Sesquiterpene alcohols from Chamaecyparis obtusa leaf oil

Chamobtusin A, a Novel Skeleton Diterpenoid Alkaloid from Chamaecyparis obtusa cv. tetragon

“…Most species of this family are good wood, and 12 of them are used in folk medicines to treat a wide variety of ailments; in particular, the leaves and seeds of Platycladus orientalis are used in traditional Chinese medicine . Plants of Cupressaceae have a rich source of sesquiterpenes, diterpenes, flavones and lignans, − and some of them are considered to possess antitumor, antimalarial, and antibacterial activities. − Chamaecyparis obtusa cv . tetragon belongs to the genus Chamaecyparis and is distributed naturally in Japan…”

Hedycaryol – Central Intermediates in Sesquiterpene Biosynthesis, Part II

“…Elemol ( 2 ) was later reisolated from various plants including Juniperus sabina and J. scopulorum , [26,27] Chamaecyparis obtusa , [28] Citrus sinensis and C. nobilis , [29–31] Saussurea lappa , [32] Cinnamomum camphora , [33] Fokiena hodginsii , [34] Calycanthus floridus , [35] Bunium cylindricum , [36] Gingko biloba , [37] Amyris balsamifera , [38] Canarium zeylanicum , [39] Bothriocloa intermedia , [40] Commiphora abyssimica , [41] Santolina oblongifolia , [42] Cymbopogon proximus , [43] Eremophila flaccida , [44] Piper ribesioides , [45] Monocyclanthus vignei , [46] Neocallitropsis pancheri , [47] Cryptomeria japonica , [48] and Eucalyptus maculata , [49] which demonstrates the widespread occurrence of 1 in nature. After its first report from H. angustifolia , [23] compound 1 was subsequently also isolated from the undistilled oils of the plants Phebalium ozothamnoides , [50] Rubus rosifolius , [51] Thujopsis dolabrata , [52] Thymus praecox , [53] Cryptomeria japonica and C. fortunei , [54] and Chamaecyparis obtusa [55] . For the optical rotation of 2 low negative values between [α] D =−2 and −9.7 are given in the literature, [24,26,27,30,32,43,46,48] while for 1 positive values between [α] D =+24.5 and +32.7 were reported [23,50–52] .…”

“…After its first report from H. angustifolia, [23] compound 1 was subsequently also isolated from the undistilled oils of the plants Phebalium ozothamnoides, [50] Rubus rosifolius, [51] Thujopsis dolabrata, [52] Thymus praecox, [53] Cryptomeria japonica and C. fortunei, [54] and Chamaecyparis obtusa. [55] For the optical rotation of 2 low negative values between [α] D = À 2 and À 9.7 are given in the literature, [24,26,27,30,32,43,46,48] while for 1 positive values between [α] D = + 24.5 and + 32.7 were reported. [23,[50][51][52] The enantiomer (À )-1 is only known from the bacterial hedycaryol synthase (HcS) from Kitasatospora setae ([α] D 25 = À 21.3) whose Cope rearrangement gives (+)-2 ([α] D 25 = + 10.0).…”

Natural sesquiterpenoids

“…In this study, the absolute configurations of 95 and 96 were established by synthesis from ( )menthone. 117 The sesquiterpene (+)-10 -hydroxy-4-muurolen-3-one 98, a new inhibitor of leukotriene biosynthesis, has been obtained from fermentations of a Favolaschia species. 118 Other inhibitors of this type have been found in Leutinellus cochleatus.…”