Microbial oxidation of tricyclic sesquiterpenoids containing a dimethylcyclopropane ring

Sedative effects of vapor inhalation of agarwood oil and spikenard extract and identification of their active components

“…Separation and isolation were carried out using various column chromatographies on the extract to isolate calarene (452 mg). NMR spectra and the chemical shifts of the isolated compound agreed with the literature data [13].…”

Biotransformation of three aromadendrane‐type sesquiterpenoids by Aspergillus wentii

“…The biotransformation of aromadendranes by Bacillus megaterium, 13 Mycobacterium smegmatis, 13 and Mucor plumbeus, 14 has been reported previously. The biotransformation of 1 and 2 by the plant pathogenic fungus Glomerella cingulata yielded (−)-10α,13,14-trihydroxyaromadendrane and (−)-10β,13,14-trihydroxyalloaromadendrane, respectively, has also been reported.…”

“…The 1 H-chemical shifts of cyclopropane hydrogens (H-6 and H-7) were similar to those of aromadendrene (H-6; 0.60 ppm, H-7; 0.67 ppm) and not so close to that of alloaromadendrene (H-6; 0.24 ppm, H-7; 0.55 ppm). 13 Spin decoupling supported the presence of an aromadendrene skeleton with a 1α-hydroxy group. Thus, compound 5 was identified as (+)-(1S,11S)-1,13-dihydroxyaromadendrene (5) + m/z 236.1780).…”

Erratum: Microbial transformation of isopinocampheol and caryophyllene oxide

“…On the other hand, (+)-b-pinene (22) is metabolized to (-)-trans-pinocarveol (23), (-)-pinocarvone (24), (+)-3-pinanone (25, isopinocamphone), 2 and 8 by A. niger TBUYN-2 [9,10] Compound 2 is metabolized to 6, 7 and 8 by A. niger TBUYN-2. Compound 25 is easily metabolized to give (-)-2-hydroxy-3-pinanone (26) and (-)-2, 5-dihydroxy-3-pinanone (27) as the main products.…”

“…In the biotransformation of (-)-cyclocolorenone and (+)-cyclocolorenone, [9] calarene, [10] (-)-globulol, [10][11][12]14] (-)-epiglobulol, [10,11,14] (+)-ledol, [12] (+)-aromadendrene [13,15] and (-)-allo-aromadendrene, [13] which have the cyclopropane ring with geminal methyl groups, were mainly hydroxylated at geminal methyl groups of the cyclopropane ring to give the corresponding compounds. Compound 3 was also stereo-and regioselectively hydroxylated at the geminal methyl groups (C-12) to give 10.…”