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MedKoo Cat#: 464674 | Name: Prangol
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Description:

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

Prangol is a furanocoumarin that has been found in A. japonica and has diverse biological activities. It is active against the Gram-positive bacteria B. cereus, S. aureus, and S. faecalis (MICs = 9.76-78.12 µg/ml), the Gram-negative bacteria E. coli, S. dysenteriae, P. aeruginosa, K. pneumoniae, and S. typhi (MICs = 39.06-625 µg/ml), and the fungi C. albicans and M. audouinii (MIC = 39.06 µg/ml for both). Prangol inhibits proliferation of human MK-1 gastric and HeLa cervical cancer cells, as well as murine B16/F10 melanoma cells (EC50s = 47.2, 80.3, and 42 µg/ml, respectively). It also inhibits proliferation of sensitive and multidrug-resistant murine L5178Y lymphoma cells (IC50s = 41.96 and 60.58 µM, respectively).

Chemical Structure

Prangol
Prangol
CAS#2643-85-8

Theoretical Analysis

MedKoo Cat#: 464674

Name: Prangol

CAS#: 2643-85-8

Chemical Formula: C16H16O6

Exact Mass: 304.0947

Molecular Weight: 304.30

Elemental Analysis: C, 63.15; H, 5.30; O, 31.55

Price and Availability

Size Price Availability Quantity
5mg USD 260.00 2 Weeks
10mg USD 430.00 2 Weeks
25mg USD 750.00 2 Weeks
50mg USD 1,120.00 2 Weeks
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Related CAS #
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Synonym
Prangol; Prangolarin hydrate; (+)-Aviprin; (+) Aviprin; (+)-Oxypeucedanin hydrate; (+) Oxypeucedanin hydrate;
IUPAC/Chemical Name
(R)-4-(2,3-dihydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one
InChi Key
PEWFWDOPJISUOK-CYBMUJFWSA-N
InChi Code
InChI=1S/C16H16O6/c1-16(2,19)13(17)8-21-15-9-3-4-14(18)22-12(9)7-11-10(15)5-6-20-11/h3-7,13,17,19H,8H2,1-2H3/t13-/m1/s1
SMILES Code
CC(O)([C@@H](COC1=C2C=COC2=CC(O3)=C1C=CC3=O)O)C
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Oxypeucedanin hydrate ((+)-Oxypeucedanin hydrate) is a natural product isolated from D. anethifolia. Prangol exhibits mild toxicity on fibroblasts and parental lymphoma cells.
In vitro activity:
Microsomal incubation with oxypeucedanin induced a time-, concentration-, and NADPH-dependent inhibition of CYPs2B6 and 2D6 with kinetic values of KI/kinact 1.82 μM/0.07 min-1 (CYP2B6) and 8.47 μM/0.044 min-1 (CYP2D6), respectively. Ticlopidine and quinidine attenuated the observed time-dependent enzyme inhibitions. An epoxide and/or γ-ketoenal intermediate(s) derived from oxypeucedanin was/were trapped in microsomal incubations. CYP3A4 was the primary enzyme involved in the bioactivation of oxypeucedanin. Reference: Curr Drug Metab. 2021;22(11):882-892. https://pubmed.ncbi.nlm.nih.gov/34191696/
In vivo activity:
Using myeloperoxidase activity measurement, ELISA, qRT-PCR, and Western blotting, this study found that oxypeucedanin modulated the activity of myeloperoxidase and decreased the expression levels of inflammatory mediators such as TNF-α, IL-6, IL-1β, MPO, COX-2 and iNOS in LPS-induced inflammation models. Meanwhile, oxypeucedanin inhibited the activation of PI3K/AKT and its downstream NF-κB and MAPK signaling pathways. In addition, oxypeucedanin significantly decreased the pulmonary vascular permeability, which was induced by LPSs, and the enhanced expression of tight junction proteins (Occludin and Claudin 3). Reference: Aging (Albany NY). 2022 Aug 18;14(16):6626-6641. https://pubmed.ncbi.nlm.nih.gov/35985771/
Solvent mg/mL mM comments
Solubility
DMF 30.0 98.59
DMSO 30.0 98.59
DMSO:PBS (pH 7.2) (1:2) 0.3 1.08
Ethanol 5.0 16.43
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 304.30 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:
1. Zhang K, Li Y, Fu Y, Cui T, Wang Q, Mao X, Peng Y, Zheng J. Oxypeucedanin is a Mechanism-based Inactivator of CYP2B6 and CYP2D6. Curr Drug Metab. 2021;22(11):882-892. doi: 10.2174/1389200222666210629114830. PMID: 34191696. 2. Park SH, Hong JY, Park HJ, Lee SK. The Antiproliferative Activity of Oxypeucedanin via Induction of G2/M Phase Cell Cycle Arrest and p53-Dependent MDM2/p21 Expression in Human Hepatoma Cells. Molecules. 2020 Jan 23;25(3):501. doi: 10.3390/molecules25030501. PMID: 31979361; PMCID: PMC7037124. 3. Du L, Zhang J, Zhang X, Li C, Wang Q, Meng G, Kan X, Zhang J, Jia Y. Oxypeucedanin relieves LPS-induced acute lung injury by inhibiting the inflammation and maintaining the integrity of the lung air-blood barrier. Aging (Albany NY). 2022 Aug 18;14(16):6626-6641. doi: 10.18632/aging.204235. Epub 2022 Aug 18. PMID: 35985771; PMCID: PMC9467393.
In vitro protocol:
1. Zhang K, Li Y, Fu Y, Cui T, Wang Q, Mao X, Peng Y, Zheng J. Oxypeucedanin is a Mechanism-based Inactivator of CYP2B6 and CYP2D6. Curr Drug Metab. 2021;22(11):882-892. doi: 10.2174/1389200222666210629114830. PMID: 34191696. 2. Park SH, Hong JY, Park HJ, Lee SK. The Antiproliferative Activity of Oxypeucedanin via Induction of G2/M Phase Cell Cycle Arrest and p53-Dependent MDM2/p21 Expression in Human Hepatoma Cells. Molecules. 2020 Jan 23;25(3):501. doi: 10.3390/molecules25030501. PMID: 31979361; PMCID: PMC7037124.
In vivo protocol:
1. Du L, Zhang J, Zhang X, Li C, Wang Q, Meng G, Kan X, Zhang J, Jia Y. Oxypeucedanin relieves LPS-induced acute lung injury by inhibiting the inflammation and maintaining the integrity of the lung air-blood barrier. Aging (Albany NY). 2022 Aug 18;14(16):6626-6641. doi: 10.18632/aging.204235. Epub 2022 Aug 18. PMID: 35985771; PMCID: PMC9467393.
1: Ali I, Mu Y, Atif M, Hussain H, Li J, Li D, Shabbir M, Bankeu JJK, Cui L, Sajjad S, Wang D, Wang X. Separation and anti-inflammatory evaluation of phytochemical constituents from Pleurospermum candollei (Apiaceae) by high-speed counter-current chromatography with continuous sample load. J Sep Sci. 2021 Apr 29. doi: 10.1002/jssc.202100155. Epub ahead of print. PMID: 33914393. 2: Kiyonga AN, Hong G, Kim HS, Suh YG, Jung K. Facile and Rapid Isolation of Oxypeucedanin Hydrate and Byakangelicin from Angelica dahurica by Using [Bmim]Tf2N Ionic Liquid. Molecules. 2021 Feb 5;26(4):830. doi: 10.3390/molecules26040830. PMID: 33562719; PMCID: PMC7915976. 3: Tan SRS, Eser BE, Han J. Gut Metabolism of Furanocoumarins: Proposed Function of Co O-Methyltransferase. ACS Omega. 2020 Nov 17;5(47):30696-30703. doi: 10.1021/acsomega.0c04879. PMID: 33283118; PMCID: PMC7711939. 4: Shimada A, Ueno H, Inagaki M, Yoshimitsu H. Glutaminase inhibitory activity of umbelliferone isolated from kabosu (Citrus sphaerocarpa Hort. ex Tanaka). Nat Prod Res. 2020 Jul 3:1-5. doi: 10.1080/14786419.2020.1788553. Epub ahead of print. PMID: 32619101. 5: Lee BW, Ha TKQ, Cho HM, An JP, Kim SK, Kim CS, Kim E, Oh WK. Antiviral activity of furanocoumarins isolated from Angelica dahurica against influenza a viruses H1N1 and H9N2. J Ethnopharmacol. 2020 Sep 15;259:112945. doi: 10.1016/j.jep.2020.112945. Epub 2020 May 7. PMID: 32389854. 6: Seo CS, Shin HK. Quality assessment of traditional herbal formula, Hyeonggaeyeongyo-tang through simultaneous determination of twenty marker components by HPLC-PDA and LC-MS/MS. Saudi Pharm J. 2020 Apr;28(4):427-439. doi: 10.1016/j.jsps.2020.02.003. Epub 2020 Feb 17. PMID: 32273801; PMCID: PMC7132628. 7: Shi B, Liu J, Zhang Q, Wang S, Jia P, Bian L, Zheng X. Effect of co- administration of Acori Tatarinowii Rhizoma volatile oil on pharmacokinetic fate of xanthotoxol, oxypeucedanin hydrate, and byakangelicin from Angelicae Dahuricae Radix in rat. J Sep Sci. 2020 Jun;43(12):2349-2362. doi: 10.1002/jssc.201901250. Epub 2020 Apr 23. PMID: 32222035. 8: Yu M, Li T, Raza A, Wang L, Song H, Zhang Y, Li L, Hua Y. Sensory-guided identification of bitter compounds in Hangbaizhi (Angelica Dahurica). Food Res Int. 2020 Mar;129:108880. doi: 10.1016/j.foodres.2019.108880. Epub 2019 Dec 5. PMID: 32036877. 9: Urbagarova BM, Shults EE, Taraskin VV, Radnaeva LD, Petrova TN, Rybalova TV, Frolova TS, Pokrovskii AG, Ganbaatar J. Chromones and coumarins from Saposhnikovia divaricata (Turcz.) Schischk. Growing in Buryatia and Mongolia and their cytotoxicity. J Ethnopharmacol. 2020 Oct 28;261:112517. doi: 10.1016/j.jep.2019.112517. Epub 2020 Jan 10. PMID: 31931162. 10: Ramírez-Pelayo C, Martínez-Quiñones J, Gil J, Durango D. Coumarins from the peel of citrus grown in Colombia: composition, elicitation and antifungal activity. Heliyon. 2019 Jun 15;5(6):e01937. doi: 10.1016/j.heliyon.2019.e01937. PMID: 31245648; PMCID: PMC6582165. 11: Zhang YB, Deng GG, Wang TX, Liu L, Yang XW. Tissue distribution study of Angelica dahurica cv. Yubaizhi in rat by ultra-performance liquid chromatography with tandem mass spectrometry. J Pharm Biomed Anal. 2019 Sep 10;174:43-49. doi: 10.1016/j.jpba.2019.05.046. Epub 2019 May 22. PMID: 31153136. 12: Mottaghipisheh J, Nové M, Spengler G, Kúsz N, Hohmann J, Csupor D. Antiproliferative and cytotoxic activities of furocoumarins of Ducrosia anethifolia. Pharm Biol. 2018 Dec;56(1):658-664. doi: 10.1080/13880209.2018.1548625. PMID: 31070540; PMCID: PMC6300088. 13: Zhang Q , Tan C , Cai L , Xia F , Gao D , Yang F , Chen H , Xia Z . Characterization of active antiplatelet chemical compositions of edible Citrus limon through ultra-performance liquid chromatography single quadrupole mass spectrometry-based chemometrics. Food Funct. 2018 May 23;9(5):2762-2773. doi: 10.1039/c8fo00403j. PMID: 29687827. 14: Yang YF, Zhang L, Yang XW. Distribution Assessments of Coumarins from Angelicae Pubescentis Radix in Rat Cerebrospinal Fluid and Brain by Liquid Chromatography Tandem Mass Spectrometry Analysis. Molecules. 2018 Jan 20;23(1):225. doi: 10.3390/molecules23010225. PMID: 29361720; PMCID: PMC6017000. 15: Numonov S, Bobakulov K, Numonova M, Sharopov F, Setzer WN, Khalilov Q, Begmatov N, Habasi M, Aisa HA. New coumarin from the roots of Prangos pabularia. Nat Prod Res. 2018 Oct;32(19):2325-2332. doi: 10.1080/14786419.2017.1413558. Epub 2017 Dec 11. PMID: 29224384. 16: Mileski KS, Trifunović SS, Ćirić AD, Šakić ŽM, Ristić MS, Todorović NM, Matevski VS, Marin PD, Tešević VV, Džamić AM. Research on Chemical Composition and Biological Properties Including Antiquorum Sensing Activity of Angelica pancicii Vandas Aerial Parts and Roots. J Agric Food Chem. 2017 Dec 20;65(50):10933-10949. doi: 10.1021/acs.jafc.7b04202. Epub 2017 Dec 8. PMID: 29129053. 17: Chen L, Yang H, Yu C, Yuan M, Li H. High hepatic exposure of furanocoumarins in Radix Angelica dahuricae is associated with transporter mediated active uptake. J Ethnopharmacol. 2018 Feb 15;212:74-85. doi: 10.1016/j.jep.2017.10.014. Epub 2017 Oct 18. PMID: 29055720. 18: Tavakoli S, Delnavazi MR, Hadjiaghaee R, Jafari-Nodooshan S, Khalighi- Sigaroodi F, Akhbari M, Hadjiakhoondi A, Yassa N. Bioactive coumarins from the roots and fruits of Ferulago trifida Boiss., an endemic species to Iran. Nat Prod Res. 2018 Nov;32(22):2724-2728. doi: 10.1080/14786419.2017.1375915. Epub 2017 Sep 27. PMID: 28954543. 19: Yuan ZM, Wang J, Jia TZ, Chen JF. [Determination of four coumarin constituents before and after Angelicae Dahuricae Radix stewed with yellow rice wine and research on its mutual transformation mechanism]. Zhongguo Zhong Yao Za Zhi. 2016 Aug;41(16):3032-3035. Chinese. doi: 10.4268/cjcmm20161615. PMID: 28920344. 20: Deng GG, Yang XW, Zhang YB, Xu W, Wei W, Li ZG. [Chemical constituents from lipophilic parts in roots of Angelica dahurica cv.Yubaizhi]. Zhongguo Zhong Yao Za Zhi. 2017 Jun;42(11):2102-2109. Chinese. doi: 10.19540/j.cnki.cjcmm.20170223.023. PMID: 28822155.