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1. A New Neolignan Glucoside from the Stems of “Baekma” Cultivar, Chrysanthemum morifolium

Author:
Hyoung-Geun Kim; Hyun-Ji Oh; Jung-Hwan Ko; Sun-Woo Joo; Yeong-Geun Lee; Yun-Su Baek; Dae Young Lee; Nam-In Baek
Source:
Chemistry of natural compounds 2019 v.55 no.4 pp. 610-613
ISSN:
0009-3130
Subject:
Chrysanthemum morifolium; chemical structure; cultivars; glucosides; lignans; nuclear magnetic resonance spectroscopy; silica gel; spectral analysis; stems
Abstract:
... A new neolignan glucoside has been isolated from Chrysanthemum morifolium ‘Baekma’ cultivar through repeated silica gel and octadecyl silica gel (ODS) column chromatographies. On the basis of spectroscopic data including NMR, MS, and IR, the chemical structure of the new neolignan glucoside was determined to be (7S,8S)-7-O-[1′-(4′,5′-dihydroxy-3′-methoxyphenyl)propanol]guaiacylglycerol 4-O-β-D-glu ...
DOI:
10.1007/s10600-019-02760-1

2. Two new secoiridoid glucosides and a new lignan from the roots of Ilex pubescens

Author:
Yang Zhang; Bowen Deng; Yida Cui; Xue Chen; Jiayi Bi; Guogang Zhang
Source:
Natural medicines 2018 v.72 no.4 pp. 946-953
ISSN:
1340-3443
Subject:
Ilex pubescens; chemical structure; glucosides; lignans; nuclear magnetic resonance spectroscopy; roots
Abstract:
... Two new secoiridoid glucosides, ilexpublignoside (1), pubzenoside (2), and a new lignan, ilexlignan B (3), along with seven known compounds (4–10) were isolated from the roots of Ilex pubescens for the first time. Their chemical structures were elucidated on the basis of extensive spectroscopic methods, including IR, UV, HR-ESI–MS, CD, NMR experiments, as well as comparison with the reported data. ...
DOI:
10.1007/s11418-018-1227-5

3. 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

4. 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

5. 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

6. Two new lignan-iridoid glucoside diesters from the leaves of Vaccinium bracteatum and their relative and absolute configuration determination by DFT NMR and TDDFT-ECD calculation

Author:
Yong-Mei Ren; Chang-Qiang Ke; Attila Mándi; Tibor Kurtán; Chunping Tang; Sheng Yao; Yang Ye
Source:
Tetrahedron 2017 pp. -
ISSN:
0040-4020
Subject:
Vaccinium bracteatum; biochemical pathways; chemical reactions; chemical structure; circular dichroism spectroscopy; glucosides; iridoids; leaves; lignans; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:
... Two new lignan-iridoid glucoside diesters (2 and 3), together with their putative biosynthetic precursor 10-O-trans-caffeoyl-6α-hydroxyl-dihydromonotropein (1), were characterized from the leaves of Vaccinium bracteatum. Their planar structures and relative configuration were elucidated by spectroscopic measurements and DFT C NMR calculations, and their absolute configurations were determined by t ...
DOI:
10.1016/j.tet.2017.04.040

7. Antioxidant components as potential neuroprotective agents in sesame (Sesamum indicum L.)

Author:
Park, Si-Hyung; Ryu, Su-Noh; Bu, Youngmin; Kim, Hocheol; Simon, James E.; Kim, Kwan-Su
Source:
Food reviews international 2010 v.26 no.2 pp. 103-121
ISSN:
8755-9129
Subject:
Sesamum indicum; oilseed crops; oil crops; sesame seed; chemical constituents of plants; lignans; glucosides; vitamin content; tocopherols; neuroprotective effect; oxidative stability; antioxidants; antioxidant activity; chemical structure; biosynthesis; biochemical pathways
DOI:
10.1080/87559120903564464

8. The unusual canangafruticosides A–E: Five monoterpene glucosides, two monoterpenes and a monoterpene glucoside diester of the aryldihydronaphthalene lignan dicarboxylic acid from leaves of Cananga odorata var. fruticosa

Author:
Nagashima, Jiro; Matsunami, Katsuyoshi; Otsuka, Hideaki; Lhieochaiphant, Duangporn; Lhieochaiphant, Sorasak
Source:
Phytochemistry 2010 v.71 no.13 pp. 1564-1572
ISSN:
0031-9422
Subject:
Cananga odorata; monoterpenoids; glucosides; essential oils; dicarboxylic acids; lignans; spectroscopy; chemical structure
Abstract:
... From the leaves of Cananga odorata var. fruticosa, five unusual monoterpene glucosides, named canangafruticosides A–E (1–5), along with two unusual non-glucosidic monoterpenes (6, 7) were isolated. An aryldihydronaphthalene-type lignan dicarboxylate (8) was also isolated, with two moles of canangafruticoside A (1) on its ester moiety. This lignan also showed strong blue fluorescence emission under ...
DOI:
10.1016/j.phytochem.2010.06.009

9. Absolute configuration of (+)-pinoresinol 4-O-[6"-O-galloyl]-β-d-glucopyranoside, macarangiosides E, and F isolated from the leaves of Macaranga tanarius

Author:
Matsunami, Katsuyoshi; Otsuka, Hideaki; Kondo, Kazunari; Shinzato, Takakazu; Kawahata, Masatoshi; Yamaguchi, Kentaro; Takeda, Yoshio
Source:
Phytochemistry 2009 v.70 no.10 pp. 1277-1285
ISSN:
0031-9422
Subject:
Macaranga tanarius; lignans; glucosides; chemical constituents of plants; chemical structure; spectral analysis; stereochemistry; antioxidant activity; Japan
Abstract:
... A lignan glucoside, (+)-pinoresinol 4-O-[6"-O-galloyl]-β-d-glucopyranoside (1), and two megastigmane glucosides, named macarangiosides E and F (2, 3), together with 15 known compounds (4-18) were isolated from leaves of Macaranga tanarius (L.) Müll.-Arg. (Euphorbiaceae). Their structures were elucidated by spectroscopic and chemical analyses. In addition, the absolute stereochemistry of macarangi ...
DOI:
10.1016/j.phytochem.2009.07.020

10. Sesquiterpenoids and Cytotoxic Lignans from the Bark of Libocedrus chevalieri

Author:
Zhang, Y.J.; Litaudon, M.; Bousserouel, H.; Martin, M.T.; Thoison, O.; Léonce, S.; Dumontet, V.; Sévenet, T.; Guéritte, F.
Source:
Journal of natural products 2007 v.70 no.8 pp. 1368-1370
ISSN:
0163-3864
Subject:
sesquiterpenoids; Libocedrus; humans; cytotoxicity; anticarcinogenic activity; glucosides; lignans; diterpenoids; spectral analysis; cultured cells; chemical structure; New Caledonia
DOI:
10.1021/np070124q
PubMed:
17676899

11. HPLC analysis of sesaminol glucosides in sesame seeds

Author:
Moazzami, A.A.; Andersson, R.E.; Kamal-Eldin, A.
Source:
Journal of agricultural and food chemistry 2006 v.54 no.3 pp. 633-638
ISSN:
0021-8561
Subject:
sesame seed; lignans; glucosides; chemical structure; food composition; high performance liquid chromatography
Abstract:
... An HPLC method was developed and validated for the quantification of sesaminol triglucoside and a sesaminol diglucoside in sesame seeds. These two lignans were isolated, and their structures were characterized by mass and nuclear magnetic resonance spectroscopy. Defatted sesame flour was extracted first with 85% ethanol for 5 h followed by 70% ethanol for 10 h at room temperature using naringenin ...
DOI:
10.1021/jf051541g

12. Abscisic acid related compounds and lignans in prunes (Prunus domestica L.) and their oxygen radical absorbance capacity (ORAC)

Author:
Kikuzaki, H.; Kayano, S.; Fukutsuka, N.; Aoki, A.; Kasamatsu, K.; Yamasaki, Y.; Mitani, T.; Nakatani, N.
Source:
Journal of agricultural and food chemistry 2004 v.52 no.2 pp. 344-349
ISSN:
0021-8561
Subject:
prunes; plant extracts; abscisic acid; lignans; glucosides; chemical structure; antioxidant activity; free radicals; antioxidants
Abstract:
... Four new abscisic acid related compounds (1-4), together with (+)-abscisic acid (5), (+)-β-D-glucopyranosyl abscisate (6), (6S,9R)-roseoside (7), and two lignan glucosides ((+)-pinoresinol mono-β-D-glucopyranoside (8) and 3-(β-D-glucopyranosyloxymethyl)-2- (4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofuran (9)) were isolated from the antioxidative ethanol extract o ...
DOI:
10.1021/jf034954v

13. The first report on the occurrence of furofuranoid lignan glucosides Acanthaceae

Author:
El-Domiaty, M.M.; El-Shafae, A.M.; Abdel-Aal, M.M.; Abou-Hashem, M.M.
Source:
Pharmaceutical biology 2002 v.40 no.2 pp. 96-102
ISSN:
1388-0209
Subject:
Acanthaceae; medicinal plants; medicinal properties; glucosides; furans; lignans; steroids; terpenoids; flavonoids; chemotaxonomy; enzyme inhibitors; phosphodiesterase I; chemical structure; chemical constituents of plants; Egypt
DOI:
10.1076/phbi.40.2.96.5848

14. Biosynthesis of (+)-syringaresinol inLiriodendron tulipifera I: feeding experiments withL-[U-14C]phenylalanine and [8-14C]sinapyl alcohol

Author:
Takeshi Katayama; Atsushi Ogaki
Source:
Journal of wood science 2001 v.47 no.1 pp. 41-47
ISSN:
1435-0211
Subject:
biosynthesis; isotope labeling; stems; chemical reactions; beta-glucosidase; chemical structure; Liriodendron tulipifera; lignans; resinols; phenylalanine; glucosides; leaves; Japan
Abstract:
... To clarify the biosynthesis of syringyl lignans and lignan formation by stereoselective coupling of monolignols, formation of (+)-syringaresinol and (+)-pinoresinol inLiriodendron tulipifera were investigated by means of feeding experiments. Following individual administration ofL-[U-¹⁴C]phenylalanine and [8-¹⁴C]sinapyl alcohol to excised shoots ofL. tulipifera and their subsequent metabolism for ...
DOI:
10.1007/BF00776644

15. Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethl glutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed. [Erratum: May 2002, v. 65 (5), p. 800.]

Author:
Ford, J.D.; Huang, K.S.; Wang, H.B.; Davin, L.B.; Lewis, N.G.
Source:
Journal of natural products 2001 v.64 no.11 pp. 1388-1397
ISSN:
0163-3864
Subject:
Linum usitatissimum; seeds; resinols; glucosides; lignans; glutaric acid; spectral analysis; chemical structure; antineoplastic agents; biosynthesis; chemical reactions; biochemical pathways; chemical constituents of plants
DOI:
10.1021/np010367x

16. Three novel constituents from Curculigo capitulata and revision of C-2 stereochemistry in nyasicoside

Author:
Chang, W.L.; Chen, C.H.; Lee, S.S.
Source:
Journal of natural products 1999 v.62 no.5 pp. 734-739
ISSN:
0163-3864
Subject:
Curculigo; rhizomes; glucosides; lignans; chemical structure; stereochemistry; chemical constituents of plants; nuclear magnetic resonance spectroscopy; spectral analysis; Taiwan
DOI:
10.1021/np980364t

17. Bioactive norlignan glucosides from Curculigo capitulata

Author:
Chang, W.L.; Su, M.J.; Lee, S.S.
Source:
Journal of natural products 1997 v.60 no.2 pp. 76-80
ISSN:
0163-3864
Subject:
Curculigo; medicinal plants; rhizomes; lignans; glucosides; spectral analysis; chemical structure; epinephrine; heart rate; medicinal properties; chemical constituents of plants; Taiwan
DOI:
10.1021/np9604902