Monoterpene, Sesquiterpene und dimere Phellandrene aus Manila-Elemi*

Abstract

From Manila-Elemi, the oleoresin of Canarium luzonicum (Miq) Asa Gray (Burseraceae) we have additionally isolated: six monoterpene and eleven sesquiterpene hydrocarbons, one mono- and two sesquiterpene alcohols, six dimers of alpha-phellandrene, carvacrol.

A chemical investigation by headspace SPME and GC–MS of volatile and semi-volatile terpenes in various olibanum samples

“…Conversely, dimer 2 (111) occurring in B. carteri, B. sacra and B. serrata olibanum, is lacking in B. frereana olibanum. The hypothetical structures of these dimers of a-phellandrene can be related to the photosensitized dimerization of a-phellandrene (Baldwin and Nelson, 1966) and were also evidenced in an oleoresin of Canarium luzonicum, a tree that also belongs to the Burseraceae family (Brieskorn and Krauss, 1986).…”

Focusing on Volatile Organic Compounds of Natural Resins by Selected-Ion Flow Tube-Mass Spectrometry

“…The mass spectrum with [H 3 O] + for elemi resin (Figure c) shows the characteristic peaks of monoterpenes with a molecular weight of 136, 150, and 152 Da (protonated molecular ion at m / z 137, 151, and 153) and of sesquiterpenes with a molecular weight of 204 and 208 Da (in the mass spectrum they occur as protonated molecular ion at m / z 205 and 209). Literature data , and results obtained by HS-GC/MS confirm that the main components are indeed monoterpenes with a molecular weight of 136 Da (limonene, pinene, thujene, sabinene, and phellandrene) and sesquiterpenes (elemicin with molecular weight of 208 Da). The high intensity of the peak at m / z 117 cannot be ascribed only to the secondary fragmentation of terpenes, but also to adduct ions of acetone.…”

“…Moreover, thanks to the interpretation of HS-GC/MS chromatograms, we assigned the peak at m / z 155 to a reaction product between water and analyte [C 10 H 18 O] + and not to the protonated form of a monoterpenoid with a molecular weight of 154 Da (as a minor compound , ). Comparing HS-GC/MS results with SIFT-MS data, we can attribute the peak at m / z 209 (in the [H 3 O] + SIFT mass spectrum) to the protonated molecular ion of elemicin, a phenylpropanoid compound specific for elemi resin. , This terpenoid is also identified in the [NO] + spectrum reagent ion as a [M] + cation at m / z 208.…”

Hedycaryol – Central Intermediates in Sesquiterpene Biosynthesis, Part II

“…Guaiol was first described from guaiacwood by Gandurin ([α] D 25 =−26.64) as a bicyclic tertiary alcohol with one double bond [203] . The compound is widespread and has also been isolated from Callitris intratropica , [204] Eucalyptus maculata , [205] Drimys lanceolata , [206] Cinnamomum camphora , [207] Callitris columellaris , [208] Guillonea scabra , [209] Thapsia villosa , [210] Canarium luzonicum (Manila elemi), [211] Murraya gleinei , [212] Neocallitropsis pancheri , [213] Eriostemon fitzgeraldii , [214] Ferula ferulioides [215] and Uvaria puguensis , [216] and is a product of the above mentioned terpene synthase TlTPS509 from Thapsia laciniata [200] . After establishment of its constitution, [217] the absolute configuration was clarified by chemical correlation [196,198,218,219] …”