new lignans, namely, (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4′-O-β-d-glucopyranoside (1), (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4-O-β-d- glucopyranoside (2) ...
DOI:
10.1016/j.phytol.2017.03.002

11. Lignans and diterpenes isolated from Tirpitzia ovoidea and their biological activities

Author:
Xue-Yan YANG; Yi-Fan ZHANG; Li-Jia LIU; Yi WANG; Ming-Ying SHANG; Feng XU; Guang-Xue LIU; Shao-Qing CAI
Source:
Chinese journal of natural medicines 2017 v.15 no.12 pp. 938-943
ISSN:
1875-5364
Subject:
Linaceae; Oriental traditional medicine; aerial parts; anti-inflammatory activity; cell lines; cytotoxicity; diterpenoids; ethanol; ethyl acetate; inflammation; inhibitory concentration 50; lignans; macrophages; mice; models; nitric oxide; spectral analysis
Abstract:
... A new lignan, tirpitzin A (17) together with 20 known compounds (1–16, and 18–21) were isolated from the ethyl acetate soluble fraction of ethanol extract of the aerial parts of Tirpitzia ovoidea. The structure of new compound was elucidated by means of spectroscopic analysis. Of the known compounds, 7–21 were isolated from Linaceae family for the first time. The pharmacological activity of the cr ...
DOI:
10.1016/S1875-5364(18)30010-4

12. Lignans from the shed trunk barks of the critically endangered plant Abies beshanzuensis and their anti-neuroinflammatory activities

Author:
Chang-Ling Hu; Juan Xiong; Peng Xu; Ke-Jun Cheng; Guo-Xun Yang; Jin-Feng Hu
Source:
Natural product research 2017 v.31 no.12 pp. 1358-1364
ISSN:
1478-6427
Subject:
Abies; inhibitory concentration 50; lignans; mice; nitric oxide; plants (botany); spectral analysis
Abstract:
... During a further and comprehensive phytochemical investigation on the shed trunk barks of the critically endangered plant Abies beshanzuensis , one new (1) and ten known (2 – 11) lignans with diverse structures were isolated. On the basis of spectroscopic methods, the new structure was established to be (7 S ,8 R ,8′ R)-4′-methoxyl- α -conidendrin (1). Among the isolated lignans, (−)-matairesinol ...
DOI:
10.1080/14786419.2016.1247082

13. Lipoxygenase-inhibiting lignans from Clematis mandshurica

Author:
Qiang Fu; Chuang Zhou; Yu Ma; Min Yang; Hai-Mei Yuan; Jiang Chen; Pei-Xi Liu
Source:
Journal of Asian natural products research 2017 v.19 no.9 pp. 884-889
ISSN:
1477-2213
Subject:
linoleate 13S-lipoxygenase; Clematis terniflora var. mandshurica; lignans; hydrolysis; spectral analysis; rhizomes; ethanol; roots
Abstract:
... The EtOH extract of the roots and rhizomes of Clematis mandshurica afforded two new lignans clemomanshurinane C (1) and clemomanshurinane D (2), and three known compounds (3–5). Their structures were elucidated on the basis of spectroscopic means and hydrolysis products. All compounds displayed moderate inhibitory activity against enzyme lipoxygenase. ...
DOI:
10.1080/10286020.2016.1251419

14. Mass spectrometry-based analysis of whole-grain phytochemicals

Author:
Ville Mikael Koistinen; Kati Hanhineva
Source:
Critical reviews in food science and nutrition 2017 v.57 no.8 pp. 1688-1709
ISSN:
1549-7852
Subject:
alkylresorcinols; barley; benzoxazinoids; flavonoids; lignans; liquid chromatography; mass spectrometry; noninfectious diseases; oats; phytosterols; risk; rye; spectral analysis; wheat; whole grain foods
Abstract:
... Whole grains are a rich source of several classes of phytochemicals, such as alkylresorcinols, benzoxazinoids, flavonoids, lignans, and phytosterols. A high intake of whole grains has been linked to a reduced risk of some major noncommunicable diseases, and it has been postulated that a complex mixture of phytochemicals works in synergy to generate beneficial health effects. Mass spectrometry, esp ...
DOI:
10.1080/10408398.2015.1016477

15. Neolignan and megastigmane glucosides from the aerial parts of Isodon japonicus with cell protective effects on BaP-induced cytotoxicity

Author:
Takahiro Matsumoto; Seikou Nakamura; Souichi Nakashima; Tomoe Ohta; Keiko Ogawa; Masashi Fukaya; Junko Tsukioka; Tomohiro Hasei; Tetsushi Watanabe; Hisashi Matsuda
Source:
Phytochemistry 2017 v.137 pp. 101-108
ISSN:
0031-9422
Subject:
aerial parts; chemical structure; cytotoxicity; glucosides; lignans; nuclear magnetic resonance spectroscopy; protective effect; spectral analysis; Japan
Abstract:
... Six neolignan glucosides, named isodonosides I–VI, and a megastigmane glucoside named isodonmegastigmane I, were isolated together with 15 known compounds from the methanolic extract of aerial parts of Isodon japonicus cultivated in Tokushima, Japan. The chemical structures of the compounds were elucidated based on their MS and NMR spectroscopic analysis. The absolute configurations of the neolign ...
DOI:
10.1016/j.phytochem.2017.02.007

16. Neolignan and monoterpene glycoside from the seeds of Pharbitis nil

Author:
Seoung Rak Lee; Eunjung Moon; Ki Hyun Kim
Source:
Phytochemistry letters 2017 v.20 pp. 98-101
ISSN:
1874-3900
Subject:
Ipomoea nil; anti-inflammatory activity; chemical structure; cytotoxicity; ethanol; glycosides; inhibitory concentration 50; lignans; lipopolysaccharides; mice; monoterpenoids; nitric oxide; nuclear magnetic resonance spectroscopy; seeds; spectral analysis
Abstract:
... Phytochemical investigation of an EtOH extract of Pharbitis nil seeds (Convolvulaceae) resulted in the isolation and identification of a new neolignan, 7R,8S-threo-dihydroxydehydrodiconiferyl alcohol (1), and a new monoterpene glycoside, (3Z,7S)-7-hydroxy-3,7-dimethyl-3,8-octadienyl-β-d-glucopyranoside (2), together with a known compound, ethyl α-l-arabinofuranoside (3). The chemical structures of ...
DOI:
10.1016/j.phytol.2017.04.019

17. Neuroprotective Lignans from the Fruits of Schisandra bicolor var. tuberculata

Author:
Liu Ye; Yu Heng-Yi; Wang Yan-Mei; Tian Tian; Wu Wen-Ming; Zhou Ming; Meng Xiang-Gao; Ruan Han-Li
Source:
Journal of natural products 2017 v.80 no.4 pp. 1117-1124
ISSN:
1520-6025
Subject:
Schisandra; X-ray diffraction; chemical structure; fruits; hydrogen peroxide; irradiation; lignans; models; neuroprotective effect; spectral analysis
Abstract:
... Nine new lignans (1–9) and ten known analogues (10–19) were isolated from the fruits of Schisandra bicolor var. tuberculata. The structures of compounds 1–9 were established on the basis of spectroscopic data analysis. The absolute configuration of compound 1 was determined by single-crystal X-ray diffraction analysis with Cu Kα irradiation techniques, and the absolute configurations of compounds ...
DOI:
10.1021/acs.jnatprod.7b00035

18. A New Insecticidal Lignan Glucoside from Galium verum

Author:
Jia Chen; Chun-Chao Zhao; Jian-Hua Shao; Ju-Di Fan; Xu-Hua Huang
Source:
Chemistry of natural compounds 2017 v.53 no.4 pp. 626-628
ISSN:
0009-3130
Subject:
Galium verum; Helicoverpa armigera; Scorpiones; chemical structure; glucosides; insecticidal properties; lignans; mortality; poisoning; scorpion venoms; spectral analysis; stomach; toxicity
Abstract:
... A new lignan glucoside, galiveroside A (1), and seven known compounds (2–8), were isolated from Galium verum L. The structure of 1 was elucidated on the basis of extensive spectroscopic analyses. Compound 1, at the concentration of 5 mg/mL, showed insecticide activity to 3 age cotton bollworm with a mortality of 16.3% through stomach poisoning. When combined with a recombinant scorpion toxin rLqh ...
DOI:
10.1007/s10600-017-2075-3

19. A New Lignan Glucoside from Cyclea racemosa

Author:
Jian-Hua Shao; Xue-Wei Zhang; Zi-Ling Dong; Si-Hui Li; Ben-Jie Miao; Ke-Zhi Cheng
Source:
Chemistry of natural compounds 2017 v.53 no.6 pp. 1025-1027
ISSN:
0009-3130
Subject:
Cyclea; chemical structure; glucosides; lignans; spectral analysis
Abstract:
... A new lignan glucoside 1, along with two known lignans (2, 3), was isolated from Cyclea racemosa Oliv. Its structure was elucidated as (+)-7′-methoxylariciresinol 4-O-β-D-glucopyranoside on the basis of extensive spectroscopic analyses. ...
DOI:
10.1007/s10600-017-2193-y

20. Phytochemical study of Joannesia princeps Vell. (Euphorbiaceae) leaves

Author:
César Muñoz Camero; Abeer Temraz; Alessandra Braca; Marinella De Leo
Source:
Biochemical systematics and ecology 2017 v.70 pp. 69-72
ISSN:
0305-1978
Subject:
Euphorbiaceae; chemotaxonomy; flavonoids; glycosylation; leaves; lignans; metabolites; methanol; monoterpenoids; spectral analysis
Abstract:
... A phytochemical study of chloroform-methanol and methanol extracts of Joannesia princeps Vell. Leaves led to the isolation of twenty eight compounds, including two α-ionones (2, 5), three glycosylated monoterpenes (1, 3, 4), eight phenolic compounds (6, 8, 9, 12, 14, 17, 18, 24), two gallotannins (10, 11), twelve flavonoids (7, 15, 16, 19, 20–23, 25–28), and one lignan (13). The structural charact ...
DOI:
10.1016/j.bse.2016.10.023