Secondary metabolites of the lichen-associated fungus Apiospora montagnei

Hao Wang; Blessing O. Umeokoli; Peter Eze; Christian Heering; Christoph Janiak; Werner E. G. Mueller; Raha S. Orfali; Rudolf Hartmann; Haofu Dai; Wenhan Lin; Zhen Liu; Peter Proksch

doi:10.1016/J.TETLET.2017.03.052

Secondary metabolites of the lichen-associated fungus Apiospora montagnei

Hao Wang, Blessing O. Umeokoli, Peter Eze, Christian Heering, Christoph Janiak, Werner E. G. Mueller, Raha S. Orfali, Rudolf Hartmann, Haofu Dai, Wenhan Lin, Zhen Liu^*, Peter Proksch^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

Abstract

The endolichenic fungus Apiospora montagnei isolated from the lichen Cladonia sp. was cultured on solid rice medium, yielding the new diterpenoid libertellenone L (1), the new pyridine alkaloid, 23-O-acetyl-N-hydroxyapiosporamide (2) and the new xanthone derivative 8-hydroxy-3-hydroxymethyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ether (3) together with 19 known compounds (4–22). The structures of the new compounds were elucidated by 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of the new 6,7-seco-libertellenone derivative 1 was determined by single-crystal X-ray diffraction. Four additional known compounds 23–26 were isolated when NaCl or NH4Cl were added to solid rice medium. Compounds 7–9, 18 and 26 exhibited significant cytotoxicity against the L5178 murine lymphoma cell line with IC50 values of 2.6, 0.2, 2.1, 2.7 and 1.7 μM, respectively.

Original language	English
Pages (from-to)	1702-1705
Journal	Tetrahedron Letters
Volume	58
Issue number	17
Early online date	01 Apr 2017
DOIs	https://doi.org/10.1016/J.TETLET.2017.03.052
Publication status	Published - 26 Apr 2017
Externally published	Yes

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@article{cf7e35bbf2ba4804af1e4b3975ded616,

title = "Secondary metabolites of the lichen-associated fungus Apiospora montagnei",

abstract = "The endolichenic fungus Apiospora montagnei isolated from the lichen Cladonia sp. was cultured on solid rice medium, yielding the new diterpenoid libertellenone L (1), the new pyridine alkaloid, 23-O-acetyl-N-hydroxyapiosporamide (2) and the new xanthone derivative 8-hydroxy-3-hydroxymethyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ether (3) together with 19 known compounds (4–22). The structures of the new compounds were elucidated by 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of the new 6,7-seco-libertellenone derivative 1 was determined by single-crystal X-ray diffraction. Four additional known compounds 23–26 were isolated when NaCl or NH4Cl were added to solid rice medium. Compounds 7–9, 18 and 26 exhibited significant cytotoxicity against the L5178 murine lymphoma cell line with IC50 values of 2.6, 0.2, 2.1, 2.7 and 1.7 μM, respectively.",

author = "Hao Wang and Umeokoli, {Blessing O.} and Peter Eze and Christian Heering and Christoph Janiak and Mueller, {Werner E. G.} and Orfali, {Raha S.} and Rudolf Hartmann and Haofu Dai and Wenhan Lin and Zhen Liu and Peter Proksch",

year = "2017",

month = apr,

day = "26",

doi = "10.1016/J.TETLET.2017.03.052",

language = "English",

volume = "58",

pages = "1702--1705",

journal = "Tetrahedron Letters",

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T1 - Secondary metabolites of the lichen-associated fungus Apiospora montagnei

AU - Wang, Hao

AU - Umeokoli, Blessing O.

AU - Eze, Peter

AU - Heering, Christian

AU - Janiak, Christoph

AU - Mueller, Werner E. G.

AU - Orfali, Raha S.

AU - Hartmann, Rudolf

AU - Dai, Haofu

AU - Lin, Wenhan

AU - Liu, Zhen

AU - Proksch, Peter

PY - 2017/4/26

Y1 - 2017/4/26

N2 - The endolichenic fungus Apiospora montagnei isolated from the lichen Cladonia sp. was cultured on solid rice medium, yielding the new diterpenoid libertellenone L (1), the new pyridine alkaloid, 23-O-acetyl-N-hydroxyapiosporamide (2) and the new xanthone derivative 8-hydroxy-3-hydroxymethyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ether (3) together with 19 known compounds (4–22). The structures of the new compounds were elucidated by 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of the new 6,7-seco-libertellenone derivative 1 was determined by single-crystal X-ray diffraction. Four additional known compounds 23–26 were isolated when NaCl or NH4Cl were added to solid rice medium. Compounds 7–9, 18 and 26 exhibited significant cytotoxicity against the L5178 murine lymphoma cell line with IC50 values of 2.6, 0.2, 2.1, 2.7 and 1.7 μM, respectively.

AB - The endolichenic fungus Apiospora montagnei isolated from the lichen Cladonia sp. was cultured on solid rice medium, yielding the new diterpenoid libertellenone L (1), the new pyridine alkaloid, 23-O-acetyl-N-hydroxyapiosporamide (2) and the new xanthone derivative 8-hydroxy-3-hydroxymethyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ether (3) together with 19 known compounds (4–22). The structures of the new compounds were elucidated by 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of the new 6,7-seco-libertellenone derivative 1 was determined by single-crystal X-ray diffraction. Four additional known compounds 23–26 were isolated when NaCl or NH4Cl were added to solid rice medium. Compounds 7–9, 18 and 26 exhibited significant cytotoxicity against the L5178 murine lymphoma cell line with IC50 values of 2.6, 0.2, 2.1, 2.7 and 1.7 μM, respectively.

U2 - 10.1016/J.TETLET.2017.03.052

DO - 10.1016/J.TETLET.2017.03.052

M3 - Article

SN - 0040-4039

VL - 58

SP - 1702

EP - 1705

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Secondary metabolites of the lichen-associated fungus Apiospora montagnei

Abstract

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