A pregnane ester and its glycoside from Orthenthera viminea

A new pregnane ester named ornogenin and its diglycoside designated as ornine were isolated from the dried twigs of Orthenthera viminea. On the basis of chemical and spectroscopic evidence, their structures were established as 12,20-di-O-cinnamoyl-sarcostin and 12,20-di-O-cinnamoyl-sarcostin-3-O-α-L-oleandropyranosyl(1 → 4)-O-β-D-cymaropyranoside, respectively.     

A pregnane ester diglycoside from Sarcostemma brevistigma

A pregnane ester diglycoside, brevinine, has been isolated from the dried twigs of Sarcostemma brevistigma. Its chemical and spectroscopic data are consistent with the structure 11-O-benzoyl-sarcogenin-3-O-α-L-diginopyranosyl-(1 → 4)-α-L-diginopyranoside.     

A pregnane ester diglycoside from periploca calophylla

A new pregnane ester diglycoside of ornogenin named as plocinine was isolated from the dried twigs of Periploca calophylla. On the basis of chemical and spectroscopic evidences its structure was established as 12,20-di-O-cinnamoyl sarcostin-3-O-α-L-oleandropyranosyl (1 → 4)-O-α-L-oleandropyranoside.     

A pregnane ester triglycoside from Sarcostemma brevistigma

A new pregnane ester glycoside, brevine, was isolated from the dried twigs of Sarcostemma brevistigma. Its chemical and spectroscopic properties were consistent with the structure 11-O-benzoyl-sarcogenin-3-O-α-L-diginopyranosyl (1 → 4)-O-α-L-diginopyranosyl(1 → 4)-O-α-L-diginopyranoside.     

A pregnane ester diglycoside from hemidesmus indicus

A new pregnane ester diglycoside named desinine has been isolated from the dried twigs of Hemidesmus indicus. On the basis of chemical and spectroscopic evidence, its structure has been established as drevogenin B-3-O-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranoside.     

A pregnane ester glycoside from Periploca calophylla

A new pregnane ester genin, plocigenin, and a new pregnane ester diglycoside, plocin, have been isolated from the dried twigs of Periploca calophylla. The chemical and spectroscopic properties are consistent with the structures 12,20-di-O-benzoyl drevogenin-D and 12,20-di-O-benzoyl drevogenin-D-3-O-β-D-oleandropyranosyl (1 → 4)-O-β-oleandropyranoside, respectively.     

Two pregnane ester glycosides from Pergularia pallida

Two new pregnane ester glycosides designated as pallidine and pallidinine have been isolated from the dried twigs of Pergularia pallida. Chemical and spectroscopic evidences are consistent with the structure 12,20-di-O-benzoyl sarcostin-3-O-β-d-oleandroside and 12,20-di-O-benzoyl-sarcostin-3-O-β-d-cymaropyranosyl(1 → 4)-β-d-oleandropyranoside for pallidine and pallidinine respectively.     

Cissogenin,a pregnane genin from Marsdenia tenacissima

A new polyhydroxy pregnane designated as cissogenin has been isolated from the seeds of Marsdenia tenacissima. Its structure has been established as 3β,11α,12β,14β,20 S-pentahydroxy-pregn-5-ene.     

Tenasogenin,a pregnane ester from Marsdenia tenacissima

A new polyhydroxy pregnane ester named tenasogenin was isolated from the seeds of Marsdenia tenacissima. On the basis of chemical and spectroscopic evidence and identification of its hydrolysis products, its structure has been established as 11α-O-β,β-dimethylacryloyl-3β,12β,14β,20R-tetrahydroxypregn-5-ene.     

Acylated pregnane glycosides from Caralluma russeliana

The chloroform extract of the aerial parts of Caralluma russeliana yielded four acylated pregnane glycosides, namely russeliosides E-H, three were found now. The structures of the compounds were elucidated using MS, 1H NMR, 13C NMR, 1H-1H COSY, HMQC, NOESY and HMBC experiments.     

Melanogenesis inhibitory pregnane glycosides from Cynanchum atratum

Bioassay-guided fractionation of the methanolic extract from the roots of Cynanchum atratum has resulted in the isolation of three new pregnane glycosides (1–3) along with four known compounds (4–7). Their structures were identified by analysis of the spectroscopic data including extensive 2D NMR. All of the isolates were evaluated for their potential to inhibit the melanin production in α-melanocyte stimulating hormone (α-MSH)-activated B16 melanoma cells. Of these, compounds 4–7 dose-dependently inhibited the melanin production with the IC₅₀ values ranging from 4?μM to 33?μM.     

Twelve pregnane glycosides from Cynanchum atratum

Eleven new 14,15-seco-pregnane-type steroidal glycosides, cynanosides P₁-P₅, Q₁-Q₃, R₁-R₃, and a novel 12,13-seco-14,18-nor-pregnane-type steroidal glycoside, cynanoside S, were isolated from the roots of Cynanchum atratum, together with four known compounds, atratoside C, sublanceoside E₃, chekiangensoside C and cynatroside B. Their structures were determined on the basis of spectroscopic analysis and chemical evidence.     

Flavescin: A new 1-ketopolyhydroxypregnene from Marsdenia flavescens

A new polyhydroxy-1-ketosteroid, flavescin, was isolated from Marsdenia flavescens A. Cunn. Its structure was elucidated as 12-O-acetyl-3β,8β,12β,14β-20-pentahydroxy-Δ⁵- pregnene-1-one.     

Separation of the pentacyclic triterpenes tylolupenols A and B from Tylophora kerrii

Tylolupenols A and B from Tylophora kerrii were separated and identified as D:C-friedolup-8(9)-en-3β-ol and D:C-friedolup-9(11)-en-3β-ol, respectively.     

New pregnane glycosides from Caralluma dalzielii

Twenty-seven new pregnane glycosides were isolated from the whole plant of Caralluma dalzielii, and their structures elucidated from extensive 2D NMR analysis as well as ESI-MS experiments. All isolated compounds were tested for their antiproliferative activity on J774.A1, HEK-293, and WEHI-164 cell lines. Moderate to high potency of cytotoxicities were found in almost all tested compounds, confirming the significant cytotoxic activity of pregnane glycosides.     

Three new cardenolides from the milkweeds Asclepias eriocarpa and A. Labriformis

Asclepias eriocarpa and A. labriformis contain three new cardenolides, the structures of which have been partially assigned by their spectral properties and comparison with the known cardenolides of A. curassavica. They include labriformin (C₃₁H₃₉O₁₀NS), labriformidin (C₂₉H₃₁O₁₁) and eriocarpin.     

Sarcogenin,a pregnane derivative from Pergularia pallida and Sarcostemma brevistigma

A new pregnane genin, designated as sarcogenin has been isolated from Pergularia pallida and Sarcostemma brevistigma and characterized as 3β,8β,11α,12β,14β,17β-hexahydroxypregn-5-en-20-one.     

Buchananine,a novel pyridine alkaloid from Cryptolepis buchanani

A new alkaloid, buchananine, was isolated from the stems of Cryptolepis buchanani. Its structure was determined as 6-O-nicotinoyl-α-d-glucopyranose by chemical and spectroscopic investigations.     

Tylophorinicine,a phenanthroindolizidine alkaloid from tylophora asthmatica and pergularia pallida

Tylophorinicine, a minor alkaloid isolated from the roots of Tylophora asthmatica and Pergularia pallida has been characterized as 14-hydroxytylophorine from physical and chemical evidence.     

Phenolic hydroxyl ionization in calotropins from Calotropis gigantea latex

The ionization of the phenolic hydroxyl groups in calotropins DI and DII isolated from the latex of Calotropis gigantea has been studied by spectrophotometric titration at 295 nm in the pH range 6–13.2. Of the 12 tyrosine residues of calotropin DI and 13 tyrosine residues of calotropin DII, only four residues were ionized reversibly in the pH range 8.9–10.7 with the apparent pK of 9.7. The remaining tyrosine residues were ionized irreversibly in the pH range 11.2–13.2 with the apparent pK of 11.5. Both calotropins showed time-dependent ionization of phenolic groups at 295 nm in the pH range 11.5–12.0. Chemical modification with tetranitromethane suggested the presence of three tyrosine residues on the surface of each calotropin molecule.