Spathulenol

Structural formula
	(+) - Spathulenol
General
Surname	Spathulenol
other names	Espatulenol; (1a R , 4a R , 7 S , 7a R , 7b R ) -1,1,7-trimethyl-4-methylidene-1a, 2,3,4a, 5,6,7a, 7b-octahydrocyclopropa [ h ] azulene -7-ol ( IUPAC );
Molecular formula	C 15 H 24 O
Brief description	colorless, viscous compound with an earthy-aromatic smell and bitter-spicy taste
External identifiers / databases
PubChem	92231
Wikidata	Q1376658
properties
Molar mass	220.35 g mol −1
Physical state	liquid
boiling point	269-270 ° C
solubility	easily soluble in ethanol ; soluble in water vapor;
Refractive index	1.5088
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Spathulenol is a Guajan - derivative , which is found in various plants. The substance is a tricyclic sesquiterpene alcohol , which has a basic structure similar to that of azulene .

History and occurrence

An essential oil was obtained from mugwort ( Artemisia vulgaris ) and tarragon ( Artemisia dracunculus ) by steam distillation, from which the sesquiterpene alcohol Spathulenol was isolated for the first time in 1975 as a colorless, viscous compound with an earthy-aromatic smell and bitter-spicy taste.

Chamomile flower heads ( Matricaria chamomilla )

It is also found in other plants such as real chamomile and other species of the Artemisia genus (e.g. Salvia mirzayanii ) as well as in cotton species ( Gossypium ). In the St. John's wort family Hypericum perforatum and Hypericum scabrum contents between 6 and 7.2% were found in the essential oil of the plants. In various Nepeta species such as N. phyllochlamys , N. viscida , N. sorgerae and N. trachonitica , up to 22% of the essential oil is spathulenol.

presentation

The synthesis of spathulenol is possible through a modification of the Büchi synthesis of aroma dendrons from (-) - β-pinene .

properties

Spathulenol is a colorless, viscous compound that dissolves well in ethanol and water vapor. The substance has an earthy-aromatic smell and a bitter-spicy taste. During dehydration , the β- spathulence occurs .

Biological effect and use

The biologically active substance Spathulenol has an immunosuppressive effect. Tests have shown dose-dependent death ( apoptosis ) of lymphocytes . Due to the inhibition of the MDR protein 1 (also PGP pump ) in vitro , Spathulenol has the potential to support chemotherapy in cancer .

For leaf-cutting ants of the species Atta cephalotes a was repellent effect of spathulenol detected. The cotton boll beetle ( Anthonomus grandis ) and the parasitic wasp Campoletis sonorensis, on the other hand, are attracted to a mixture of different sesquiterpenes , which also contains spathulenol , in cotton species .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h S. Monrad-Krohn Juell, Rudolf Hansen and Hellmut Jork: New substances from essential oils of different Artemisia species, 1. Mitt. Spathulenol, an azulenogenic sesquiterpene alcohol. Archives of Pharmacy , Vol. 309, Iss. 6, pp. 458-466, June 6, 1975.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Ziaei, A. et al. (2011): Identification of spathulenol in Salvia mirzayanii and the immunomodulatory effects. In: Phytother Res . 25 (4); 557-562. doi : 10.1002 / ptr.3289 ; PMID 20857430 .
^ ^A ^b G. W. Elzen, HJ Williams, SB Vinson: Isolation and Identification of Cotton Synmones Mediating Searching Behavior by Parasitoid. Journal of Chemical Ecology, Vol. 10, No. 8, 1984, pp. 1251-1264.
↑ KHC Baser, T. Ozek, HR Nuriddinov, AB Demirci: Essential Oils of two Hypericum Species from Uzbekistan. Chemistry of Natural Compounds, Vol. 38, No. 1, 2002, pp. 54-57.
↑ KHC Baser, N. Kirimer, M. Kurkcuoglu, B. Demirci: Essential Oils of Nepeta Species Growing in Turkey. Chemistry of Natural Compounds, Vol. 36, No. 4, 2000, pp. 356-359.
↑ JR Hanson, JS Roberts: Terpenoids and Steroids , 1983, 12, pp. 75-185: Sesquiterpenoids. P. 183. doi : 10.1039 / 9781847557117-00075 .
↑ A. Martins, Z. Hajdú, A. Vasas, B. Csupor-Löffler, J. Molnár, J. Hohmann: Spathulenol inhibit the human ABCB1 efflux pump. In: Planta Med . 2010; 76, doi : 10.1055 / s-0030-1264906 .
↑ Jeffrey B. Harborne: Chemical Signals in the Ecosystem. Annals of Botany 60, 1987. Supplement 4, pp. 39-57.

[jork-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h S. Monrad-Krohn Juell, Rudolf Hansen and Hellmut Jork: New substances from essential oils of different Artemisia species, 1. Mitt. Spathulenol, an azulenogenic sesquiterpene alcohol. Archives of Pharmacy , Vol. 309, Iss. 6, pp. 458-466, June 6, 1975.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] Ziaei, A. et al. (2011): Identification of spathulenol in Salvia mirzayanii and the immunomodulatory effects. In: Phytother Res . 25 (4); 557-562. doi : 10.1002 / ptr.3289 ; PMID 20857430 .

[elzen-4] A ^b G. W. Elzen, HJ Williams, SB Vinson: Isolation and Identification of Cotton Synmones Mediating Searching Behavior by Parasitoid. Journal of Chemical Ecology, Vol. 10, No. 8, 1984, pp. 1251-1264.

[5] KHC Baser, T. Ozek, HR Nuriddinov, AB Demirci: Essential Oils of two Hypericum Species from Uzbekistan. Chemistry of Natural Compounds, Vol. 38, No. 1, 2002, pp. 54-57.

[6] KHC Baser, N. Kirimer, M. Kurkcuoglu, B. Demirci: Essential Oils of Nepeta Species Growing in Turkey. Chemistry of Natural Compounds, Vol. 36, No. 4, 2000, pp. 356-359.

[7] JR Hanson, JS Roberts: Terpenoids and Steroids , 1983, 12, pp. 75-185: Sesquiterpenoids. P. 183. doi : 10.1039 / 9781847557117-00075 .

[8] A. Martins, Z. Hajdú, A. Vasas, B. Csupor-Löffler, J. Molnár, J. Hohmann: Spathulenol inhibit the human ABCB1 efflux pump. In: Planta Med . 2010; 76, doi : 10.1055 / s-0030-1264906 .

[9] Jeffrey B. Harborne: Chemical Signals in the Ecosystem. Annals of Botany 60, 1987. Supplement 4, pp. 39-57.