An Unsuccessful Attempt to Confirm the Occurrence of 4′-O-β-d-Glucosyl-9-O-(6″-deoxysaccharosyl)olivil in Valerian Root

Jandirk Sendker; Matthias Lechtenberg; Andreas Hensel

doi:10.1055/a-1078-5195

Planta Medica, Table of Contents

Planta Med 2020; 86(15): 1133-1139
DOI: 10.1055/a-1078-5195

Natural Product Chemistry and Analytical Studies

Original Papers

An Unsuccessful Attempt to Confirm the Occurrence of 4′-O-β- d-Glucosyl-9-O-(6″-deoxysaccharosyl)olivil in Valerian Root^{[
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Authors

Jandirk Sendker

Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany
Matthias Lechtenberg

Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany
Andreas Hensel

Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany

Abstract

The lignan 4′-O-β- d-glucosyl-9-O-(6″-deoxysaccharosyl)olivil had previously been discovered in a methanolic extract of valerian root (Valeriana officinalis agg.) and characterized as a potent partial agonist at the A₁ adenosine receptors. Today, countless scientific sources, webpages, and press articles mention this compound and discuss it as an active constituent for the sedative effect of this herbal drug. As no second report confirmed the occurrence of this lignan in valerian root during the 20 years since its first description in 1998, we intended to re-prove its presence by means of LCMS using other genuine or added lignans as a quantitative benchmark. Whilst those lignans were clearly detectable in methanolic valerian extracts of all six investigated batches of valerian root, no positive proof of 4′-O-β- d-glucosyl-9-O-(6″-deoxysaccharosyl)olivil was achieved. Our result suggests that this compound does not occur regularly in valerian root in the amounts expected from the single report on the occurrence of this compound.

Key words

Valeriana officinalis - Valeriana edulis - Caprifoliaceae - lignans - olivil - LCMS

Full Text

References

References
1 Schumacher B, Scholle S, Hölzl J, Khudeir N, Hess S, Müller CE. Lignans isolated from valerian: identification and characterization of a new olivil derivative with partial agonistic activity at A1 adenosine receptors. J Nat Prod 2002; 65: 1479-1485
2 Balduini W, Cattabeni F. Displacement of [3H]-N6-cyclohexylandenosine binding to rat cortical membranes by an hydroalcoholic extract of Valeriana officinalis . Med Sci Res 1989; 17: 639-640
3 Müller CE, Schumacher B, Brattström A, Abourashed EA, Koetter U. Interactions of valerian extracts and a fixed valerian-hop extract combination with adenosine receptors. Life Sci 2002; 71: 1939-1949
4 Holzgrabe U. Rätsel gelöst – warum Baldrian/Hopfen-Extrakte schläfrig machen. Pharm Unserer Zeit 2004; 33: 348
5 Knopf D. Warum Baldrian beruhigt. PZ 2004; 149: 565
6 Passreiter CM. Lignane – Pflanzliche Sekundärstoffe mit großem Potential (Teil 2). Zertifizierte Fortbildung. Available at (Accessed October 18, 2019): https://www.thieme.de/statics/dokumente/thieme/final/de/dokumente/zw_thieme-en/02_plantamedica_Autorenrichtlinien_Online-PDF.pdf
7 Abtei Pharma Vertriebs GmbH. Wirkmechanismus von Baldrian entdeckt!. PZ 2004; 149: 3517 (Advertisement)
8 Unger M. Pflanzliche Sedativa: Neue Aspekte zu altbewährten Arzneipflanzen. Pharm Unserer Zeit 2007; 36: 206-212
9 Ghedira K, Goetz P, Le Jeune R. Valeriana officinalis L. Phytothérapie 2008; 6: 253-257
10 Nell PG, Albrecht-Küpper B. The adenosine A1 receptor and its ligands. Prog Med Chem 2009; 47: 163-201
11 Van Rensen I. Baldrian, Hopfen, Baldrian und Hopfen – pflanzliche Beruhigungsmittel. Z Phytother 2011; 32: 65-70
12 Sticher O. Isoprenoide als Inhaltsstoffe. In: Sticher O, Heilmann J, Zündorf I. eds. Pharmakognosie – Phytopharmazie, 10th edition. Stuttgart: Wissenschaftliche Verlagsgesellschaft mbH; 2015: 535
13 Laubscher S. Ich kann nicht schlafen!. DAZ 2016; 44: 46
14 Baldrianwurzel. Heilpflanzen online. Available at (Accessed September 25, 2019): https://www.heilpflanzen.online/pflanzenportraits/baldrianwurzel
15 European Medicines Agency. Assessment report on Valeriana officinalis L., radix and Valeriana officinalis L., aetherolum. Available at (Accessed October 7, 2019): https://www.ema.europa.eu/en/documents/herbal-report/final-assessment-report-valeriana-officinalis-l-radix-valeriana-officinalis-l-aetheroleum_en.pdf
16 Scholle S. Neue Lignane aus Valeriana officinalis L.: Isolierung, Strukturaufklärung, Analytik und Rezeptorassays [dissertation]. Marburg: University of Marburg/Lahn; 1998
17 Goppel M, Franz G. Stability control of valerian ground material and extracts: a new HPLC-method for the routine quantification of valerenic acids and lignans. Pharmazie 2004; 59: 446-452
18 Navarette A, Avula B, Choi YW. Chemical fingerprinting of Valeriana species: simultaneous determination of valerenic acids, flavonoids, and phenylpropanoids using liquid chromatography with ultraviolet detection. J AOAC Int 2006; 89: 8-15
19 Wang PC, Ran XH, Chen R, Luo HR, Ma QY, Liu YQ, Hu JM, Huang SZ, Jiang HZ, Chen ZQ, Zhuo J, Zhao YX. Sesquiterpenoids and lignans from the roots of Valeriana officinalis L. Chem Biodivers 2011; 8: 1908-1913
20 Wang PC, Ran XH, Luo HR, Ma QY, Liu YQ, Zhou J, Zhao YX. Phenolic compounds from the roots of Valeriana officinalis var. latifolia . J Braz Chem Soc 2013; 24: 1544-1548
21 Wang C, Xiao Y, Yang B, Wang Z, Wu L, Su X, Brantner A, Kuang H, Wang Q. Isolation and screened neuroprotective active constituents from the root and rhizomes of Valeriana amurensis . Fitoterapia 2014; 96: 48-55
22 Hashmi MA, Khan A, Hanif M, Farooq U, Perveen S. Traditional uses, phytochemistry, and pharmacology of Olea europea (Olive). Evid Based Complementary Alternat Med 2015; 2015: 541591
23 Brandenstein C. Phytochemische Untersuchungen zu Lignanen in Valeriana officinalis L. [masterʼs thesis]. Münster: University of Münster; 2007
24 Schulze-Dieckhoff J, Lechtenberg M, Sendker J, Luftmann H, Hensel A. Isolierung und Charakterisierung von Lignanen aus Baldrianwurzel [masterʼs thesis]. Münster: University of Münster; 2008
25 Schulze-Dieckhoff J. Fractionation of a hydroalcoholic extract from valerian root using flash chromatography and fast centrifugal partition chromatography. Poster (ref. code 5579 0435), International Symposium on Chromatography (ISC 2008) in Münster, Germany. Available at (Accessed October 18, 2019): https://www.researchgate.net/publication/335992712_Fractionation_of_a_Hydroalcoholic_Extract_from_Valerian_Root_using_Flash_Chromatography_and_Fast_Centrifugal_Partition_Chromatography
26 Sarshar S, Sendker J, Qin X, Goycoolea FM, Asadi Karam MR, Habibi M, Bouzari S, Dobrindt U, Hensel A. Antiadhesive hydroalcoholic extract from Apium graveolens fruits prevents bladder and kidney infection against uropathogenic E. coli . Fitoterapia 2018; 127: 237-244
27 Ma Q, Wan Q, Huang S, Dai H, Wu Y, Zhou J, Luo H, Zhao Y. Phenolic constituents with inhibitory activities on acetylcholinesterase from rhizomes of Gastrodia elata . Chem Nat Compd 2015; 51: 158-160
28 Sendker J, Sheridan H. Composition and Quality Control of herbal Medicines. In: Pelkonen O, Vuorela PM, Duez P, Vuorela H. eds. Toxikology of herbal Products. Switzerland: Springer International Publishing; 2017: 29-65
29 Dimpfel W, Brattström A, Koetter U. Central action of a fixed Valerian-hops extract combination (Ze 91019) in freely moving rats. Eur J Med Res 2006; 11: 496-500
30 Lacher SK, Mayer R, Sichardt K, Nieber K, Müller CE. Interaction of valerian extracts of different polarity with adenosine receptors: identification of isovaltrate as an inverse agonist at A1 receptors. Biochem Pharmacol 2007; 73: 248-258

Supplementary Material

Supporting Information (PDF)

An Unsuccessful Attempt to Confirm the Occurrence of 4′-O-β- d-Glucosyl-9-O-(6″-deoxysaccharosyl)olivil in Valerian Root[ # ]

Authors

An Unsuccessful Attempt to Confirm the Occurrence of 4′-O-β- d-Glucosyl-9-O-(6″-deoxysaccharosyl)olivil in Valerian Root^{[
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