Novel biflavonoids from the stem bark of Ochna integerrima

Two new biflavonoids, namely, 6'"-hydroxylophirone B (1) and 6'"-hydroxylophirone B 4"'-O-beta-glucoside (2), were isolated from the stem bark of Ochna integerrima, together with five known compounds. The structures of 1 and 2 were determined by spectral data interpretation.     

7-Hydroxyceratinamine, a new cyanoformamide-containing metabolite from a sponge, Aplysinella sp.

7-Hydroxyceratinamine (1) and the known compounds moloka'iamine (2), ceratinamine (3), and N,N,N-trimethyl-3,5-dibromotyramine (4), were isolated from a Micronesian sponge, Aplysinella sp. The structure of 1, which contains the unusual cyanoformamide moiety, was solved by spectroscopic analysis.     

Halisulfate 7, a new sesterterpene sulfate from a sponge, Coscinoderma sp.

A new sesterterpene sulfate, halisulfate 7 (1), has been isolated from a Coscinoderma sp. of sponge collected at Yap, Federated States of Micronesia. The structure was determined from spectroscopic evidence.     

Two new styryl lactones, 9-deoxygoniopypyrone and 7-epi-goniofufurone, from Goniothalamus giganteus.

Two new styryl lactones, 9-deoxygoniopypyrone [1] and 7-epi-goniofufurone [3], and a known styryl lactone, goniodiol [5], were isolated from the stem bark of Goniothalamus giganteus. The structures were elucidated by ir, ms, 1H-nmr, 13C-nmr, and 1H-1H COSY spectra; the relative configurations were determined by X-ray crystallographic analysis. Unlike goniopypyrone [2] and goniofufurone [4], neither of the new styryl lactones 1 and 3 showed significant bioactivities to human tumor cells. However, goniodiol [5] showed significant and selective cytotoxicity against human lung tumor cells (A-549).     

(2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a new amino alcohol from the caribbean sponge Haliclona vansoesti

The Caribbean marine sponge Haliclona vansoesti was found to contain a high amount (5% dry wt) of a new analogue of 4-sphingenine, (2R,3R, 7Z)-2-aminotetradec-7-ene-1,3-diol (1). Its structure was determined by detailed spectroscopic analysis. The relative configuration was deduced from the NMR data of the corresponding acetonide 5, while the absolute configuration was secured via protection of the primary alcohol and amino groups, and esterification of the secondary alcohol with Mosher's reagent.     

Taraxacin, a new guaianolide from Taraxacum wallichii

A new guaianolide, taraxacin (1), and a known sesquiterpene ketolactone (2) have been isolated from an ethyl acetate-soluble part of a methanolic extract of Taraxacum wallichii. The structure of 1 was established using NMR, MS, and X-ray crystallographic methods. The (13)C NMR data of 2 is also being reported for the first time.     

Nummularogenin, a new spirostane from Zizyphus nummularia

From the C6H6 extract of the whole plant of Zizyphus nummularia, a new (25 S)-spirostane was isolated and characterized as nummularogenin, (25 S)-3 alpha-hydroxy-5 alpha-spirostane-2, 12-dione.     

7-O-6'-O-malonylcachinesidic acid, a new macrocyclic iridoid ester of malonic acid from the Tunisian plant Ajuga pseudoiva

A new iridoid glucoside, 7-O-6'-O-malonylcachinesidic acid (1), was isolated from the leaves of Ajuga pseudoiva and characterized as its triacetyl derivative (1a). Its structure was established by spectroscopic methods and showed an unusual feature, in which an alcoholic function of the iridoid moiety and the primary alcohol of a glucopyranose unit form a 13-membered heterocycle with malonic acid.     

Coproverdine,a novel,cytotoxic marine alkaloid from a new zealand ascidian

The crude extract of a New Zealand ascidian displayed antitumor activity. Bioassay-directed fractionation yielded a novel alkaloid, coproverdine (1). The structure of 1 was assigned on the basis of detailed spectroscopic analysis. Coproverdine (1) was responsible for the antitumor activity of the crude extract.     

Pulcherralpin, a new diterpene ester from Caesalpinia pulcherrima

From the stems of Caesalpinia pulcherrima, the new cassane-type diterpene ester pulcherralpin (1) has been isolated and characterized. The structure of 1 was established through spectroscopic studies, including the 1H-1H homonuclear and 1H-13C heteronuclear correlation studies.     

seco-Hinokiol, a new abietane diterpenoid from Rosmarinus officinalis

seco-Hinokiol (1), a new abietane diterpenoid, has been isolated from the leaves of Rosmarinus officinalis. Its structure was elucidated on the basis of extensive spectroscopic analysis. To our knowledge, this is the fourth report of a seco-abietane having been isolated. In addition, methyl carnosate (4) was synthesized from carnosic acid (3), and detailed NMR spectroscopic data are provided to clarify previous literature reports.     

Genipatriol,a new cycloartane triterpene from Genipa spruceana

Genipatriol (1), a new 2alpha,3beta-dihydroxylated cycloartane triterpene, was isolated from the aerial parts of Genipa spruceana. The structure of genipatriol was determined by a combination of spectroscopic methods.     

Verbaspinoside, a new iridoid glycoside from Verbascum spinosum

A new iridoid glycoside, verbaspinoside (1), was isolated from the aerial parts of Verbascum spinosum. Its structure was elucidated on the basis of chemical and spectral data as 6-O-[(2' '-O-trans-cinnamoyl)-alpha-L-rhamnopyranosyl]-catalpol. Additionally, three known iridoids (aucubin, catalpol, and ajugol) and three phenylpropanoid glycosides [acteoside, angoroside A (2), and angoroside C (3)] were isolated and identified.     

Siamenol, a new carbazole alkaloid from Murraya siamensis

A new carbazole alkaloid, siamenol (1), and two known alkaloids, mahanimbine (2) and mahanimbilol (3), have been isolated from the organic extract of Murraya siamensis. The novel compound exhibited HIV-inhibitory activity.     

Rankinidine, a new indole alkaloid from Gelsemium rankinii

A new oxindole alkaloid, rankinidine (1), has been isolated from the MeOH extract of the stem of Gelsemium rankinii. Its structure was elucidated by comparison with an analog, humantenirine (3), which also occurred in this plant.     

A new anti-HIV alkaloid, drymaritin, and a new C-glycoside flavonoid, diandraflavone, from Drymaria diandra

A novel anti-HIV alkaloid, drymaritin (1), and a new C-glycoside flavonoid, diandraflavone (2), along with eight known compounds, torosaflavone A, isovitexin, spinasterol beta-d-glycoside, p-hydroxybenzoic acid, p-hydroxybenzaldehyde, cis-p-coumarate, methyl 5-hydroxy-4-oxopentanoate, and glycerol-alpha-lignocerate, were isolated from Drymaria diandra. Drymaritin (1) exhibited anti-HIV effects in H9 lymphocytes with an EC(50) value of 0.699 microg/mL and a TI of 20.6. Compound 2 showed significantly selective inhibition on superoxide anion generation from human neutrophils stimulated by fMLP/CB with an IC(50) value of 10.0 microg/mL.     

Retamatrioside, a new flavonol triglycoside from Retama sphaerocarpa

A new flavonol triglycoside, retamatrioside (1), has been isolated from the aerial parts of Retama sphaerocarpa. The structure of 1 has been determined as rhamnazin 3-O-beta-D-glucopyranosyl-(1-->5)-[beta-D-apiofuranosyl(1-->2)]-al pha -L-arabinofuranoside, using spectroscopic methods.     

Sileneoside H, a new phytoecdysteroid from Silene brahuica

Sileneoside H (1), a new phytoecdysteroid, has been isolated from the roots of Silene brahuica and identified as 22-O-alpha-D-galactosylintegristerone A 25-acetate by MS and NMR analysis.