Cadinane sesquiterpenoids

Silva GH et al., Cadinane sesquiterpenoids of Phomopsis cassiae, an endophytic fungus associated with Cassia spectabilis (Leguminosae), Phytochemistry 67 1964-1969, 2006. 

New cadinane sesquiterpenoids include (—)-cadala-l,4,9-triene (163) Acorns calamus) dihydroisochromolaenin (164), 1,6-dihydrochromolaenin (165),... 

The structures of notonipetrone (185) ° and the two abrotanifolone derivatives (186) and (187) have been deduced on the basis of n.m.r. spectral evidence. A different type of ring-contracted cadinane sesquiterpenoid is seen in the structure of mutisianthol (188). Another synthesis of oplopanone (189) has been reported (Scheme 31). ... 

The ring-contracted cadinane sesquiterpenoid, oplopanone (111) has now been synthesized in racemic form using a key photochemical step to construct the requisite perhydroindane skeleton. The synthetic sequence is outlined in Scheme 10. 

New cadinane sesquiterpenoids include isokhusinoloxide (192) and raimondal (193). A number of timbers undergo a colour change on exposure to daylight. 

Figure 12.3 GC/MS (a) and THM GC/MS (b) curves of aged dammar. Peak assignments 2, a cubebene 3, copaene 4, ft bourbonene 8,10 12, cadinane type pyrolysis fragments 14 16, cadinene type pyrolysis fragments 17, calamanene type pyrolysis fragments 18 21, unidentified sesquiterpenoids 22, dammaradienone 23, dammaradienol 24, nor a amyrone 25, 28 nor olean 17 en 3 one 26, dammarenolic acid methyl ester 27, oleanonic acid 28, hydroxydammarenone 29, oleanonic aldehyde 30, ursonic acid methyl ester 31, ursonic aldehyde 32, nor (3 amyrone 34, 20,24 epoxy 25 hydroxy 3,4 seco 4(28) dammaren 3 oic acid methyl ester 35, 20,24 epoxy 25 hydroxy dammaren 3 one 36, dammaradienol...

An investigation of the constituents of Mexican species of the genus Eupatorium has resulted in the isolation of sesquiterpenoids belonging to the eudesmane (294a and b), eudesmanolide (295a and b), cadinane (296), and guanolide (297) groups. 

Several new sesquiterpenoids having normal (168) and rearranged (169—172) cadinane structures have been isolated from the aerial parts of the plant Heterotheca... 

Cadinane, Amorphane, Muurolane, Bulgarane, and related Tricyclic Sesquiterpenoids... 

Apart from the n-alkanes discussed above, epicuticular wax hydrocarbons contain sesqui- and diterpenoids. These compounds are based on the structural skeletons of cadinane and abietane, respectively, which are shown in Fig. 7-24. The sesquiterpenoids recovered by Simoneit and Mazurek (1982) in the rural aerosol were calamenene, tetrahydrocadalane, and cadalene. These compounds presumably are degradation products of cadinane derivatives (various isomers of cadinenes and cadinols), which are ubiquitous in essential oils of many higher plants (Simonsen and Barton, 1961). The major diterpenoid hydrocarbons observed in the aerosol samples were dehy-droabietane, dehydroabietin, and retene. The main source of abietane derivatives are coniferous resins. The parent compounds dehydrate fairly rapidly to yield the more stable hydrocarbons found in the aerosols. These may then serve as markers for hydrocarbons arising from vegetation, in addition to the odd-to-even carbon number preference in the n-alkanes. 

Figure 6. Cadinane-type Sesquiterpenoid Stress Metabolites from Elm.

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