Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5216062 | Tetrahedron | 2014 | 6 Pages |
Neomacrophorins I (1), II (2), and III (3) were isolated from the culture broth of Trichoderma sp. 1212-03, which was collected at Shirakami Mountainous area in Japan. Structural analyses disclosed that these resemble known macrophorins but possess axial-hydroxy group at C3 as well as different side chains at C7â². These are diastereomeric forms of macrophorins for 5â²,6â²-epoxide functionality. The NMR analyses suggested their relative configurational relationship between the C1-C15 drimene and C1â²-C7â² epoxyquinone moieties. ECD spectral discussions verified them particularly for C5â²,C6â²-epoxyquinone (1), C5â²,C6â²-epoxysemiquinone (2 and 3), and 2â³,3â³-dihydroxybutanoate moiety in 1 and 2. The configuration of C3â³-stereocenter of 3 was determined by chiral GC-MS after converting into methyl (S)-3â³-hydroxybutanoate by basic of 3 methanolysis. Biological assays disclosed that 1 induces hyphal branching of Cochliobolus miyabeanus as well as cytotoxicity against human colorectal cancer COLO 201.
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