Study on chemical constituents of Cyclocarya paliurus

A new dammarane triterpenoid glycoside named cyclocarioside J (1) and other three known triterpenoid glycosides were isolated from the leaves of Cyclocarya paliurus. Based on ESI-MS, HR-ESI-MS, ¹H NMR, ¹³C NMR, and 2D NMR techniques including ¹H–¹H COSY, HMBC, HMQC, and NOESY correlations, the structure of cyclocarioside J was elucidated as (20S,24R)-epoxydammarane 3β,12β,25-trihydroxy-12-O-β-d-quinovopyranosyl-3-O-α-l-arabinopyranoside.     

Cytotoxic triterpenoid saponins from Vaccaria segetalis

By the guidance of bioassay, one new cytotoxic triterpenoid saponin, 3-O-[β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranosyl] quillaic acid 28-O-β-d-glucopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-fucopyranosyl-(1 → 4)]-β-d-fucopyranoside (1), and five known cytotoxic triterpenoid saponins, vaccaroside E (2), vaccaroside G (3), vaccaroside B (4), segetoside H (5) and segetoside I (6), were isolated from Vaccaria segetalis. Their structures were established on the basis of ESI-MS, IR, extensive NMR (¹H NMR, ¹³C NMR, TOCSY, ¹H–¹H COSY, DEPT, HMQC, HMBC and ROESY) analyses, chemical degradation, and by comparing with previously reported data. Compounds 1–6 showed moderate cytotoxic activities against LNcap, P-388 and A-549 cell lines with IC₅₀ values in the range 0.1–12.9 μM.     

Cytototoxic constituents from the bark of Chisocheton cumingianus (Meliaceae)

A new lanostane-type triterpenoid, 3β-hydroxy-25-ethyl-lanost-9(11),24(24′)-diene (1), along with 3β-hydroxy-lanost-7-ene (2) and β-sitosterol-3-O-acetate (3) was isolated from the stem bark of C. cumingianus. The chemical structure of the new compound was elucidated on the basis of spectroscopic data. All of the compounds were evaluated for their cytotoxic effects against P-388 murine leukemia cells. Compounds 1-3 showed cytotoxicity against P-388 murine leukemia cells with IC₅₀ values of 28.8 ± 0.10, 4.29 ± 0.03, and 100.18 ± 0.16 μg/ml, respectively.     

Diterpenoids from the freshwater green algae Rhizoclonium hieroglyphicum with antibacterial activity

Three new isopimarane diterpenes 7β-hydroxy-19α-methylmalonyloxy-isopimara-8(14),15-diene (1), 7β-hydroxy-14-oxo-isopimara-8(9),15-dien-19oic acid (2), and 7β-hydroxy-14-oxo-19α-methylmalonyloxy-isopimara-9(11),15-diene (3) in addition to the known compounds isopimaric acid (4), 7oxo-13-epi-pimara-14,15-dien-18oic acid (5), 7oxo-13-epi-pimara-8,15-dien-18oic acid (6), and 6β-hydroxyisopimaric acid (7) were isolated from the hexane extract of Rhizoclonium hieroglyphicum. The structures of compounds 1–7 were established by 1D and 2D NMR techniques. The isolated diterpenoids were screened for antimicrobial activity against gram-positive and gram-negative bacteria and yeast strains.     

Four new minor taxanes from cell cultures of Taxus chinensis

Four new minor taxanes (1–4) have been isolated from Ts-19 cell cultures of Taxus chinensis together with five known taxanes (5–9) by silica gel chromatography combined with semi-preparative HPLC chromatography. On the basis of the analyses of the chemical and spectroscopic (IR, MS, 1D, and 2D NMR) data, the structures of new compounds were elucidated as 5α-hydroxy-2α,10β-diacetoxy-14β-(3-hydroxy-2-methyl-butyryl)oxytaxa-4(20),11-diene (1), 2α,5α,10β-triacetoxy-14β-(2-hydroxy-propionyl)oxytaxa-4(20),11-diene (2), 2α,5α,10β-triacetoxy-14β-(2-hydroxy-3-methyl-butyryl)oxytaxa-4(20),11-diene (3), and 2α-benzoxy-4α,9α,10β,13α-tetraacetoxytax-11-ene (4), respectively. Compounds 1–5 were pharmacologically evaluated for their cytotoxicities against five human cancer cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780) and their reversing activity towards multi-drug resistance A549/taxol tumor cell line, and the results showed that all of the tested compounds exhibited very low cytotoxicities, while compound 4 possessed twice the reversing activity as that of verapamil at 10 μM.     

Two new triterpenoid glycosides from Cyclocarya paliurus

Two new dammarane triterpenoid glycosides named cyclocarosides B (1) and C (2) were isolated from the leaves of Cyclocarya paliurus. Based on FAB-MS, HRESI-MS, IR, ¹H NMR, ¹³C NMR, and 2D-NMR (HMQC, HMBC, COSY, ROESY) data, the structures of cyclocarosides B (1) and C (2) were elucidated as (20S,24R)-epoxydammarane (3β,12β)-25-hydroxyl-12-O-β-d-quinovopyranosyl-3-O-β-d-quinovopyranoside (1), and (20S,24R)-epoxydammarane (3β, 12β)-25-hydroxyl-12-O-α-l-arabinopyranosyl-3-O-(5′-O-acetyl)-α-l-arabinofuranoside (2).     

Two new steroidal saponins from the biotransformation product of the rhizomes of Dioscorea nipponica

Two new steroidal saponins, dioscins E (1) and F (2), along with nine known steroidal saponins, were isolated from the biotransformation product of the rhizomes of Dioscorea nipponica using Aspergillus oryzae. The structures of new compounds were established as 25(R)-spirost-5-en-21β-methyl-3β-ol-3-O-α- l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside (1) and (25R)-spirost-5-en-3β-ol-7-one 3-O-α- l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside (2) by detailed spectroscopic analyses including 1D and 2D NMR spectral data (¹H–¹H COSY, HSQC, and HMBC) and MS spectrometry.     

New steroidal glycosides from the rhizome of Anemarrhena asphodeloides

Two new steroidal saponins, timosaponin X (1) and timosaponin Y (2), and one new pregnane glycoside, timopregnane B (3), were isolated from the rhizomes of Anemarrhena asphodeloides, as well as three known compounds 25S-timosaponin BII (4), protodesgalactotigonin (5), and timosaponin BII-a (6) isolated from this plant for the first time. By the detailed analysis of 1D, 2D NMR, MS spectra, and chemical evidences, the structures of new compounds were elucidated as 26-O-β-d-glucopyranosyl-(25S)-5β-22-methoxy-furost-3β,26-diol 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranoside (1), 5β-pseudo-spirost-3β,15α,23α-triol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (2), (5β,17α)-Δ¹⁶⁽¹⁷⁾-20-one-pregn-2β,3β-diol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside (3).     

Water-soluble constituents from the leaves of Ilex oblonga

Four new water-soluble constituents, oblongaroside A (1), oblongar ester A (2), oblongaroside B (3), and oblongaroside C (4), were isolated along with four known compounds: 4-O-β-d-glucopyranosyl-3-hydroxybenzalcohol (5), 7-methoxyl-4-O-β-d-glucopyranosyl-3-hydroxybenzalcohol (6), 4-O-β-d-glucopyranosyl-3-hydroxybenzoic acid (7), and 3,4-dihydroxybenzoic acid (8) from the leaves of Ilex oblonga. Identification of their structures was achieved by 1D and 2D NMR experiments, including ¹H–¹H COSY, NOESY, HMQC, and HMBC methods and FAB mass spectral data.     

Two new furostanol saponins from the fibrous root of Ophiopogon japonicus

Two new furostanol saponins ophiopogonins J (1) and K (2) were isolated from the fibrous roots of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-14-hydroxy-furost-5,20(22)-diene 3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (1), and (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-furost-5,20(22)-diene 3-O-α-l-rhamnopyranosyl-(1 → 2)[(β-d-xylopyranosyl-(1 → 4)-β-d-glucopyranoside)] (2) on the basis of spectroscopic means including HRESIMS, 1D, and 2D NMR experiments.     

Two new triterpenoid saponins from Ilex cornuta

Two new triterpenoid saponins (1 and 2) were isolated from the stems of Ilex cornuta, along with two known triterpenoids (3 and 4). The structures of compounds 1 and 2 were determined as ursane-12,19-diene-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (1), 3α,23α-dihydroxy-olean-9(11),12-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (2), on the basis of hydrolysis and spectral evidence, including 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) analyses. Protective effects of compounds 1–4 were tested against H₂O₂-induced H9c2 cardiomyocyte injury, and the data showed that all these compounds had no cell-protective effect.     

Ergostane steroids from the ethanol extract of Dysoxylum mollissimum

Three new ergostane steroids, 7α-acetoxyl-ergosta-5,24(28)-diene-3β,4β,20S-triol (1), 7α-acetoxyl-ergosta-5,24(28)-diene-3β,4β-diol (2), and 7α-acetoxyl-ergosta-5,24(28)-3β-ol (3) were isolated from the ethanol extract of stem bark of Dysoxylum mollissimum BI. Structural elucidation of all the compounds was performed by spectral methods such as 1D and 2D (¹H-¹H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. All the isolated steroids were in vitro evaluated for their anti-inflammatory activity against COX-1 and COX-2. As a result, steroids 1–3 exhibited modest selective inhibition for COX-1 (>60%).     

Schisanlactone H and sphenanthin A,new metabolites from Schisandra sphenanthera

From the fruits of Schisandra sphenanthera (Schisandraceae), a new 3,4-seco-lanostane triterpenoid, schisanlactone H (1), and a new monocyclofarnesane sesquiterpenoid, sphenanthin A (2), were isolated. Their structures were elucidated by spectroscopic methods including extensive 1D and 2D NMR techniques.     

Triterpenoid Saponin from Primula Elatior Subsp. Meyeri

Abstract

A new triterpenoid saponin, protoprimuloside B (2), has been isolated from the roots of Primula elatior subsp. meyeri and its structure deduced as 3β-O-{[α-L-rhamnopyranosyl-(1–2)-β-D-galactopyranosyl-(1–3)]-[β-D-glucopyranosyl-(1–2)]-β-D-glucopyranosyl}-protoprimuloside B by means of spectral data, especially NMR (400 MHz), including ¹H, ¹³C, DEPT, COSY, HMBC, HMQC, NOESY techniques and (+)FAB-MS spectrum.     

Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum

Three new germacrane sesquiterpenes, eupalinolides C–E (1–3), along with three known germacrane sesquiterpenes, eupalinolide A (4), eupalinolide B (5), and 3β-acetoxy-8β-(4′-hydroxytigloyloxy)-14-hydroxycostunolide (6), were isolated from Eupatorium lindleyanum. They were tested for cytotoxicity against A-549, BGC-823, SMMC-7721, and HL-60 tumour cell lines. The results showed that these compounds demonstrated potent cytotoxicity. The structures of the compounds were elucidated by means of ¹H and ¹³C NMR spectroscopic analysis, including 2D NMR experiments.     

Note: A new compound from Rhododendren anthopogonosides maxim

A new compound, (2R)-4-phenyl-2-O-[β-d-xylopyranosyl(1→6)-β-d-glucopyranosyl]butane (1), has been isolated from the aerial parts of Rhododendren anthopogonoides, together with two known compounds, fraxin (2), and lyoniside (3). Their structures were determined by means of physico-chemical evidence and spectral analyses, including UV, IR, HR-FABMS, ¹H and ¹³C NMR, and 2D NMR data.     

Microbial transformation of hederagenin by Cunninghamella echinulate,Mucor subtilissimus,and Pseudomonas oleovorans

The pentacyclic triterpenoid hederagenin (1) was subjected to biotransformation by Cunninghamella echinulate CGMCC 3.2000, Mucor subtilissimus CGMCC 3.2454 and Pseudomonas oleovorans CGMCC 1.1641. Three metabolites were obtained. On the basis of nuclear magnetic resonance and high-resolution mass spectral analyses, their structures were characterized as 3β, 23-dihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranosyl ester (2), 3β, 15α, 23-trihydroxyolean-12-en-28-oic acid (3), 1β, 3β, 23-trihydroxyolean-12-en-28-oic acid (4), and metabolite (3) was a new compound. This was the first report on the biotransformation of hederagenin.     

Soulieoside O,a new cyclolanostane triterpenoid glycoside from Souliea vaginata

A new cyclolanostane triterpenoid glycoside, soulieoside O (1), together with 25-O-acetylcimigenol-3-O-β-d-xylopyranoside (2) and cimigenol-3-O-β-d-xylopyranoside (3), was isolated from the rhizomes of Souliea vaginata. Their structures were characterized by spectroscopic analysis and chemical methods. The new compound showed moderate inhibitory activity against three human cancer cell lines with IC₅₀ values of 9.3–22.5 μM.     

Four new taraxastane-type triterpenoic acids from Cirsium setosum

Four new taraxastane-type triterpenoids acids 3β,22α-dihydroxy-20-taraxasten-30-oic acid (1), 3β-hydroxy-22-oxo-20-taraxasten-30-oic acid (2), 3-oxo-22α-hydroxy-20- taraxasten-30-oic acid (3), and 3β,19β-dihydroxy-20-taraxasten-30-oic acid (4) were isolated and characterized from Cirsium setosum (Willd.) MB. Their structures were determined by the combination of 1D and 2D NMR experiments (¹H-¹HCOSY, HSQC, HMBC and ROESY) and mass spectrometry. Compound 2 exhibited potent selective cytotoxicity against human ovarian cancer cell line A2780 with an IC₅₀ value of 3.9 μM.     

A New Triterpenoid from Stelmatocrypton khasianum

Abstract

A new triterpenoid, 2α-,3β-,19α-trihydroxy-urs-12-ene-24,28-dioic acid (1), along with two known compounds, 3β-acetoxy-urs-12-ene-11-one (2) and vomifoliol (3), was isolated from stems of Stelmatocrypton khasianum for the first time. Their structures were elucidated on the basis of chemical and spectroscopic methods.