1177-14-6Relevant articles and documents
Acyl glycosides lignans, coumarins, and terpenes from the stems of Erycibe obtusifolia
Liu, Zhao-Zhen,Zhan, Zhi-Lai,Liu, Fu,Yang, Ya-Nan,Feng, Zi-Ming,Jiang, Jian-Shuang,Zhang, Pei-Cheng
, p. 47 - 54 (2013)
Nine new acyl glycosides, obtusifosides A-I (1-9), and eight known compounds have been isolated from an EtOH extract of the stems of Erycibe obtusifolia. Their structures were elucidated on the basis of a spectroscopic data analysis (NMR, HRESIMS, and CD) and chemical evidence. The hepatoprotective effects of some of the compounds from d-galactosamine-induced cytotoxicity in HL-7702 hepatic cells were evaluated. Compounds 1, 10, 11, 13, 16, and 17 showed significant hepatoprotective activities compared with the positive control bicyclol at concentrations of 1 × 10-5 M.
Neuritogenesis of herbal (+)- and (-)-syringaresinols separated by chiral HPLC in PC12h and neuro2a Cells
Chiba, Kenzo,Yamazaki, Matsumi,Umegaki, Emiko,Ming, Run Li,Zhen, Wen Xu,Terada, Sumio,Taka, Michihiro,Naoi, Noriyuki,Mohri, Tetsuro
, p. 791 - 793 (2002)
Syringaresinol isolated from Epimedium koreanum NAKAI and Magnolia officinalis REHB. et WILS. was subjected to optical resolution by chiral HPLC to give (+)- and (-)-enantiomers. The two syringaresinol enantiomers, as well as a mixture of their glucosides, showed dose-dependent neuritogenesis in a concentration range from 0.24 to 24 μM in PC12h cells.
Pinoresinol-lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties
Davin, Laurence B.,Hwang, Julianne K.,Lewis, Norman G.,Moinuddin, Syed G. A.
, (2020/03/26)
Two western red cedar pinoresinol-lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8- and 8′-linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can enantiospecifically metabolize different furofuran lignans with modified aromatic ring substituents, but where phenolic groups at both C4/C4′ are essential for catalysis. These results are consistent with quinone methide intermediate formation in the PLR active site. Site-directed mutagenesis and kinetic measurements provided additional insight into factors affecting enantioselectivity and kinetic properties. From these data, PLRs can be envisaged to allow for the biotechnological potential of generation of various lignan skeleta, that could be differentially “decorated” on their aromatic ring substituents, via the action of upstream dirigent proteins.
Syringaresinol inhibits UVA-induced MMP-1 expression by suppression of mapk/ap-1 signaling in hacat keratinocytes and human dermal fibroblasts
Joo, Yung Hyup,Karadeniz, Fatih,Ko, Jaeyoung,Kong, Chang-Suk,Oh, Jung Hwan
, (2020/06/08)
Ultraviolet (UV) irradiation induces detrimental changes in human skin which result in photoaging. UV-induced intracellular changes cause degradation of extracellular matrix (ECM). UV-stimulated cleavage of collagen in ECM occurs via matrix metalloproteinases (MMPs). (±)syringaresinol (SYR), a phytochemical which belongs to the lignan group of polyphenols, was investigated for its ability to reverse the UVA-induced changes in human HaCaT keratinocytes and dermal fibroblasts (HDFs) in vitro. Effect of SYR on UVA-induced changes was investigated by production and activation of MMPs and its transcriptional upstream effectors; mitogen-activated protein kinases (MAPKs) and pro-inflammatory mediators. Levels of expression were determined using ELISA, RT-PCR and immunoblotting. UVA irradiation stimulated the production of MMP-1 and inhibited collagen production. SYR treatment suppressed MMP-1 and enhanced collagen production in UVA-irradiated HaCaT keratinocytes and HDFs. SYR repressed the UV-induced phosphorylation of p38, ERK and JNK MAPKs in HaCaT keratinocytes while only suppressing JNK phosphorylation in HDFs. In addition, SYR was able to inhibit UVA-induced production of inflammatory cytokines; TNF-α, COX-2, IL-1β and IL-6. Moreover, SYR suppressed the activator protein-1 (AP-1), a heterodimer of phosphorylated transcription factors c-Jun and c-Fos. SYRtreatment decreased nuclear levels of activated c-Fos and c-Jun as a mechanism to inhibit UVAinduced transcriptional activities leading to MMP-1 production. In conclusion, current results demonstrated that SYR could inhibit UVA-induced upregulation of MMP-1 by suppressing MAPK/AP-1 signaling in HaCaT keratinocytes and HDFs. Therefore, SYR was suggested as a potential compound with antiphotoaging properties against UVA-induced skin aging.
