Ardeemins and cytochalasins from Aspergillus terreus residing in Artemisia annua.
Three new alkaloids, 15b-dehydro-5- N-acetylardeemin ( 3), 10-phenyl-[12]-cytochalasins Z16 ( 6) and Z17 ( 7), were characterized from the liquid culture of the endophytic fungus ASPERGILLUS TERREUS IFB-E030 along with six known derivatives, 5- N-acetylardeemin ( 1), 15b- β-hydroxyl-5- N-acetylardeemin ( 2), cytochalasin E ( 4), rosellichalasin ( 5), cytochalasins Z11 ( 8), and Z13 ( 9). The structures of the new metabolites were established mainly by a combination of their 1D- and 2D-NMR spectra, single crystal X-ray diffraction, and the modified Mosher reaction. Biological assays indicated that cytochalasin Z17 ( 7) had moderate cytotoxicity against human nasopharyngeal epidermoid tumor KB cell line with an IC (50) value of 26.2 µM.
Zhang
Hua-Wei
HW
School of Medicine, Nanjing University, Nanjing, China.
Zhang
Jie
J
Hu
Sha
S
Zhang
Zun-Jian
ZJ
Zhu
Cheng-Jian
CJ
Ng
Seik Weng
SW
Tan
Ren-Xiang
RX
D031172:Artemisia annua / Q000382:microbiology*; D001230:Aspergillus / Q000737:chemistry*; D005591:Chemical Fractionation; D003572:Cytochalasins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007624:KB Cells; D019906:Nuclear Magnetic Resonance, Biomolecular; D011744:Pyrimidinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014961:X-Ray Diffraction
C555982:10-phenyl-(12)-cytochalasins Z16; C555983:10-phenyl-(12)-cytochalasins Z17; C555981:15b-dehydro-5- N-acetylardeemin; D003572:Cytochalasins; D003603:Cytotoxins; D026121:Indole Alkaloids; D011744:Pyrimidinones; C534892:ardeemin