Oxidative Transformations of Lignans

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2019 Jan 18

PMID 30650623

Citations 11

Authors

Patrik A Runeberg

Yury Brusentsev

Sabine M K Rendon

Patrik C Eklund

Affiliations

Soon will be listed here.

Abstract

Numerous oxidative transformations of lignan structures have been reported in the literature. In this paper we present an overview on the current findings in the field. The focus is put on transformations targeting a specific structure, a specific reaction, or an interconversion of the lignan skeleton. Oxidative transformations related to biosynthesis, antioxidant measurements, and total syntheses are mostly excluded. Non-metal mediated as well as metal mediated oxidations are reported, and mechanisms based on hydrogen abstractions, epoxidations, hydroxylations, and radical reactions are discussed for the transformation and interconversion of lignan structures. Enzymatic oxidations, photooxidation, and electrochemical oxidations are also briefly reported.

Citing Articles

Unveiling the Power of Flax Lignans: From Plant Biosynthesis to Human Health Benefits.

Gao Z, Cao Q, Deng Z Nutrients. 2024; 16(20).

PMID: 39458513 PMC: 11510306. DOI: 10.3390/nu16203520.

Dietary Polyphenols Effects on Focal Adhesion Plaques and Metalloproteinases in Cancer Invasiveness.

Carrano R, Grande M, Leti Maggio E, Zucca C, Bei R, Palumbo C Biomedicines. 2024; 12(3).

PMID: 38540096 PMC: 10968611. DOI: 10.3390/biomedicines12030482.

Polyketides as Secondary Metabolites from the Genus .

Bai X, Sheng Y, Tang Z, Pan J, Wang S, Tang B J Fungi (Basel). 2023; 9(2).

PMID: 36836375 PMC: 9962652. DOI: 10.3390/jof9020261.

Rationally Guided Improvement of NOV1 Dioxygenase for the Conversion of Lignin-Derived Isoeugenol to Vanillin.

De Simone M, Alvigini L, Alonso-Cotchico L, Brissos V, Caroli J, Lucas M Biochemistry. 2022; 62(2):419-428.

PMID: 35687874 PMC: 9851154. DOI: 10.1021/acs.biochem.2c00168.

Natural Enantiomers: Occurrence, Biogenesis and Biological Properties.

Yu J, Yu Z, Capon R, Zhang H Molecules. 2022; 27(4).

PMID: 35209066 PMC: 8880303. DOI: 10.3390/molecules27041279.

References

Molander G, George K, Monovich L . Total synthesis of (+)-isoschizandrin utilizing a samarium(II) iodide-promoted 8-endo ketyl-olefin cyclization. J Org Chem. 2003; 68(25):9533-40. DOI: 10.1021/jo0347361. View

Bobe G, Murphy G, Albert P, Sansbury L, Lanza E, Schatzkin A . Dietary lignan and proanthocyanidin consumption and colorectal adenoma recurrence in the Polyp Prevention Trial. Int J Cancer. 2011; 130(7):1649-59. PMC: 3235262. DOI: 10.1002/ijc.26184. View

Pezzella C, Guarino L, Piscitelli A . How to enjoy laccases. Cell Mol Life Sci. 2015; 72(5):923-40. PMC: 11113763. DOI: 10.1007/s00018-014-1823-9. View

Magoulas G, Papaioannou D . Bioinspired syntheses of dimeric hydroxycinnamic acids (lignans) and hybrids, using phenol oxidative coupling as key reaction, and medicinal significance thereof. Molecules. 2014; 19(12):19769-835. PMC: 6271182. DOI: 10.3390/molecules191219769. View

Davidson S, Pearce A, Copp B, Barker D . Total Synthesis of (-)-Bicubebin A, B, (+)-Bicubebin C and Structural Reassignment of (-)-cis-Cubebin. Org Lett. 2017; 19(19):5368-5371. DOI: 10.1021/acs.orglett.7b02644. View

Huang X, Bai M, Zhou L, Lou L, Liu Q, Zhang Y . Food Byproducts as a New and Cheap Source of Bioactive Compounds: Lignans with Antioxidant and Anti-inflammatory Properties from Crataegus pinnatifida Seeds. J Agric Food Chem. 2015; 63(32):7252-60. DOI: 10.1021/acs.jafc.5b02835. View

Albertson A, Lumb J . A bio-inspired total synthesis of tetrahydrofuran lignans. Angew Chem Int Ed Engl. 2015; 54(7):2204-8. DOI: 10.1002/anie.201408641. View

Roulland E, Magiatis P, Arimondo P, Bertounesque E, Monneret C . Hemi-synthesis and biological activity of new analogues of podophyllotoxin. Bioorg Med Chem. 2002; 10(11):3463-71. DOI: 10.1016/s0968-0896(02)00255-9. View

Koprowski M, Balczewski P, Owsianik K, Rozycka-Sokolowska E, Marciniak B . Total synthesis of (±)-epithuriferic acid methyl ester via Diels-Alder reaction. Org Biomol Chem. 2016; 14(5):1822-30. DOI: 10.1039/c5ob02368h. View

10.

Ozanne A, Pouysegu L, Depernet D, Francois B, Quideau S . A stabilized formulation of IBX (SIBX) for safe oxidation reactions including a new oxidative demethylation of phenolic methyl aryl ethers. Org Lett. 2003; 5(16):2903-6. DOI: 10.1021/ol0349965. View

11.

Kende A, Liebeskind L, Mills J, Rutledge P, Curran D . Oxidative aryl-benzyl coupling. A biomimetic entry to podophyllin lignan lactones. J Am Chem Soc. 1977; 99(21):7082-3. DOI: 10.1021/ja00463a062. View

12.

Kosina P, Kren V, Gebhardt R, Grambal F, Ulrichova J, Walterova D . Antioxidant properties of silybin glycosides. Phytother Res. 2002; 16 Suppl 1:S33-9. DOI: 10.1002/ptr.796. View

13.

Prestianni A, Ferrante F, Simakova O, Duca D, Murzin D . Oxygen-assisted hydroxymatairesinol dehydrogenation: a selective secondary-alcohol oxidation over a gold catalyst. Chemistry. 2013; 19(14):4577-85. DOI: 10.1002/chem.201202957. View

14.

Yang X, Gao M, Hu H, Zhang H . Electrochemical detection of honokiol and magnolol in traditional Chinese medicines using acetylene black nanoparticle-modified electrode. Phytochem Anal. 2011; 22(4):291-5. DOI: 10.1002/pca.1279. View

15.

Fernandez E, Vidal L, Canals A . Rapid determination of hydrophilic phenols in olive oil by vortex-assisted reversed-phase dispersive liquid-liquid microextraction and screen-printed carbon electrodes. Talanta. 2018; 181:44-51. DOI: 10.1016/j.talanta.2017.12.075. View

16.

Whiting D . Lignans, neolignans, and related compounds. Nat Prod Rep. 1987; 4(5):499-525. DOI: 10.1039/np9870400499. View

17.

Xia Z, Costa M, Pelissier H, Davin L, Lewis N . Secoisolariciresinol dehydrogenase purification, cloning, and functional expression. Implications for human health protection. J Biol Chem. 2001; 276(16):12614-23. DOI: 10.1074/jbc.M008622200. View

18.

Pohmakotr M, Pinsa A, Mophuang T, Tuchinda P, Prabpai S, Kongsaeree P . General strategy for stereoselective synthesis of 1-substituted exo,endo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: total synthesis of (+/-)-gmelinol. J Org Chem. 2006; 71(1):386-9. DOI: 10.1021/jo0519110. View

19.

Xiao J, Cong X, Yang G, Wang Y, Peng Y . Divergent Asymmetric Syntheses of Podophyllotoxin and Related Family Members via Stereoselective Reductive Ni-Catalysis. Org Lett. 2018; 20(6):1651-1654. DOI: 10.1021/acs.orglett.8b00408. View

20.

Moya R, Saastamoinen P, Hernandez M, Suurnakki A, Arias E, Mattinen M . Reactivity of bacterial and fungal laccases with lignin under alkaline conditions. Bioresour Technol. 2011; 102(21):10006-12. DOI: 10.1016/j.biortech.2011.08.046. View