Friedelin | CAS# 559-74-0 | antifungal and antimicrobial

MedKoo Cat#: 581095 | Name: Friedelin

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Description:

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

Friedelin is a triterpene natural product isolated from the Quercus suber L. cork tree bark. Friedelin have antifungal and antimicrobial properties.

Chemical Structure

Friedelin

CAS#559-74-0

Theoretical Analysis

MedKoo Cat#: 581095

Name: Friedelin

CAS#: 559-74-0

Chemical Formula: C30H50O

Exact Mass: 426.3862

Molecular Weight: 426.73

Elemental Analysis: C, 84.44; H, 11.81; O, 3.75

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 485.00	2 Weeks
25mg	USD 1,250.00	2 Weeks

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Related CAS #

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Synonym

Friedelin; Friedeline; Friedelan-3-one; Friedelanone; NSC 55141; NSC55141; NSC-55141;

IUPAC/Chemical Name

(4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one

InChi Key

OFMXGFHWLZPCFL-SVRPQWSVSA-N

InChi Code

InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1

SMILES Code

[H][C@]12CC[C@]3(C)[C@@H](C)C(=O)CC[C@@]3([H])[C@]1(C)CC[C@]1(C)[C@]2(C)CC[C@@]2(C)CCC(C)(C)C[C@@]12[H]

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

>2 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

1: Antonisamy P, Duraipandiyan V, Aravinthan A, Al-Dhabi NA, Ignacimuthu S, Choi KC, Kim JH. Protective effects of friedelin isolated from Azima tetracantha Lam. against ethanol-induced gastric ulcer in rats and possible underlying mechanisms. Eur J Pharmacol. 2015 Mar 5;750:167-75. doi: 10.1016/j.ejphar.2015.01.015. Epub 2015 Jan 22. PubMed PMID: 25617794. 2: Sunil C, Duraipandiyan V, Ignacimuthu S, Al-Dhabi NA. Antioxidant, free radical scavenging and liver protective effects of friedelin isolated from Azima tetracantha Lam. leaves. Food Chem. 2013 Aug 15;139(1-4):860-5. doi: 10.1016/j.foodchem.2012.12.041. Epub 2013 Jan 4. PubMed PMID: 23561182. 3: Pires RA, Aroso I, Silva SP, Mano JF, Reis RL. Isolation of friedelin from black condensate of cork. Nat Prod Commun. 2011 Nov;6(11):1577-9. PubMed PMID: 22224263. 4: Souza-Moreira TM, Alves TB, Pinheiro KA, Felippe LG, De Lima GM, Watanabe TF, Barbosa CC, Santos VA, Lopes NP, Valentini SR, Guido RV, Furlan M, Zanelli CF. Friedelin Synthase from Maytenus ilicifolia: Leucine 482 Plays an Essential Role in the Production of the Most Rearranged Pentacyclic Triterpene. Sci Rep. 2016 Nov 22;6:36858. doi: 10.1038/srep36858. PubMed PMID: 27874020; PubMed Central PMCID: PMC5118845. 5: Antonisamy P, Duraipandiyan V, Ignacimuthu S. Anti-inflammatory, analgesic and antipyretic effects of friedelin isolated from Azima tetracantha Lam. in mouse and rat models. J Pharm Pharmacol. 2011 Aug;63(8):1070-7. doi: 10.1111/j.2042-7158.2011.01300.x. Epub 2011 Jun 11. PubMed PMID: 21718291. 6: Susanti D, Amiroudine MZ, Rezali MF, Taher M. Friedelin and lanosterol from Garcinia prainiana stimulated glucose uptake and adipocytes differentiation in 3T3-L1 adipocytes. Nat Prod Res. 2013 Mar;27(4-5):417-24. doi: 10.1080/14786419.2012.725399. Epub 2012 Sep 19. PubMed PMID: 22988818. 7: Vistuba JP, Piovezan M, Pizzolatti MG, Rebelo AM, Azevedo MS, Vitali L, Costa AC, Amadeu Micke G. Increasing the instrumental throughput of gas chromatography method using multiple injections in a single experimental run: application in determination of friedelan-3-ol and friedelin in Maytenus ilicifolia. J Chromatogr A. 2013 Jan 25;1274:159-64. doi: 10.1016/j.chroma.2012.11.087. Epub 2012 Dec 11. PubMed PMID: 23276648. 8: Wang Z, Yeats T, Han H, Jetter R. Cloning and characterization of oxidosqualene cyclases from Kalanchoe daigremontiana: enzymes catalyzing up to 10 rearrangement steps yielding friedelin and other triterpenoids. J Biol Chem. 2010 Sep 24;285(39):29703-12. doi: 10.1074/jbc.M109.098871. Epub 2010 Jul 7. PubMed PMID: 20610397; PubMed Central PMCID: PMC2943309. 9: Aswar UM, Bhaskaran S, Mohan V, Bodhankar SL. Estrogenic activity of friedelin rich fraction (IND-HE) separated from Cissus quadrangularis and its effect on female sexual function. Pharmacognosy Res. 2010 May;2(3):138-45. doi: 10.4103/0974-8490.65507. PubMed PMID: 21808556; PubMed Central PMCID: PMC3141304. 10: Queiroga CL, Silva GF, Dias PC, Possenti A, de Carvalho JE. Evaluation of the antiulcerogenic activity of friedelan-3beta-ol and friedelin isolated from Maytenus ilicifolia (Celastraceae). J Ethnopharmacol. 2000 Oct;72(3):465-8. PubMed PMID: 10996287. 11: Jiao J, Zhang Y, Lou D, Wu X, Zhang Y. Antihyperlipidemic and antihypertensive effect of a triterpenoid-rich extract from bamboo shavings and vasodilator effect of friedelin on phenylephrine-induced vasoconstriction in thoracic aortas of rats. Phytother Res. 2007 Dec;21(12):1135-41. PubMed PMID: 17639555. 12: Lee JA, Ha SK, Kim YC, Choi I. Effects of friedelin on the intestinal permeability and bioavailability of apigenin. Pharmacol Rep. 2017 Oct;69(5):1044-1048. doi: 10.1016/j.pharep.2017.04.012. Epub 2017 Apr 23. PubMed PMID: 28939344. 13: Onishi Y, Hanaoka M. [Studies on the chemical components of Quercus stenophylla Makino. I. Isolation of friedelin from the leaves of Quercus stenophylla Makino]. Yakugaku Zasshi. 1968 Sep;88(9):1244-5. Japanese. PubMed PMID: 5751298. 14: Kohen F, Stevenson R. Photodecarbonylation of Friedelin. Chem Ind. 1966 Oct 29;44:1844-5. PubMed PMID: 5977499. 15: Wei Q, Ji XY, Xu F, Li QR, Yin H. [Chemical Constituents from Leaves of Hibiscus syriacus and Their α-Glucosidase Inhibitory Activities]. Zhong Yao Cai. 2015 May;38(5):975-9. Chinese. PubMed PMID: 26767290. 16: Chen C, Wei G, Zhu H, Guo Y, Li XN, Zhang J, Liu Y, Yao G, Luo Z, Xue Y, Zhang Y. A new 3,4-seco-oleanane-type triterpenoid with an unusual enedione moiety from Hypericum ascyron. Fitoterapia. 2015 Jun;103:227-30. doi: 10.1016/j.fitote.2015.04.009. Epub 2015 Apr 12. PubMed PMID: 25870936. 17: Bin Ismail AA, Ee GC, Bin Daud S, Teh SS, Hashim NM, Awang K. Venuloxanthone, a new pyranoxanthone from the stem bark of Calophyllum venulosum. J Asian Nat Prod Res. 2015;17(11):1104-8. doi: 10.1080/10286020.2015.1047353. Epub 2015 May 29. PubMed PMID: 26023810. 18: Kikuchi T, Niwa M. [Studies on the neutral constituents of Pachysandra terminalis Sieb. et Zucc. VI. Isolation and structure determination of pachysantriol, a new Friedelin-type triterpene (author's transl)]. Yakugaku Zasshi. 1973 Oct;93(10):1378-82. Japanese. PubMed PMID: 4798515. 19: Farozi A, Banday JA, Shah SA. Genicunolide A, B and C: three new triterpenoids from Euphorbia geniculata. Beilstein J Org Chem. 2015 Dec 23;11:2707-12. doi: 10.3762/bjoc.11.291. eCollection 2015. PubMed PMID: 26877792; PubMed Central PMCID: PMC4734298. 20: Subash-Babu P, Li DK, Alshatwi AA. In vitro cytotoxic potential of friedelin in human MCF-7 breast cancer cell: Regulate early expression of Cdkn2a and pRb1, neutralize mdm2-p53 amalgamation and functional stabilization of p53. Exp Toxicol Pathol. 2017 Oct 2;69(8):630-636. doi: 10.1016/j.etp.2017.05.011. Epub 2017 Jun 12. PubMed PMID: 28619518.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Friedelin is a noncompetitive inhibitor of CYP3A4 with IC50 and Kivalues of 10.79 μM and 6.16 μM, respectively.

In vitro activity:

The results showed Friedelin inhibited the proliferation of the human AML-196 cells with little effects on the normal cells. Investigation of the underlying mechanisms showed that Friedelin induced apoptosis in AML-196 cells. Reference: J BUON. 2020 May-Jun;25(3):1594-1599. https://pubmed.ncbi.nlm.nih.gov/32862609/

In vivo activity:

Friedelin at the doses of 20 and 40 mg/kg was used to treated STZ-induced diabetic rats for 28 days. Later 28 days of treatment, the bodyweight changes, levels of blood glucose, insulin, SGOT, SGPT, SALP, liver glycogen and total protein were assessed. Friedelin significantly brought these altered levels to near normal. Moreover, friedelin also enhanced the translocation as well as activation of GLUT2 and GLUT4 through PI3K/p-Akt signaling cascade in skeletal muscles and liver on diabetic rats. Reference: J Ethnopharmacol. 2021 Mar 25;268:113659. https://pubmed.ncbi.nlm.nih.gov/33271243/

Preparing Stock Solutions

The following data is based on the product molecular weight 426.73 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

Formulation protocol:

1. Chang W, Wang J, Xiao Y. Friedelin inhibits the growth and metastasis of human leukemia cells via modulation of MEK/ERK and PI3K/AKT signalling pathways. J BUON. 2020 May-Jun;25(3):1594-1599. PMID: 32862609. 2. Wei J, Zhang H, Zhao Q. In vitro inhibitory effects of Friedelin on human liver cytochrome P450 enzymes. Pharm Biol. 2018 Dec;56(1):363-367. doi: 10.1080/13880209.2018.1491999. PMID: 30122094; PMCID: PMC6130513. 3. Sunil C, Irudayaraj SS, Duraipandiyan V, Alrashood ST, Alharbi SA, Ignacimuthu S. Friedelin exhibits antidiabetic effect in diabetic rats via modulation of glucose metabolism in liver and muscle. J Ethnopharmacol. 2021 Mar 25;268:113659. doi: 10.1016/j.jep.2020.113659. Epub 2020 Dec 1. PMID: 33271243. 4. Antonisamy P, Duraipandiyan V, Aravinthan A, Al-Dhabi NA, Ignacimuthu S, Choi KC, Kim JH. Protective effects of friedelin isolated from Azima tetracantha Lam. against ethanol-induced gastric ulcer in rats and possible underlying mechanisms. Eur J Pharmacol. 2015 Mar 5;750:167-75. doi: 10.1016/j.ejphar.2015.01.015. Epub 2015 Jan 22. PMID: 25617794.

In vitro protocol:

In vivo protocol:

1. Sunil C, Irudayaraj SS, Duraipandiyan V, Alrashood ST, Alharbi SA, Ignacimuthu S. Friedelin exhibits antidiabetic effect in diabetic rats via modulation of glucose metabolism in liver and muscle. J Ethnopharmacol. 2021 Mar 25;268:113659. doi: 10.1016/j.jep.2020.113659. Epub 2020 Dec 1. PMID: 33271243. 2. Antonisamy P, Duraipandiyan V, Aravinthan A, Al-Dhabi NA, Ignacimuthu S, Choi KC, Kim JH. Protective effects of friedelin isolated from Azima tetracantha Lam. against ethanol-induced gastric ulcer in rats and possible underlying mechanisms. Eur J Pharmacol. 2015 Mar 5;750:167-75. doi: 10.1016/j.ejphar.2015.01.015. Epub 2015 Jan 22. PMID: 25617794.