Tigliane diterpene

The phorbol 33 is a tigliane diterpene whose 12, 13-diesters play a principal role in efforts to understand biological activities such as carcinogenesis and... 

M3) (tigliane diterpene PE) sailors of Christopher leaf-poisoned water... 

Deoxyphorbol 13-phenylacetate (phorbol ester tigliane diterpene)... 

In the first formal asymmetric synthesis of phorbol, a tigliane diterpene, Wender and co-workers utilized a chiral oxazolidinone-based asymmetric aldol reaction to produce chiral alcohol 43, a non-Evans syn product as a single diastereomer in 96% yield. ... 

Lee et al. reported an intermolecular [4+3] cycloaddition route to the skeleton of tigliane diterpene phorbol 59... 

Tigliane (G5 C7 C61 C3) diterpenes include the highly irritant, toxic, co-carcinogenic, PKC activating phorbol esters from Euphorbiaceae plants. While not being activated by the parent compound phorbol, PKC is activated by plant-derived esters of phorbol, 4-deoxyphor-bol and 12-deoxyphorbol (e.g. 12-0-palmitoyl-16-hydroxy-phorbol 13-acetate, 12-deoxyphorbol 13-benzoate, 12-deoxyphorbol 13-phenylacetate, 12-deoxyphorbol 13-phenylacetate-20-acetate, sapintoxin A (4-deoxyphorbol 12-(2-methylamino)benzoate-l3-acetate) and 12-tetradecanoylphorbol 13-acetate (TPA)), as well as by synthetic phorbol esters. 

A liquid chromatography-tandem mass spectrometry (LC-MS-MS) method was developed to detect tumor-promoting diterpene esters of the tigliane and ingenane types within plant extracts. Fractionation on a Cig HPLC column was followed by MS-MS-multiple reaction monitoring (MRM). 

Croton is endemic to the tropical parts of Asia it has been imported to Mauritius and to East Africa. Croton oil was a well-known purgative in human as well as in veterinary medicine (57, 58). The active compounds are esters of phorbol, a tetracyclic, tiglian-type diterpen. Croton oil possesses a burning taste and causes vomiting and diarrhea applied locally it produces skin irritation followed by formation of blisters and edema. Closely related to phorbol is huratoxin (daphnan-type frame) from Hura crepitans, a tree endemic to the tropical part of America (59). 

Mandnellin. C36H52O8, Mr 612.80, ester of 6,7-epoxy-4,5,9,13,20-pentahydtoxy-1 -tiglien-3-one, a diterpene of the tigliane type. M. can be isolated firom the Hippomane mancinella (Euphorbiaceae) growing in... 

Many plants of the Euphorbiaceae and Thymelaeaceae have long been known to be intensely irritating to the skin. Some produce severe skin lesions in humans and in livestock (Evans and Schmidt, 1980). Members of the genus Euphorbia are especially well known for their irritant and poisonous properties. Polyfunctional diterpene esters of the tigliane, ingenane, and daphnene types are responsible for the acrid... 

The major stmctural types known are the phorbol esters [e.g., a tigliane from Sapium japonicum (17)] Croton, Sap-ium, Aleurites, Mancinella, Baliospermum, and Euphorbia), ingenol esters [e.g., ingenane (18)] Euphorbia), and daph-nanes [e.g., daphnetoxin (19)] Euphorbia, Hura, Hip-pomane, Excoecaria, Baliospermum, Thymelaeaceae) (Fig. 22.7) most of the plants that contain these diterpenes are in subfamilies Crotonoideae and Euphorbioideae (Kinghom, 1979 Webster, 1975). 

Evans, F. J. and C, J. Soper, The tigliane, daphnane, and ingenane diterpenes. Their chemistry, distribution, and biological activities, Lloydia, 41, 193-233 (1978). 

Evans, F.J., and C.J. Soper The tigliane, daphnane and ingenane diterpenes, their chemistry, distribution and biological activities. A review. Lloydia 41, 193 (1978). 

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