Shinorine
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Raw Materials of Healthcare Products |
| Catalog number | BBF-05887 |
| CAS | 73112-73-9 |
| Molecular Weight | 332.31 |
| Molecular Formula | C13H20N2O8 |
| Purity | ≥95% |
Online Inquiry
Description
Shinorine, a mycosporine-like amino acid (MAA) and an analog of porphyra-344, is a small molecule sunscreen produced by some bacteria with antioxidant, anti-UV, and sun protection properties. Shinorine ameliorates chromium-induced toxicity in zebrafish hepatocytes through facultatively activating the Nrf2-Keap1-ARE pathway. Both porphyrin-334 and Shinorine antioxidants and direct antagonists of Keap1-Nrf2 binding. Shinorine may be an effective drug to prevent or delay the progression of a variety of degenerative aging diseases.
Specification
| Synonyms | L-Serine, N-[3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxy-2-cyclohexen-1-ylidene]-; demethyl-analog of Porphyra 334; N-[3-[(Carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxy-2-cyclohexen-1-ylidene]-L-serine |
| Storage | Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years) |
| IUPAC Name | (2S)-2-[[3-(carboxymethylimino)-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohexen-1-yl]amino]-3-hydroxypropanoic acid |
| Canonical SMILES | COC1=C(CC(CC1=NCC(=O)O)(CO)O)NC(CO)C(=O)O |
| InChI | InChI=1S/C13H20N2O8/c1-23-11-7(14-4-10(18)19)2-13(22,6-17)3-8(11)15-9(5-16)12(20)21/h9,15-17,22H,2-6H2,1H3,(H,18,19)(H,20,21)/t9-,13?/m0/s1 |
| InChI Key | HXQQNYSFSLBXQJ-LLTODGECSA-N |
Properties
| Appearance | Solid Powder |
| Boiling Point | 626.9±55.0°C (Predicted) |
| Density | 1.54±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in DMSO |
Reference Reading
1. Efficient production of shinorine, a natural sunscreen material, from glucose and xylose by deleting HXK2 encoding hexokinase in Saccharomyces cerevisiae
Chaeyeon Jin, Sojeong Kim, Seokjun Moon, Hyunbin Jin, Ji-Sook Hahn FEMS Yeast Res. 2021 Oct 12;21(7):foab053. doi: 10.1093/femsyr/foab053.
Mycosporine-like amino acids (MAAs), microbial secondary metabolites with ultraviolet (UV) absorption properties, are promising natural sunscreen materials. Due to the low efficiency of extracting MAAs from natural producers, production in heterologous hosts has recently received attention. Shinorine is a well characterized MAA with strong UV-A absorption property. Previous, we developed Saccharomyces cerevisiae strain producing shinorine by introducing four shinorine biosynthetic genes from cyanobacterium Nostoc punctiforme. Shinorine is produced from sedoheptulose 7-phosphate (S7P), an intermediate in the pentose phosphate pathway. Shinorine production was greatly improved by using xylose as a co-substrate, which can increase the S7P pool. However, due to a limited xylose-utilizing capacity of the engineered strain, glucose was used as a co-substrate to support cell growth. In this study, we further improved shinorine production by attenuating glucose catabolism via glycolysis, which can redirect the carbon flux from glucose to the pentose phosphate pathway favoring shinorine production. Of the strategies we examined to reduce glycolytic flux, deletion of HXK2, encoding hexokinase, was most effective in increasing shinorine production. Furthermore, by additional expression of Ava3858 from Anabaena variabilis, encoding a rate-limiting enzyme 2-demethyl 4-deoxygadusol synthase, 68.4 mg/L of shinorine was produced in an optimized medium containing 14 g/L glucose and 6 g/L xylose, achieving a 2.2-fold increase compared with the previous strain.
2. Sustainable Production of Shinorine from Lignocellulosic Biomass by Metabolically Engineered Saccharomyces cerevisiae
So-Rim Kim, Minseok Cha, Taeok Kim, Sihoon Song, Hye Jee Kang, Younghoon Jung, Jeong-Yong Cho, Sang Hyun Moh, Soo-Jung Kim J Agric Food Chem. 2022 Dec 21;70(50):15848-15858. doi: 10.1021/acs.jafc.2c07218. Epub 2022 Dec 7.
Mycosporine-like amino acids (MAAs) have been used in cosmetics and pharmaceuticals. The purpose of this work was to develop yeast strains for sustainable and economical production of MAAs, especially shinorine. First, genes involved in MAA biosynthetic pathway from Actinosynnema mirum were introduced into Saccharomyces cerevisiae for heterologous shinorine production. Second, combinatorial expression of wild and mutant xylose reductase was adopted in the engineered S. cerevisiae to facilitate xylose utilization in the pentose phosphate pathway. Finally, the accumulation of sedoheptulose 7-phosphate (S7P) was attempted by deleting transaldolase-encoding TAL1 in the pentose phosphate pathway to increase carbon flux toward shinorine production. In fed-batch fermentation, the engineered strain (DXdT-M) produced 751 mg/L shinorine in 71 h. Ultimately, 54 mg/L MAAs was produced by DXdT-M from rice straw hydrolysate. The results suggest that shinorine production by S. cerevisiae might be a promising process for sustainable production and industrial applications.
3. Shinorine and porphyra-334 isolated from laver ( Porphyra dentata) inhibit adipogenesis in 3T3-L1 cells
Su-Young Choi, Su Yeon Lee, Hyung Gyun Kim, Jae Cheon Jeong, Don Carlo Batara, Sung-Hak Kim, Jeong-Yong Cho Food Sci Biotechnol. 2022 Mar 28;31(5):617-625. doi: 10.1007/s10068-022-01055-6. eCollection 2022 May.
Mycosporine-like amino acids (MAAs) such as shinorine and porphyra-334 from Porphyra spp. are bioactive compounds with strong photoprotective and antioxidant properties. In this study, the anti-adipogenic effect of shinorine and porphyra-334 was examined in vitro utilizing 3T3-L1 preadipocytes. Shinorine and porphyra-334 were extracted from laver (Porphyra dentata) 50% methanolic (MeOH) extract of and their structures were elucidated by MS and NMR spectroscopy. Both compounds had no cytotoxic effect in 3T3-L1 cells (< 200 μg/mL) and inhibited the accumulation of lipid droplets in 3T3-L1 mature adipocytes in a dose-dependent manner (0.1 and 1.0 μM). Interestingly, both compounds had also significantly reduced the expression of adipogenic-related genes such as peroxisome proliferator-activated receptor γ2 (PPARγ2), CCAAT/enhancer-binding protein α (C/EBPα), adiponectin, and leptin in 3T3-L1 cells. The findings suggest that shinorine and porphyra-334 have the potential to inhibit adipogenesis in 3T3-L1 preadipocytes.
Recommended Products
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
