S. K. Adesina, O. Idowu, A. O. Ogundaini, H. Oladimeji, T. A. Olugbade, G. O. Onawunmi and M. Pais, 'Antimicrobial constituents of the leaves of EAcalypha wilkesiana and acalypha hispida'. Phytotherapy research14(5) 2000, 371-374

The original article to which this Erratum refers was published in Phytotherapy Research 14(5) 2000, 371-374. Following publication of this paper in the August 2000 issue of Phytotherapy Research (14(5):371-374), it has come to our attention that the dates of receipt and acceptance were printed incorrectly. The corrected dates appear below. The publishers would like to apologise for any confusion caused. Received 28 August 1996 Accepted 15 June 1997     

Antineoplastic agents. 42. The butterfly, Prioneris thestylis.

Isoguanine (2) was found to be an antineoplastic constituent of Prioneris thestylis Dbldy. wings. Three other purine components of the butterfly wings were identified as hypoxanthine (3), uric acid (4) and xanthine (5). Isolation of urocanic acid (6) from the same wing material represented the first detection of this interesting histidine derivative in an arthropod.     

Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth.

The sensitivity of the human keratinocyte cell line HaCaT to several lichen metabolites isolated from Parmelia nepalensis and Parmelia tinctorum was evaluated. The tridepside gyrophoric acid (6), the dibenzofuran derivative (+)-usnic acid (1), and the didepside diffractaic acid (5) were potent antiproliferative agents and inhibited cell growth, with IC50 values of 1.7, 2.1, and 2.6 microM, respectively. Methyl beta-orcinolcarboxylate (2), ethyl hematommate (3), the didepside atranorin (4), and (+)-protolichesterinic acid (7) did not influence keratinocyte growth at concentrations of 5 microM. Keratinocytes were further tested for their susceptibility to the action of the potent antiproliferative agents on plasma membrane integrity. The release of lactate dehydrogenase activity into the culture medium was unchanged as compared to controls, documenting that the activity of gyrophoric acid (6), (+)-usnic acid (1), and diffractaic acid (5) was due to cytostatic rather than cytotoxic effects.     

Isolation, purification, and cytotoxicity of 5-methoxypodophyllotoxin, a lignan from a root culture of Linum flavum.

A method has been developed for the large scale isolation of 5-methoxypodophyllotoxin [1] from a high-producing root culture derived from Linum flavum. A closely related lignan, 5'-demethoxy-5-methoxypodophyllotoxin [2], was also present in the root culture and was the cause of the main isolation difficulties. Essential steps in the isolation procedure are CH2Cl2 and XAD-4 extraction and XAD-8 cc followed by Si gel chromatography, using two different mobile phases. The isolated 5-methoxypodophyllotoxin [1] was very pure (greater than 99%) and possessed the desired stereochemical configuration, namely (-)-5-methoxypodophyllotoxin [1]. The in vitro cytotoxicity of 5-methoxypodophyllotoxin [1] against EAT and HeLa cells was determined and compared with those of podophyllotoxin [3], etoposide (VP-16-213) [4], teniposide (VM-26) [5], and 5-methoxypodophyllotoxin-4-beta-D-glucoside [6]. It appeared that 5-methoxypodophyllotoxin [1] has about the same cytotoxic potency as podophyllotoxin [3].     

Gelliusterols A--D, new acetylenic sterols from a sponge, Gellius species.

New acetylenic sterols, gelliusterol A (1, 26,27-bisnorcholest-5-en-23-yn-3 beta,7 alpha-diol), its corresponding 7-ketone, gelliusterol B (2, 26,27-bisnorcholest-5-en-23-yn-3 beta-ol-7-one), and gelliusterols C (4, cholest-5-en-23-yn-3 beta,7-one) and D (5, cholest-5-en-23-yn-3 beta,25-diol-7-one), were isolated from an unidentified species of sponge, Gellius sp. The structures of the steroids were established from spectroscopic data.     

R. Daudt, G. L. Von poser, G. Neves and S. M. K. Rates, 'Screening for the antidepressant activity of some species of hypericum from south Brazil'. Phytotherapy research14(5) 2000, 344-346

The original article to which this Erratum refers was published in Phytotherapy Research 14(5) 2000, 344-346. Following the publication of this paper in the August 2000 issue of Phytotherapy Research (14(5):344-346), it has come to our attention that there is a misleading statement regarding conclusions cited from the work of Butterweck et al. 1998. The discussion in the recent PTR paper states that those authors are 'in favour of the hypothesis that the antidepressant activity is due to the hypericin only'. We wish to make it clear that this is not the case, and the Butterweck paper actually concludes that 'both naphthodianthrones must be considered as active constituents of the crude extract of H. perforatum. However, previous studies indicate that the other consitutuents of the crude drug also have activity'. The authors apologize for this error and are happy to correct it.     

Antineoplastic agents, 99. Amaryllis belladonna

Amaryllis belladonna bulbs were examined for constituents inhibitory against the murine P-388 lymphocytic leukemia (PS system). Two in vitro active alkaloids, acetylcaranine (2; 9PS ED50 0.23 microgram/ml) and ambelline (3; 9PS ED50 1.6 micrograms/ml), were isolated accompanied by undulatine. However, the non-chiral anhydrolycorinium chloride (5) was found to be the principal antineoplastic (3 PS, 64-69% life extension at dose levels 10 to 20 mg/kg in vivo, ED50 1.4 micrograms/ml in vitro) component. Quaternary chloride 5 has not been located previously among plant or animal biosynthetic products.     

Antitumor agents. 228. five new agarofurans, Reissantins A-E, and cytotoxic principles from Reissantia buchananii

Twenty-one compounds, including five new agarofuran sesquiterpenes, reissantins A-E (1-5), were isolated from Reissantia buchananii by means of bioassay-directed fractionation and their structures identified from spectral data. Reissantins A-C are the first reported simple agarofuran sesquiterpenes to contain a 5-carboxy-N-methyl-2-pyridone (CNMP) substituent, which has previously been found only in macroring agarofuran pyridine alkaloids. The major terpenoid components, celastrol (6) and its methyl ester derivative, pristimerin (7), were significantly active against nine cancer cell lines, including A549, MCF-7, HCT-8, KB, KB-VIN, U-87-MG, PC-3, 1A9, and PTX10 cell lines, with ED(50) values ranging from 0.076 to 0.34 microg/mL.     

Antineoplastic agents 430. Isolation and structure of cribrostatins 3, 4, and 5 from the republic of maldives cribrochalina species

Continued investigation of cancer-cell growth-inhibitory constituents of the blue marine sponge Cribrochalina sp. has led to discovery of cribrostatins 3 (4a), 4 (5), and 5 (4b) in 10(-5) to 10(-7) % of the wet weight. The structure of cribrostatin 3 (4a) was determined by results of high field (500 MHz) (1)H and (13)C NMR and HRMS interpretations. The same general approach to the structures of cribrostatins 4 (5) and 5 (4b) was completed by X-ray crystal structure determinations. Cribrostatins 3, 4, and 5 provided significant cancer cell line inhibitory activities. Cribrostatins 1 and 2(2) and the newly isolated cribrostatins 3-5 displayed antibacterial and/or antifungal activities.     

Studies on terpenoids produced by actinomycetes: oxaloterpins A, B, C, D, and E, diterpenes from Streptomyces sp. KO-3988

Following screening for terpenoids produced by Streptomyces sp. KO-3988, five new diterpenes named oxaloterpins A (1), B (2), C (3), D (4), and E (5) together with the known viguiepinone (6) were isolated from culture broth, and their structures were established on the basis of extensive NMR and MS analyses. The absolute configuration of oxaloterpin A was determined by the modified Mosher's method as 3 R, 5 S, 8 S, 10 R, 13 S.     

Binding studies for serotoninergic, dopaminergic and noradrenergic receptors of Valeriana adscendens Trel. extracts

Valeriana adscendens Trel. (Valerianaceae) is a psychoactive plant usually used in magical-therapeutic rituals in traditional practices of the Northern Peruvian Andes. Previous studies have been carried out on extracts of aerial parts in order to validate its traditional use. The results indicated that Valeriana adscendens exerts important effects on the central nervous system. Aim of the present study is to evaluate if the effects on the central nervous system of Valeriana adscendens extracts can be associated with interaction with some CNS receptors. In this work we examined affinity and selectivity of two Valeriana adscendens extracts (methanolic and aqueous) towards 5-HT(1A), 5-HT(2A), 5-HT(2C) serotononergic, D(1) and D(2) dopaminergic, alpha(1) and alpha(2) noradrenergic receptors by a preliminary binding screen. The results show weak affinity to 5-HT(1A) for the aqueous extract. Both extracts showed affinity for D(1) receptors, but only for the methanolic extract the IC(50) value was determinable (30.14 microg/ml). No affinity for 5-HT(2A), 5-HT(2C) serotononergic receptors, alpha(1) and alpha(2) noradrenergic receptors and D(2) receptors was recorded for the extracts.     

Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1)

The synthesis of sodium narcistatin (8) was improved (88% overall yield) and the modified reaction sequence was utilized to synthesize three new 3,4-cyclic phosphate prodrugs, sodium 7-deoxynarcistatin (5), sodium 7-deoxy-trans-dihydronarcistatin (6), and sodium trans-dihydronarcistatin (7). The human cancer cell line inhibitory isocarbostyril precursors were isolated from the bulbs of Hymenocallis littoralis obtained by horticultural production or reduction of narciclasine (1a --> 4) from the same source.     

Antineoplastic agents, 88. Pimelea prostrata

The aerial portion of Pimelea prostrata (Thymelaeaceae) collected in New Zealand was evaluated as a source of substances that inhibit growth of the murine P-388 lymphocytic leukemia (PS). Simplexin (1) and Pimelea factor P2 (2) were found to strongly inhibit growth (ED50 5 X 10(-3) and 8 X 10(-4) micrograms/ml, respectively) of the PS in vitro cell line. The cyclic orthoester (2) was also found to inhibit growth (T/C 132 at 20 micrograms/kg) of the PS in vivo system. Detailed 1H-nmr (at 400 MHz) and 13C-nmr studies combined with fast atom bombardment mass spectral evidence were employed to confirm the structural assignments.     

Biological activities of Indian celery, Seseli diffusum (Roxb. ex Sm.) Sant. & Wagh

In continuation of our work on Indian celery (Seseli diffusum (Roxb. ex Sm.) Santapau & Wagh; Umbelliferae), the fractionation of the 80% MeOH-H(2) O extract of the seeds was performed to identify the principles responsible for its folk use as an antispasmodic and diuretic. Several compounds were isolated as active components: seselin (1) and anthriscinol methyl ether (4) showed a selective cytotoxicity to some yeast strains. Compound 1 also showed spasmolytic activity. On the other hand, isopimpinellin (3) and isorutarin (5) exhibited a spasmogenic effect on the smooth muscle preparations. Compound 5 was also found to have antioxidant activity. Among them, compound 4 was isolated for the first time from this plant.     

Novel isoflavone, cinnamic acid, and triterpenoid glycosides in soybean molasses.

Seven known isoflavones, genistein (4), daidzein (5), glycitein (6), formononetin (7), genistin (8), daidzin (9), and glycitein 7-O-beta-D-(6' '-O-acetylglucopyranoside) (10), ferulic acid, and two known saponin glycosides, soysaponin I (14) and soysaponin A2 (15), were isolated from soybean molasses. Several new compounds were also isolated and identified, including three isoflavones (1-3), two cinnamic acid ester glycosides (11) and (12), and a new saponin hexaglycoside (13). The structures of the new compounds were established on the basis of spectral data interpretation.     

Glaciapyrroles A, B, and C, pyrrolosesquiterpenes from a Streptomyces sp. isolated from an Alaskan marine sediment

A Streptomyces sp. (NPS008187) isolated from a marine sediment collected in Alaska was found to produce three new pyrrolosesquiterpenes, glyciapyrroles A (1), B (2), and C (3), along with the known diketopiperazines cyclo(leucyl-prolyl) (4), cyclo(isoleucyl-prolyl) (5), and cyclo(phenylalanyl-prolyl) (6). The structures of 1, 2, and 3 were established using spectroscopic methods.     

Studies on zoapatle, II. Leucanthanolide, a novel sesquiterpene lactone from Montanoa leucantha ssp. leucantha

A sesquiterpene lactone given the trivial name leucanthanolide, from the Mexican zoapatle plant (Montanoa leucantha), long used as an herbal remedy, was isolated and was found to have cytotoxicity but no uterine activity. The compound was isolated from the fraction containing zoapatanol, a substance being investigated for its ability to induce menses, abortion and labor. The compound has a molecular formula of C19H2606, a 5-membered lactone ring, an ester group, and a germacradienolide skeleton. It was evaluated for abortifacient activity in pregnant guinea pigs by intraperitoneal injection on day 22 of gestation. 3 of 5 animals had abnormal fetuses, but there was no evidence of early uterine activity. Cytotoxic testing in vitro was done on KB and P-388 test systems in cell culture. The ED50 of leucanthanolide was 0.57 mcg/ml (KB) and 0.93 (P-388). In comparison, the ethyl acetate fraction had an ED50 of 1.35 mcg/ml and 5.2 mcg/ml respectively.     

Platanionosides A-C, megastigmane diglycosides from the leaves of Alangium platanifolium.

From the leaves of Alangium platanifolium var. platanifolium collected in Fukuoka Prefecture, Japan, three megastigmane diglycosides (1-3) were isolated, along with two known compounds, benzyl alcohol 7-O-beta-D-(6'-O-beta-D-xylopyranosyl)glucopyranoside and Z-hex-3-en-1-ol 1-O-beta-D-glucopyranoside. The structures of the new compounds, named platanionosides A (1), B (2), and C (3) were elucidated by spectroscopic evidence to be 3S,5R,6R,9R, 7E-megastigma-3,9-diol 3,9-di-O-beta-D-glucopyranoside, 3R,9R, 7E-megastigma-5,7-diene-3,9-diol 3,9-di-O-beta-D-glucopyranoside, and 5R,6S,7E-megastigma-3-on-7-en-9-ol 9-O-beta-D-(6'-O-beta-D-xylopyranosyl)glucopyranoside, respectively.     

Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium

Four new polysulfur aromatic alkaloids, lissoclibadins 4 (1), 5 (2), 6 (3), and 7 (4), were isolated from the ascidian Lissoclinum cf. badium collected in Indonesia, together with seven known alkaloids, lissoclibadins 1 (5), 2 (6), and 3 (7), lissoclinotoxins E (8) and F (9), 3,4-dimethoxy-6-(2'-N,N-dimethylaminoethyl)-5-(methylthio)benzotrithiane (10), and N,N-dimethyl-5-(methylthio)varacin (11). Compounds 1-11 were isolated from the ascidian collected in March (wet season), while 5-11 have been obtained previously from the organism collected in September (dry season) at the same site. The structures of the new compounds were assigned on the basis of their spectroscopic data. Lissoclibadins 4-7 (1-4) inhibited the colony formation of Chinese hamster V79 cells with EC50 values of 0.71, 0.06, 0.06, and 0.17 microM, respectively. Compounds 1-4 showed also weak antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Saccharomyces cerevisiae.     

Prismatomerin, a new iridoid from Prismatomeris tetrandra. Structure elucidation, determination of absolute configuration, and cytotoxicity

A new complex iridoid, prismatomerin (1), has been isolated from the leaves of Prismatomeris tetrandra, together with the known glucoside gaertneroside (4). The structures of 1 and 4 were determined by spectroscopic analysis, notably 2D NMR techniques. The (1R,5S,8S,9S,10S)-(-) absolute configuration of prismatomerin (1) was determined by comparison of the vibrational circular dichroism (VCD) spectrum calculated using density functional theory and the experimental VCD spectrum of the O-acetyl derivative 3. Prismatomerin (1) showed remarkable antitumor activity and also interfered with mitotic spindle formation.