201: J Nat Prod 1988 Nov-Dec;51(6):1062-74

Irritant principles of the spurge family (Euphorbiaceae). XIII. Oligocyclic and macrocyclic diterpene esters from latices of some Euphorbia species utilized as source plants of honey.

Sosath S, Ott HH, Hecker E.

German Cancer Research Center, Institute of Biochemistry, Heidelberg.

The latices of the three South African species Euphorbia ledienii, Euphorbia coerulescens, and Euphorbia triangularis, belonging to a group of cactiform Euphorbias locally called "Noors," were shown to contain four 12-mono- and three 13,20-diesters of the tetracyclic tigliane type parent alcohol 12-deoxyphorbol [1]. In addition, two 13,16-di- and two 13,16,20-triesters of the related 12-deoxy-16-hydroxyphorbol [9] were obtained. Ester groups in 1 and 9 are made up of acetic, isobutyric, tiglic, angelic, and 2-methylbutyric acid; their positions in the parent alcohols were identified. The free parent alcohols were not detected in the latices. On the mouse ear all esters isolated showed moderate irritant activity as compared to the tigliane-type standard TPA. In addition to the oligocyclics listed above, the latex of E. ledienii also yielded five esters of the macrocylic, lathyrane type parent alcohol ingol [14]. In the two triesters and three teraesters the ester groups were made up of acetic, tiglic, and 2-methylbutyric acid (positions in 14 unidentified). None of the ingol esters showed irritant activity.

202: J Biol Chem 1988 Sep 5;263(25):12373-7

Mass spectrometric determination of the inorganic carbon species assimilated by photoautotrophic cells of Euphorbia characias L.

Rebeille F, Gans P, Chagvardieff P, Pean M, Tapie P, Thibault P.

Department de Biologie, C.E.N. de Cadarache, Saint-Paul-lez-Durance, France.

The chemical forms of inorganic carbon, CO2 or HCO3-, incorporated during photosynthesis in photoautotrophic Euphorbia characias cell suspension cultures were determined in experiments using 13CO2 and a mass spectrometry technique. From the equations of the CO2 hydration reaction, a kinetic model was first developed, and the effect of photosynthesis on the external CO2 concentration was simulated. It was predicted from this model that CO2 and HCO3- uptakes could be differentiated by recording only the CO2 variation rate in the external medium, successively in absence then in presence of an exogenous carbonic anhydrase activity. The results obtained with either CO2-grown or air-grown photoautotrophic cells were in good agreement with the model and demonstrated that CO2 was the sole species taken up during photosynthesis. In addition no accumulation of inorganic carbon within the cells was observed in the light. Similarly, in dark, CO2 was the only species released by respiration in the external medium.

203: Zhong Yao Tong Bao 1988 May;13(5):35-6, 63

[Isolation and identification of antitumor constituents of diterpenoids lactone in Euphorbia fischeriana Steud]

[Article in Chinese]

Liu GF.

204: Indian J Med Res 1988 Apr;87:395-7

Antibacterial activity of Euphorbia thymifolia Linn.

Khan NH, Rahman M, Nur-e-Kamal MS.

205: Zhong Yao Tong Bao 1987 Aug;12(8):36-8, 64

[Isolation and identification of the lipophilic constituents from the root of Euphorbia fischeriana Steud.]

[Article in Chinese]

Liu GF, Yang SS, Yang ZQ.

206: Lancet 1987 May 30;1(8544):1257-8

African Burkitt's lymphoma and an Epstein-Barr virus-enhancing plant Euphorbia tirucalli.

Osato T, Mizuno F, Imai S, Aya T, Koizumi S, Kinoshita T, Tokuda H, Ito Y, Hirai

N, Hirota M, et al.

207: J Nat Prod 1987 Jan-Feb;50(1):36-40

3,3',5'-Tri-O-methylpiceatannol and 4,3',5'-tri-O-methylpiceatannol: improvements over piceatannol in bioactivity.

Gill MT, Bajaj R, Chang CJ, Nichols DE, McLaughlin JL.

Piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene) (NSC 365798) has recently been isolated and was subsequently synthesized for NCI tumor panel testing as a new antileukemic natural product from the seeds of Euphorbia lagascae. During the synthesis, a bioactive reaction mixture of several partially O-methylated piceatannol analogues was obtained. This mixture has now been maximized and subjected to bioactivity-directed fractionation, using brine shrimp lethality, to yield 3,3',5'-tri-O-methylpiceatannol (NSC 381281); this new compound has improved stability and better bioactivity in several systems than piceatannol itself. To confirm the structure, 5 was synthesized from vanillin. In addition, the isovanillin analogue, 4,3',5'-tri-O-methylpiceatannol (NSC 381864), another new compound, was synthesized and found to be bioactive.

208: AIDS Res 1986 Dec;2 Suppl 1:S151-5

Epstein-Barr virus-enhancing plant promoters in east Africa.

Mizuno F, Osato T, Imai S, Koizumi S, Aya T, Kinoshita T, Hirai N, Hirota M, Ohigashi H, Koshimizu K, et al.

The extracts of a certain African plant species, Euphorbia tirucalli, were found to have markedly enhancing effects on the activation of latent Epstein-Barr virus (EBV) genomes in the EBV carrying lymphoblastoid cells and also on EBV-induced transformation of human lymphocytes. The Euphorbia tirucalli was especially noticeable in highly endemic areas of Burkitt's lymphoma (BL), an EBV-associated malignancy, in Kenya and Tanzania. The activation of the latent EBV genome and the EBV-induced transformation enhancement were also observed with the soil and drinking water taken around the plants, strongly indicating that the people living in BL endemic areas are frequently exposed to such an EBV-enhancing plant promoter substance.

209: Zhong Yao Tong Bao 1986 Nov;11(11):48-9

[Mutagenic evaluation of the Chinese drug C, L, T, G pill consisting of Daphne genkwa, Euphorbia kansui, Euphorbia pekinensis, Glycyrrhiza uralensis tested in Salmonella typhimurium and B. subtilis]

[Article in Chinese]

Lin TG.

210: Mem Inst Oswaldo Cruz 1986 Oct-Dec;81(4):475-6

Latex of "coroa de cristo" (Euphorbia splendens): an effective molluscicide.

de Vasconcellos MC, Schall VT.

An aqueous solution of the latex of "coroa de cristo" (Euphorbia splendens var. hislopii) showed molluscicide action (LD90) at a concentration lower than 0.5 ppm on Biomphalaria glabrata and B. tenagophila reared in laboratory and at a concentration lower than 4.0 ppm for field B. tenagophila.

211: Lakartidningen 1986 Aug 20;83(34):2756

[Euphorbia and high chapparall--hazardous pot plants in fashion]

[Article in Swedish]

Hallen L.

212: Virology 1986 Jul 15;152(1):219-27

3-Methylquercetin is a potent and selective inhibitor of poliovirus RNA synthesis.

Castrillo JL, Vanden Berghe D, Carrasco L.

3-Methylquercetin (3MQ) is a natural compound isolated from Euphorbia grantii that selectively inhibits poliovirus replication, but has no effect on encephalomyocarditis virus. When the compound is present from the beginning of infection, the bulk of viral protein synthesis is prevented, but the shut-off of host protein synthesis still occurs. Addition of 3MQ 3 hr after infection has a slight effect on viral protein synthesis, suggesting that this compound blocks a step of viral replication different from translation. Indeed, poliovirus RNA synthesis is potently blocked by 3MQ, i.e., 50% inhibition at 2 micrograms/ml (6.3 X 10(-6) M). No effect on encephalomyocarditis, nor on cellular RNA synthesis is observed even at 20 micrograms/ml. The inhibitory effect of 3MQ is reversible, since cells treated with this compound from the beginning of infection start to synthesize viral RNA and proteins when the compound is removed. Strikingly, other natural compounds structurally related to 3-methylquercetin such as quercetin, naringenin, naringin, morin, catechin, kaempferol, myricetin, phloretin, phlorizdin, and rutin do not block poliovirus replication.

213: J Nat Prod 1986 May-Jun;49(3):386-97

On the active principles of the Euphorbiaceae, XII. Highly unsaturated irritant diterpene esters from Euphorbia tirucalli originating from Madagascar.

Furstenberger G, Hecker E.

The latex of Euphorbia tirucalli originating from Madagascar contains as irritant constituents ingenane- and tigliane-type diterpene esters derived from the parent alcohols ingenol and phorbol. The main irritant constituents are isomeric 12,13-acetates, acylates of phorbol as well as 3-acylates of ingenol. As acyl groups, they carry homologous, highly unsaturated aliphatic acids of the general structure CH3-(CH2)m-(CH = CH)n-COOH (m = 2,4; n = 2,3,4,5; total number N of C-atoms = 2n + m + 2). The lack of 4-deoxyphorbol esters in this latex as compared to latex of South African origin is probably indicative of the existence of chemical races of E. tirucalli. In the acyl moiety of phorbol esters investigated in detail, an increasing number of C-atoms or an increasing number of double bonds at a fixed number of C-atoms leads to an increase of irritant activity. As compared to their saturated analogs, corresponding unsaturated phorbol esters exhibit similar irritant activities. On the other hand, by an increasing number of conjugated double bonds in the acyl moieties of phorbol esters, the promoting activity is decreased, thus indicating that irritant activity is a necessary, but insufficient, requirement for promoting activity of phorbol esters. An assessment of a potential carcinogenic risk involved in mass production and handling of the plant should point to the very weak tumor-promoting activity and the chemical instability demonstrated for the diterpene constituents in the latex and hence in all plant parts.

214: Mem Inst Oswaldo Cruz 1985 Oct-Dec;80(4):423-7

Molluscicide activity of the "avelos" plant (Euphorbia tirucalli, L.) on Biomphalaria glabrata, the mollusc vector of schistosomiasis.

Jurberg P, Cabral Neto JB, Schall VT.

An aqueous solution of the latex of Euphorbia tirucalli collected at sites receiving large amounts of sunlight showed molluscicide action on Biomphalaria glabrata, with LD50 obtained at the concentration of 28,0 ppm and LD90 at the concentration of 85,0 ppm. The toxicity of the product for fish was similar to that of Bayluscide and of copper sulfate used for comparison. However, the wide distribution of the plant, its easy propagation and the simple procedure for extraction of the active substance, which is biodegradable, favor "avelos" as a promising agent in the control of schistosomiasis.

215: Z Naturforsch [C] 1985 Sep-Oct;40(9-10):631-46

On the active principles of the spurge family (Euphorbiaceae). XI. [1] The skin irritant and tumor promoting diterpene esters of Euphorbia tirucalli L. originating from South Africa.

Furstenberger G, Hecker E.

The irritant and tumor-promoting constituents of latex of Euphorbia tirucalli L. originating from South Africa were isolated. They were identified as irritant ingenane and tigliane type diterpene esters derived from unsaturated aliphatic acids and acetic acid and the polyfunctional diterpene parent alcohols 4-deoxyphorbol, phorbol and ingenol, respectively. The irritant and tumor-promoting esters of 4-deoxyphorbol are predominant and were fully characterized chemically and biologically. They are positionally isomeric 12,13-acylates, acetates e.g. Euphorbiafactors Ti1-Ti4. As acyl groups they carry homologous, highly unsaturated aliphatic acids of the general structure CH3-(CH2)m-(CH = CH)n-COOH (m = 2,4; n = 1,2, 3,4,5; N = 2n + m + 2). Corresponding diesters of 4-deoxy-4 alpha-phorbol are also present which are biologically inactive. Comparison of structures and biological activities of 12,13-diesters of 4-deoxyphorbol indicates that--for a distinct total number of C-atoms (N) in the acyl moiety--an increasing number of conjugated double bonds (n) may increase the irritant but decrease the tumor-promoting activity. Replacement of the hydroxyl function at C-4 (phorbol-12,13-diesters) by hydrogen (corresponding 4-deoxyphorbol-12,13-diesters) does not essentially alter biological activities. Epimerization of 4-deoxyphorbol-12,13-diesters at C-4 abolishes biological activities. The specific chemical properties demonstrated for the diterpene ester irritants contained in the latex of E. tirucalli and hence in all plant parts may be useful in trials to abolish the potential risk of cancer involved especially in occupational mass production and handling of the plant. Some of the structure activity relations of the Euphorbia factors isolated made them excellent tools in experimental cancer research for the analysis of mechanisms of tumorigenesis.

216: Contact Dermatitis 1985 Jul;13(1):44

Irritant dermatitis due to Euphorbia marginata.

Pinedo JM, Saavedra V, Gonzalez-de-Canales F, Llamas P.

217: Klin Monatsbl Augenheilkd 1985 May;186(5):380-1

[Euphorbiae keratoconjunctivitis]

[Article in German]

Rossler G.

This paper reports on 6 cases of keratoconjunctivitis caused by the latex of Euphorbiaceae, one of them with slight systemic intoxication. Phorbolesters are considered to be responsible for the toxicity of the latex of Euphorbiaceae, e.g., in the case of Euphorbia helioscopia, 12-Desoxyphorbol-13-phenylacetate-2-O-acetate. Since all of the cases of keratoconjunctivitis Euphorbiae described here, as well as the majority of those cited in the literature, have resulted in a restitutio ad integrum, a benign course may be expected, even in cases of keratoconjunctivitis Euphorbiae with initially severe clinical pictures.

218: Contact Dermatitis 1985 May;12(5):285-6

Contact dermatitis from Euphorbia pulcherrima.

Santucci B, Picardo M, Cristaudo A.

219: Q J Exp Physiol 1984 Oct;69(4):809-18

Function of the lower intestine and osmoregulation in the ostrich: preliminary anatomical and physiological observations.

Skadhauge E, Warui CN, Kamau JM, Maloiy GM.

The gross anatomy of the lower intestine of the African ostrich (Struthio camelus) was investigated in four adult birds shot in the wild. The presence of 80 cm long paired caeca, and approximately 10 m of colon between ileum and the cloaca was confirmed. Urine, but not faeces, was found in the coprodeum. Retrograde flow into the colon was not observed. Samples of contents from the lower intestine were secured from these birds and the water content, osmolality and concentrations in the supernatant of short-chain fatty acids (SCFA), acetate, Na, K and Cl and pH were measured. In the caeca and the orad wide part (2-3 m) of the colon an avid production of SCFA takes place since the concentration of SCFA reached around 200 mM in these segments. As judged from a pronounced fall in the concentrations of Na and SCFA along the length of the colon, these ions are absorbed together with water. The water content falls from 92 to 67% (i.e. from 11.5 to 2.0 ml H2O/g dry matter). The mid-gut fermentation of carbohydrate is in agreement with the observation that the birds were feeding exclusively on Euphorbia heterochroma. This succulent plant (water content 87%) apparently makes the birds independent of surface water. Laboratory studies were performed on two captive male chicks. Hyperosmotic NaCl loading was unable to activate the nasal glands to secretion. Their ducts passed directly from the frontal/lacrimal bone to the nasal cavity. Dehydration confirmed a maximal osmolality of the cloacal urine of around 800 mosmol/l, the osmotic urine to plasma ratio being 2.5. Feeding of either a low- or a high-NaCl diet did not affect the transepithelial electrical potential difference of the coprodeal wall. It remained less than 5 mV, lumen negative.

220: Planta Med 1984 Aug;50(4):319-22

Active principles of the Euphorbiaceae. VII. Milliamines H and I, peptide esters of 20-deoxy-5 epsilon-hydroxyphorbol from Euphorbia milii.

Marston A, Hecker E.

221: J Nat Prod 1984 Jul-Aug;47(4):702-5

Correlation of the anticholinesterase and molluscicidal activity of the latex of Euphorbia royleana on the snail Lymnaea acuminata.

Singh DK, Agarwal RA.

222: Planta Med 1984 Jun;50(3):259-61

Macrocyclic lathyrane type diterpene esters (jolkinols) from callus cultures and roots of Euphorbia lathyris.

Adolf W, Hecker E, Becker H.

223: Toxicol Lett 1984 Jun;21(3):309-14

Alteration in biogenic amine levels in the snail Lymnaea acuminata by the latex of Euphorbia royleana.

Singh DK, Agarwal RA.

The latex of Euphorbia royleana which has high molluscicidal and anti-cholinesterase activity against Lymnaea acuminata reduced the levels of 5-hydroxytryptamine (5HT) and dopamine (DA) in the nervous tissue of L. acuminata. There was, however, no significant change in the level of 5-hydroxyindole acetic acid (5HIAA). The changes were found to be dependent on concentration of the latex extract. Similar changes were produced by both water and organic solvent extracts of the latex. The latex of E. royleana thus affects all the known neurotransmission mechanisms in the snail either separately or through a complex interaction between the different neurotransmitters. This may account for its high toxicity to snails.

224: J Ethnopharmacol 1984 Apr;10(2):225-33

Anti-inflammatory activity of Euphorbia acaulis Roxb.

Singh GB, Kaur S, Satti NK, Atal CK, Maheshweri JK.

From various extracts of Euphorbia acaulis , the n-hexane fraction showed marked anti-inflammatory activity in carrageenan induced oedema in rats and mice as compared to phenylbutazone and was equipotent in adrenal- ectomised rats. In chronic models of formaldehyde and adjuvant arthritis, its anti-arthritic activity was found to be superior to that of phenylbutazone. It had a diuretic effect but did not show any analgesic or antipyretic activity.

225: Planta Med 1984 Apr;50(2):138-42

Effects of Euphorbia prostrata and Fumaria parviflora in normoglycaemic and alloxan-treated hyperglycaemic rabbits.

Akhtar MS, Khan QM, Khaliq T.

226: J Nat Prod 1984 Mar-Apr;47(2):347-52

Use of potato disc and brine shrimp bioassays to detect activity and isolate piceatannol as the antileukemic principle from the seeds of Euphorbia lagascae.

Ferrigni NR, McLaughlin JL, Powell RG, Smith CR Jr.

EtOH extracts of the seeds of Euphorbia lagascae inhibited crown gall tumors on potato discs, were active against 3PS (in vivo) and 9PS (in vitro) mouse leukemia, and were toxic to brine shrimp. Using the potato disc and brine shrimp bioassays to monitor fractionation, piceatannol (3,4,3',5'- tetrahydroxystilbene) was isolated as the 3PS active principle. Aesculetin (6,7-dihydroxycoumarin) was isolated in large quantity, was weakly cytotoxic in 9KB , but was inactive in the other bioassay systems. Sucrose was also isolated. A combination of the simple crown gall and brine shrimp bioassays can thus be used both to detect and to isolate plant antitumor substances, minimizing the need for extensive antitumor testing in vivo.

227: J Cancer Res Clin Oncol 1984;108(1):98-109

On the active principles of the spurge family (Euphorbiaceae). V. Extremely skin-irritant and moderately tumor-promoting diterpene esters from Euphorbia resinifera Berg.

Hergenhahn M, Kusumoto S, Hecker E.

The irritant and tumor-promoting principles were isolated from the latex of Euphorbia resinifera Berg. and from the resin derived from latex (euphorbium), which is commercially available as a drug. The irritant Euphorbia factors RL 5 (mixture), RL 6, RL 7, RL 8, and RL 10 were identified as tigliane-type 12-deoxyphorbol esters each bearing, in the 13 position, either long-chain, partially methyl-substituted acyl residues (10-16 carbon atoms) or short-chain acyl residues (4 or 5 carbon atoms) or a (substituted) phenylacetyl group with a 20-acetoxy group. Euphorbia factors RL 15 (mixture), RL 16, RL 17, RL 18, and RL 21 are the corresponding 20-deacetylated derivatives thereof. The irritant Euphorbia factors RL 11, RL 12, RL 22, RL 23 were characterized as esters of the tigliane type 12-deoxy-16-hydroxyphorbol, i.e., 13-0-phenylacetyl-16-0-benzoyl-12-deoxy16-hydroxyphorbol-20- acetate (RL 11) and 13, 16-0-phenylacetyl, tigloyl-12-deoxy-16-hydroxy-phorbol-20-acetate (RL 12), RL 22 and RL 23 representing the respective 20-deacetylated derivatives. A mixture of irritant factors, RL 13, was shown to represent long-chain 3-esters of ingenane-type ingenol with similar acyl residues (10-16 carbon atoms, partially methyl-substituted) to RL 5 (RL 15) above. A further group of E. resinifera factors was of the daphnane type: RL 9 was identified as the extremely irritant 9,13,14-orthophenylacetate of resiniferonol-20-(4-hydroxy-3-methoxy)phenylacetate (Resiniferatoxin), RL 14 as the corresponding 9,13,14-orthophenylacetate of resiniferonol, and RL 20 as 14-0-phenylacetylresiniferonol-20-(4-hydroxy-3-methoxy)-phenylacet ate (Proresiniferatoxin). The irritant factors specified below were accompanied by nonirritant esters of the tigliane type 12,20-dideoxyphorbol, i.e., RL 1 and RL 2, and of the lathyrane type ingol, i.e., RL 3 and RL 4. In tumor promotion experiments the mixture of homologous irritant factors RL 13 was equipotent with the standard tumor promoter TPA, but at 10 times the dose of TPA. Several others of the irritant factors had low activity as tumor promotors, but of the few tumors obtained in these experiments a high percentage was malignant. The very high irritant activity of the latex may be ascribed to resiniferatoxin (RL 9), representing a new class of rapidly acting skin irritants. No promoting activity was detected on administration of the highly irritant resiniferatoxin.

228: Neoplasma 1984;31(3):347-50

Tumor promoting activity of Euphorbia striatella (Boiss) and skin irritant activity of some Euphorbia species.

Upadhyay RR, Sater AM, Moinzadeh F, Bunakdari A, Sedehi F, Samin R.

Out of seven plants selected due to their use in folk medicine, five possessing ingenol as diterpene parent, exhibited mild skin irritancy where as E. striatella latex was highly skin irritant and produced papilloma, in initiation-promotion experiment on mouse back skin. This tumor promoting activity has been demonstrated due to the presence of ingenol-3-O-decanoate.

229: Zhong Xi Yi Jie He Za Zhi 1984 Jan;4(1):46-7

[Antineoplastic effect of Euphorbia fischeriana Steud on mice with implanted

tumor]

[Article in Chinese]

Shen TJ.

230: Biochem J 1983 Dec 1;215(3):433-9

Purification and properties of two lectins from the latex of the euphorbiaceous plants Hura crepitans L. (sand-box tree) and Euphorbia characias L. (Mediterranean spurge).

Barbieri L, Falasca A, Franceschi C, Licastro F, Rossi CA, Stirpe F.

1. From the latex of two members of the plant family Euphorbiaceae, Hura crepitans L. (sand-box tree) and Euphorbia characias L. (Mediterranean spurge), two lectins were purified by affinity chromatography on acid-treated Sepharose 6B followed by elution with D-galactose.

2. The lectin from E. characias is a single molecular species with Mr 80 000, made up of two identical subunits with Mr 40 000, and is a glycoprotein containing 11% carbohydrate.

3. The lectin from H. creptians appears as a mixture of three isolectins with Mr 140 000, consisting of four different subunits with Mr values 37 500, 35 500, 31 000, and 29 000.

4. Both lectins have haemagglutinating activity, with no specificity for

human blood groups. The haemagglutinating activity is inhibited by D-galactose and by galactose-containing oligosaccharides.

5. The lectin from H. crepitans is mitogenic to human T-, but not to B-, lymphocytes. The latex of E. characias is mitogenic to T- and, to a lesser extent, to B-, lymphocytes, but the purified E. characias lectin has no mitogenic activity.

6. The lectin from H. crepitans, but not that from E. characias, inhibits protein synthesis by a rabbit reticulocyte lysate.

231: Biochem J 1983 Oct 1;215(1):141-5

Isolation and partial characterization of a lectin from Euphorbia heterophylla seeds.

Nsimba-Lubaki M, Peumans WJ, Carlier AR.

An N-acetylgalactosamine-specific lectin was isolated from Euphorbia heterophylla seeds by affinity chromatography on cross-linked arabinogalactan. It is a dimeric protein of two identical subunits of Mr 32 000, and differs structurally from all previously known Euphorbiaceae lectins. Its distribution over the seed is typical in that it is merely confined to the primary axes.

232: J Nat Prod 1983 Sep-Oct;46(5):723-31

The dermatitis-producing constituents of Euphorbia hermentiana latex.

Lin LJ, Marshall GT, Kinghorn AD.

Five ingenane derivatives, 3-O-n-(deca-2,4,6-trienoyl)-16-O-[(Z)-2-methyl-2-butenoyl]-16-hydroxyingenol (1), 3-O-[(Z)-2-methyl-2-butenoyl]-5,16,20-O-triacetyl-16-hydroxyingenol (2), 3-O-[(Z)-2-methyl-2-butenoyl]-16,20-O-diacetyl-16-hydroxyingenol (3), 3-O-[(Z)-2-methyl-2-butenoyl]-20-O-acetylingenol (4), and 3-O-[(Z)-2-methyl-2-butenoyl]-16-O-acetyl-20-deoxy-16-hydroxyingenol (5) were isolated with a new procedure that uses droplet counter-current chromatography, from a dermatitis-producing fraction of the latex of Euphorbia hermentiana Lem. The structures of the new compounds 2,3, and 5 were established by the interpretation of their spectroscopic data and those of their hydrolytic and acetylated derivatives.

233: Antonie Van Leeuwenhoek 1983 Apr;49(1):51-9

Pichia euphorbiae sp. nov., a new haploid heterothallic yeast species.

van der Walt JP, Opperman A.

Representatives of an undescribed, haploid, heterothallic yeast species, Pichia euphorbiae, have been recovered from insect-infested specimens of Euphorbia ingens. The new species is considered to be another representative of the apparently related group of heterothallic species, comprising Pichia rhodanensis, Pichia wickerhamii, Pichia veronae, Pichia amylophila, Pichia mississippiensis and Pichia meyerae. While no mating response was observed in interspecific mixtures of the mating types of the new species with the mating types of the first five mentioned species, a sexual response, manifested by the formation of non-sporulating zygotes, was nevertheless detected with the mating types of P. meyerae. Prototrophic hybrids obtained by crossing auxotrophic mutants of the mating types of P. euphorbiae and P. meyerae were found to be only partial recombinants. A description of the new species is given.

234: Arch Biochem Biophys 1983 Feb 1;220(2):623-7

Essential sulfhydryl groups in diamine oxidase from Euphorbia characias latex.

Floris G, Giartosio A, Rinaldi A.

Diamine oxidase from Euphorbia characias latex contains two sulfhydryl groups per mole of dimeric enzyme. The sulfhydryl groups are unreactive in the native enzyme but can be readily titrated by 4,4'-dithiodipyridine after protein denaturation, or anaerobically in the presence of the amine substrate. In the presence of both substrates (diamine and oxygen) they react sluggishly. The sulfhydryl groups show different reactivity toward various reagents, but in every case their modification inhibits catalytic activity. The insensitivity of the native enzyme to specific reagents suggests that the sulfhydryl groups are positioned in the interior of the protein and shielded from the solvent. Their reactivity in the presence of the amine substrate could be attributed to a conformational change occurring upon substrate binding or after substrate oxidation.

235: Planta Med 1982 Dec;46(4):215-8

Skin irritant ingenol esters from Euphorbia esula.

Seip EH, Hecker E.

236: Arch Pharm (Weinheim) 1982 Dec;315(12):1026-32

[Constituents of Euphorbiaceae, 7. 20-Deoxyingenol Monoesters and ingenol diesters from Euphorbia biglandulosa Desf.]

[Article in German]

Falsone G, Crea AE, Noack EA.

237: Eur J Biochem 1982 Oct;127(2):417-22

Purification and properties of diamine oxidase from Euphorbia latex.

Rinaldi A, Floris G, Finazzi-Agro A.

A diamine oxidase has been purified to homogeneity from the latex of an herbaceous shrub, Euphorbia characias. This enzyme has a relative molecular mass of 144,000 and is composed of two identical subunits. It contain two Cu(II) and two carbonyl-like groups per dimer. The purified enzyme is pink and shows a broad absorption in the visible region centered at 480 nm, which is modified by the addition of phenylhydrazine or semicarbazide. The electron paramagnetic resonance spectrum is typical of copper(II) in a tetragonal symmetry. This enzyme oxidizes putrescine and cadaverine at fairly high rate and, less efficiently a few related compounds, but not histamine, spermine or spermidine.

238: J Cancer Res Clin Oncol 1982;103(3):255-68

On the active principles of the spurge family (Euphorbiaceae). IV. Skin irritant and tumor promoting diterpene esters from Euphorbia ingens E.Mey.

Opferkuch HJ, Hecker E.

The irritant and tumor-promoting principles of the latex of Euphorbia ingens E. Mey have been isolated together with several nonirritant compounds. The Euphorbia factors I1, I5, and I6 are esters of ingenane-type poly-functional diterpene alcohols. Euphorbia factor I1 is characterized as the 3-hexadecanoate of the polyfunctional parent alcohol ingenol and Euphorbia factor I6 as the 3-deca-2.4.6-trienoic acid ester of ingenol. Euphorbia factor I5 is the 16-angelate-3-deca-2.4.6-trienoate of 16-hydroxyingenol. Nonirritant diterpenes of the latex are I2, the ingenol-20-hexadecanoate - an isomer of Euphorbia factor I1 - and I4, the 3.7.12-triacetate-8-nicotinate of the macrocyclic lathyrane-type polyfunctional diterpene alcohol ingol. The diterpene alcohols ingenol and 16-hydroxyingenol are inactive as irritants and tumor promoters of mouse skin. Compared to croton oil factor A1 (TPA), the Euphorbia factor I1 exhibits about 1/10 of the irritant and tumor-promoting activity in mouse skin. I1 shows no reasonable tumorigenic activity. Compared with I1, Eupohorbia factors I5 and I6 are more potent irritants and less potent tumor promoters.

239: J Ethnopharmacol 1982 Jan;5(1):91-112

A neglected Mayan galactagogue - ixbut (Euphorbia lancifolia).

Rosengarten F Jr.

A herbal tea, made of leaves of ixbut (Euphorbia lancifolia Schlecht.), has been used for several centuries by postpartum Mayan women in Guatemala to stimulate and increase the flow of mother's milk. Ixbut, when mixed with cattle fodder, is reputed to have increased milk yields in cows. To date, the active principle of ixbut has never been isolated. However, this medicinal herb, a natural galactagogue of Central American origin, would appear to be worthy of further chemical and pharmacological study. The following illustrated article describes the history and use of ixbut, and includes chromatographic analyses of dried ixbut leaves from Guatemala.

240: Bull Environ Contam Toxicol 1981 Dec;27(6):894-902

Testing for tumor promoters in Euphorbia lathyris: analysis of possible health hazards.

Bissell MJ, Nemethy EK, Riddle L, Calvin M.

241: Ann Ophthalmol 1981 Jun;13(6):739-40

Euphorbia peplus latex keratoconjunctivitis.

Biedner BZ, Sachs U, Witztum A.

242: Cancer Lett 1981 Apr;12(3):175-80

Combined effect of the extracts from Croton tiglium, Euphorbia lathyris or Euphorbia tirucalli and n-butyrate on Epstein-Barr virus expression in human lymphoblastoid P3HR-1 and Raji cells.

Ito Y, Kawanishi M, Harayama T, Takabayashi S.

The combined usage of n-butyrate and 12-O-tetradecanoylphorbol-13-acetate (TPA) or the oily extracts from Croton tiglium, Euphorbia lathyris or Euphorbia tirucalli exerted a marked effect on induction of Epstein-Barr virus (EBV)-associated early (EA) and viral capsid (VCA) antigens in EBV genome-carrying human lymphoblastoid cell lines. In producer P3HR-1 cells, the enhancing effect of the 2 components was additive both for EA and VCA, while in non-producer Raji cells, a synergistic increase of EA was observed. The possible implication of these findings relating to the cause of EBV-associated diseases is discussed.

243: J Pharm Sci 1981 Mar;70(3):329-31

Dry column chromatographic procedure for rapid concentration of biological activity in natural products fractionation.

Hokanson GC, Matyunas NJ.

A dry column chromatographic procedure is described. It allows for the rapid concentration of biologically active materials in natural products fractionation. The potential value of the technique is described, utilizing as an example the separation of an anticancer active fraction obtained from Euphorbia cyparissias.

244: Contact Dermatitis 1981 Jan;7(1):19-22

Irritant contact dermatitis from an ornamental Euphorbia.

Worobec SM, Hickey TA, Kinghorn AD, Soejarto DD, West D.

An ornamental succulent plant sold in many plant stores in the Chicago area has been identified as Euphorbia hermentiana Lem. Open and closed patch testing using undiluted latex from this species was performed on five Caucasian volunteers. Open testing on flexor forearms resulted in irritant follicular dermatitis, while closed testing to the flexor surfaces of both upper arms in each subject produced bullae and vesiculation with residual desquamation and hyperpigmentation. Dermatological signs persisted for over a week following latex application.

245: Toxicon 1981;19(3):383-92

Effects of a 4-deoxyphorbol triester from the latex sap of Euphorbia biglandulosa Desf. on isolated spinach chloroplasts.

Santarius KA, Crea AE, Falsone G.

246: Neoplasma 1981;28(5):555-8

Tumor promoting and skin irritant diterpene esters of Euphorbia virgata latex.

Upadhyay R, Samiyeh R, Tafazuli A.

The mouse ear irritant latex of E. virgata, has been found to contain various skin irritant and non-irritant esters of the diterpene ingenol. In cocarcinogenic assay on dorsal back skin of NMRI mice, acetone extract of this latex produces squamous cell papilloma. Using a combination of biologic and chemical separation techniques one of the initiator-promotor for skin carcinogenesis has been identified as 3-0-2 methyl-decanoyl ingenol.

247: Experientia 1980 Oct 15;36(10):1206-7

Constituents of Egyptian Euphorbiaceae. IX. Irritant and cytotoxic ingenane esters from Euphorbia paralias L.

Sayed MD, Riszk A, Hammouda FM, El-Missiry MM, Williamson EM, Evans FJ.

The irritant and cytotoxic constituents of the latex of Euphorbia paralias L. were separated from the hydrocarbon fraction by means of solvent partition. 3 new ingenane esters were identified from the toxic ether fraction. The major compound was 3-angelyl-20-deoxyingenol and the 2 minor compounds were 3-hexanoyl-20-deoxyingenol and 3-angelyl-ingenol. These compounds were of a similar potency to podophyllin in the inhibition of 3H-thymidine uptake by TLX/5 mouse lymphoma cells. In addition the compounds produced a persistent erythema of the mouse ear in sub-microgram doses.

248: Gann 1980 Aug;71(4):557-9

Presence of a tumor-promoting factor in honey.

Upadhyay RR, Islampanah S, Davoodi A.

Honey samples collected from the Saidabad area of Azarbaijan province of Iran were found to be moderately irritant, and this activity was associated with the presence of tri-acylates of the diterpene ingenol, which are transferred from the nectar of Euphorbia seguieriana Neck by honey bees to the honey. The acylates of ingenol are known promoters of carcinogenesis.

249: Clin Toxicol 1980 Apr;16(2):167-73

Toxicity of fresh poinsettia (Euphorbia pulcherrima) to Sprague-Dawley rats.

Runyon R.

Fresh leaves and bracts of poinsettia (Euphorbia pulcherrima) were fed to 46 Sprague-Dawley rats. The animals were observed for 1 week for changes in weight or behavior. The animals were then sacrificed in ether and examined for changes in thyroid and adrenal weights. One group was also examined for damage to the duodenum, jejunum, and ileum. No lesions or other signs of intestinal damage were observed. None of the groups showed any change in behavior or any significant change in body weight or adrenal weight. Only one group showed a significant increase in thyroid weight.

250: Contact Dermatitis 1980 Apr;6(3):204-10

Skin irritants of the sun spurge (Euphorbia helioscopia L.).

Schmidt RJ, Evans FJ.

Euphorbia helioscopia is a common herbaceous week found in the British Isles and parts of Europe. It has been responsible for poisoning of livestock resulting in severe inflammation particularly of mucous membranes and the eyes. Four esters of 12-deoxyphorbol were isolated from the fresh aerial parts of the plant and their irritant doses 50% (I.D.50) ascertained using female L.A.C.A. mice, 12-Deoxyphorbol-13-phenylacetate-20-acetate was found to be the major component of the toxic fraction and occurred in yields of 0.0012% w/w. This compound was also the most irritant substance isolated and exhibited an I.D.50 of 0.038microgram, and is accordingly considered to be responsible for the major part of the toxicity of E. helioscopia. A high molecular weight aliphatic ester, 12-deoxyphorbol-13-dodecdienoate-20-acetate, was also obtained in low yields. This compound exhibited an I.D.50 of 0.12microgram. The final two esters obtained from the toxic fraction of the plant were the low molecular weight homologues, 12-deoxyphorbol-13-[2-methyl-cis-2-butenoate]-20-acetate and 12-deoxyphorbol-13-[2-methyl-cis-2-butenoate]. These compounds exhibited I.D.50 of 3.09 and 0.72 microgram, respectively and were the least irritant of the series of compounds isolated.

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