Cadinanes

Benzenoid (-)-(75, 105)-calamenene is isolated from Ulmus thomasii (Uhnaceae), and (-l-)-3,8-calamenenediol from Heterotheca subaxillaris. The naphthalene sesquiterpene cadalene oeeurs in eonifers, for example in flie resin of fir Abies sibirica (Pinaceae). The wood of several trees contains 3-cadalenol. Cadalen-2,3-qutnone, also known as mansonone C, is a constituent of Mansonia altissima and Ulmus lactinata (Table 3). [Pg.34]

Hibiscones and various reddish-brown hibiscoquinones from Hibiscus elatus (Malvaceae) represent furanoid derivatives of eadinane. [Pg.34]

B.G.K. Van Aarssen, H.C. Cox, P. Hoogendoorn, and J.W. De Leeuw, A Cadinene Biopolymer Present in Fossil and Extant Dammar Resins as a Source for Cadinanes and Bicadinanes in Crude Oils from South East Asia, Geochim. Cosmochim. Acta, 54, 3021 3031 (1990). [Pg.162]

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...

On the other hand, thermolysis of (400) at 250 °C in xylene afforded the cadinane dienol (407) in 40% yield, via also the olefin metathesis-transannular ene sequence... [Pg.142]

As indicated in Figure 3, the cadlnanes (170 - 187) are formed from the humulane (205) system, which also is the progenitor of the caryophyllanes (206 - 208). Of these last three compounds, caryophyllene (206) itself is of particular Importance, since it can account for 20 - 25% of the essential oil of some samples (lA). Other major constituents in the same sample were copaene (173, another cadinane) and a-humulene (205), each near 15%. It is therefore apparent that the pathway involving initial conversion of Z,E-farnesyl pyrophosphate to the humulane system is dominant in Gossypiwn terpenoid biogenesis. [Pg.292]

Silva GH et al., Cadinane sesquiterpenoids of Phomopsis cassiae, an endophytic fungus associated with Cassia spectabilis (Leguminosae), Phytochemistry 67 1964-1969, 2006. [Pg.574]

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. [Pg.101]

Sesquit. cadinanes gossypol (Gossypium spp., Malvales, and other widely cultivated Ang. MI). [Pg.23]

As mentioned, qinghaosu chemically belongs to the cadinane sesquiterpene therefore, the other sesquiterpene components in A. annua have been given preferential attention. From indigenous A. annua L., continuous phytochemical studies by Chinese researches in the early 1980s led to the excavation of another ten sesquiterpenes including deoxy-artemisinin (14), artemisinin D (15), artemisinin... [Pg.188]

Misra, L. N. Ahmad, A. Thakur, R. S. Jakupovic, J. Bisnor-cadinanes fmmArtemisia annua and definitive C-13 NMR assignments of beta-arteether. Phytochemistry, 1993, 33(6) 1461-1464. [Pg.242]

Brown, G. D. Cadinanes from Artemisia annua that may be intermediates in the biosynthesis of artemisinin. Phytochemistry, 1994, 36(3) 637-641. [Pg.242]

Sy, L. K. Cheung, K. K. Zhu, N. Y Brown, G. D. Stmcture elucidation of Arteannuin-O, a novel cadinane diol from Artemisia annua and the s3mthesis of Arteannuin-K, Arteannuin-L, Arteannuin-M and Arteannuin-O. Tetrahedron, 2001, 57(40) 8481-8493. [Pg.242]

Cadinane, Muurolane, Copaane, Cyclosesquifenchane, Sativane, Copacamphane, Picrotoxane... [Pg.28]

New cadinane sesquiterpenoids include (—)-cadala-l,4,9-triene (163) Acorns calamus) dihydroisochromolaenin (164), 1,6-dihydrochromolaenin (165),... [Pg.28]

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). ... [Pg.30]

Another important class of diagnostic plant terpenoids is the cadinane group derived from cadinene-based polymers of resinous tropical... [Pg.3952]

Several new sesquiterpenoids having normal (168) and rearranged (169—172) cadinane structures have been isolated from the aerial parts of the plant Heterotheca... [Pg.72]

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