[Isolation and preparation of sesquiterpenols from the Japanese cedar, Cryptomeria japonica D. Don, by preparative reversed-phase high performance liquid chromatography and its characterization].

A method for the isolation of sesquiterpenols from the Japanese Cedar, Cryptomeria japonica D. Don by preparative reversed-phase high performance liquid chromatography (RP-HPLC) was established. The preparation of the sesquiterpenols was carried out on a preparative liquid chromatograph with a YWC-Pack C18 column, and the mobile phase was isopropanol-methanol-hexane-water (50:35:10:5, v/v) at a flow rate of 5.0 mL/min. The two sesquiterpenols, (-)-cubebol and (+)-2,7(14),10-bisabolatrien-1-ol-4-one, were separated by liquid chromatography and identified by spectroscopic analyses (ultraviolet (UV), infrared (IR), nuclear magnetic resonance (NMR), electrospray ionization mass spectrometry (ESI-MS)). The purities of the two sesquiterpenols were 98.7% and 99.1%, respectively.

Determination of the absolute configuration of (+)-2,7(14),10-bisabolatrien-1-ol-4-one from Japanese cedar, Cryptomeria japonica.

The absolute configuration of (+)-2,7(14),10-bisabolatrien-1-ol-4-one, a peculiar sesquiterpenol in the Japanese cedar, Cryptomeria japonica, was determined as (1S,6R)-2,7(14),10-bisabolatrien-1-ol-4-one by comparing the specific rotation values of cryptomeriones respectively converted from (+)-2,7(14),10-bisabolatrien-1-ol-4-one and synthesized from (R)-(-)-carvone.

Repellents in the Japanese cedar, Cryptomeria japonica, against the pill-bug, Armadillidium vulgare.

Sandaracopimarinol and (1S,6R)-2,7(14),10-bisabolatrien-1-ol-4-one were isolated and identified from Cryptomeria japonica as repellents against Armadillidium vulgare which is well known as an unpleasant pest in the house and as vegetable pest in Japan. These compounds strongly repelled A. vulgare when they were combined, although each compound alone did not show any activity.