Bostrycin | CAS# 21879-81-2 | Anthraquinone

MedKoo Cat#: 574245 | Name: Bostrycin

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Description:

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

Bostrycin is an anthraquinone with antibacterial, antiproliferative, and phytotoxic properties. It is active against Gram-positive bacteria, including methicillin-resistant S. aureus (MRSA), M. tuberculosis, and C. botulinum. Bostrycin inhibits proliferation of A549 lung adenocarcinoma cells as well as halts the cell cycle at the G0/G1 phase and induces apoptosis in A549 cells. Bostrycin has been used as a cross-linking agent for protein immobilization that retains bacteriostatic activity when immobilized on nonwoven polypropylene fabric.

Chemical Structure

Bostrycin

CAS#21879-81-2

Theoretical Analysis

MedKoo Cat#: 574245

Name: Bostrycin

CAS#: 21879-81-2

Chemical Formula: C16H16O8

Exact Mass: 336.0845

Molecular Weight: 336.29

Elemental Analysis: C, 57.14; H, 4.80; O, 38.06

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 550.00	2 Weeks
5mg	USD 1,450.00	2 Weeks

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Related CAS #

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Synonym

Bostrycin, Rhodosporin

IUPAC/Chemical Name

(5S,6R,7S)-5,6,7,8-tetrahydro-5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-1,4-anthracenedione

InChi Key

ZQNOLGRKZRDRQO-XHSDSOJGSA-N

InChi Code

InChI=1S/C16H16O8/c1-16(23)4-5-8(14(21)15(16)22)13(20)9-6(17)3-7(24-2)12(19)10(9)11(5)18/h3,14-15,18,20-23H,4H2,1-2H3/t14-,15+,16-/m0/s1

SMILES Code

O=C(C(OC)=C1)C2=C(C(O)=C([C@H](O)[C@@H](O)[C@](O)(C)C3)C3=C2O)C1=O

Appearance

Solid powder

Purity

>95% (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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 336.29 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.

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: Chen SY, Huang C, Zhang CL, Chen YZ, Lin FC. Bostrycin. Acta Crystallogr Sect E Struct Rep Online. 2008 Oct 31;64(Pt 11):o2226. doi: 10.1107/S1600536808032030. PMID: 21581081; PMCID: PMC2959567. 2: Jie J, Shi L, Yue S, Wang M, Zhang J. Bostrycin inhibits growth of tongue squamous cell carcinoma cells by inducing mitochondrial apoptosis. Transl Cancer Res. 2020 Jun;9(6):3926-3936. doi: 10.21037/tcr-19-2076. PMID: 35117759; PMCID: PMC8798930. 3: Huang YH, Yang WJ, Cheng CY, Sung HM, Lin SF. Bostrycin production by agro- industrial residues and its potential for food processing. Food Sci Biotechnol. 2017 May 29;26(3):715-721. doi: 10.1007/s10068-017-0082-6. PMID: 30263596; PMCID: PMC6049593. 4: Li J, Shi L, Xu S, Gu S, Wen X, Xu D, Luo J, Huang Y, Wang M. Optimal fermentation time for Nigrospora-fermented tea rich in bostrycin. J Sci Food Agric. 2021 Apr;101(6):2483-2490. doi: 10.1002/jsfa.10874. Epub 2020 Nov 10. PMID: 33058154. 5: Chen WS, Hou JN, Guo YB, Yang HL, Xie CM, Lin YC, She ZG. Bostrycin inhibits proliferation of human lung carcinoma A549 cells via downregulation of the PI3K/Akt pathway. J Exp Clin Cancer Res. 2011 Feb 8;30(1):17. doi: 10.1186/1756-9966-30-17. PMID: 21303527; PMCID: PMC3041691. 6: Yuan P, He L, Chen D, Sun Y, Ge Z, Shen D, Lu Y. Proteomic characterization of Mycobacterium tuberculosis reveals potential targets of bostrycin. J Proteomics. 2020 Feb 10;212:103576. doi: 10.1016/j.jprot.2019.103576. Epub 2019 Nov 6. PMID: 31706025. 7: Yang WJ, Yang CS, Huang CJ, Chen KS, Lin SF. Bostrycin, a novel coupling agent for protein immobilization and prevention of biomaterial-centered infection produced by Nigrospora sp. No. 407. Enzyme Microb Technol. 2012 May 10;50(6-7):287-92. doi: 10.1016/j.enzmictec.2012.02.002. Epub 2012 Feb 22. PMID: 22500894. 8: Noda T, Take T, Watanabe T, Abe J. The structure of bostrycin. Tetrahedron. 1970 Mar;26(5):1339-46. doi: 10.1016/s0040-4020(01)93004-2. PMID: 5463237. 9: Charudattan R, Rao KV. Bostrycin and 4-deoxybostrycin: two nonspecific phytotoxins produced by Alternaria eichhorniae. Appl Environ Microbiol. 1982 Apr;43(4):846-9. doi: 10.1128/aem.43.4.846-849.1982. PMID: 6805431; PMCID: PMC241930. 10: Xu C, Wang J, Gao Y, Lin H, Du L, Yang S, Long S, She Z, Cai X, Zhou S, Lu Y. The anthracenedione compound bostrycin induces mitochondria-mediated apoptosis in the yeast Saccharomyces cerevisiae. FEMS Yeast Res. 2010 May;10(3):297-308. doi: 10.1111/j.1567-1364.2010.00615.x. Epub 2010 Mar 3. PMID: 20345898. 11: Chen DN, Chen H, She ZG, Lu YJ. Identification of Bostrycin Derivatives as Potential Inhibitors of Mycobacterium tuberculosis Protein Tyrosine Phosphatase (MptpB). Med Chem. 2016;12(3):296-302. doi: 10.2174/1573406411666151005105857. PMID: 26434800. 12: Noda T, Take T, Otani M, Miyauchi K, Watanabe T, Abe J. Structure of bostrycin. Tetrahedron Lett. 1968 Dec;(58):6087-90. doi: 10.1016/s0040-4039(00)70801-x. PMID: 5750419. 13: Chen H, Zhong L, Long Y, Li J, Wu J, Liu L, Chen S, Lin Y, Li M, Zhu X, She Z. Studies on the synthesis of derivatives of marine-derived bostrycin and their structure-activity relationship against tumor cells. Mar Drugs. 2012 Apr;10(4):932-952. doi: 10.3390/md10040932. Epub 2012 Apr 24. PMID: 22690152; PMCID: PMC3366684. 14: Bhatia A, Bharti SK, Tripathi T, Mishra A, Sidhu OP, Roy R, Nautiyal CS. Metabolic profiling of Commiphora wightii (guggul) reveals a potential source for pharmaceuticals and nutraceuticals. Phytochemistry. 2015 Feb;110:29-36. doi: 10.1016/j.phytochem.2014.12.016. Epub 2015 Jan 2. PMID: 25561401. 15: Wang H, Guo Y, Luo Z, Gao L, Li R, Zhang Y, Kalaji HM, Qiang S, Chen S. Recent Advances in Alternaria Phytotoxins: A Review of Their Occurrence, Structure, Bioactivity, and Biosynthesis. J Fungi (Basel). 2022 Feb 9;8(2):168. doi: 10.3390/jof8020168. PMID: 35205922; PMCID: PMC8878860. 16: Feng S, Wang W. Bioactivities and Structure-Activity Relationships of Natural Tetrahydroanthraquinone Compounds: A Review. Front Pharmacol. 2020 May 27;11:799. doi: 10.3389/fphar.2020.00799. PMID: 32536871; PMCID: PMC7267002. 17: Safwan S, Hsiao G, Lee TH, Lee CK. Bioactive compounds from an endophytic fungi Nigrospora aurantiaca. Bot Stud. 2021 Oct 26;62(1):18. doi: 10.1186/s40529-021-00324-7. PMID: 34698886; PMCID: PMC8548483. 18: Suwannarach N, Kumla J, Nishizaki Y, Sugimoto N, Meerak J, Matsui K, Lumyong S. Optimization and characterization of red pigment production from an endophytic fungus, Nigrospora aurantiaca CMU-ZY2045, and its potential source of natural dye for use in textile dyeing. Appl Microbiol Biotechnol. 2019 Sep;103(17):6973-6987. doi: 10.1007/s00253-019-09926-5. Epub 2019 Jun 26. PMID: 31243502. 19: Takenaka A, Furusaki A, Watanabé T. The crystal and molecular structure of bostrycin pi-bromobenzoate, A derivative of bostrycin. Tetrahedron Lett. 1968 Dec;(58):6091-4. doi: 10.1016/s0040-4039(00)70802-1. PMID: 5750420. 20: Xu J, Nakazawa T, Ukai K, Kobayashi H, Mangindaan RE, Wewengkang DS, Rotinsulu H, Namikoshi M. Tetrahydrobostrycin and 1-deoxytetrahydrobostrycin, two new hexahydroanthrone derivatives, from a marine-derived fungus Aspergillus sp. J Antibiot (Tokyo). 2008 Jul;61(7):415-9. doi: 10.1038/ja.2008.57. PMID: 18776653.