Atropurosides A-G, new steroidal saponins from Smilacina atropurpurea

Atropurosides A-G (1-7), seven new steroidal saponins, which possess new polyhydroxylated aglycones, were isolated from the rhizomes of Smilacina atropurpurea (Convallariaceae), together with a known saponin, dioscin (8). Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR techniques and chemical methods. Antifungal testing of the eight compounds indicated that atropurosides B (2) and F (6) were fungicidal against Candida albicans, Candida glabrata, Cryptococcus neoformans, and Aspergillus fumigatus with minimum fungicidal concentrations (MFCs) < or = 20 microg/ml, while dioscin (8) was selectively active against C. albicans and C. glabrata (MFC < or = 5.0 microg/ml). Furthermore, the antifungal saponins 2, 6, and 8 were evaluated for their in vitro cytotoxicities in a panel of human cancer cell lines (SK-MEL, KB, BT-549, SK-OV-3, and HepG2) and non-cancerous Vero cells. All showed moderate cytotoxicities. It appears that the antifungal activity of these steroidal saponins correlates with their cytotoxicity against mammalian cells.     

Bis-iridoids and other constituents from Scabiosa semipapposa

Six undescribed bis-iridoids named Semipapposiridoids A–F (1–6) together with seventeen known compounds were obtained from the roots and aerial parts of Scabiosa semipapposa Salzm. ex DC. Among the known compounds, three lignans were isolated for the first time in Scabiosa species, whereas the other known constituents including iridoids, phenol glycosides and flavonoids were previously isolated from Scabiosa sp. Their structures were assigned on the basis of extensive 1D- and 2D NMR experiments (¹H, ¹³C, COSY, TOCSY, NOESY, HSQC, HMBC), mass spectrometry HR-ESI-MS and by comparison of their spectral data with those of literature values. To the best of our knowledge, this should be the first report on the bis-iridoids content of this plant; furthermore, the fact that the plant is rich in mono-and bis-iridoids will support chemotaxonomy of the genus. The total phenolic and flavonoid contents of the 80% MeOH extracts and fractions were evaluated, with their antioxidant activities using three different methods, namely DPPH, ABTS and CUPRAC. Most of the fractions showed a moderate to good antioxidant activity compared to the standards BHA and BHT.     

Alkylated benzoquinones from Iris kumaonensis

Six novel alkylated p-Benzoquinones irisoquin (A-F) (1-2, 4-7) together with a known cytotoxic quinone, irisoquin (3) along with three known isoflavones, tectoregenin, iristectorin and irigenin were isolated from the rhizomes of Iris kumaonensis and characterized. The structures of compounds 1-2, 4-7 were confirmed by extensive spectroscopic analysis, IR, MS, HRMS, GC, GC-MS, 1D (1H, 13C, NOE) and 2D (HMQC and HMBC) NMR and comparison with literature data of known compounds.     

Hopane-type saponins from Glinus lotoides Linn

Seven hopane-type saponins were isolated from the methanol extract of Glinus lotoides. Six of them were identified as novel compounds and designated as lotoideside A [3-O-beta-D-xylopyranosyl (1-->2)-alpha-L-rhamnopyranosyl-6 alpha-O-beta-D-xylopyranosyl-22-beta-O-beta-D-glucopyranosyl-16 beta-hydroxy hopane (1)], lotoideside B [3-O-beta-D-xylopyranosyl (1-->2)-alpha-L-rhamnopyranosyl-22-beta-O-beta-D-glucopyranosyl-6 alpha,16 beta-dihydroxyhopane (2)], lotoideside C [3-OD-xylopyranosyl-6 alpha-O-beta-D-xylopyranosyl-16 beta-O-beta-D-xylopyranosyl-22 beta-hydroxyhopane (3)], lotoideside D [3-O-beta-D-xylopyranosyl-16 beta-O-alpha-L-arabinopyranosyl-6 alpha,22-beta-dihydroxyhopane (4)], lotoideside E [3-O-beta-D-xylopyranosyl-6 alpha-O-beta-D-xylopyranosyl-16 beta,22-beta-dihydroxyhopane (5)], and lotoideside F [3-O-beta-D-xylopyranosyl-22-beta-O-beta-D-glucopyranosyl-16 beta-hydroxyhopan-6-one (6)]. The known compound succulentoside B (7) was also encountered. Their structures were elucidated on the basis of one-and two-dimensional NMR spectroscopic techniques, ESIMS and chemical evidences.     

Gracillosides A-F, six new 8,14-seco-pregnane glycosides from Adelostemma gracillimum

Six new 8,14-seco-pregnane glycosides, gracillosides A-F (1-6), were isolated from the roots of Adelostemma gracillimum (Asclepiadaceae). All of them had the same aglycone as gracigenin with a rare 8,14-seco-pregnane type skeleton in nature and possessed an oligosaccharide chain consisting of four to six sugar units at C-3 of the aglycone. Their structures were determined on the basis of detailed spectroscopic analysis and chemical evidence.     

Steroidal saponins from the stem of Yucca elephantipes

Ten steroidal saponins with cis-fused A/B ring, including a smilagenin glycoside, elephanoside A (4), and the five furostanol bisdesmosides, elephanosides B-F (6-10), were isolated from the stems of Yucca elephantipes Regel. (Agavaceae). Their structures were determined by detailed chemical and spectroscopic analysis. All the isolated compounds were tested for their in vitro antifungal and antibacterial activities. Only the two known spirostanol glycosides Ys-II (1) and Ys-IV (2) showed moderate inhibitory activity against the growth of Candida albicans and Cryptococcus neoformans.     

Gerronemins A-F, cytotoxic biscatechols from a Gerronema species

The gerronemins A-F (1-6) were isolated as the cytotoxic components of an extract of a Gerronema species detected in a screening for new cytotoxic metabolites from basidiomycetes. Their structures were elucidated by spectroscopic techniques, and they are composed of a C12-C16 alkane or alkene substituted at both ends by 2,3-dihydroxyphenyl groups. The gerronemins blocked the inducible expression of a hCOX-2 and iNOS promoter driven reporter gene with IC50-values of 1-5 microg/ml. In addition, cytotoxic activities were observed which were due the inhibition of cellular macromolecular syntheses.     

New cassane diterpenes from the fruits of Caesalpinia mimosoides Lam.

Six new cassane diterpenes, caesmimosins A-F (1–6) were isolated from the fruits of Caesalpinia mimosoides Lam. Their structures were identified by 1D and 2D NMR spectral data. Compounds 1–6 were evaluated for their cytotoxicity on HL-60, SMMC-7721, A-549, MCF-7 and SW-480 human cancer cell lines, they did not show inhibitory cytotoxic activities at a concentration of 40 μM against the five cell lines.     

Terpenoids from Dysoxylum densiflorum

Three degraded limonoids, dysodensiols A-C (1-3), and three sesquiterpenoids, dysodensiols D-F (4-6), along with 17 known compounds, were isolated from the twigs and leaves of Dysoxylum densiflorum. The structures of compounds 1-6 were established on the basis of extensive spectroscopic analysis.     

Fungitoxic dihydrofuranoisoflavones and related compounds in white lupin,Lupinus albus

Chromatographic investigation of a methanolic extract of white lupin roots has revealed the presence of six new dihydrofuranoisoflavones (lupinisoflavones A-F). Three monoprenylated (3,3-dimethylallyl-substituted) isoflavones (wighteone, luteone and licoisoflavone A), two diprenylated isoflavones [6,3′-di(3,3-dimethylallyl)genistein (lupalbigenin) and 6,3′-di(3,3-dimethylallyl)-2′-hydroxygenistein (2′-hydroxylupalbigenin)] and two pyranoisoflavones (parvisoflavone B and licoisoflavone B) have also been isolated from the same source. In addition to genistein, leaf extracts of L. italbus contain 3′-O-methylorobol which is presumed to be the precursor of lupisoflavone [5,7,4′-trihydroxy-3′-methoxy-6-(3,3-dimethylallyl)isoflavone]. Probable biogenetic relationships between the prenylated, and dihydrofurano-and pyrano-substituted isoflavones in roots and leaves of L. albus are briefly discussed.