Sekikaic acid
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| Category | Others |
| Catalog number | BBF-05484 |
| CAS | 607-11-4 |
| Molecular Weight | 418.44 |
| Molecular Formula | C22H26O8 |
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Specification
| Synonyms | Benzoic acid, 2-hydroxy-3-[(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy]-4-methoxy-6-propyl-; Sekikasaeure; 6-Hydroxy-5-(6-hydroxy-4-methoxy-2-propyl)-4-methoxy-2-propyl-benzoesaeure; 6-Oxy-4-methoxy-5-(6-oxy-4-methoxy-2-propyl-benzoyloxy)-2-propyl-benzoesaeure |
| IUPAC Name | 2-hydroxy-3-(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy-4-methoxy-6-propylbenzoic acid |
| Canonical SMILES | CCCC1=CC(=C(C(=C1C(=O)O)O)OC(=O)C2=C(C=C(C=C2O)OC)CCC)OC |
| InChI | InChI=1S/C22H26O8/c1-5-7-12-9-14(28-3)11-15(23)17(12)22(27)30-20-16(29-4)10-13(8-6-2)18(19(20)24)21(25)26/h9-11,23-24H,5-8H2,1-4H3,(H,25,26) |
| InChI Key | CPHXGYQLOSNELY-UHFFFAOYSA-N |
Reference Reading
1. Sekikaic acid modulates pancreatic β-cells in streptozotocin-induced type 2 diabetic rats by inhibiting digestive enzymes
Vinay Bharadwaj Tatipamula, Satya Sowbhagya Priya Annam, Ha Thi Nguyen, Haritha Polimati, Rajendra Prasad Yejella Nat Prod Res. 2021 Dec;35(23):5420-5424. doi: 10.1080/14786419.2020.1775226. Epub 2020 Jun 5.
The antioxidant and antidiabetic effects of sekikaic acid (SA) were investigated using in vitro and in vivo study models. SA possessed good antioxidant activity as assessed through hydroxyl radicals (IC50 value = 41.5 µg/mL) and ferric ions assay (IC50 value = 42.0 µg/mL). SA exhibited stronger α-glucosidase and α-amylase inhibition than that of aldose-reductase and protein tyrosine phosphatase 1B. The hypoglycemic activity of SA caused significant reduction of plasma glucose levels in normal and glucose loaded rats. The anti-hyperglycemic activity of SA (2 mg/Kg body weight) was indicated by the reduction of blood glucose by 44.17 ± 3.78% in the third week in streptozotocin-induced diabetic rats. The hypolipidaemic action of SA was evident by the significant decrease in the levels of low-density lipoprotein, total cholesterol, and total glycerides. Histologically, the pancreas of the treated groups showed significant regeneration of the pancreatic β-cells compared to diabetic control, possibly due to the inhibition of digestive enzymes.
2. Potential of Lichen Compounds as Antidiabetic Agents with Antioxidative Properties: A Review
Vinitha M Thadhani, Veranja Karunaratne Oxid Med Cell Longev. 2017;2017:2079697. doi: 10.1155/2017/2079697. Epub 2017 Apr 12.
The advancement in the knowledge of potent antioxidants has uncovered the way for greater insight in the treatment of diabetic complications. Lichens are a rich resource of novel bioactive compounds and their antioxidant potential is well documented. Herein we review the antidiabetic potential of lichens which have received considerable attention, in the recent past. We have correlated the antidiabetic and the antioxidant potential of lichen compounds. The study shows a good accordance between antioxidant and antidiabetic activity of lichens and points out the need to look into gathering the scarce and scattered data on biological activities for effective utilization. The review establishes that the lichen extracts, especially of Parmotrema sp. and Ramalina sp. have shown promising potential in both antidiabetic and antioxidant assays. Ubiquitous compounds, namely, zeorin, methylorsellinate, methyl-β-orcinol carboxylate, methyl haematommate, lecanoric acid, salazinic acid, sekikaic acid, usnic acid, gyrophoric acid, and lobaric acid have shown promising potential in both antidiabetic as well as antioxidant assays highlighting their potential for effective treatment of diabetic mellitus and its associated complications. The available compilation of this data provides the future perspectives and highlight the need for further studies of this potent herbal source to harvest more beneficial therapeutic antidiabetic drugs.
3. Three new species of Krogia (Ramalinaceae, lichenised Ascomycota) from the Paleotropics
Sonja Kistenich, Jouko K Rikkinen, Holger Thüs, Charles S Vairappan, Patricia A Wolseley, Einar Timdal MycoKeys. 2018 Sep 26;(40):69-88. doi: 10.3897/mycokeys.40.26025. eCollection 2018.
Krogiaborneensis Kistenich & Timdal, K.isidiata Kistenich & Timdal and K.macrophylla Kistenich & Timdal are described as new species, the first from Borneo and the two latter from New Caledonia. The new species are supported by morphology, secondary chemistry and DNA sequence data. Krogiaborneensis and K.isidiata contain sekikaic and homosekikaic acid, both compounds reported here for the first time from the genus. Krogiamacrophylla contains an unknown compound apparently related to boninic acid as the major compound. DNA sequences (mtSSU and nrITS) are provided for the first time for Krogia and a phylogeny of the genus based on 15 accessions of five of the six accepted species is presented. Krogiaantillarum is reported as new to Brazil, Guatemala and Mexico.
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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 ╳
