Abietane diterpene

Milanova R, M Moore, Y Hirai (1994) Hydroxylation of synthetic abietane diterpenes by Aspergillus and Cunninghamella species novel route to the family of diterpenes isolated from Tripterygium wilfordii. J Nat Prod 5T 882-889. 

Topcu, G. Ulubelen, A. Abietane and rearranged abietane diterpenes from Salvia montbretii. J. Nat. Prod. 1996, 59, 734—737. 

Cerqueira, F. Corderio-Da-Silva, A. Gaspar-Marques, C. Simoes, F. Pinto, M. M. M. Nascimento, M. S. J. Effect of abietane diterpenes from Plectranthus grandidentatus on T- and B-lymphocyte proliferation. Bioorg. Med. Chem. 2004, 12, 217-223. 

Yang, Z. Kitano, Y. Chiha, K. Shibata, N. Kurokawa, H. Doi, Y. Arakawa, Y. Tada, M. Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRS A and VRE. Bioorg. Med. Chem. 2001, 9, 347-356. 

In a series of publications over the past few years, the group of Barriault has reported on microwave-assisted tandem oxy-Cope/Claisen/ene and closely related reactions [175-178], These pericyclic transformations typically proceed in a highly stereoselective fashion and can be exploited for the synthesis of complex natural products possessing decalin skeletons, such as the abietane diterpene wiedamannic... 

These processes are normally enzyme-catalyzed. Purefy ctemical processes are seldom encountered with carbon conq)ounds in nature. The few exceptions include the very act of phenol coupling (by which racemic compounds are obtained), cyclization reactions ofpolyprenyl compoimds (which benefit from the preferred conformation of the reaction partners, suitable for the cyclization, Wendt 2000), and Diels-Alder cycloadditions. The latter have been advocated for the biosynthesis of celastroidine A (= volubilide) from a lupane triterpene and an abietane diterpene in two different plants, Hippocratea celastroides Kunth from Mexico (Jimenez-Estrada 2000) and Hippocratea volubilis Linnaeus (Alvarenga 2000). 

The abietane diterpene carnosic acid (89), a derivative of ferruginol, is found in the popular Labiatae herb, sage and rosemary and is considered a precursor of other diterpenoid constituents in the herb [20,21]. Wenkert et al [22] have established the structure of carnosic acid (89). Carnosic acid (89) and related diterpenes such as camasol (90) and rosemanol (91) Fig. (11) possess powerful antioxidant activities [23] but carnosic acid (89) is the most powerful potency among these diterpenes. Carnosic acid (89)... 

Fig (11) Camosic acid (89) is an abietane diterpene and has been isolated from the leaves of sage as pale-yellow powder, m.p. 194.5 - 195°C (crystallized from acetic acid). Its oxidation products have been identified as (92), an orange powder, m.p. 129°C and (93), a yellow powder, m.p. 172 - 173°C. 

Camosol (abietane diterpene) Rosmarinus officinalis. Salvia officinalis (Lamiaceae) HIV-1 protease (> 30 pM) [54]... 

Abietane diterpenes (C61C61C6 with varying degrees of unsaturation) include the 5-LOX inhibitor abietane, the GABA(A) receptor antagonist taxodione and the bitter tastant carnosol. 

Hydroxyierruginol (abietane diterpene) Salacia obbnga (Celastraceae) [root] AR (rat lens) (> 100)... 

Top9u, G., Eris, C., Ulubelen, A. 1996. Rearranged abietane diterpenes from salvia limbata. Phytochemistry 41 1143-1147. 

In the following section, bioactivities of abietane diterpenes and related activities of rosemary and sage are discussed. 

Luis, J.G., Grillo, T.A. 1993. Abietane diterpenes from Salvia munzii. Phytochemistry. 34 863-864. 

Munne-Bosch, S., Schwarz, K. and Alegre, L. 1999. Enhanced formation of a-tocopherol and highly oxidized abietane diterpenes in water-stressed rosemary plants. Plant Physiol. 121 1047-1052. 

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