Three Novel, Structurally Unique Spirocyclic Alkaloids from the Halotolerant B-17 Fungal Strain of Aspergillus variecolor

During our search for novel antitumor lead compounds from microorganisms living under extreme conditions, three novel alkaloids, variecolortides A–C (1–3), were isolated from the mycelia of the halotolerant fungal strain Aspergillus variecolor B‐17. The new compounds were found to share an unprecede...

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Bibliographic Details
Published in:Chemistry & biodiversity 2007-12, Vol.4 (12), p.2913-2919
Main Authors: Wang, Wen-Liang, Zhu, Tian-Jiao, Tao, Hong-Wen, Lu, Zhen-Yu, Fang, Yu-Chun, Gu, Qian-Qun, Zhu, Wei-Ming
Format: Article
Language:English
Subjects:
Alkaloids
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - toxicity
Antioxidant activity
Aspergillus - chemistry
Aspergillus - classification
Aspergillus variecolor
Cell Line, Tumor
Cell Survival - drug effects
Drug Resistance - drug effects
Halotolerant fungi
Humans
Macrocyclic Compounds - chemistry
Macrocyclic Compounds - toxicity
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Neoplasms - pathology
Salts - pharmacology
Spiro Compounds - chemistry
Spiro Compounds - toxicity
Spiro-anthronopyranoid diketopiperazine
Variecolortides A - C
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Summary:During our search for novel antitumor lead compounds from microorganisms living under extreme conditions, three novel alkaloids, variecolortides A–C (1–3), were isolated from the mycelia of the halotolerant fungal strain Aspergillus variecolor B‐17. The new compounds were found to share an unprecedented ‘spiro‐anthronopyranoid diketopiperazine’ structure, with a stable hemiaminal function, as corroborated by in‐depth NMR‐spectroscopic and mass‐spectrometric analyses, as well as by a single‐crystal X‐ray analysis of 1. All compounds were shown to exhibit weak cytotoxic and antioxidant activities.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.200790240