410:. Chorismate mutase then converts chorismic acid to prephenate via a Claisen rearrangement (1,3-sigmatropic rearrangement). Phenolpyruvate is generated by the decarboxylation of prephenate, and the loss of a water molecule. Phenylalanine ammonia lyase (PAL) then converts phenolpyruvate to phenylalanine by using L-glutamate as an amine donor, which is used in rosavin biosynthesis. In the first step of rosavin synthesis, PAL converts phenylalanine to cinnamic acid. From cinnamic acid, cinnamyl-CoA ester is formed through hydroxycinnamate: CoA ligase (4CL). This CoA ester is reduced to cinnamaldehyde by cinnamyl-CoA reductase (CCR). The cinnamaldehyde is further reduced by cinnamyl alcohol dehydrogenase (CAD) to cinnamyl alcohol. The enzymes that take part in the formation of the glycosides of cinnamyl alcohol are not yet known. By one glucose transfer, rosin is formed, which is the simplest glycoside of
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extract have reported positive efficacy on fatigue, depression, mountain sickness, and cardiovascular disease. Extracts used in most clinical trials are standardized to a minimum of 3% cinnamyl alcohol glycosides and 0.8–1.0% salidroside, as the naturally occurring ratio of these compounds in the
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Cinnamyl alcohol glycosides are products of phenylpropanoid metabolism, derived from phenylalanine, which is produced from the shikimic-chorismic acid pathway. Shikimic acid is made from the precursor compounds erythrose-4-phosphate, and phosphoenolpyruvate. Shikimic acid is then converted to
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Rosavin is formed by the addition of an arabinose residue to rosin, while rosarin is generated by the addition of an arabinofuranose residue to rosin. Depending on the sugar type, and the site it is attached to, various other glycosides may be formed.
452:-induced pulmonary fibrosis, and induced antidepressant-like effects in mouse models. The low content of rosavins in plants has limited further investigation of their activities, and there is great interest in producing rosavins using biotechnology.
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roots and rhizomes. The production of rosavins increases in plants as they get older, and the amount of the cinnamyl alcohol glycosides depends on the place of origin of the plant.
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InChI=1S/C20H28O10/c21-12-9-28-19(17(25)14(12)22)29-10-13-15(23)16(24)18(26)20(30-13)27-8-4-7-11-5-2-1-3-6-11/h1-7,12-26H,8-10H2/b7-4+/t12-,13+,14-,15+,16-,17+,18+,19-,20+/m0/s1
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plant rhizomes is approximately 3:1. Rosavins have also been reported to display immunomodulatory effects, radiation protection, anti-cancer activities, protective effects on
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L. by
Analyzing the Salidroside and Rosavin Content and the Electrophysiological Activity in Hippocampal Long-Term Potentiation, a Synaptic Model of Memory"
478:"Biosynthesis of a rosavin natural product in Escherichia coli by glycosyltransferase rational design and artificial pathway construction"
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is an important medicinal plant commonly used throughout Europe, Asia, and North
America, that has been recognized as a botanical
582:"Biotransformation of cinnamyl alcohol to rosavins by non-transformed wild type and hairy root cultures of Rhodiola kirilowii"
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Grech-Baran M, Sykłowska-Baranek K, Krajewska-Patan A, Wyrwał A, Pietrosiuk A (March 2014).
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Except where otherwise noted, data are given for materials in their
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Biosynthetic
Pathway to Produce Rosavins (Rosin, Rosavin, Rosarin)
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Bi H, Qu G, Wang S, Zhuang Y, Sun Z, Liu T, Ma Y (January 2022).
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Rosavins are considered to be the major active components of
351:(also known as rosin, rosavin, and rosarin) are a family of
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Glycoside production by in vitro
Rhodiola rosea cultures
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chorismic acid through various enzymes derived from the
525:Dimpfel W, Schombert L, Panossian AG (2018-05-24).
273:C1((((O1)OC2((((O2)OC/C=C/C3=CC=CC=C3)O)O)O)O)O)O
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393:of these glycosides occurs spontaneously in
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83:)-2-{oxy}-6-({oxy}methyl)oxane-3,4,5-triol
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381:. Rosavin production is specific to
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430:Biosynthesis of L-Phenylalanine
408:shikimic-chorismic acid pathway
333:(at 25 °C , 100 kPa).
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656:. Oulu: University of Oulu.
359:that are key ingredients of
495:10.1016/j.ymben.2021.10.010
44:)-3-Phenylprop-2-en-1-yl α-
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692:Phenylpropanoid glycosides
48:-arabinopyranosyl-(1→6)-α-
598:10.1007/s10529-013-1401-5
535:Frontiers in Pharmacology
379:European Medicines Agency
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443:and clinical trials of
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586:Biotechnology Letters
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59:Systematic IUPAC name
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337:Infobox references
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650:György Z (2006).
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592:(3): 649–656.
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90:Identifiers
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282:Properties
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389:, and the
357:glycosides
162:ChemSpider
118:3D model (
107:84954-92-7
97:CAS Number
37:IUPAC name
672:141381688
512:240229184
488:: 15–25.
450:bleomycin
441:R. rosea,
412:R. rosea.
375:adaptogen
686:Category
616:24190481
567:29881348
504:34715353
445:R. rosea
395:Rhodiola
383:R. rosea
371:R. rosea
367:R. rosea
353:cinnamyl
17:Rosavin
607:3964300
558:5976749
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377:by the
349:Rosavin
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196:9823887
183:PubChem
171:4945006
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266:SMILES
31:Names
508:S2CID
365:L., (
244:InChI
142:ChEBI
120:JSmol
668:OCLC
658:ISBN
612:PMID
563:PMID
500:PMID
385:and
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602:PMC
594:doi
553:PMC
543:doi
490:doi
213:EPA
186:CID
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