https://cancerres.aacrjournals.org/content/canres/28/11/2338.full.pdf

Cocarcinogenic principles from the seed oil of Croton tiglium and from other Euphorbiaceae.

Families Hong-Bing Wang,*,† Xiao-Yang Wang,†,‡ Li-Ping Liu,† Guo-Wei Qin, and Ting-Guo Kang‡ †Research Center for Translational Medicine, Shanghai East Hospital, School of Life Sciences and Technology, Tongji University, Shanghai 200092, People’s Republic of China ‡School of Pharmacy, Liaoning University of Traditional Chinese Medicine, Dalian 116600, People’s Republic of China Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People’s Republic of China

Tigliane Diterpenoids from the Euphorbiaceae and Thymelaeaceae Families

[1] FISCHER, t~. W. : Z. Naturforsch. 12a, 753 (~957). [2] FRIEDEL, J . : Dislocations. Oxford: Pergamon Press 1964. E3] FRIEDRIcH, W., P. KNIPPINO U. M.v . LANE: Bayer. akad. Bet. 303 (1912). E4] GEIL, P. H., e t al. : J. Po lymer Sci. A 2, 3707 (t964). [5] HOLLAND, V. F.: J . Appl. Phys. 3S, 3235 (1964). [6] HosE~A~N, R., u. S. N. BAOCHI: Direct ana lys i s of diffract ion b y mat te r . A m s t e r d a m : Nor th -Hol land Publ. Co. ~962. [7] HOSEMANN, R., W. WILDE u. F. J . BALTA CALLEJA: Ac ta Cryst. 21, I18 (1966). [8] HOSEMA~N, R., A. PREISINGER U. W. VOOEL: Bet. der Bunsenges. fiir phys ik . Chemic 70, 796 (t966). [9] KELLER, A.: Phil. Mag. [8] 2, 1t71 ( 1 9 5 7 ) . [10] P E c t I n O L D , W . : Fachber ieh t der Tagung der Dtseh. Physikal . Ges., Mfinehen 1966. [11] PREDECKI, P., u. W. O. S'rATTON: Vortrag, Meeting of Divis. of High Polymer Physics. Am. Physic Sot., M~irz 1966. [12] RENEGER, D. H. : J. Po lymer Sei. 59, 539 (t962). [13] STAUmNGER, H., U. M. Lt~THI: Helv. Chim. Ac ta 8, 41 (1925). [ld] TILL jr., P. H. : J . Po lymer Sci. 24, 30t (1957).

Phorbol esters from croton oil chemical nature and biological activities

A new type of phorbol ester, which has a macrocyclic dicarboxylic acid diester structure, was isolated from the seed oil of Jatropha curcas L. (Euphorbiaceae). Based on the results of spectroscopic analyses of the compound and its chemical degradation products, its structure is proposed to be an intramolecular 13,16-diester of 12-deoxy-16-hydroxyphorbol, 12-deoxy-16-hydroxyphorbol-4'-[12',14'-butadienyl]-6'-[16',18',20' - nonatrienyl]-bicyclo[3.1.0]hexane-(13-O)-2'-[carboxylate]-(16-O)-3 '- [8'-butenoic-10']ate (DHPB). DHPB showed slightly weaker biological and biochemical activities than 12-O-tetradecanoylphorbol-13-acetate (TPA). DHPB induced ornithine decarboxylase in mouse skin (2.8 nmol CO2/30 min/mg protein/34 nmol application), inhibited the specific binding of [3H]-12-O-tetradecanoylphorbol-13-acetate to phorbol ester receptors (50% effective dose, 17.0 nM), and activated protein kinase C in vitro (50% effective dose, 36.0 nM). Also, a weak tumor-promoting activity of DHPB was found in a two-stage carcinogenesis experiment on mouse skin. One week after initiation of mice with 100 micrograms of 7,12-dimethyl-benz(a)anthracene, topical application, twice a week, of 2 micrograms of DHPB until week 17, followed by application of 5 microgram of DHPB until week 30 at the same rate, resulted in 46.7% incidence of tumors by week 30. The groups treated with 7,12-dimethylbenz(a)anthracene alone or DHPB alone did not produce significant numbers of tumors. These results indicate that the new phorbol ester, DHPB, is a tumor promoter with weaker activity than 12-O-tetradecanoylphorbol-13-acetate.

https://cancerres.aacrjournals.org/content/canres/48/20/5800.full.pdf

A New Tumor Promoter from the Seed Oil of Jatropha curcas L., an Intramolecular Diester of 12-Deoxy-16-hydroxyphorbol

Pc19 a new tumor promoter from the seed oil of jatropha curcas l. : an intramolecular diester of 12-deoxy-16-hydroxyphorbol

Structure and stereochemistry of the tetracyclic diterpene phorbol from croton tiglium L.

Aus Crotonol konnten durch Anwendung multiplikativer Verteilungs- und chromatographischer Verfahren die entzundlichen und cocarcinogenen Substanzen A1–A4 und B1–B7 rein dargestellt werden. Diese Substanzen sind Diester des polyfunktionellen Diterpenalkohols Phorbol, C20H28O6 mit jeweils einer kurzkettigen (Essig-, (+)-S-2-Methylbutter-, Tiglinsaure) und einer langkettigen Fettsaure (Capryl-, Caprin-, Laurin-, Myristin-, Palmitinsaure). Die Teilsynthese einiger Substanzen wird angegeben. Aus den UV-, IR- und KMR-Daten und chemischen Befunden werden Teilformeln fur Phorbol abgeleitet und diskutiert.

H. W. Thielmann

Papers

Structure and stereochemistry of the tetracyclic diterpene phorbol from croton tiglium L.

Kombination wirksamer Trennverfahren mit modernen analytischen Methoden in der Naturstoffchemie