Presence of Cyclopropane Fatty Acids (CPFA) in Human Plasma

NCT03612700 | Completed

• 1 other identifier: DDR-CPFA
• Study Type: interventional
• Target: 10
• Locations: 1 country
• Sites: 1

Brief Summary

Fatty acids containing a cyclopropane ring in their structure (CPFA) have been found in plants, fungi, a wide variety of bacteria and recently detected in dairy products and bovine meat. Little is known about CPFA in mammals, especially in human tissues. This work aims at investigating the presence of CPFA in plasma of humans after a regular consumption of CPFA from milk and cheese. A free living diet controlled in CPFA, mainly deriving from Grana Padano cheese and whole milk containing CPFA, will be consumed by 10 healthy normal weight volunteers for three weeks, after one week of dairy products and bovine meat restricted diet. Plasma of volunteers will be collected at 8 different timepoints for lipid extraction, CPFA identification and quantification by GC-MS. A preliminary pilot in vivo acute study (involving only 1 subject) will be performed for investigating the post-prandial response curve of CPFA after a portion of Grana Padano cheese.

Conditions

Biological Availability

Keywords

Cyclopropane fatty acids; GC-MS

Outcome Measures

Primary Outcomes (1)

• CPFA plasmatic concentration

  Fasting concentration of CPFA

  Fasting CPFA plasma concentration [time -7 days, time 0 (after 1 week of CPFA restricted diet), time 3, 6, 9, 12, 15, 18 days]

Study Arms (1)

CPFA-rich diet

EXPERIMENTAL

Free living diet controlled in CPFA intake

Other: CPFA-rich foods

Interventions

CPFA-rich foods OTHER

Daily consumption of Grana Padano cheese (50 g) and whole milk (250 mL) for 3 weeks.

CPFA-rich diet

Eligibility Criteria

• Age: 18 Years+
• Sex: all
• Healthy Volunteers: Yes
• Age Groups: Adult (18-64), Older Adult (65+)

You may qualify if:

• \- BMI 19-29 (kg/m2)

You may not qualify if:

• pregnancy and lactation
• gastrointestinal disorders
• metabolic diseases
• drugs and food supplements interfering with lipid metabolism

Sponsors & Collaborators

• University of Parma: lead

Study Sites (1)

Department of Food and Drugs, University of Parma

Parma, 43125, Italy

Location

Related Publications (17)

• Moore BS, Floss HG. Biosynthesis of Cyclic Fatty Acids Containing Cyclopropyl-, Cyclopentyl-, Cyclohexyl-, and Cycloheptyl-rings. Reference Module in Chemistry, Molecular Sciences, and Chemical Engineering, from Comprehensive Natural Products Chemistry 1:61-82, 1999

  BACKGROUND

• Montanari C, Sado Kamdem SL, Serrazanetti DI, Etoa FX, Guerzoni ME. Synthesis of cyclopropane fatty acids in Lactobacillus helveticus and Lactobacillus sanfranciscensis and their cellular fatty acids changes following short term acid and cold stresses. Food Microbiol. 2010 Jun;27(4):493-502. doi: 10.1016/j.fm.2009.12.003. Epub 2010 Jan 6.

  PMID: 20417398 BACKGROUND

• Poger D, Mark AE. A ring to rule them all: the effect of cyclopropane Fatty acids on the fluidity of lipid bilayers. J Phys Chem B. 2015 Apr 30;119(17):5487-95. doi: 10.1021/acs.jpcb.5b00958. Epub 2015 Apr 16.

  PMID: 25804677 BACKGROUND

• Marseglia A, Caligiani A, Comino L, Righi F, Quarantelli A, Palla G. Cyclopropyl and omega-cyclohexyl fatty acids as quality markers of cow milk and cheese. Food Chem. 2013 Oct 15;140(4):711-6. doi: 10.1016/j.foodchem.2013.01.029. Epub 2013 Jan 23.

  PMID: 23692757 BACKGROUND

• Caligiani A, Marseglia A, Palla G. An overview on the presence of cyclopropane fatty acids in milk and dairy products. J Agric Food Chem. 2014 Aug 6;62(31):7828-32. doi: 10.1021/jf4057204. Epub 2014 Jul 24.

  PMID: 25033416 BACKGROUND

• Sledzinski T, Mika A, Stepnowski P, Proczko-Markuszewska M, Kaska L, Stefaniak T, Swierczynski J. Identification of cyclopropaneoctanoic acid 2-hexyl in human adipose tissue and serum. Lipids. 2013 Aug;48(8):839-48. doi: 10.1007/s11745-013-3806-2. Epub 2013 Jun 11.

  PMID: 23754307 BACKGROUND

• Bichi E, Toral PG, Hervas G, Frutos P, Gomez-Cortes P, Juarez M, de la Fuente MA. Inhibition of ∆9-desaturase activity with sterculic acid: effect on the endogenous synthesis of cis-9 18:1 and cis-9, trans-11 18:2 in dairy sheep. J Dairy Sci. 2012 Sep;95(9):5242-5252. doi: 10.3168/jds.2012-5349.

  PMID: 22916929 BACKGROUND

• Jones SE, Whitehead K, Saulnier D, Thomas CM, Versalovic J, Britton RA. Cyclopropane fatty acid synthase mutants of probiotic human-derived Lactobacillus reuteri are defective in TNF inhibition. Gut Microbes. 2011 Mar-Apr;2(2):69-79. doi: 10.4161/gmic.2.2.15282. Epub 2011 Mar 1.

  PMID: 21637024 BACKGROUND

• Kadegowda AK, Burns TA, Pratt SL, Duckett SK. Inhibition of stearoyl-CoA desaturase 1 reduces lipogenesis in primary bovine adipocytes. Lipids. 2013 Oct;48(10):967-76. doi: 10.1007/s11745-013-3823-1. Epub 2013 Aug 9.

  PMID: 23929455 BACKGROUND

• Mika A, Stepnowski P, Chmielewski M, Malgorzewicz S, Kaska L, Proczko M, Ratnicki-Sklucki K, Sledzinski M, Sledzinski T. Increased Serum Level of Cyclopropaneoctanoic Acid 2-Hexyl in Patients with Hypertriglyceridemia-Related Disorders. Lipids. 2016 Jul;51(7):867-73. doi: 10.1007/s11745-016-4141-1. Epub 2016 Mar 22.

  PMID: 27003900 BACKGROUND

• Schneider AC, Beguin P, Bourez S, Perfield JW 2nd, Mignolet E, Debier C, Schneider YJ, Larondelle Y. Conversion of t11t13 CLA into c9t11 CLA in Caco-2 cells and inhibition by sterculic oil. PLoS One. 2012;7(3):e32824. doi: 10.1371/journal.pone.0032824. Epub 2012 Mar 12.

  PMID: 22427892 BACKGROUND

• Grogan DW, Cronan JE Jr. Cyclopropane ring formation in membrane lipids of bacteria. Microbiol Mol Biol Rev. 1997 Dec;61(4):429-41. doi: 10.1128/mmbr.61.4.429-441.1997.

  PMID: 9409147 BACKGROUND

• WOOD R, REISER R. CYCLOPROPANE FATTY ACID METABOLISM: PHYSICAL AND CHEMICAL IDENTIFICATION OF PROPANE RING METABOLIC PRODUCTS IN THE ADIPOSE TISSUE. J Am Oil Chem Soc. 1965 Apr;42:315-20. doi: 10.1007/BF02540137. No abstract available.

  PMID: 14279117 BACKGROUND

• Wessjohann LA, Brandt W, Thiemann T. Biosynthesis and metabolism of cyclopropane rings in natural compounds. Chem Rev. 2003 Apr;103(4):1625-48. doi: 10.1021/cr0100188. No abstract available.

  PMID: 12683792 BACKGROUND

• Kim BH, Kim S, Kim HG, Lee J, Lee IS, Park YK. The formation of cyclopropane fatty acids in Salmonella enterica serovar Typhimurium. Microbiology (Reading). 2005 Jan;151(Pt 1):209-218. doi: 10.1099/mic.0.27265-0.

  PMID: 15632439 BACKGROUND

• Lolli V, Marseglia A, Palla G, Zanardi E, Caligiani A. Determination of Cyclopropane Fatty Acids in Food of Animal Origin by 1H NMR. J Anal Methods Chem. 2018 Apr 1;2018:8034042. doi: 10.1155/2018/8034042. eCollection 2018.

  PMID: 29805838 BACKGROUND

• Bao X, Katz S, Pollard M, Ohlrogge J. Carbocyclic fatty acids in plants: biochemical and molecular genetic characterization of cyclopropane fatty acid synthesis of Sterculiafoetida. Proc Natl Acad Sci U S A. 2002 May 14;99(10):7172-7. doi: 10.1073/pnas.092152999. Epub 2002 May 7.

  PMID: 11997456 RESULT

Study Officials

• Daniele Del Rio, Professor

  Department of Food and Drugs

  PRINCIPAL INVESTIGATOR

• Augusta Caligiani, Professor

  Department of Food and Drugs

  PRINCIPAL INVESTIGATOR

Study Design

• Study Type: interventional
• Phase: not applicable
• Allocation: NA
• Masking: NONE
• Purpose: BASIC SCIENCE
• Intervention Model: SINGLE GROUP
• Sponsor Type: OTHER
• Responsible Party: PRINCIPAL INVESTIGATOR
• PI Title: Professor

Study Record Dates

• First Submitted: July 27, 2018
• First Posted: August 2, 2018
• Study Start: August 6, 2018
• Primary Completion: September 28, 2018
• Study Completion: September 28, 2018
• Last Updated: October 17, 2018

Record last verified: 2018-10

Data Sharing

• IPD Sharing: Will not share

Locations

IT (1)