Biotransfomation of cyperenoic acid by Cunninghamella elegans AS 3.2028 and the potent anti-angiogenic activities of its metabolites.

Cyperenoic acid (1) is one of the major sesquiterpenes isolated from Croton crassifolius, which exhibited potent anti-angiogenic activity. Traditional structural modification of 1 is difficult to perform by chemical technology due to the remarkable stability of the patchoulane skeleton. In order to overcome chemical synthesis difficulties and obtain structurally diverse derivations, microbial transformation of 1 by using Cunninghamella elegans AS 3.2028 was studied for the first time. Five new hydroxylated products 2-6 were obtained. Furthermore, cytotoxicity and anti-angiogenic activities of all the biotransformation products were evaluated by MTT assay and ELISA in HepG2 and MCF-7 cells. These results indicated that hydroxylated modification products 2-4 significantly inhibited VEGF release, which suggest the potential use of hydroxylated modification products for cancer therapy.

Two new compounds from Atractylodes macrocephala with neuroprotective activity.

In the present study, two new compounds, together with six known compounds, were isolated from rhizome of Atractylodes macrocephala Koidz by a series of silica gel, ODS column chromatography, and preparative HPLC. Their structures were characterized as atractylenolide II (1), atractylenolide I (2), biepiasterolid (3), isoatractylenolide I (4), atractylenolide III (5), 3ß-acetoxyl atractylenolide I (6), (4E,6E,12E)-tetradeca-4,6,12-triene-8,10-diyne-13,14-triol (7), (3S,4E,6E,12E)-1-acetoxy-tetradeca-4,6,12-triene-8,10-diyne-3,14-diol (8) on the basis of 1D, 2D NMR, and circular dichroism analyses. Among them, compounds 6 and 8 were novel compounds. In addition, their neuroprotective activity against MPP+-induced SH-SY5Y cells was evaluated by MTT colorimetry. The results showed that all these compounds have definite protective effect on MPP+-induced SH-SY5Y cells.

N-[(R)-(6-Bromo-2-meth-oxy-quinolin-3-yl)(phen-yl)meth-yl]-N-[(S)-1-(4-meth-oxy-phen-yl)eth-yl]-2-(piperazin-1-yl)acetamide.

In the title compound, C(32)H(35)BrN(4)O(3), the piperazine ring exists in a chair conformation. The quinoline ring system is oriented at dihedral angles of 82.70 (17) and 19.54 (17)° to the phenyl and meth-oxy-phenyl rings, respectively. Weak inter-molecular C-H⋯π inter-actions are present in the crystal structure.

21-(3-Carboxy-propano-yl)-11ß,17-dihydroxy-pregn-4-ene-3,20-dione monohydrate.

In the title compound, C(25)H(34)O(8)·H(2)O, the two crylohexane rings adopt chair conformations. In the crystal, the organic mol-ecule and the water mol-ecule are linked by O-H⋯O hydrogen bonds, generating a three-dimensional network.

N-[(6-Bromo-2-meth-oxy-3-quinol-yl)phenyl-meth-yl]-2-morpholino-N-(1-phenyl-ethyl)acetamide.

In the title compound, C(31)H(32)BrN(3)O(3), the morpholine ring adopts a chair conformation, and the planar quinoline system is twisted with respect to the phenyl rings, with dihedral angles of 17.6 (4) and 75.1 (3)°. Intramolecular C-H⋯O and C-H⋯N hydrogen bonds are present. The crystal packing is stabilized by weak C-H⋯O hydrogen bonding and C-H⋯π interactions.