9-Norlignans: Occurrence, Properties and Their Semisynthetic Preparation from Hydroxymatairesinol

Eklund, Patrik; Raitanen, Jan-Erik

doi:10.3390/molecules24020220

Cited by 22 publications

(16 citation statements)

References 40 publications

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“…1 H, 13 C, DEPT 45 • , DEPT 90 • , DEPT 135 • , COSY, NOESY, HSQC, and HMBC NMR data are shown in Table 1, while COSY, NOESY, and HMBC correlations are shown in Figure 2. The 1 H and 13 C data of 2 are in agreement with the literature, which confirmed that 2 was a 9,9 -bisnorlignan, 5,7,8-trimethoxy-1-(2,4,5-trimethoxyphenyl)-1,2-dihydronaphthalene or pachypostaudin B [35,36].…”

Section: Isolation and Identification Of Compounds From P Pellucida supporting

confidence: 88%

Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities

et al. 2020

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Extracts of Peperomia pellucida [L.] Kunth have previously been demonstrated to have in vivo estrogenic-like effects, thereby functioning as an anti-osteoporotic agent. However, the compounds responsible for these effects have not yet been determined. Therefore, the aim of this study is to isolate and elucidate potential compounds with estrogenic activity. The structures of the isolated compounds were identified using 1D 1H and 13C-NMR and confirmed by 2D FT-NMR. The estrogenic activity was evaluated using the E-SCREEN assay, and a molecular docking study was performed to predict the binding affinity of the isolated compounds to estrogen receptors. In this experiment, we successfully isolated three phenylpropanoids and two lignan derivatives, namely, 6-allyl-5-methoxy-1,3-benzodioxol-4-ol (1), pachypostaudin B (2), pellucidin A (3), dillapiole (4), and apiol (5). Among these compounds, the isolation of 1 and 2 from P. pellucida is reported for the first time in this study. Activity assays clearly showed that the ethyl acetate extract and its fractions, subfractions, and isolated compounds exerted estrogenic activity. Methanol fraction of the ethyl acetate extract produced the highest estrogenic activity, while 1 and 2 had partial agonist activity. Some compounds (derivates of dillapiole and pellucidin A) also had, in addition, anti-estrogenic activity. In the docking study, the estrogenic activities of 1–5 appeared to be mediated by a classical ligand-dependent mechanism as suggested by the binding interaction between the compounds and estrogen receptors; binding occurred on Arg 394 and His 524 of the alpha receptor and Arg 346 and His 475 of the beta receptor. In summary, we reveal that P. pellucida is a promising anti-osteoporotic agent due to its estrogenic activity, and the compounds responsible for this activity were found to be lignan and phenylpropanoid derivatives. The presence of other compounds in either the extract or fraction may contribute to a synergistic effect, as suggested by the higher estrogenic activity of the methanol fraction. Hence, we suggest further research on the osteoporotic activity and safety of the identified compounds, especially regarding their effects on estrogen-responsive organs.

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Section: Isolation and Identification Of Compounds From P Pellucida supporting

confidence: 88%

Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities

et al. 2020

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“…NMR solvents were purchased from VWR Chemicals (CD 3 OD, CDCl 3 ). All norlignan substrates were synthesized from the natural lignan hydroxymatairesinol at Johan Gadolin Process Chemistry Center, Åbo Akademi University [9]. The [MoO 2 (SAP)] 2 and [MoO 2 (SATP)] 2 complexes were synthesized according to published procedures at the IUT-LCC, Castres.…”

Section: Methodsmentioning

confidence: 99%

“…The prefix "nor" indicates the lack of one or more carbon in the parent skeleton, and the term 9-norlignan is used when the lignan structure lacks C-9 (or γ carbon). As lignans, norlignans are also found in plants, having a range of biological activity [8,9].…”

Section: Introductionmentioning

confidence: 99%

“…The lignan 7-hydroxymatairesinol (HMR) can be isolated in large-scale from the knotwood of Norway spruce (Picea abies) as it constitutes up to 24% of the dry weight [10]. HMR can be used as raw material for the semi-synthesis of a range of different lignans, among others are a family of norlignans belonging to the imperanene family [9]. Some of these semi-synthetic and unsaturated 9-norlignans were used as substrates in this study (Figure 2, substrates 1-4).…”

Section: Introductionmentioning

confidence: 99%

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Formation of Tetrahydrofurano-, Aryltetralin, and Butyrolactone Norlignans through the Epoxidation of 9-Norlignans

Runeberg

Eklund

2020

Molecules

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Epoxidation of the C=C double bond in unsaturated norlignans derived from hydroxymatairesinol was studied. The intermediate epoxides were formed in up to quantitative conversions and were readily further transformed into tetrahydrofuran, aryltetralin, and butyrolactone products—in diastereomeric mixtures—through ring-closing reactions and intramolecular couplings. For epoxidation, the classical Prilezhaev reaction, using stoichiometric amounts of meta-chloroperbenzoic acid (mCPBA), was used. As an alternative method, a catalytic system using dimeric molybdenum-complexes [MoO2L]2 with ONO- or ONS-tridentate Schiff base ligands and aqueous tert-butyl hydroperoxide (TBHP) as oxidant was used on the same substrates. Although the epoxidation was quantitative when using the Mo-catalysts, the higher temperatures led to more side-products and lower yields. Kinetic studies were also performed on the Mo-catalyzed reactions.

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“…Geographically, the intakes are greater in the European population relative to the Asian population (Bhakta et al, 2006). The main common dietary lignans are secoisolariciresinol, lariciresinol, matairesinol, pinoresinol, medioresinol, and syringaresinol (Durazzo et al, 2018); the range of components is very wide and efforts on isolation of new compounds are being carried out (Eklund and Raitanen, 2019;Xiao et al, 2019). Plant lignans are metabolized to enterodiol and enterolactone, called enterolignans or mammalian lignans (Landete, 2012).…”

Section: Introductionmentioning

confidence: 99%

Lignans: Quantitative Analysis of the Research Literature

et al. 2020

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The current study provides a comprehensive overview and analysis of the lignan literature. Data for the current study were extracted from the electronic Web of Science Core Collection database via the search string TOPIC = ("lignan*") and processed by the VOSviewer software. The search yielded 10,742 publications. The ratio of original articles to reviews was 14.6:1. Over 80% of the analyzed papers have been published since the year 2000 and nearly 50% since the year 2010. Many of the publications were focused on pharmacology, chemistry, and plant sciences. The United States and Asian countries, such as China, Japan, South Korea, and India, were the most productive producers of lignan publications. Among the 5 most productive institutions was the University of Helsinki in Finland, the country that ranked 9 th . Nineteen journals collectively published 3,607 lignan publications and were considered as core journals. Their impact factor did not correlate with the proportion of uncited papers. Highly cited publications usually mentioned phytoestrogen, isoflavone, daidzein, enterodiol, enterolactone, equol, genistein, and isoflavonoid. Cancer (e.g., breast cancer), cardiovascular disease, and antioxidation were the major themes. Clinical trials were estimated to contribute to 0.2-1.1% of the analyzed body of literature, so more of them should be conducted in the future to substantiate the beneficial effects and optimal dose of lignan intake in humans. Moreover, researchers can refer to these findings for future research directions and collaborations.

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9-Norlignans: Occurrence, Properties and Their Semisynthetic Preparation from Hydroxymatairesinol

Cited by 22 publications

References 40 publications

Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities

Isolation and Characterization of Phenylpropanoid and Lignan Compounds from Peperomia pellucida [L.] Kunth with Estrogenic Activities

Formation of Tetrahydrofurano-, Aryltetralin, and Butyrolactone Norlignans through the Epoxidation of 9-Norlignans

Lignans: Quantitative Analysis of the Research Literature

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