1. //
  2. Start
  3. //
  4. Publications
  5. Calopins and cyclocalopins
  6. Output formats
  7. //

Calopins and cyclocalopins: bitter principles from Boletus calopus and related mushrooms

Research output: Journal contributions › Journal articles › Research

Standard

Calopins and cyclocalopins: bitter principles from Boletus calopus and related mushrooms. / Hellwig, Veronika; Dasenbrock, Johannes; Gräf, Claudia et al.
In: European Journal of Organic Chemistry, Vol. 2002, No. 17, 09.2002, p. 2895-2904.

Research output: Journal contributions › Journal articles › Research

Harvard

Hellwig, V, Dasenbrock, J, Gräf, C, Kahner, L, Schumann, S & Steglich, W 2002, 'Calopins and cyclocalopins: bitter principles from Boletus calopus and related mushrooms', European Journal of Organic Chemistry, vol. 2002, no. 17, pp. 2895-2904. https://doi.org/10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S

APA

Hellwig, V., Dasenbrock, J., Gräf, C., Kahner, L., Schumann, S., & Steglich, W. (2002). Calopins and cyclocalopins: bitter principles from Boletus calopus and related mushrooms. European Journal of Organic Chemistry, 2002(17), 2895-2904. https://doi.org/10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S

Vancouver

Hellwig V, Dasenbrock J, Gräf C, Kahner L, Schumann S, Steglich W. Calopins and cyclocalopins: bitter principles from Boletus calopus and related mushrooms. European Journal of Organic Chemistry. 2002 Sept;2002(17):2895-2904. doi: 10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S

Bibtex

@article{9507c427b1e14635b2236853765b8e02,
title = "Calopins and cyclocalopins: bitter principles from Boletus calopus and related mushrooms",
abstract = "Boletus calopus and closely related mushrooms of the Boletus section Calopodes are characterized by their bitter taste, which is caused mainly by O-acetylcyclocalopin A (6a), a member of a series of unique δ-lactone derivatives. Besides the simple lactone calopin (1b) and its O-acetyl derivative la, the more complex cyclocalopins 6-12 have been isolated and their structures elucidated. Cyclocalopin D (10a) is an unprecedented α-glucoside in which the sugar residue is bound to an enolic hydroxy group., The chemical conversion of 6b into la established the same stereochemistry for the calopin and cyclocalopin types of metabolites.",
keywords = "Chemistry, calopins, lactones, mushrooms, natural products, spiro compounds",
author = "Veronika Hellwig and Johannes Dasenbrock and Claudia Gr{\"a}f and Lydia Kahner and Susanne Schumann and Wolfgang Steglich",
year = "2002",
month = sep,
doi = "10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S",
language = "English",
volume = "2002",
pages = "2895--2904",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "17",

}

RIS

TY - JOUR

T1 - Calopins and cyclocalopins

T2 - bitter principles from Boletus calopus and related mushrooms

AU - Hellwig, Veronika

AU - Dasenbrock, Johannes

AU - Gräf, Claudia

AU - Kahner, Lydia

AU - Schumann, Susanne

AU - Steglich, Wolfgang

PY - 2002/9

Y1 - 2002/9

N2 - Boletus calopus and closely related mushrooms of the Boletus section Calopodes are characterized by their bitter taste, which is caused mainly by O-acetylcyclocalopin A (6a), a member of a series of unique δ-lactone derivatives. Besides the simple lactone calopin (1b) and its O-acetyl derivative la, the more complex cyclocalopins 6-12 have been isolated and their structures elucidated. Cyclocalopin D (10a) is an unprecedented α-glucoside in which the sugar residue is bound to an enolic hydroxy group., The chemical conversion of 6b into la established the same stereochemistry for the calopin and cyclocalopin types of metabolites.

AB - Boletus calopus and closely related mushrooms of the Boletus section Calopodes are characterized by their bitter taste, which is caused mainly by O-acetylcyclocalopin A (6a), a member of a series of unique δ-lactone derivatives. Besides the simple lactone calopin (1b) and its O-acetyl derivative la, the more complex cyclocalopins 6-12 have been isolated and their structures elucidated. Cyclocalopin D (10a) is an unprecedented α-glucoside in which the sugar residue is bound to an enolic hydroxy group., The chemical conversion of 6b into la established the same stereochemistry for the calopin and cyclocalopin types of metabolites.

KW - Chemistry

KW - calopins

KW - lactones

KW - mushrooms

KW - natural products

KW - spiro compounds

UR - http://www.scopus.com/inward/record.url?scp=0036712011&partnerID=8YFLogxK

U2 - 10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S

DO - 10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S

M3 - Journal articles

VL - 2002

SP - 2895

EP - 2904

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 17

ER -

Related by journal

Simplification in Synthesis.

Bertz, S. H., Rücker, C., Rücker, G. & Sommer, T. J., 01.12.2003, In: European Journal of Organic Chemistry. 16, 24, p. 4737-4740 4 p.

Research output: Journal contributions › Comments / Debate / Reports › Research

Retipolides - unusual spiromacrolactones from the mushrooms Retiboletus retipes and R. ornatipes

Justus, K., Herrmann, R., Klamann, J-D., Gruber, G., Hellwig, V., Ingerl, A., Polborn, K., Steffan, B. & Steglich, W., 01.11.2007, In: European Journal of Organic Chemistry. 2007, 33, p. 5560-5572 13 p.

Research output: Journal contributions › Journal articles › Research

Other publications by the same author(s)

Accelerated dereplication of natural products, supported by reference libraries

Bitzer, J., Köpcke, B., Stadler, M., Hellwig, V., Ju, Y-M., Seip, S. & Henkel, T., 27.06.2007, In: Chimia. 61, 6, p. 332-338 7 p.

Research output: Journal contributions › Journal articles › Research

Activities of prenylphenol derivatives from fruitbodies of Albatrellus spp. on the human and rat vanilloid receptor 1 (VR 1) and characterisation of the novel natural product, confluentin

Hellwig, V., Nopper, R., Mauler, F., Freitag, J., Ji-Kai, L., Zhi-Hui, D. & Stadler, M., 01.04.2003, In: Archiv der Pharmazie. 336, 2, p. 119-126 8 p.

Research output: Journal contributions › Journal articles › Research

Altersetin, a new antibiotic from cultures of endophytic Alternaria spp. taxonomy, fermentation, isolation, structure elucidation and biological activities: taxonomy, fermentation, isolation, structure elucidation and biological activites

Hellwig, V., Grothe, T., Mayer-Bartschmid, A., Endermann, R., Geschke, F-U., Henkel, T. & Stadler, M., 01.10.2002, In: Journal of Antibiotics. 55, 10, p. 881-892 12 p.

Research output: Journal contributions › Journal articles › Research

Analysis of polychlorinated biphenyl (PCB)-induced modification of protein expression in primary hepatocytes from harbour seals

Behr, A., Wargel, A., Siebert, U. & Hellwig, V., 2008, In: Organohalogen Compounds. 70, p. 1079-1082 4 p.

Research output: Journal contributions › Conference article in journal › Research

Chemotaxonomy of Pochonia and other conidial fungi with Verticillium-like anamorphs

Stadler, M., Tichy, H-V., Katsiou, E. & Hellwig, V., 01.05.2003, In: Mycological Progress. 2, 2, p. 95-122 28 p.

Research output: Journal contributions › Journal articles › Research › peer-review

DOI