MedKoo Cat#: 585159 | Name: Skimmianine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Skimmianine is a furanoquinoline alkaloid from Teclea (RUTACEAE).

Chemical Structure

Skimmianine
Skimmianine
CAS#83-95-4

Theoretical Analysis

MedKoo Cat#: 585159

Name: Skimmianine

CAS#: 83-95-4

Chemical Formula: C14H13NO4

Exact Mass: 259.0845

Molecular Weight: 259.26

Elemental Analysis: C, 64.86; H, 5.05; N, 5.40; O, 24.68

Price and Availability

Size Price Availability Quantity
5mg USD 550.00 2 Weeks
10mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Skimmianine, Skimmianin
IUPAC/Chemical Name
Furo(2,3-b)quinoline, 4,7,8-trimethoxy-
InChi Key
SLSIBLKBHNKZTB-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H13NO4/c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2/h4-7H,1-3H3
SMILES Code
COC1=C2N=C(OC=C3)C3=C(OC)C2=CC=C1OC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 259.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Gotsurve KN, Das J, Kutre S, Teja PK, Rathod R, Chauthe SK, Behera SK. In- silico and In-vitro Investigation of Flavonoids and Alkaloids from Artocarpus heterophyllus, Tinospora cordifolia, and Glycosmis pentaphylla as Potential NF- κB Inhibitors in Oral Cancer. Chem Biodivers. 2024 Oct 10:e202401886. doi: 10.1002/cbdv.202401886. Epub ahead of print. PMID: 39387347. 2: Alqhtani HA, Othman SI, Aba Alkhayl FF, Altoom NG, Lamsabhi AM, Kamel EM. Unraveling the mechanism of carbonic anhydrase IX inhibition by alkaloids from Ruta chalepensis: A synergistic analysis of in vitro and in silico data. Biochem Biophys Res Commun. 2024 Nov 12;733:150685. doi: 10.1016/j.bbrc.2024.150685. Epub 2024 Sep 11. PMID: 39270414. 3: Yoshita M, Funaki M, Shimakami T, Kakuya M, Murai K, Sugimoto S, Kawase S, Matsumori K, Kawane T, Nishikawa T, Nakamura A, Suzuki R, Ishida A, Kawasaki N, Sato Y, Li YY, Sumiyadorj A, Nio K, Takatori H, Kawaguchi K, Kuroki K, Kato T, Honda M, Yamashita T. High-Throughput Screening of Antiviral Compounds Using a Recombinant Hepatitis B Virus and Identification of a Possible Infection Inhibitor, Skimmianine. Viruses. 2024 Aug 22;16(8):1346. doi: 10.3390/v16081346. PMID: 39205320; PMCID: PMC11360121. 4: Ayaz H, Aşır F, Korak T. Skimmianine Showed Neuroprotection against Cerebral Ischemia/Reperfusion Injury. Curr Issues Mol Biol. 2024 Jul 12;46(7):7373-7385. doi: 10.3390/cimb46070437. PMID: 39057078; PMCID: PMC11276333. 5: Barazorda-Ccahuana HL, Cárcamo-Rodriguez EG, Centeno-Lopez AE, Galdino AS, Machado-de-Ávila RA, Giunchetti RC, Coelho EAF, Chávez-Fumagalli MA. Targeting with Structural Analogs of Natural Products the Purine Salvage Pathway in Leishmania (Leishmania) infantum by Computer-Aided Drug-Design Approaches. Trop Med Infect Dis. 2024 Feb 3;9(2):41. doi: 10.3390/tropicalmed9020041. PMID: 38393130; PMCID: PMC10891554. 6: Wang R, Yu C, Shang Y, Wen J, Wei W, Du K, Li J, Fang S, Chang Y. Quantification and discovery of quality markers from Toddalia asiatica by UHPLC- MS/MS coupled with chemometrics. Phytochem Anal. 2024 Jun;35(4):634-646. doi: 10.1002/pca.3318. Epub 2024 Jan 8. PMID: 38191127. 7: Huo CL, Wang B, Zhang X, Sun ZG. Skimmianine attenuates liver ischemia/reperfusion injury by regulating PI3K-AKT signaling pathway-mediated inflammation, apoptosis and oxidative stress. Sci Rep. 2023 Oct 25;13(1):18232. doi: 10.1038/s41598-023-45354-2. PMID: 37880319; PMCID: PMC10600244. 8: Kimani NM, Ochieng CO, Ogutu MD, Yamo KO, Onyango JO, Santos CBR. Inhibition Kinetics and Theoretical Studies on Zanthoxylum chalybeum Engl. Dual Inhibitors of α-Glucosidase and α-Amylase. J Xenobiot. 2023 Feb 21;13(1):102-120. doi: 10.3390/jox13010009. PMID: 36976158; PMCID: PMC10059848. 9: Szewczyk A, Grabowski M, Zych D. Ruta chalepensis L. In Vitro Cultures as a Source of Bioactive Furanocoumarins and Furoquinoline Alkaloids. Life (Basel). 2023 Feb 6;13(2):457. doi: 10.3390/life13020457. PMID: 36836814; PMCID: PMC9959614. 10: Ogunrinade FA, Iwuanyanwu VU, Sarker SD, Olajide OA. Neuroprotection by Skimmianine in Lipopolysaccharide-Activated BV-2 Microglia. Molecules. 2023 Jan 30;28(3):1317. doi: 10.3390/molecules28031317. PMID: 36770987; PMCID: PMC9920223. 11: Szewczyk A, Paździora W, Ekiert H. The Influence of Exogenous Phenylalanine on the Accumulation of Secondary Metabolites in Agitated Shoot Cultures of Ruta graveolens L. Molecules. 2023 Jan 11;28(2):727. doi: 10.3390/molecules28020727. PMID: 36677781; PMCID: PMC9864388. 12: Son NT. Skimmianine: Natural Occurrence, Biosynthesis, Synthesis, Pharmacology and Pharmacokinetics. Med Chem. 2023;19(6):556-569. doi: 10.2174/1573406419666221213124847. PMID: 36518041. 13: Szewczyk A, Marino A, Molinari J, Ekiert H, Miceli N. Phytochemical Characterization, and Antioxidant and Antimicrobial Properties of Agitated Cultures of Three Rue Species: Ruta chalepensis, Ruta corsica, and Ruta graveolens. Antioxidants (Basel). 2022 Mar 20;11(3):592. doi: 10.3390/antiox11030592. PMID: 35326242; PMCID: PMC8945450. 14: Liu Y, Kang L, Shi SM, Li BJ, Zhang Y, Zhang XZ, Guo XW, Fu G, Zheng GN, Hao H, Zhao HF. Skimmianine as a novel therapeutic agent suppresses proliferation and migration of human esophageal squamous cell carcinoma via blocking the activation of ERK1/2. Neoplasma. 2022 May;69(3):571-582. doi: 10.4149/neo_2022_211118N1640. Epub 2022 Feb 10. PMID: 35144474. 15: Guetchueng ST, Nahar L, Ritchie KJ, Sarker SD. Evaluation of the chemopreventive effect of selected medicinal plants extracts via induction of the Nrf2 in a modified model of breast cancer cells: identification of bioactive lead compounds. Eur J Cancer Prev. 2022 Jan 1;31(1):50-53. doi: 10.1097/CEJ.0000000000000668. PMID: 34871198. 16: Deng Y, Ding T, Deng L, Hao X, Mu S. Active constituents of Zanthoxylum nitidium from Yunnan Province against leukaemia cells in vitro. BMC Chem. 2021 Jul 23;15(1):44. doi: 10.1186/s13065-021-00771-0. PMID: 34301301; PMCID: PMC8305521. 17: Heredia Díaz Y, Tuenter E, Garcia-Díaz J, Ochoa Pacheco A, Cos P, Pieters L, Escalona Arranz JC. Novel flavonol-3-O-methylethers from Zanthoxylum pistaciifolium Griseb. (Rutaceae). Nat Prod Res. 2022 Oct;36(19):4869-4878. doi: 10.1080/14786419.2021.1906240. Epub 2021 Apr 5. PMID: 33813981. 18: Ogunrinade FA, Guetchueng ST, Katola FO, Aderogba MA, Akande IS, Sarker SD, Olajide OA. Zanthoxylum zanthoxyloides inhibits lipopolysaccharide- and synthetic hemozoin-induced neuroinflammation in BV-2 microglia: roles of NF-κB transcription factor and NLRP3 inflammasome activation. J Pharm Pharmacol. 2021 Mar 1;73(1):118-134. doi: 10.1093/jpp/rgaa019. PMID: 33791805. 19: Sabu V, Krishnan S, Peter J, Aswathy IS, Lal Preethi SS, Simon M, Radhakrishna GP, Helen A. Synergistic effect of Betulinic acid, Apigenin and Skimmianine (BASk) in high cholesterol diet rabbit: Involvement of CD36-TLR2 signaling pathway. Cytokine. 2021 Jun;142:155475. doi: 10.1016/j.cyto.2021.155475. Epub 2021 Mar 2. PMID: 33667961. 20: Dofuor AK, Ayertey F, Bolah P, Djameh GI, Kyeremeh K, Ohashi M, Okine LK, Gwira TM. Isolation and Antitrypanosomal Characterization of Furoquinoline and Oxylipin from Zanthoxylum zanthoxyloides. Biomolecules. 2020 Dec 13;10(12):1670. doi: 10.3390/biom10121670. PMID: 33322191; PMCID: PMC7763825.