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Oxyfunctionalization of Pharmaceuticals by Fungal Peroxygenases
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2019
Jan Kiebist, Martin Hofrichter, Ralf Zuhse, Katrin Scheibner
Especially if activated polyaromatic structures should be oxygenated, the presence of radical scavengers will be necessary to prevent further oxidation and coupling reactions. Thus, in the presence of ascorbic acid, diverse flavonoids and stilbenoids were shown to be hydroxylatable by UPOs, in first place by AaeUPO (Aranda et al., 2018a; Barková et al., 2011). UPO reactions with flavonoids, including flavones, flavonols, flavanones and isoflavones, yielded mainly in monohydroxy derivatives (predominantly hydroxylated at position C6). For example, quercetin (27, pentahydroxyflavonol), widely distributed in plants and used as an ingredient in dietary supplements, beverages, and foods, was hydroxylated to 6-hydroxyquercetin (28) by AaeUPO (94%, Fig. 18.14) (Barková et al., 2011). In a similar manner, pinosylvin (29) was converted into resveratrol (30, 3,4′,5-trihydroxy-trans-stilbene) by AaeUPO (61%, Fig. 18.14), rCciUPO (32%) and MroUPO (11%), and further into oxyresveratrol (Aranda et al., 2018a). Resveratrol (30) is a phytoalexin naturally found in grapes and wine, which accomplishes antioxidative and anti-proliferative activities. It has emerged as a promising bioactive compound with diverse biological effects such as protection against metabolic, cardiovascular and other age-related complications including neurodegeneration and cancer (Kulkarni and Cantó, 2015). Structure-activity studies revealed the molecular determinants of 30, which are necessary for its biological effects, namely the 4′-hydroxy group along with trans-conformation. In that context, 4,4′-dihydroxy-trans-stilbene (DHS) was prepared from stilbene (51) by UPOs. DHS is known for its pronounced cytotoxic, anti-proliferative and anti-tumor properties (Aranda et al., 2018a). Selective hydroxylation of the flavonol quercetin (27) and the stilbenoid pinosylvin (29) by AaeUPO.
The traditional herb Polygonum hydropiper from China: a comprehensive review on phytochemistry, pharmacological activities and applications
Published in Pharmaceutical Biology, 2023
Yi-Dan Kong, Ying Qi, Na Cui, Zhi-Hong Zhang, Na Wei, Chang-Fu Wang, Yuan-Ning Zeng, Yan-Ping Sun, Hai-Xue Kuang, Qiu-Hong Wang
Gallic acid (320), which is the tannin monomer, was isolated from PH extract with 75% ethanol (Huang et al. 2012). Ellagic acid (321), a tannin component, was obtained from PH (Li et al. 2017). An acidic polysaccharide named PFMP (322) was separated by DEAE column chromatography and authenticated to consist of d-mannose, l-rhamnose, d-glucuronic acid, d-galactose, d-glucose, and l-arabinose by HPLC (Zhu 2020). Pinosylvin (323) and 5,6-dehydrokawain (324) were isolated from chloroform extract (Xiao 2018). Rich metallic elements, such as Ca, Mg, Al, K, Fe, Mn, Ag, and Zn, and several harmful metals, such as Pb, As, Cu, Hg, and Cd, were discovered by microscopic with identification combined inductively coupled emission spectrometry (Wang et al. 2019). The contents of four heavy metals, Pb, Cd, As, and Hg, were detected by flame atomic absorption spectroscopy, and all met the Green Trade Standard (Lai et al. 2011). The structures of 320, 321, 323 and 324 are shown in Figure 8.
Extract of Pinus densiflora needles suppresses acute inflammation by regulating inflammatory mediators in RAW264.7 macrophages and mice
Published in Pharmaceutical Biology, 2022
Seul-Yong Jeong, Won Seok Choi, Oh Seong Kwon, Jong Seok Lee, Su Young Son, Choong Hwan Lee, Sarah Lee, Jin Yong Song, Yeon Jin Lee, Ji-Yun Lee
Phytochemical analysis of PINE putatively identified a total of 14 metabolites, including two organooxygen (quinic acid and caffeoylquinic acid), one benzene (dihydrobenzoic acid), nine flavonoids (pinobanksin, kaempferol glucoside, kaempferol 6″-coumaroyl-glucose, kaempferol 3″,6″-dicoumaroyl-glucoside, quercetin glucoside, quercetin coumaroyl hexoside, taxifolin, taxifolin glucoside and dihydromyricetin), one stilbene (pinosylvin) and one long-chain fatty acid (pinellic acid). These tentatively identified metabolites were annotated based on their retention times, and tandem mass spectrometric fragment patterns, with reference to data from published studies. These metabolites are marked on the chromatograms derived from the UHPLC-LTQ-Orbitrap-MS analysis (Figure 1 and Table 1).