Diterpene esters

Materials. I-EGF was either made by iodinating mouse EGF (Biomedical Technologies Inc.) by the chloramine T method, to a specific activity of approximately 1-2 Ci/ xmol, using Na- I (Amersham) or purchased from New England Nuclear. Phorbol diterpene esters were purchased from Sigma. Palytoxin was isolated from Palythoa tuberculosa as previously described (1). 

Gotta H, Adolf W, Opferkuch HJ, Hecker E. (1984) On the active principles of the Enphorbiaceae, IX. Ingenane type diterpene esters from five Euphorbia species. Z Naturforsch B 39 683-694 Hohmann J, Evanics E, Berta L, Bartok T. (2000) Diterpenoids from Euphorbia peplus. Planta Med 66 291-294 Ivanova A, Khozin-Goldberg 1, Kamenarska Z, Nechev J, Cohen Z, Popov S, Stefanov K. (2003) Lipophylic componnds from Euphorbia peplis L. — a halophytic plant from the Bnlgarian black sea coast. Z. Naturforsch 58c 783-788. 

CN048 Ito, Y., S. Yanase, H. Tokuda, M. Kishishita, H. Ohigashi, M. Hirota, and K. Koshimizu. Epstein-Barr virus activation by tung oil, extracts of CN059 Aleurite fordii and its diterpene ester 12 0 hexadecanoyl 16 hydroX yphorbol 13-acetate. Chem Lett 1983 ... 

Pettitt Jr, B. C. Identification of the diterpene esters in arabica and cane-phora coffees. J Agr Food Chem 1987 35(4) 549-551. 

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). 

Diterpene esters are primary dermal and gastrointestinal irritants. The amount of toxin found in the common greenhouse variety of poinsettia is minimal and very rarely causes symptoms. Irritation, whether dermal or oral, is rare. The poinsettia, despite its unfavorable reputation, appears for the most part to be innocuous. 

Tetradecanoylphorbol 13-acetate (TPA) and other diterpene esters from the plant family Euphorbiaceae are well-known as tumor-promotion agents [85]. Thus, inhibition of the biological effects induced by TPA has been considered as a promising strategy [68]. To date, two short-term cell-based in vitro bioassays using TPA as a tumor-promoter have been developed to evaluate the potential cancer chemopreventive activities of several lignans isolated from Hernandia species, namely, inhibition of Epstein-Barr virus early antigen activation [6] and the inhibition of the transformation of JB6 mouse epidermal cells [7]. 

Caseana tremula Diterpene ester (19) Gibbons el a/, (1996) Silica gel Toluene EtOAc AcOH (88 10 2) Rf= 0 71 Petrol EtOAc, (1 1) Two developments ... 

The potential anti-inflammatory properties of southern African soft coral metabolites were further exemplified by the isolation of five diterpene esters valdivones A (101), B (102), their corresponding methoxy ketals (103, 104) and dihydrovaldivone A (105) from Alcyonium valdivae (Family Alcyoniidae) collected off Coffee Bay on the warm temperate east coast of southern Africa (Figure 1) [94]. The structures of these compounds were determined from analysis of their 2D-NMR data with coupling constant analysis and nOe data providing the relative stereochemistry of 101 and 102. Valdivones A and B showed fairly strong inhibition of chemically-induced inflammation in the mouse ear assay (93% and 72% inhibition at 50 pg/ear respectively) but did not significantly inhibit bee venom phospholipase A2 (ca. 43% at 16 pgmL1) [94]. 

A. heterophylla [249,251] and a diterpene ester of aristolochic acid from the roots and stems of A. elegans [252] and thus, A. heterophylla is considered to be a rich source of sesquiterpene esters of aristolochic acids. Aristoloterpenate I (40) and III (42) are esters of aristolochic acid I (5) with the sesquiterpenes, madolin M (305) and L (306), respectively, whereas aristoloterpenate II (39) and IV (41) are esters of aristolochic acid II (1) [249]. In these four esters C-ll of the aristolochic acid and C-4 of sesquiterpene were involved in the ester linkage. The stereochemistry at... 

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... 

Hecker, E., New toxic, irritant and cocarcinogenic diterpene esters from Euphorbiaceae and from Thymelaeaceae, Pure Appl. Chem., 49, 1423-1431 (1977). 

Hecker, E., Cocarcinogens of the diterpene ester type as principal risk factors of cancer in Curacao and possibly in South China, in Cancer of the Liver, Esophagus and Nasopharynx (G. Wagner and Z. You-Hui, eds.), 101-il3, Springer-Verlag, Berlin, 1987a. 

Hecker, E., Tumour promoters of the irritant diterpene ester type as risk factors of cancer in man, Bot. J. Linn. Soc., 94,197-219 (1987b). 

SosATH, S., H. H. Ott, and E. Hecker, Irritant principles of the spurge family (Euphorbiaceae). XIII. Oligocyclic and macrocy-clic diterpene esters from latices of some Euphorbia species utilized as source plants of honey, J. Nat. Prod., 51,1062-1074 (1988). 

Vogg, G. Achatz, A. Kettrap, A. Sandermann, A., Jr. Fast, sensitive and selective liquid chromatographic-tandem mass spectrometric determination of tumor-promoting diterpene esters. J. Chromatogr. A, 1999, 855, 563 573. 

Keller, R., Reist R., Adolf, W., Opferkuch, H. J., Schmidt, R., and Hecker, E. (1982). Tumor promoting diterpene esters prevent macrophage activation and suppress macrophage tumori-cidal capacity, p. Cell Biol. 50 121-134. 

Goerttler, K., Loehrke, H., Schweizer, J. and Hesse, B. 1982, Diterpene ester-mediated two-stage carcinogenesis, Jn "Carcinogenesis, Vol 7, Cocarcinogens and Biological Effects of Tumor-Promoters", E. Hecker, N.E. Fusenig, W. Kunz, F. Marks and H.W. Thielmann, eds.. Raven Press, New York. 

Diterpene (phorbol) esters Diterpene esters are tricyclic compounds often containing a combination of five-, six-, and seven-membered rings and a variety of phertolic or alkyl side chains or esters. They are soluble in water and other polar solvents. 

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