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Phytochemistry and pharmacology of natural prenylated flavonoids
Hua-Wei Lv,Qiao-Liang Wang,Meng Luo,Meng-Di Zhu,Hui-Min Liang,Wen-Jing Li,Hai Cai,Zhong-Bo Zhou,Hong Wang,Sheng-Qiang Tong,Xing-Nuo Li 대한약학회 2023 Archives of Pharmacal Research Vol.46 No.4
Prenylated flavonoids are a special kind of flavonoid derivative possessing one or more prenyl groups in the parent nucleus of the flavonoid. The presence of the prenyl side chain enriched the structural diversity of flavonoids and increased their bioactivity and bioavailability. Prenylated flavonoids show a wide range of biological activities, such as anti-cancer, anti-inflammatory, neuroprotective, anti-diabetic, anti-obesity, cardioprotective effects, and anti-osteoclastogenic activities. In recent years, many compounds with significant activity have been discovered with the continuous excavation of the medicinal value of prenylated flavonoids, and have attracted the extensive attention of pharmacologists. This review summarizes recent progress on research into natural active prenylated flavonoids to promote new discoveries of their medicinal value.
홉의 주요 Phloroglucinol 및 Prenylated Flavonoid의 생물활성
김현정,윤구,조영창,이익수,강복윤 한국생약학회 2018 생약학회지 Vol.49 No.3
Hop cones (Humuli Strobili) are the female inflorescences of hop plants (Humulus lupulus L.) belonging to the family Cannabaceae. They have been used as herbal remedies to treat mood and sleep disturbances, and mainly to add as a bittering ingredient in brewing process. Considerable interests on pharmacological and biological activities of hop cones have been focused on their major constituents, namely, phloroglucinols (humulone, lupulone), terpenes (myrcene, humulene), and prenylated flavonoids (xanthohumol, isoxanthohumol, 6-prenylnaringenin, and 8-prenylnaringenin). The present review describes and discusses biological activity profiles of these major compounds in the hop cones.
Chi, Yeon Sook,Jong, Hyon Gun,Son, Kun Ho,Chang, Hyeun Wook,Kang, Sam Sik,Kim, Hyun Pyo 영남대학교 약품개발연구소 2002 영남대학교 약품개발연구소 연구업적집 Vol.11 No.-
Prenylated flavonoids are chemical entities having an isoprenyl, a geranyl, a l, l-dimethylallyl, and/or a lavandulyl moiety as part of their cyclooxygenase (COX)-1 and COX-2 and on 5-lipoxygenase (5-LOX) and 12-LOX were investigated using [^14C]arachidonic acid as a substrate. The homogenates of bovine platelets and polymorphonuclear leukocytes were used as COX-1, 12-LOX, and 5-LOX enzyme sources;the homogenate of aspiring-pretreated lipopolysaccharide-induced RAW 264.7 cells was used for the COX-2 enzyme source. Among the 19 prenylated flavonoids, morusin, kuwanon C, sanggenon B, sanggenon D and kazinol B inhibited COX-2 activity (ic_30=73-100 ??M), but the potencies were far less than that of NS-398 (ic_50=2.9 ??M). In contrast, many prenylated flavonoids, such as kuraridin, kuwanon C and sophoraisoflavanone A, inhibited COX-1 activity. Of the COX-1 inhibiting prenylated flavonoids, kuraridin, kurarinone, and sophoraflavanone G, all having a C-8 lavandulyl moicty, showed potent activity (ic_50=0.1 to 1 ??M) comparable to that of indomethacin (ic_50=0.7 M). Most of the prenylated flavonoids tested inhibited 5-LOX activity with ic-50 values ranging from 0.09 to 100 M. Of these, only kuwanon C, papyriflavonol A and sophoraflavanone G showed inhibitory activity against 12-LOX at low concentration ranges (ic_50=19-69 ??M) comparable to that of NDGA (ic_50=2.6 ??M). Our results suggest that the position and the nature of the preayl substitution grealy influence in vitro biological activities of these molecules.
Hak Ju Lee,마응천,Da Hyun Lyu,Uk Koo,남궁우,홍성수,Kem Ok Kim,김경호,이동호 대한약학회 2012 Archives of Pharmacal Research Vol.35 No.1
Seven prenylated flavanoids, licoflavone C (1), cyclomulberrin (2), neocyclomorusin (3), sanggenon I (4), morusin (5), kuwanon U (6) and kuwanon E (7), and three 2-arylbenzofurans, moracin P (8), moracin O (9), and mulberrofuran Q (10) were isolated from the MeOH extract of Mori Cortex Radicis. Among these, compounds 2-7 enhanced cell viability in a dose-dependent manner against sodium nitroprusside-induced cell death in neuroblastoma SH-SY5Y cells, which was measured by MTT reduction assay (EC50 values of 4.4, 5.6, 8.0, 6.4, 8.7, and 11.9 μg/mL, respectively). Among 10 compounds, C-3 prenylated flavones (2, 3, and 5) and prenylated flavanones (4, 6, and 7) showed cell protection. However, compound 1 which lacks the prenyl group at C-3 and three 2-arylbenzofurans (8-10) did not show protective effect. The order of cell protection was as follow: C-3 prenylated flavones (2, 3, and 5) > prenylated flavanones (4, 6, and 7) > 2-arylbenzofurans (8-10) and flavone (1). From this result, we show that some prenylated flavones and flavanones might protect neuronal cells against nitrosative stress-mediated cell death. Even though further evaluations are necessary in vitro and in vivo study, we carefully suggest that some prenylated flavonoids from Mori Cortex Radicis might protect neuronal cells from neurodegenerative diseases.
Cheon, Bong Sun,Kim, Young Ha,Son, Kun So,Chang, Hyeun Wook,Kang, Sam Sik,Kim, Hyun Pyo 영남대학교 약품개발연구소 2001 영남대학교 약품개발연구소 연구업적집 Vol.11 No.-
Certain flavonoid derivatives possess anti-inflammatory activity in vitro and in vivo. Besides their antioxidative properties and effects on the arachidonic acid metabolism including cycloosygenase/lipoxygenase inhibition. some flavones and flavondls were previously found to show inhibitiory activity on nitric oxide production by inducible nltric oxide synthase (iNOS; NOS type 2) through suppression of iNOS induction. As part of our continuing investigations, the effects of unique and minor flavonoids (prenylated flavonoids and biflavonoids) on nitric oxide production from lipopolysaccharide-induced macrophage cell line (RAW 264.7) were evaluated in order to establish their inhibitory activity on NO production and correlate this action with their in vivo anti-inflammatory potentlal. Among the derivatives tested, prenylated compounds including morusin, kuwanon C. and sanggenon D and biflavonoids such as bilobetin and ginkgetin were found to inhibit NO production fom lipopolysaccharide (LPS)-induced RAW 264.7 cells at ? 10㎛. Lnhibition of nitric oxide production was mediated by suppressinon of iNOS enzyme induction but not by direct inhibition of iNOS enzyme activity. An execption was echinoisoflavanone that inhibited iNOS enzyme activity (IC_(50) = 83㎛) and suppressed iNOS enzyme induction as well. While most prenylated derivatives showed cytotoxicity to RAW cells at 10-100㎛, all biflavonoids tested were not cytotoxic. Since nitric oxide (NO) produced by inducible NO synthase (iNOS) plays an important role in inflammatory disorders, inhibition of NO production by these flavonoids may contribute, at least in part, to their antiinflammatory and immunoregulating potentlal in vivo.
Tran, Phi-Long,Tran, Phuong Thao,Tran, Huynh Nguyen Khanh,Lee, Suhyun,Kim, Okwha,Min, Buyng-Sun,Lee, Jeong-Hyung ELSEVIER 2018 INTERNATIONAL IMMUNOPHARMACOLOGY Vol.55 No.-
<P><B>Abstract</B></P> <P>Prenylated flavonoids are a unique class of naturally occurring flavonoids that have various pharmacological activities. In the present study, we investigated the anti-inflammatory effect in murine macrophages of a prenylated flavonoid, 10-oxomornigrol F (OMF), which was isolated from the twigs of <I>Morus alba</I> (Moraceae). OMF inhibited the lipopolysaccharide (LPS)-induced production of nitric oxide (NO), tumor necrosis factor-α (TNF-α), interleukin (IL)-1β, and IL-6 in RAW264.7 cells, as well as in mouse bone marrow-derived macrophages (BMMs). OMF also rescued LPS-induced septic mortality in ICR mice. LPS-induced expression of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), TNF-α and IL-6 was also significantly suppressed by OMF treatment in RAW264.7 cells. Treatment of RAW264.7 cells with OMF induced heme oxygenase (HO)-1 mRNA and protein expression and increased the nuclear translocation of the nuclear factor-E2-related factor 2 (Nrf2) as well as the expression of Nrf2 target genes, such as NAD(P)H:quinone oxidoreductase 1 (NQO1). Treatment of RAW264.7 cells with OMF increased the intracellular level of reactive oxygen species (ROS) and the phosphorylation levels of p38 mitogen-activated protein kinase (MAPK); co-treatment with the antioxidant <I>N</I>-acetyl-cysteine (NAC) blocked this OMF-induced p38 MAPK phosphorylation. Moreover, NAC, or SB203580 (a p38 MAPK inhibitor), blocked the OMF-induced nuclear translocation of Nrf2 and HO-1 expression, suggesting that OMF induces HO-1 expression by activating Nrf2 through the p38 MAPK pathway. Consistent with the notion that the Nrf2/HO-1 pathway has anti-inflammatory properties, inhibiting HO-1 significantly abrogated the anti-inflammatory effects of OMF in LPS-stimulated RAW264.7 cells. Taken together, these findings suggest that OMF exerts its anti-inflammatory effect by activating the Nrf2/HO-1 pathway, and may be a potential Nrf2 activator to prevent or treat inflammatory diseases.</P> <P><B>Highlights</B></P> <P> <UL> <LI> The anti-inflammatory effect of 10-oxomornigrol F, a prenylated flavonoid from <I>Morus alba</I>, is demonstrated. </LI> <LI> The Nrf2/HO-1 pathway is attributable to the anti-inflammatory properties of 10-oxomornigrol F. </LI> <LI> 10-Oxomornigrol F activates the Nrf2/HO pathway via the p38 MAPK pathway. </LI> <LI> The mechanism explains the anti-inflammatory effect of 10-oxomornigrol F. </LI> </UL> </P>
Prenylated Flavonoids as Tyrosinase Inhibitors
Lee, Nan-Kyoung,Son, Kun-Ho,Chang, Hyeun-Wook,Kang, Sam-Sik,Park, Hae-Il,Heo, Moon-Young,Kim, Hyun-Pyo The Pharmaceutical Society of Korea 2004 Archives of Pharmacal Research Vol.27 No.11
In order to find new tyrosinase inhibitors and the effects of prenyl residue on flavonoid molecules, eight prenylated and three synthetic vinylated flavonoids were examined on their inhibitory effect against tyrosinase activity. From the results, kuwanon C, papyriflavonol A, sanggenon D and sophoflavescenol were found to possess the considerable inhibitory activity. Especially, sanggenon D is revealed as a potent inhibitor ($IC_{50}$ =7.3$\mu$ M), compared to the reference compound, kojic acid ($IC_{50}$ =24.8 $\mu$M). However, the prenylation with isoprenyl group or the vinylation to flavonoid molecules did not enhance tyrosinase inhibitory activity.
Jang, JunPil,Na, MinKyun,Thuong, Phuong Thien,Njamen, Dieudonné,Mbafor, Joseph Tanyi,Fomum, Zacharias Tanee,Woo, Eun-Rhan,Oh, Won Keun The Pharmaceutical Society of Japan 2008 Chemical & pharmaceutical bulletin Vol.56 No.1
<P>Phytochemical study on an EtOAc-soluble extract of the root bark of <I>Erythrina mildbraedii</I> resulted in the isolation of six prenylated flavonoids 1—6. Based on physicochemical and spectroscopic analyses, their structures were determined to be new natural products licoflavanone-4′-<I>O</I>-methyl ether (1), 2′,7-dihydroxy-4′-methoxy-5′-(3-methylbut-2-enyl)isoflavone (2), and (3<I>R</I>)-2′,7-dihydroxy-3′-(3-methylbut-2-enyl)-2‴,2‴-dimethylpyrano[5‴,6‴ :4′,5′]isoflavan (3), along with three known compounds erythrinin B (4), abyssinin II (5), and parvisoflavone B (6). All the isolates, except for compound 4, inhibited PTP1B activity <I>in vitro</I> with IC<SUB>50</SUB> values ranging from 5.3 to 42.6 μ<SMALL>M</SMALL>. This result further suggests that the prenyl group on the B ring of flavonoids plays an important role in suppressing the enzyme PTP1B.</P>
Synthesis and $PGE_2$ Inhibitory Activity of Vinylated and Allylated Chrysin Analogues
Dao, Tran-Thanh,Oh, Jeong-Won,Chi, Yeon-Sook,Kim, Hyun-Pyo,Sin, Kwan-Seog,Park, Hae-Il The Pharmaceutical Society of Korea 2003 Archives of Pharmacal Research Vol.26 No.8
Vinylated and allylated chrysin analogues were prepared as congeners of prenylated flavonoids and evaluated their anti-inflammatory activity. 8-Substituted chrysin analogues were prepared from 2 -hydroxy-3 -iodo-4 ,6 -dimethoxyacetophenone in 3 steps. 3-Allylated chrysin analogues were prepared from chrysin in 3 steps. Synthesized chrysin analogues (4, 5 and 8) showed moderate inhibitory activities of $PGE_2$ production from LPS-induced RAW 264.7 cells.