Angucycline

1,2,3,4-Tetrahydrobenzo [ a ] anthracene-7,12-dione: basic structure of the aglycone of the angucyclines

Angucyclines are a group of substances isolated from Streptomyces species with antibiotic and anti- neoplastic effects.

Chemically, they are glycosides , the aglycon of which has a cyclohexane - fused anthraquinone skeleton, the 1,2,3,4-tetrahydrobenzo [ a ] anthracene-7,12-dione . In addition to other substituents , the angucyclines have several hydroxyl groups . The glycosidic bond with the carbohydrate is in many cases on the A-ring of the aglycone.

They are related to the anthracyclines ; they differ from them in the cyclohexane ring fused to the anthracene at an angle (lat .: angulus ) .

properties

Angucyclines are mainly formed by actinomycetes . Over 100 metabolites of the angucycline have been described. They have a weak antibiotic effect against Gram-positive bacteria. The angucyclines include z. B. the aquayamycin and the dynemicin A as well as the landomycins , moromycins , saquayamycins , urdamycins and vineomycins . The aglycones of the angucyclines are called angucylinones .

use

Angucyclines are being studied for use as cytostatics against various types of cancer ( chemotherapy ).

literature

J. Rohr and R. Thiericke: Angucycline group antibiotics , Natural Product Reports , 1992, 9 (2), pp. 103-137 ( doi: 10.1039 / NP9920900103 ).
MK Kharel, P. Pahari, MD Shepherd, N. Tibrewal, SE Nybo, KA Shaaban, J. Rohr: Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis , Natural Product Reports , 2012, 29 (2 ), Pp. 264-325 ( doi: 10.1039 / c1np00068c , PMID 22186970 ).

Individual evidence

^ RS Coleman, ML Madaras: Carboaromatic compounds . In: Karl J. Hale (Ed.): The Chemical Synthesis of Natural Products . Blackwell Publishing Ltd., Oxford 2000, ISBN 1-84127-039-3 , pp. 171 ( limited preview in Google Book search).
↑ entry to angucyclins. In: Römpp Online . Georg Thieme Verlag, accessed on April 26, 2019.
↑ ^a ^b ^c ^d ^e Burkhard Fugmann: RÖMPP Encyclopedia Natural Products, 1st Edition, 2000. Georg Thieme Verlag, 2014, ISBN 978-3-131-79311-9 , p. 35.
^ Severian Dumitriu: Polysaccharides in Medicinal Applications. CRC Press, 1996, ISBN 978-0-824-79540-5 , p. 353.
↑ KA Shaaban, S. Srinivasan, R. Kumar, C. Damodaran, J. Rohr: Landomycins PW, cytotoxic angucyclines from Streptomyces cyanogenus S-136. In: Journal of Natural Products . Volume 74, number 1, 2011, pp. 2–11, doi : 10.1021 / np100469y , PMID 21188999 , PMC 3070852 (free full text).
↑ KA Shaaban, C. Stamatkin, C. Damodaran, J. Rohr: 11-Deoxylandomycinone and landomycins XZ, new cytotoxic angucyclin (on) es from a Streptomyces cyanogenus K62 mutant strain. In: The Journal of Antibiotics . Volume 64, number 1, 2011, pp. 141–150, doi : 10.1038 / ja.2010.121 , PMID 20978514 , PMC 3030652 (free full text).
↑ OV Tymchyk, BP Matseliukh, VI Lavrinchuk: Sensitivity of Streptomyces globisporus 3-1-a highly active producer of landomycin E to its own and the other polyketide antibiotics. In: Mikrobiolohichnyi zhurnal . Volume 66, Number 2, 2004, pp. 69-73, PMID 15208856 .
↑ Georg Thieme Verlag: RÖMPP Lexikon Chemie, 10th edition, 1996-1999. Georg Thieme Verlag, 2014, ISBN 978-3-132-00071-1 . Keyword urdamycine .

Web links

Commons : Angucycline - collection of images, videos and audio files

Total synthesis of the angucycline antibiotics , Department of Chemistry, Otago University, PO Box 56, Dunedin 9054, Union Place West, Dunedin 9016, New Zealand.

[1] RS Coleman, ML Madaras: Carboaromatic compounds . In: Karl J. Hale (Ed.): The Chemical Synthesis of Natural Products . Blackwell Publishing Ltd., Oxford 2000, ISBN 1-84127-039-3 , pp. 171 ( limited preview in Google Book search).

[2] try to angucyclins. In: Römpp Online . Georg Thieme Verlag, accessed on April 26, 2019.

[Fugmann-3] Burkhard Fugmann: RÖMPP Encyclopedia Natural Products, 1st Edition, 2000. Georg Thieme Verlag, 2014, ISBN 978-3-131-79311-9 , p. 35.

[Dumitriu-4] Severian Dumitriu: Polysaccharides in Medicinal Applications. CRC Press, 1996, ISBN 978-0-824-79540-5 , p. 353.

[5] KA Shaaban, S. Srinivasan, R. Kumar, C. Damodaran, J. Rohr: Landomycins PW, cytotoxic angucyclines from Streptomyces cyanogenus S-136. In: Journal of Natural Products . Volume 74, number 1, 2011, pp. 2–11, doi : 10.1021 / np100469y , PMID 21188999 , PMC 3070852 (free full text).

[6] KA Shaaban, C. Stamatkin, C. Damodaran, J. Rohr: 11-Deoxylandomycinone and landomycins XZ, new cytotoxic angucyclin (on) es from a Streptomyces cyanogenus K62 mutant strain. In: The Journal of Antibiotics . Volume 64, number 1, 2011, pp. 141–150, doi : 10.1038 / ja.2010.121 , PMID 20978514 , PMC 3030652 (free full text).

[7] OV Tymchyk, BP Matseliukh, VI Lavrinchuk: Sensitivity of Streptomyces globisporus 3-1-a highly active producer of landomycin E to its own and the other polyketide antibiotics. In: Mikrobiolohichnyi zhurnal . Volume 66, Number 2, 2004, pp. 69-73, PMID 15208856 .

[Römpp-8] Georg Thieme Verlag: RÖMPP Lexikon Chemie, 10th edition, 1996-1999. Georg Thieme Verlag, 2014, ISBN 978-3-132-00071-1 . Keyword urdamycine .