12,20-Epoxypregnane Glycosides from the Roots of Oxypetalum caeruleum.

The MeOH extract from dried roots of Oxypetalum caeruleum (Apocynaceae, formerly known as Asclepiadaceae) plants yielded twenty new pregnane glycosides, some of which had a new 12,20-epoxy type aglycone. The structures of these compounds were established using NMR, MS spectroscopic analysis and chemical evidence.

C21 Steroidal Glycosides from the Roots of Oxypetalum caeruleum.

The MeOH extract from dried roots of Oxypetalum caeruleum (Apocynaceae) plants yielded seventeen new pregnane glycosides, some of which had the acylated-ramanone or -isoramanone type aglycone. The structures of these compounds were established using NMR, MS spectroscopic analysis and chemical evidence.

Tetracyclic Triterpenoids, Steroids and Lignanes from the Aerial Parts of Oxypetalum caeruleum.

The MeOH extract from dried aerial parts of Oxypetalum caeruleum (Apocynaceae) plants yielded seventeen compounds, including four new tetracyclic triterpenoids, one pregnane glycoside, two lignane glycosides, and ten known compounds. The structures of the new compounds were established using NMR, MS spectroscopic analysis and chemical evidence.

An immunochromatographic assay for rapid etection of salvinorin A.

We developed an immunochromatographic assay (ICA) that enables rapid analysis of salvinorin A (Sal A) in Salvia divinorum within 10 min. The result shows that no Sal A in other samples of Lamiaceae plants was detected, but it could recognize Sal A among other substances in complex samples. The main advantage of the ICA is its high performance in combination with low cost, simplicity, and speed. Our newly developed combined ICA/indirect competitive ELISA(icELISA) system enables analysis of large numbers of samples over short periods of time without cumbersome pretreatments in complex mixtures. This method can complement other instrumental analyses for salvinorins, and could be used to deter S. divinorum abuse.

Chrotacumines G-J, chromone alkaloids from Dysoxylum acutangulum with osteoclast differentiation inhibitory activity.

Four new chromone alkaloids, chrotacumines G-J (1-4), have been isolated from the barks of Dysoxylum acutangulum. Their structures and absolute configurations were elucidated on the basis of NMR and CD data. Chrotacumines G and J (1 and 4) showed osteoclast differentiation inhibitory activity in a dose dependent manner.

Transannular cyclization of (4S,5S)-germacrone-4,5-epoxide under basic conditions to yield eudesmane-type sesquiterpenes.

Transannular cyclizations of germacrone-4,5-epoxide under acidic and thermal conditions have been reported in our previous study. However, this process gave the different and interesting results under basic conditions. (4S,5S)-Germacrone-4,5-epoxide (1) was treated under basic conditions to yield four products (2-5). Compound 2 was an isomer of 1--(4S,5S,9Z)-4,5-epoxygermacra-7(11),9-dien-8-one--and the remaining three compounds (3-5) were eudesmane-type derivatives. Compounds 4 and 5 are new compounds. The structures of the new compounds were determined using high resolution (HR)-MS, one dimensional (1D)-NMR, 2D-NMR and circular dichroism (CD) spectroscopic data. Products 3-5 had the same carbon skeleton as that of eudesmane-type compounds; however, these compounds showed different arrangement of isoprene units to the natural eudesmane-type sesquiterpenes.

Development of an enzyme immunoassay using a monoclonal antibody against the psychoactive diterpenoid salvinorin A.

Salvinorin A (1), the main active constituent in Salvia divinorum, is a highly selective kappa-opioid receptor agonist with hallucinogenic effects, which is regulated in several countries. In the present study, a monoclonal antibody (mAb) against 1 was prepared, and an indirect competitive enzyme-linked immunosorbent assay (icELISA) system was developed for the detection of salvinorins. To raise mAbs against 1, salvinorin B (2) hemisuccinate was synthesized and used to prepare the immunogen 2-bovine serum albumin conjugate. This technique was used to prepare a hybridoma cell line, 3D5, which secreted a mAb that recognized 1. The mAb was shown to have specificity for 1 and other salvinorins in cross-reactivity tests. The intra-assay calibration range by icELISA using the mAb against 1 was 0.0195-0.625 µg/mL. After validating the icELISA using intra- and interassays, a recovery experiment and analysis of several plants in the family Lamiaceae, including S. divinorum, confirmed that the analytical method based on ELISA is not only simple but also precise, accurate, sensitive, and sufficiently reliable. The results indicate that icELISA is a useful tool in the identification of S. divinorum.

Mosquito Larvicidal Activity of Compounds from Unripe Fruit Peel of Avocado (Persea americana Mill.).

Mosquitoes are important vectors responsible for spreading a number of diseases affecting both humans and animals. Many diseases as dengue, chikungunya, yellow fever, malaria, filariasis and Japanese encephalitis are spread by mosquitoes. There are many reports of plant extracts and their active constituents showing anti-mosquito activities as larvicidal, pupicidal, ovicidal and adulticidal activities. Persea americana Mill. (Lauraceae), known as avocado, has been reported to show many pharmacological and antimicrobial activities. In this communication, the mosquito larvicidal activities of the three-active constituents, avocadene, avocadyne and avocadenol-A, from the methanolic extract of the unripe fruit peel are presented. The three mosquito species studied were Aedes aegypti, Culex quinquefasciatus and Anopheles stephensi. All three compounds showed the highest larvicidal activity against An. stephensi, LC50 values being 2.80ppm for avocadene, 2.33ppm for avocadyne and 2.07ppm for avocadenol-A. Avocadene showed larvicidal activity of 3.73ppm against Ae. aegypti and 5.96ppm against Cx. quinquefasciatus. The LC50 value of avocadyne was 5.35ppm against Ae. aegypti and 3.98ppm against Cx. quinquefasciatus. Similarly, avocadenol-A showed 6.56ppm against Ae. aegypti and 2.35ppm against Cx. quinquefasciatus. The active constituents were isolated by bioactivity-guided fractionation by silica gel column chromatography and RP HPLC. The compounds were identified by physical and spectroscopic data and compared with literature values already reported.

New tricyclic alkaloids, cassiarins G, H, J, and K from leaves of Cassia siamea.

Four new alkaloids, cassiarins G, H, J, and K (1-4) which showed moderate antiplasmodial activity against Plasmodium falciparum 3D7, were isolated from the leaves of Cassia siamea (Leguminosae) and the structures of 1-4 were elucidated by 1D- and 2D-NMR analysis and X-ray crystallographic analysis.

Sabiperones A-F, new diterpenoids from Juniperus sabina.

Six new diterpenoids, sabiperones A-F (1-6) have been isolated from the aerial part of Juniperus sabina. Their structures were elucidated by spectroscopic methods including 2D NMR techniques. Sabiperone F showed moderate cell growth inhibitory activities against five human cancer cell lines.

Leishmanicidal active withanolides from a pakistani medicinal plant, Withania coagulans.

In the course of screening for leishmanicidal constituents from Asian and South American medicinal plants, a Pakistani medicinal plant, Withania coagulans, showed activity. We therefore studied the active components of the methanol extract of aerial parts of W. coagulans. From the ethyl acetate soluble fraction of the extract, four new withanolides (1-4) were isolated along with seven known withanolides (5-11). The new compounds were elucidated to be (14R,15R,17S,20S,22R)-14,15,17,20-tetrahydroxy-1-oxowitha-2,5,24-trienolide (1), (14R,15R,17S,20S,22R)-14,15,17,20-tetrahydroxy-1-oxowitha-3,5,24-trienolide (2), (14S,17R,20S,22R)-14,17,20-trihydroxy-1-oxowitha-2,5,24-trienolide (3), and (14S,17R,20S,22R)-14,17,20-trihydroxy-1-oxowitha-3,5,24-trienolide (4), from 1H-NMR, 13C-NMR, 2D-NMR and high resolution (HR)-MS data. Some of these compounds having the partial structure 1-oxo-2,5-diene showed strong leishmanicidal activity against Leishmania major.

Rupestines F-M, new guaipyridine sesquiterpene alkaloids from Artemisia rupestris.

Eight new guaipyridine sesquiterpene alkaloids, rupestines F-M (1-8) were isolated from the leaves of Artemisia rupestris and their structures were elucidated on the basis of 2D-NMR data. The absolute configurations of 1-8 have been assigned by comparison of their experimental and calculated circular dichroism (CD) spectra.

Chukranoids A-I, isopimarane diterpenoids from Chukrasia velutina.

Bioactivity guided separation of Chukrasia velutina root methanolic extract led to the isolation of nine new isopimarane diterpenoids, chukranoids A-I (1-9). The absolute configuration was then assigned by comparing the experimental CD spectra and the calculated CD spectra. Chukranoids A-I (1-9) showed moderate antimalarial activity against Plasmodium falciparum 3D7 strain. It seems that conjugate system in the isopimarane skeleton may influence their antimalarial activity.

Walsogynes H-O from Walsura chrysogyne.

Eight new limonoids, walsogynes H-O (1-8) were isolated from the barks of Walsura chrysogyne, and their structures were determined on the basis of the 1D and 2D NMR data. Walsogynes H-M (1-6) and O (8) were concluded to be 11,12-seco limonoids with a dodecahydro-1H-naphtho[1,8-bc:3,4-c']difuran skeleton, and walsogyne N (7) to be 11,12-seco limonoid sharing a unique dodecahydronaphtho[1,8-bc:5,4-b'c']difuran skeleton. Walsogynes H-O (1-8) exhibited potent antimalarial activity against Plasmodium falciparum 3D7 strain with IC50 value of 2.5, 2.6, 1.6, 2.5, 1.5, 2.6, 2.1, and 1.1 µM, respectively.

Sesquiterpenes from Blumea balsamifera.

Five new guaiane sesquiterpenes, blumeaenes E1 (1), E2 (2), K (3), L (4), and M (5), and one new eudesmane sesquiterpene, samboginone (6), along with three known compounds, cryptomeridiol, 3,3',5,7-tetrahydroxy-4'-methoxyflavanone, and austroinulin, were isolated from the leaves of the Philippine medicinal herb sambong, Blumea balsamifera. The absolute configuration of the new guaiane core was determined as 1S,7S,9S,10R by employing the modified Mosher's method. In the structure of 1, the absolute configuration of the epoxyangelic acid moiety was identified as 2S,3S using (R)-PGME as a chiral anisotropic auxiliary.

Chisomicines A-C, limonoids from Chisocheton ceramicus.

Three new limonoids, chisomicines A-C (1-3), have been isolated from the bark of Chisocheton ceramicus. Their structures were determined by 2D NMR, CD spectroscopic methods, and X-ray analysis. Chisomicine A (1) exhibited NO production inhibitory activity in J774.1 cells stimulated by LPS dose-dependently at high cell viability.

Neolamarckines A and B, new indole alkaloids from Neolamarckia cadamba.

Two new indole alkaloids, neolamarckines A and B (1, 2) were isolated from the leaves of Neolamarckia cadamba (Rubiaceae). Structural elucidation of 1 and 2 was performed by combination of 2D-NMR and circular dichroism (CD) spectra, and chemical correlations. Neolamarckine A (1) showed inhibition of inducible nitric oxide synthase (iNOS) dose dependently.

Pseuduvarines A and B, two new cytotoxic dioxoaporphine alkaloids from Pseuduvaria rugosa.

Pseuduvarines A (1) and B (2), two new dioxoaporphine alkaloids with an amino moiety, were isolated from the stem bark of Pseuduvaria rugosa and their structures were elucidated by combination of 2D-NMR spectroscopic analysis. Pseuduvarines A (1) and B (2) showed cytotoxicity against MCF7, HepG2, and HL-60 (1: IC50, 0.9, 21.7, and >50.0 µM, respectively, 2: IC50 >50.0, 15.7, and 12.4 µM, respectively).

Three new constituents from the roots of Erythrina variegata and their antibacterial activity against methicillin-resistant Staphylococcus aureus.

Two new isoflavonoids, eryvarins V and W (1 and 2, resp.), and a new chromen-4-one derivative, eryvarin X (3), along with three known isoflavonoids, 4-6, were isolated from the roots of Erythrina variegata. Their structures were established by spectroscopic analyses. Compound 1 is a rare naturally occurring isoflavanone which possesses a OH group at C(3). Among the new compounds 1-3, 2 exhibited a potent antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strains.

Triterpenoids from Walsura trichostemon.

Bioactivity guided separation of Walsura trichostemon stem methanolic extract led to the isolation of four new dammarane (1-4) and two new apotirucallane triterpenoids (5-6), together with one limonoid (7), 11,25-dideacetyltrichostemonate, 12ß, 20S, 24R-trihydroxydammar-25-en-3-one and 12ß, 20S, 25-trihydroxydammar-23-en-3-one. Compounds 1-7 showed in vitro inhibitory activity on the proliferation of A549, human lung adenocarcinoma cell line.