Alkannin
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MedKoo CAT#: 592483

CAS#: 517-88-4

Description: Alkannin is a natural compound, which can inhibit Hepatic Inflammation in Diabetic Db/Db Mice. Alkannin Inhibits the Development of Ovarian Cancer by Affecting miR-4461. Alkannin-Induced Oxidative DNA Damage Synergizes With PARP Inhibition to Cause Cancer-Specific Cytotoxicity. Alkannin displays tumor suppressive activity by initiating apoptosis. Alkannin inhibited the growth of PANC-1 cells via modulating miR-199a-Klotho node. During this process, mTOR and MEK/ERK pathways were blunted.

Chemical Structure

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Alkannin
CAS# 517-88-4
Instruction

Theoretical Analysis

MedKoo Cat#: 592483
Name: Alkannin
CAS#: 517-88-4
Chemical Formula: C16H16O5
Exact Mass: 288.10
Molecular Weight: 288.300
Elemental Analysis: C, 66.66; H, 5.59; O, 27.75

Price and Availability

Size Price Availability Quantity
10mg USD 250 2 Weeks
25mg USD 450 2 Weeks
50mg USD 800 2 Weeks
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Related CAS #: 23444-65-7  

Synonym: (–)-Alkannin, NSC-94524, NSC94524. NSC 94524

IUPAC/Chemical Name: (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione

InChi Key: NEZONWMXZKDMKF-JTQLQIEISA-N

InChi Code: InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m0/s1

SMILES Code: OC1=C2C(C(C=C([C@H](C/C=C(C)/C)O)C2=O)=O)=C(O)C=C1

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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 288.30 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Kumar N, Singh JV, Bhagat K, Gulati HK, Sharma A, Rani A, Duggal A, Gulati P, Singh H, Bedi PMS, Kaur S. Discovery of potent inhibitors for Mpro enzyme of SARS-COV2 by multi-stage in-silico screening of Alkannin/shikonin. Nat Prod Res. 2021 Dec 15:1-5. doi: 10.1080/14786419.2021.2013212. Epub ahead of print. PMID: 34906016.


2: Wang Y, Zhang J, Wang F, Chen W, Ma J, Wang H. Alkannin Inhibits the Development of Ovarian Cancer by Affecting miR-4461. Evid Based Complement Alternat Med. 2021 Nov 28;2021:5083302. doi: 10.1155/2021/5083302. PMID: 34876915; PMCID: PMC8645362.


3: Cañamares MV, Mieites-Alonso MG, Leona M. Raman, SERS and DFT analysis of the natural red dyes of Japanese origin alkannin and shikonin. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Jan 15;265:120382. doi: 10.1016/j.saa.2021.120382. Epub 2021 Sep 9. PMID: 34543990.


4: Tang C. Exploring the evolutionary process of alkannin/shikonin O-acyltransferases by a reliable Lithospermum erythrorhizon genome. DNA Res. 2021 Sep 13;28(5):dsab015. doi: 10.1093/dnares/dsab015. PMID: 34424327; PMCID: PMC8435551.


5: Ahmad M, Leroy T, Krigas N, Temsch EM, Weiss-Schneeweiss H, Lexer C, Sehr EM, Paun O. Spatial and Ecological Drivers of Genetic Structure in Greek Populations of Alkanna tinctoria (Boraginaceae), a Polyploid Medicinal Herb. Front Plant Sci. 2021 Jul 14;12:706574. doi: 10.3389/fpls.2021.706574. PMID: 34335669; PMCID: PMC8317432.


6: Yang X, Fan W, Huang R, Liu G. β-acetoxyisovaleryl alkannin (AAN-II) from Alkanna tinctoria promotes the healing of pressure-induced venous ulcers in a rabbit model through the activation of TGF-β/Smad3 signaling. Cell Mol Biol Lett. 2021 Jul 31;26(1):35. doi: 10.1186/s11658-021-00278-5. PMID: 34332546; PMCID: PMC8325215.


7: Zhang W, Zhang R, Zeng Y, Li Y, Chen Y, Zhou J, Zhang Y, Wang A, Zhu J, Liu Z, Yan Z, Huang JA. ALCAP2 inhibits lung adenocarcinoma cell proliferation, migration and invasion via the ubiquitination of β-catenin by upregulating the E3 ligase NEDD4L. Cell Death Dis. 2021 Jul 31;12(8):755. doi: 10.1038/s41419-021-04043-6. PMID: 34330894; PMCID: PMC8324825.


8: Arampatzis AS, Kontogiannopoulos KN, Theodoridis K, Aggelidou E, Rat A, Willems A, Tsivintzelis I, Papageorgiou VP, Kritis A, Assimopoulou AN. Electrospun wound dressings containing bioactive natural products: physico- chemical characterization and biological assessment. Biomater Res. 2021 Jul 16;25(1):23. doi: 10.1186/s40824-021-00223-9. PMID: 34271983; PMCID: PMC8284004.


9: Arampatzis AS, Giannakoula K, Kontogiannopoulos KN, Theodoridis K, Aggelidou E, Rat A, Kampasakali E, Willems A, Christofilos D, Kritis A, Papageorgiou VP, Tsivintzelis I, Assimopoulou AN. Novel electrospun poly-hydroxybutyrate scaffolds as carriers for the wound healing agents alkannins and shikonins. Regen Biomater. 2021 Jun 10;8(3):rbab011. doi: 10.1093/rb/rbab011. PMID: 34211727; PMCID: PMC8240617.


10: Song W, Zhuang Y, Liu T. CYP82AR Subfamily Proteins Catalyze C-1' Hydroxylations of Deoxyshikonin in the Biosynthesis of Shikonin and Alkannin. Org Lett. 2021 Apr 2;23(7):2455-2459. doi: 10.1021/acs.orglett.1c00360. Epub 2021 Mar 17. PMID: 33728922.


11: Rat A, Naranjo HD, Krigas N, Grigoriadou K, Maloupa E, Alonso AV, Schneider C, Papageorgiou VP, Assimopoulou AN, Tsafantakis N, Fokialakis N, Willems A. Endophytic Bacteria From the Roots of the Medicinal Plant Alkanna tinctoria Tausch (Boraginaceae): Exploration of Plant Growth Promoting Properties and Potential Role in the Production of Plant Secondary Metabolites. Front Microbiol. 2021 Feb 3;12:633488. doi: 10.3389/fmicb.2021.633488. PMID: 33633713; PMCID: PMC7901983.


12: Taghvaei S, Sabouni F, Minuchehr Z, Taghvaei A. Identification of novel anti-cancer agents, applying in silico method for SENP1 protease inhibition. J Biomol Struct Dyn. 2021 Feb 3:1-15. doi: 10.1080/07391102.2021.1880480. Epub ahead of print. PMID: 33533323.


13: Chang M, Wang H, Niu J, Song Y, Zou Z. Alkannin-Induced Oxidative DNA Damage Synergizes With PARP Inhibition to Cause Cancer-Specific Cytotoxicity. Front Pharmacol. 2020 Dec 22;11:610205. doi: 10.3389/fphar.2020.610205. PMID: 33519476; PMCID: PMC7844861.


14: Oshikiri H, Watanabe B, Yamamoto H, Yazaki K, Takanashi K. Two BAHD Acyltransferases Catalyze the Last Step in the Shikonin/Alkannin Biosynthetic Pathway. Plant Physiol. 2020 Oct;184(2):753-761. doi: 10.1104/pp.20.00207. Epub 2020 Jul 29. PMID: 32727911; PMCID: PMC7536692.


15: Zheng Q, Li Q, Zhao G, Zhang J, Yuan H, Gong D, Guo Y, Liu X, Li K, Lin P. Alkannin induces cytotoxic autophagy and apoptosis by promoting ROS-mediated mitochondrial dysfunction and activation of JNK pathway. Biochem Pharmacol. 2020 Oct;180:114167. doi: 10.1016/j.bcp.2020.114167. Epub 2020 Jul 20. PMID: 32702370.


16: Auber RP, Suttiyut T, McCoy RM, Ghaste M, Crook JW, Pendleton AL, Widhalm JR, Wisecaver JH. Hybrid de novo genome assembly of red gromwell (Lithospermum erythrorhizon) reveals evolutionary insight into shikonin biosynthesis. Hortic Res. 2020 Jun 1;7(1):82. doi: 10.1038/s41438-020-0301-9. PMID: 32528694; PMCID: PMC7261806.


17: Zhang G, Zhai N, Zhang X. Alkannin represses growth of pancreatic cancer cells based on the down regulation of miR-199a. Biofactors. 2020 Sep;46(5):849-859. doi: 10.1002/biof.1613. Epub 2020 Jan 22. PMID: 31967380.


18: Hong M, Li J, Li S, M Almutairi M. Acetylshikonin Sensitizes Hepatocellular Carcinoma Cells to Apoptosis through ROS-Mediated Caspase Activation. Cells. 2019 Nov 19;8(11):1466. doi: 10.3390/cells8111466. Retraction in: Cells. 2020 Jul 31;9(8): PMID: 31752383; PMCID: PMC6912742.


19: Tang CY, Li S, Wang YT, Wang X. Comparative genome/transcriptome analysis probes Boraginales' phylogenetic position, WGDs in Boraginales, and key enzyme genes in the alkannin/shikonin core pathway. Mol Ecol Resour. 2020 Jan;20(1):228-241. doi: 10.1111/1755-0998.13104. Epub 2019 Nov 15. PMID: 31625679.


20: Su J, Ma J, Mo F, Yang X, Zhang P, Zhang J. Thermosensitive hydrogels as a controlled release system for alkannin to improve localized treatment of Candida vaginitis after external beam radiotherapy in vitro and in vivo. Pathog Dis. 2019 Jun 1;77(4):ftz041. doi: 10.1093/femspd/ftz041. PMID: 31374574.