New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of <i>Lactarius deliciosus</i>

doi:10.1007/s13659-017-0130-1

Natural Products and Bioprospecting

2017, Vol. 7

Issue (3) : 269-273 DOI: 10.1007/s13659-017-0130-1

New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus

Michel Feussi Tala¹, Jianchun Qin^1,2, Joseph T. Ndongo¹, Hartmut Laatsch¹

Institute of Organic and Biomolecular Chemistry, University of Goettingen, Tammannstrasse 2, 37077 Göttingen, Germany

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Abstract In the ¹H NMR-guided fractionation of extracts from the edible mushroom Lactarius deliciosus, two new azulene-type sesquiterpenoids, 7-isopropenyl-4-methyl-azulene-1-carboxylic acid (1) and 15-hydroxy-3,6-dihydrolactarazulene (2), together with seven known compounds were characterized. Their structures were determined on basis of spectroscopic evidence, as well as by comparing with literature data. Amongst the known metabolites, the ¹³C NMR assignment of 15-hydroxy-6,7-dihydrolactarazulene (3) is reported here for the first time. Moreover, 7-acetyl-4-methylazulene-1-carbaldehyde (5) displayed a moderate antibacterial activity against Staphylococcus aureus.

Keywords Lactarius deliciosus Fungal pigments Azulene sesquiterpenoids Antibacterial activity

Fund:We thank Dr.H.Frauendorf and Dr.M.John for MS and NMR measurements,respectively.JQ thanks the Natural Science Foundation for a Chinese Government Scholarship Fund for Study Abroad (31470414,20140101126JC).

Issue Date: 06 February 2018

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Michel Feussi Tala,Jianchun Qin,Joseph T. Ndongo, et al. New Azulene-Type Sesquiterpenoids from the Fruiting Bodies of Lactarius deliciosus[J]. Natural Products and Bioprospecting, 2017, 7(3): 269-273.

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http://npb.kib.ac.cn/EN/10.1007/s13659-017-0130-1 OR http://npb.kib.ac.cn/EN/Y2017/V7/I3/269

1. Y. Yang, N.M. Bao, H.J. Shao, Y.L. Wang, L. Zhu, Y.F. Duan, Nat. Prod. Res. Dev. 25, 274-279 (2013)
2. D. Dong, G. Li, Nat. Prod. Res. Dev. 4, 66-80 (1991)
3. O. Bergendorff, O. Sterner, Phytochemistry 27, 97-100 (1988)
4. P. Spiteller, Chem. Eur. J. 14, 9100-9110 (2008)
5. J. VelíSek, K. Cejpek, J. Food Sci. 29, 87-102 (2011)
6. D.J. Bertelli, J.H. Crabtree, Tetrahedron 24, 2019-2089 (1968)
7. A.D. Harmon, K.H. Weisgraber, U. Weiss, Experientia 36, 54-56 (1979)
8. L.Z. Fang, H.J. Shao, W.Q. Yang, J.K. Liu, Helv. Chim. Acta 89, 1463-1466 (2006)
9. L.Z. Fang, Z.J. Dong, H.J. Shao, J.K. Liu, Acta Bot. Yunn. 29, 122-124 (2007)
10. G.H. Xu, J.W. Kim, I.J. Ryoo, S.J. Choo, Y.H. Kim, S.J. Seok, J.S. Ahn, I.D. Yoo, J. Antibiot. 63, 335-337 (2010)
11. G. Vidari, P. Vita-Finzi, Studies in natural products chemistry, in Stucture and Chemistry (Part D), vol. 17, ed. by Atta-ur-Rahman (Elsevier, Amsterdam, 1995), p. 153
12. K. Vokač, Z. Samek, V. Herout, F. Sorm, Collect. Czech. Chem. Commun. 35, 1296-1301 (1970)
13. X.L. Yang, D.Q. Luo, J.K. Liu, Z. Naturforsch. 61b, 1180-1182 (2006)
14. X.L. Yang, D.Q. Luo, Z.J. Dong, J.K. Liu, Helv. Chem. Acta 89, 988-990 (2006)
15. H.S. Lee, J. Microbiol. Biotechnol. 13, 529-536 (2003)
16. I. Sajid, C.B. Fotso Fondja Yao, K.A. Shaaban, S. Hasnain, H. Laatsch, World J. Microbiol. Biotechnol. 25, 601-610 (2009)

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