Apiin

Structural formula
General
Surname	Apiin
other names	Apigenin-7- (2- O -apiosylglucoside); Apiosid; Apigenin-7-apioglucoside; 7 - [(2 S , 3 R , 4 S , 5 S , 6 R ) -3 - [(2 S , 3 R , 4 R ) -3,4-dihydroxy-4- (hydroxymethyl) oxolan-2-yl ] oxy-4,5-dihydroxy-6- (hydroxymethyl) oxan-2-yl] oxy-5-hydroxy-2- (4-hydroxyphenyl) chromen-4-one;
Molecular formula	C 26 H 28 O 14
Brief description	difficult to ignite, white, odorless
External identifiers / databases
EC number	247-780-0
ECHA InfoCard	100.043.421
PubChem	5280746
ChemSpider	4444321
Wikidata	Q2858300
properties
Molar mass	564.49 g mol −1
Physical state	firmly
solubility	132 g l −1 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Apiin is a chemical compound from the group of flavones - glycosides .

properties

Apiin is a flammable, hardly ignitable substance. At room temperature, its crystals are white and odorless. Apiin decomposes when heated above 262–264 ° C. The aglycon of the apiins is apigenin . At the end there is an apiose . Apiin is anti-inflammatory by inhibiting iNOS .

Occurrence

Curly parsley

Sedum caeruleum

Apiin is found in parsley , celery ( Apium graveolens ), nettles and Sedum caerulaeum .

use

Apiin is used as a reducing agent and stabilizer in the manufacture of spherical colloids from gold or silver .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet Apiin, ≥97.0% (HPLC) from Sigma-Aldrich , accessed on August 4, 2016 ( PDF ).
↑ T. Mencherini, A. Cau, G. Bianco, R. Della Loggia, RP Aquino, G. Autore: An extract of Apium graveolens var. Dulce leaves: structure of the major constituent, apiin, and its anti-inflammatory properties. In: The Journal of pharmacy and pharmacology. Volume 59, Number 6, June 2007, pp. 891-897, doi: 10.1211 / jpp.59.6.0016 , PMID 17637182 .
↑ H. Meyer, A. Bolarinwa, G. Wolfram, J. Linseisen: Bioavailability of apigenin from apiin Rich Parsley in Humans . In: Ann Nutr Metab . 50, No. 3, 2006, pp. 167-172. doi : 10.1159 / 000090736 . PMID 16407641 .
↑ MH Farzaei, Z. Abbasabadi, MR Ardekani, R. Rahimi, F. Farzaei: Parsley: a review of Ethnopharmacology, phytochemistry and biological activities. In: Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan / sponsored by All-China Association of Traditional Chinese Medicine, Academy of Traditional Chinese Medicine. Volume 33, Number 6, December 2013, pp. 815-826, doi: 10.1016 / S0254-6272 (14) 60018-2 , PMID 24660617 .
↑ Quantitative determination of plant phenolics in Urtica dioica extracts by high-performance liquid chromatography coupled with tandem mass spectrometric detection . In: Food Chemistry . tape 143 , January 15, 2014, p. 48-53 , doi : 10.1016 / j.foodchem.2013.07.097 .
^ SR Gupta, TR Seshadri: A study of apiin from the parsley seeds and plant . In: Proceedings of the Indian Academy of Sciences - Section A . tape 35 , no. 5 , May 1952, p. 242-248 , doi : 10.1007 / BF03172503 .
↑ C. Bensouici, A. Kabouche, A. Karioti, M. Öztürk, ME Duru, AR Bilia, Z. Kabouche: Compounds from Sedum caeruleum with antioxidant, anticholinesterase, and antibacterial activities. In: Pharmaceutical biology. Volume 54, number 1, 2016, pp. 174-179, doi: 10.3109 / 13880209.2015.1028078 , PMID 25845643 .
↑ J. Kasthuri, S. Veerapandian, N. Rajendiran: Biological synthesis of silver and gold nanoparticles using apiin as reducing agent. In: Colloids and surfaces. B, biointerfaces. Volume 68, Number 1, January 2009, pp. 55-60, doi: 10.1016 / j.colsurfb.2008.09.021 , PMID 18977643 .

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f data sheet Apiin, ≥97.0% (HPLC) from Sigma-Aldrich , accessed on August 4, 2016 ( PDF ).

[2] T. Mencherini, A. Cau, G. Bianco, R. Della Loggia, RP Aquino, G. Autore: An extract of Apium graveolens var. Dulce leaves: structure of the major constituent, apiin, and its anti-inflammatory properties. In: The Journal of pharmacy and pharmacology. Volume 59, Number 6, June 2007, pp. 891-897, doi: 10.1211 / jpp.59.6.0016 , PMID 17637182 .

[3] H. Meyer, A. Bolarinwa, G. Wolfram, J. Linseisen: Bioavailability of apigenin from apiin Rich Parsley in Humans . In: Ann Nutr Metab . 50, No. 3, 2006, pp. 167-172. doi : 10.1159 / 000090736 . PMID 16407641 .

[4] MH Farzaei, Z. Abbasabadi, MR Ardekani, R. Rahimi, F. Farzaei: Parsley: a review of Ethnopharmacology, phytochemistry and biological activities. In: Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan / sponsored by All-China Association of Traditional Chinese Medicine, Academy of Traditional Chinese Medicine. Volume 33, Number 6, December 2013, pp. 815-826, doi: 10.1016 / S0254-6272 (14) 60018-2 , PMID 24660617 .

[5] Quantitative determination of plant phenolics in Urtica dioica extracts by high-performance liquid chromatography coupled with tandem mass spectrometric detection . In: Food Chemistry . tape 143 , January 15, 2014, p. 48-53 , doi : 10.1016 / j.foodchem.2013.07.097 .

[6] SR Gupta, TR Seshadri: A study of apiin from the parsley seeds and plant . In: Proceedings of the Indian Academy of Sciences - Section A . tape 35 , no. 5 , May 1952, p. 242-248 , doi : 10.1007 / BF03172503 .

[7] C. Bensouici, A. Kabouche, A. Karioti, M. Öztürk, ME Duru, AR Bilia, Z. Kabouche: Compounds from Sedum caeruleum with antioxidant, anticholinesterase, and antibacterial activities. In: Pharmaceutical biology. Volume 54, number 1, 2016, pp. 174-179, doi: 10.3109 / 13880209.2015.1028078 , PMID 25845643 .

[8] J. Kasthuri, S. Veerapandian, N. Rajendiran: Biological synthesis of silver and gold nanoparticles using apiin as reducing agent. In: Colloids and surfaces. B, biointerfaces. Volume 68, Number 1, January 2009, pp. 55-60, doi: 10.1016 / j.colsurfb.2008.09.021 , PMID 18977643 .