Agarwood oil (Aquilaria agallocha Roxb.). Its composition and eight new valencane‐, eremophilane‐ and vetispirane‐ derivatives

Abstract

The profile of the total extract of agarwood oil (Aquilaria agallocha Roxb.) is discussed and eight new sesquiter‐penoids are presented: two with the eremophilane‐skeleton (rel‐(2R,8S,8aR)‐2‐(1,2,3,5,6,7,8,8a‐octahydro‐8,8a‐dimethy1‐2‐naphthyl)‐prop‐2‐en‐1‐ol (1, eremophila‐9,11(13)‐dien‐12‐ol) and rel‐(3R,7R,9R,10S)‐9,10‐dimethyl‐6‐methylene‐4‐oxatricyclo[7.4.0.03,7]tridec‐1‐ene (2, 8,12‐epoxy‐eremophila‐9,11(13)‐diene)), one with the valencane‐skeleton (rel‐(2R,8S,8aR)‐2‐(1,2,6,7,8,8a‐hexahyro‐8,8a‐dimethyl‐2‐naphthyl)‐propan‐2‐ol (3, valenca‐1(10),8‐dien‐11‐ol)) and four with the vetispirane‐skeleton (rel‐(5R,10R)‐(2‐isopropylidene‐10‐methyl‐spiro[4,5]dec‐6‐ene‐6‐carbaldehyde (4, vetispira‐2(11),6‐dien‐14‐al), rel‐(5R,7R,10R)‐2‐isopropylidene‐10‐methyl‐6‐rnethylene‐spiro[4.5]decan‐7‐01 (5, vetispira‐2(11),6(14)‐dien‐7‐01), rel‐(1R,2R)‐9‐isopropyl‐2‐rnethyl‐8‐oxatricyclo[7.2.1.01,6]dodec‐5‐ene (6, 2,14‐epoxy‐vetispir‐6‐ene) and rel‐(1R,2R)‐(9‐isopropyl‐2‐methyl‐8‐oxatricyclo[7.2.1.01,6]dodeca‐4,6‐diene (7, 2,14‐epoxy‐vetispira‐6(14),7‐diene)). 2‐(1,2,3,5,6,7,8,8a‐octahydro‐8,8a‐dimethyl‐2‐naphthyl)‐propanal (8, valenc‐ or eremophil‐9‐en‐12‐al) is tentatively identified. Copyright © 1995 John Wiley & Sons, Ltd