Antiproliferative activity and absolute configuration of zonaquinone acetate from the Jamaican alga Stypopodium zonale.

The chemical investigation of specimens of the Jamaican brown alga Stypopodium zonale led to the isolation of a cytotoxic compound, zonaquinone acetate (1), along with known compounds flabellinone, not previously identified in S. zonale, stypoldione, 5',7'-dihydroxy-2'-pentadecylchromone and sargaol. The structures of the metabolites were established by analysis of the spectral data including 1D and 2D NMR experiments while the stereochemistry of 1 was assessed by VCD measurements. Cytotoxic activity was reported in vitro for 1 against breast cancer and colon cancer cell lines at IC(50) values of 19.22-21.62 µM and 17.11-18.35 µM respectively, comparing favorably with standard treatments tamoxifen (17.22-17.32 µM) and fluorouracil (27.03-31.48 µM). When tested with liver cancer cells (Hep G2), no activity was observed. Weak antioxidant activity was observed with 1 but sargaol exhibited high activity.

Chemical composition and biological activity of the essential oil from Jamaican Cleome serrata.

The chemical composition of the essential oil obtained from the aerial parts of Cleome serrata by hydrodistillation was analyzed by employing GC-FID, GC-MS and RI. Fourteen compounds comprising 90.4% of the total oil composition were characterized. The main components identified were (Z)-phytol (53.0%) and di(2-ethylhexyl)-phthalate (DEHP) (14.7%). The oil was evaluated for its in vitro antimicrobial activities against nine pathogenic microorganisms using the filter paper disc diffusion method. Moderate antimicrobial activity was observed against five of the pathogens assayed. In addition, the essential oil was tested against the sweet potato weevil, Cylas formicarius elegantulus. Strong knockdown insecticidal activity was observed.

Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa.

Five different essential oil extractions of the aerial parts of Cleome spinosa Jacq. were examined. The oils obtained by hydrodistillation of the whole aerial parts, aerial parts without flowers (fruit, leaves and stem), flowers, fruits and leaves have been examined by GC-FID and GC-MS. The chemical profiles of the oils reveal the dominance of oxygenated sesqui- and diterpenes, with the exception of the fruit oil, which contained a high content of fatty acids. The most abundant compounds from the whole aerial parts were (Z)-phytol (31.3%), integerrimine (5.5%) and incensole (4.0%). The major compounds from the aerial portion without flowers were caryophyllene oxide (10.5%), (-)-spathulenol (7.5%) and Z-phytol (6.9%). In the flower oil, the main components were 7-alpha-hydroxy manool (23.8%), incensole (9.2%) and sclareol (8.7%). The chief constituents in the fruit oil were tetradecanoic acid (40.6%), (Z)-phytol (6.58%) and sclareol (4.5%). In the leaf oil, (Z)-phytol (19.5%), 7-alpha-hydroxy manool (6.8%) and caryophyllene oxide (4.36%) were the predominant compounds. Antimicrobial activity of the oil obtained from the whole aerial part was evaluated against nine microbial strains using a filter paper disc-diffusion method. The volatile oil showed moderate action against seven of the eight bacteria strains used, with significant inhibitory activity against Streptococcus pyogenes Group A when compared with the standard antibiotics, ampicillin and gentamicin. The fungus, Candida albicans was less sensitive to the essential oil. The oils showed moderate insecticidal activity against Cylas formicarius elegantalus, but possessed no antioxidant activity as indicated by the DPPH method. This represents the first report on the chemical composition of the essential oils from C. spinosa found in Jamaica and the in vitro antioxidant, insecticidal and antimicrobial potential of the oil from the aerial parts.

Bioactivity of amphitoxin, the major constituent of the Jamaican sponge Amphimedon compressa.

Fractionation of the MeOH/CH2Cl2 extract of the sponge Amphimedon compressa afforded the secondary metabolite amphitoxin (1), the structure of which was elucidated by interpretation of 1H- and 13C-NMR data. The crude extract and the fractions containing the metabolite 1 were assessed for ichthyotoxic and insecticidal activity towards Xiphophorus variatus (moon fish) and Cylas formicarius elegantulus (sweet potato weevil), respectively. In addition, the ability of 1 to cause mortality (toxicity and lethal effect) in the rodent Rattus norvegicus (Norway rat) was examined. Moderate insecticidal activity was observed, while the toxicity towards the moon fish was evidenced by the high mortality rates for all the fractions tested. In contrast, the rodent was not affected by the metabolite.

Changes in the contents of oleoresin and pungent bioactive principles of Jamaican ginger (Zingiber officinale Roscoe.) during maturation.

Changes in the yields of the oleoresin and content of pungent bioactive principles: [6], [8], [10] gingerols and [6] shogaol of Jamaican ginger ( Zingiber officinale) were investigated during different stages of maturity (7-9 months). Ethanolic oleoresin extracts were prepared (95%, w/w) by cold maceration of dried ginger powder, and their percentage yields were calculated (w/w). The pungent bioactive principles in the ginger oleoresin were extracted with methanol and quantitatively analyzed by high performance liquid chromatography (HPLC). Ginger harvested at 8 months from Bourbon, Portland had the highest oleoresin yield (8.46 +/- 0.46%). [6] Gingerol was found to be the most abundant pungent bioactive principle in all the oleoresin samples investigated, with the 9 months sample from Bourbon, Portland containing the highest level (28.94 +/- 0.39%). The content of [6] gingerols was also found to be consistently high (7-9 months) in oleoresin samples from Johnson Mountain, St. Thomas (15.12 +/- 0.39 to 16.02 +/- 0.95%). The results suggest that Bourbon in Portland may be the most ideal location for cultivating ginger for high yields and quality, however, Johnson Mountain in St. Thomas could prove to be the least restrictive location, allowing for harvesting of good quality material throughout the maturity period (7-9 months).

Extraction, processing, and storage effects on curcuminoids and oleoresin yields from Curcuma longa L. grown in Jamaica.

Aromatic diarylheptanoid compounds from Curcuma longa Linn grown in Jamaica were quantified by UV-vis spectrophotometry and high-performance liquid chromatographic (HPLC) analyses. The oleoresin yields from ethanolic extracts were quantified and evaluated with regard to the effects of the type of postharvesting process and the type of extraction method conducted on the plant material. Fresh samples that were hot solvent extracted provided the highest oleoresin yields of 15.7% +/- 0.4 ( n = 3), and the lowest oleoresin yields of 7.8% +/- 0.2 ( n = 3) were from the dried milled samples that were cold solvent extracted. Data from the ASTA spectrophotometer assay confirmed that dried samples contained the highest curcuminoid content of 55.5% +/- 2.2 ( n = 6) at the fifth month of storage, and the fresh samples showed a curcuminoid content of 47.1% +/- 6.4 ( n = 6) at the third month of storage. A modified HPLC analysis was used to quantify curcumin content. Data from the HPLC analysis confirmed that the dried treated, hot extracted, room temperature stored samples had the highest curcumin content of 24.3%. A novel high-performance thin layer chromatography (HPTLC) method provided a chemical fingerprint of the C. longa with the use of a commercial curcumin standard.

Efficient synthesis of substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and evaluation of their in vitro antiproliferative/cytotoxic activities.

Substituted 7-methyl-2H,5H-pyrano[4,3-b]pyran-5-ones and related heterocycles 3 were synthesized through an efficient domino Knoevenagel condensation/6pi-electron electrocyclization. In vitro antiproliferative/cytotoxic activity evaluation was performed with human SH-SY5Y neuroblastoma cells and revealed IC(50) values ranging from 6.7 to >200microM. The compound that was most cytotoxic to the neuroblastoma cells, that is, 2-isobutyl-3-isopropyl-7-methyl-2H,5H-pyrano[4,3-b]pyran-5-one (3a), also exhibited necrotic effects on the human IPC melanoma cells.

Biological activity and chemical composition of the essential oil from Jamaican Hyptis verticillata Jacq.

The chemical composition of the essential oil obtained by hydrodistillation from the aerial parts of Hyptis verticillata Jacq. was elucidated by a combination of GC and GC-MS analyses. The oil was dominated by the sesquiterpenoids cadina-4,10(15)-dien-3-one (15.1%) (1) and aromadendr-1(10)-en-9-one (squamulosone) (30.7%) (2). The oil exhibited chemosterilant activities against the cattle tick, Boophilus microplus Canest., and toxic action against adult Cylas formicarius elegantulus Summer, the most destructive pest of sweet potato (Ipomoea species).

Angiotensin converting enzyme inhibiting and anti-dipsogenic activities of euphorbia hirta extracts

The methanol extract obtained from the leaves and stems of Euphorbia hirta inhibited the activity of angiotensin converting enzyme (ACE) by 90 percent and 50 percent at 500 ug and 160 ug respectively using enzyme linked immunosorbent assay (ELISA). The effect of the extract on thirst was examined using Wistar rats. Intraperitoneal administration of 10mg/100mg body wt of the extract significantly (p<0.05) decreased the amount of water consumed by rats. This effect lasted for 2 h.(AU)

Ascaris lumbricoides in the paranasal sinuses of a Jamaican adult

While preparing a routine sagittal section of the human head and neck for the teaching of anatomy, 3 mature Ascaris lumbricoides worms were seen in the maxillary sinus and 3 in the sphenoidal sinus. Of the worms in the maxillary sinus, 2 were males and one was female, while in the sphenoidal sinus all 3 worms were females. The worms measured 7 - 11 cm in length Light microscope examination of the maxillary sinus wall revealed a few eggs of the parasite in close relation to the epithelium. The migratory abilities of A. Lumbricoides adult worms are well documented and most often involve the bile and pancreatic ducts (Asrat & Rogers, 1995). In a endemic area of Kashmir, India, A. Lumbricoides was the cause of acute pancreatis in 23 percent of 256 patients (Khuroo et al., 1992). Worm extraction and biliary drainage were indicated in 32 percent of 156 patients who had acute hepatobiliary and pancreatic ascariasis, and this resulted in rapid relief of symptoms in most patients (Khuroo et al., 1993). In the case represented, the ostia of the sinuses were between 3 and 4 mm in width and were therefore large enough for the passage of the worms as adults. We are not aware of any other report of ectopic ascariasis involving the sinuses. Clinical data on the current case were not available to us. A. Lumbricoides has high fecundity and the fact that only a few eggs were seen in the sinuses suggests that the worms were immature or that there was a reduction in egg production due to overcrowding or lack of adequate nutrition.(AU)

Acaricidal and insecticidal activities of cadina-4, 10 (15)-dien-3-one

The novel assingment of 13C and 1HNMR data for cadina-4,10(15)-dien-3-one obtained from Hyptis verticillata is presented. The study revealed that cadina-4,10(15)-dien-3-one possesses chemosterilant activities against the economically important cattle tick, Boophilus microplus, and toxic action against adult Cylas formicarius the most destructive pest of sweet potato (I pomoea sp.) (AU)

Inactivation of strongyloides stercoralis filariform larvae in vitro by six Jamaican plant extracts and three commercial antihelminthics

In vitro bioassay of (a) aqueous methanol extracts (AME) of the green leaves of mimosa (Mimosa pudica), love weed (Cuscuta americana), vervine (Stachytarpheta jamaicensis), chicken weed (Salvia serotina) and breadfruit (Artocarpus altilis); (b) methanol-water fraction (MWF) of breadfruit leaves, and (c) commercially available drugs albendazole, thiabendazole and levamisole were assayed for nematode inactivating potential, using filariform larvae of Strongyloides stercoralis. Test larvae were obtained from a 10-day-old charcoal coproculture. Bioassays were conducted in Locke's solution, using 100 larvae in each of three replicates. Inactivation was recorded microscopically at 1, 2, 6 and 12 hours, then every 24 hours up to 5 days' incubation. It(50) (time for inactivation of 50 percent of larvae) values read: levamisole and mimosa extract < 1 hour; love weed extract, approximately 2 hours; breadfruit (MWF), 9.5 hours; chicken weed, 20 hours; albendazole, 35 hours; breadfruit (AME), 49 hours; thiabendazole, 74 hours and vervine extract, 81.5 hours. It(95) values followed a similar trend, and were approximately double the It(50) measures. A potential role for locally available natural products in the treatment of strongyloidiasis is highlighted (AU)