Discovery of new natural products by intact-cell mass spectrometry and LC-SPE-NMR: malbranpyrroles, novel polyketides from thermophilic fungus Malbranchea sulfurea.
Six photosensitive polyketides, malbranpyrroles A-F, were discovered from the thermophilic fungus Malbranchea sulfurea by using intact-cell desorption/ionization on silicon mass (ICD-MS) and LC-SPE-NMR. These two strategies facilitate the searching and structural determination of unstable natural products. The ICD-MS indicated that only brown hyphae of M. sulfurea can produce malbranpyrroles. The biosynthetic pathway of malbranpyrroles was evidenced by 13C isotope precursors and amino acid feeding experiments. The cytotoxicity data revealed that the conformation of the conjugated system in malbranpyrroles does not affect cytotoxic potency against cancer cell lines. In addition, the chlorine atom was shown to be the pharmacophore for cytotoxicity.
Yang
Yu-Liang
YL
Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan.
Liao
Wen-Ying
WY
Liu
Wan-Yun
WY
Liaw
Chih-Chuang
CC
Shen
Chia-Ning
CN
Huang
Zih-You
ZY
Wu
Shih-Hsiung
SH
D001688:Biological Products / Q000737:chemistry* / Q000633:toxicity; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D005658:Fungi / Q000737:chemistry*; D006801:Humans; D018942:Macrolides / Q000737:chemistry* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D011758:Pyrroles / Q000737:chemistry* / Q000633:toxicity; D052616:Solid Phase Extraction
D001688:Biological Products; D018942:Macrolides; D011758:Pyrroles