A new bibenzyl derivative with nuclear factor-kappaB inhibitory activity from Schefflera arboricola (Araliaceae)

A new bibenzyl derivative (1), 4-acetoxy-3,5,3′,4′-tetramethoxybibenzyl, along with eight known compounds (2–9), was isolated from the twigs and leaves of Schefflera arboricola (Araliaceae). The isolated compounds were elucidated mainly by means of one-dimensional, two-dimensional NMR and MS, and by comparison with the literature data. Compounds 2–5 and 7–9 are first reported from this plant. In the in vitro assays, compound 1 displayed moderate nuclear factor-kappaB inhibitory activity.     

Two New Triterpenoid Saponins from Stauntonia obovatifoliola Hayata ssp. intermedia

Two new hederagenin‐type saponins, staunoside G ( 1 ) and staunoside H ( 2 ), along with twelve known triterpenoid saponins, were isolated from stems of Stauntonia obovatifoliola Hayata ssp. intermedia. Their structures were determined by analysis of HR‐EI‐MS, and 1D‐ and 2D‐NMR data, and comparison with those in literature. The two new compounds showed moderate cytotoxicities against three tumor cells, i.e., A549 (lung carcinoma), 4T1 (mammary carcinoma), and HeLa (cervical carcinoma).     

Three New Triterpenoid Saponins from Ardisia crenata

Three new triterpenoid saponins, ardisicrenoside I ( 1 ), ardisicrenoside J ( 2 ), and ardisicrenoside M ( 3 ), along with eight known compounds, were isolated from the roots of Ardisia crenata Sims . Their structures were elucidated as 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 1 ), 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 2 ), 30,30‐dimethoxy‐16‐oxo‐3β‐O‐{β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 3 ), ardisiacrispin A ( 4 ), ardisiacrispin B ( 5 ), ardisicrenoside B ( 6 ), ardisicrenoside A ( 7 ), ardisicrenoside H ( 8 ), ardisicrenoside G ( 9 ), cyclamiretin A‐3β‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐arabinopyranoside ( 10 ), and cyclamiretin A‐3β‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐arabinopyranoside ( 11 ) by means of chemical and spectral analysis, and their cytotoxicities were evaluated in vitro.     

Pentacyclic Triterpenoid Saponins from Silene viscidula

Three new pentacyclic triterpenoid saponins, viscidulosides A and B ( 1 and 2 , resp.), and silenoviscoside D ( 3 ), were isolated from the roots of Silene viscidula, together with two known saponins, sinocrassulosides VIII and IX ( 4 and 5 , resp.). Their structures were elucidated by spectroscopic data and chemical methods. Compounds 1 / 2 and 4 / 5 were two inseparable mixtures, which are glycosides of quillaic acid whose fucose residue is acylated by (E)‐ or (Z)‐4‐methoxycinnamic acid.     

Triterpenoid Saponins from the Spikes of Prunella vulgaris

Three new oleanane‐skeleton triterpenoid saponins, 3β,4β,16α‐17‐carboxy‐16,24‐dihydroxy‐28‐norolean‐12‐en‐3‐yl 4‐O‐β‐D ‐xylopyranosyl‐β‐D ‐glucopyranosiduronic acid ( 1 ), (3β,4β,16α)‐17‐carboxy‐16,24‐dihydroxy‐28‐norolean‐12‐en‐3‐yl β‐D ‐glucopyranosiduronic acid methyl ester ( 2 ), and (3β,4β)‐24‐hydroxy‐16‐oxo‐28‐norolean‐12‐en‐3‐yl 4‐O‐β‐D ‐xylopyranosyl‐β‐D ‐glucopyranosiduronic acid ( 3 ), together with eight known constituents, i.e., the oleanane‐type triterpenoids 4 – 6 , and the ursane‐type triterpenoids 7 – 11 , were isolated from the spikes of Prunella vulgaris. The new structures were established by means of detailed spectroscopic analysis (IR, HR‐ESI‐MS, 1D‐ and 2D‐NMR experiments). Compounds 1 – 3 were tested for their inhibition activity against the growth of tumor cell lines; only compound 3 displayed marginal inhibition activity.     

Synthesis of a Trisaccharide Related to the Cytotoxic Triterpenoid Saponins Isolated from the Bark of Albizia procera

Chemical synthesis of a trisaccharide related to the cytotoxic triterpenoid saponins isolated from the bark of Albizia procera has been accomplished through a concise stepwise glycosylation strategy starting from commercially available D ‐xylose, 2‐acetamido‐2‐deoxy‐D ‐glucose and L ‐arabinose. The target trisaccharide was designed with a 4‐methoxyphenyl (MP) aglycone to extend the scope of conversion to suitable glycoconjugates via selective removal of 4‐methoxyphenyl (MP) group. An unexpected phenomenon, i.e., the arabinosyl residue assumed the ¹C₄ conformation instead of the typical ⁴C₁ form, was observed. Deprotection could restore the normal conformation.     

Triterpenoid Ester Saponins from Dipteronia dyeriana

The phytochemical investigation of Dipteronia dyeriana (Aceraceae) resulted in the isolation and identification of five new triterpenoid ester saponins, dipterosides A–E ( 1 – 5 ). Their structures were elucidated by spectroscopic methods and chemical evidence. The inhibitory activities of these compounds against human leukemia K562 and human hepatoma HepG2 cells were also evaluated.     

Three New Triterpenoid Saponins from the Seeds of Aesculus chinensis

Inpreviouspaperswehavereportedtheisolationandidentificationofescinsla,fo,IVa.IVbandIVel2.Nowwedescribethestructureelucidationofthreemorenewtriterpenoidsaponins.namedescinsIVc(l),IVd(2)andIVf(3).CompoundIwasisolatedaswhiteamorphouspowder.HR-SI-MSrevealedthecompositionofC,,H,,O,,bymolecularionpeakatm/z1129.5438.Comparedwiththe:3CandiHNMRspectraofescinla,compoundIisalsoaglycosideofprotoaescigeninacylatedbythetigloylandtheacetylgroup.Thesignificantdifferencesbetweenthemwerethechemicals…     

Three New E‐Secoursane Triterpenoid Saponins from the Leaves of Ilex dunniana

Three new triterpenoid saponins with an 18,19‐secours‐13(18)‐ene skeleton, dunnianaolactones A–C ( 1 – 3 , resp.), together with nine known compounds i.e., the ursane‐type triterpene saponin 4 , the two benzofuran lignans 5 and 6 , five flavonoid glycosides, and 4‐hydroxybenzoic acid, were isolated from the leaves of Ilex dunniana Levl . (Aquifoliaceae). Their structures were elucidated by means of spectroscopic and chemical methods. The configuration of dunnianaolactone A ( 1 ) was further confirmed by X‐ray crystal‐structure analysis.     

Oleanane Saponins from Rhizome of Anemone raddeana

Two new oleanolic acid‐type triterpenoid saponins, raddeanosides R₂₂ and R₂₃ ( 1 and 2 , resp.), together with four known saponins were isolated from the rhizome of Anemone raddeana Regel. The structures of the new compounds were elucidated as oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 1 ) and oleanolic acid 3‐O‐α‐L ‐arabinopyranosyl(1→3)‐α‐L ‐rhamnopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 2 ). The four known compounds were identified as oleanolic acid 3‐O‐α‐L ‐arabinopyranoside ( 3 ), oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→4)‐α‐L ‐arabinopyranoside ( 4 ), hederasaponin B ( 5 ), and hederacholchiside E ( 6 ) on the basis of chemical and spectral evidences. Compound 4 is reported for the first time from the Anemone genus, while the other three known compounds have been already found in this plant.     

Highly Polar Triterpenoid Saponins from the Roots of Saponaria officinalis L.

Five new triterpenoid saponins, including 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐β‐d ‐glucopyranosyl‐(1→3)‐β‐d ‐xylopyranosyl‐(1→4)‐α‐l ‐rhamnopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)‐(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 1 ), 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐(6‐O‐acetyl)‐β‐d ‐glucopyranosyl‐(1→3)‐[β‐d ‐xylopyranosyl‐(1→4)]‐α‐l ‐rhamnopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)‐(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 2 ), 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐β‐d ‐xylopyranosyl‐(1→4)‐α‐l ‐rhamnopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)‐(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 3 ), 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐β‐d ‐glucopyranosyl‐(1→3)‐β‐d ‐xylopyranosyl‐(1→4)‐α‐l ‐rhamnopyranosyl‐(1→2)‐[(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 4 ), 3‐O‐β‐d ‐galactopyranosyl‐(1→2)‐[β‐d ‐xylopyranosyl‐(1→3)]‐β‐d ‐glucuronopyranosyl quillaic acid 28‐O‐(6‐O‐acetyl)‐β‐d ‐glucopyranosyl‐(1→3)‐[β‐d ‐xylopyranosyl‐(1→4)]‐α‐l ‐rhamnopyranosyl‐(1→2)‐[(4‐O‐acetyl)‐β‐d ‐quinovopyranosyl‐(1→4)]‐β‐d ‐fucopyranoside ( 5 ) together with two known congeners, saponariosides A ( 6 ) and B ( 7 ) were isolated from the roots of Saponaria officinalis L. Their structures were elucidated by extensive spectroscopic methods, including 1D‐ (¹H, ¹³C) and 2D‐NMR (DQF‐COSY, TOCSY, HSQC, and HMBC) experiments, HR‐ESI‐MS, and acid hydrolysis.     

New Triterpenoid Saponins from the Roots of Gypsophila paniculata L.

The seven new triterpenoid saponins 1 – 7 were isolated from the roots of Gypsophila paniculata L. Their structures were established by 1D ‐ and 2D‐NMR techniques, HR‐MS, and acid hydrolysis. The isolated compounds include 3,28‐O‐bidesmosides with or without a 4‐methoxycinnamoyl group (see 1 vs. 2 and 3 ), and 3‐O‐monoglucosides 4 – 7 . All isolated saponins 1 – 7 and their aglycones were evaluated for their α‐glucosidase inhibition activity. Compound 1 showed inhibitory activity against yeast α‐glucosidase with an IC₅₀ value of 100.9±3.3 μM , whereas compounds 2 – 7 were inactive.     

Two New Dammarane‐Type Triterpenoid Saponins from Gynostemma pentaphyllum

Two new dammarane‐type triterpenoid saponins were isolated from the EtOH extract of Gynostemma pentaphyllum (Thunb .) Makino . Their structural elucidations were accomplished mainly on the basis of the interpretation of spectroscopic data, such as IR, NMR, and HR‐TOF‐MS. Their liver fibrosis inhibitory activities were evaluated against hepatic stellate cells using 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide (MTT) assay. Thus, G. pentaphyllum can be used as ingredient for ancillary drugs or functional food.     

Triterpenoid Saponins from Clematis tangutica

Clenlall\vlanglllica(Maxim).KorshisaTibetanherbandhasbeenusedtotreatindigestionandskindiseasesl.Nophytochemicalworkonthisplanthasbeenreportedinliterature.Inourwork.someglycosideswereobtainedtyomaerialpartofthisplant.Inthispaper.thestructureelucidationoftwonewtriterpenoidsaponins.tanguticosideAandBaredescribed.Onmineralacidhydrolysis.both1and2yieldedthesameaglycone.BycomparingMP.MS,'HNMRand13CNMRspectratheaglyconewasdeterminedtobehederagenin=.Glucoseandrhamnosewereobtainedfromhydrolysis…     

Triterpenoid Saponins from Vaccaria segetalis

Four novel triterpenoid saponins, Vaccariside B‐E (1–4), were isolated from the seeds of Vaccaria segetalis and their structures were elucidated as 3‐O‐β‐D‐galactopyranosyl‐(1–2)‐β‐D‐glucuronopyranosyl quillaic add 28‐O‐β‐D‐xylopyranosyl‐(1–3)‐α‐L rhamno‐pyranosyl‐(1–2)‐[α‐L‐arabinofura‐nosyl‐(1–3)]‐4‐O‐acetyl‐β‐D)‐fucopyranoside (1), 3‐O‐β‐D‐galactopyranosyl ‐ (1–2) ?3‐O‐acetyl‐β‐D ‐ glucuronopyranosyl quillaic acid 28‐O‐β‐D‐xylopyranosyl‐(1–3)‐α‐L‐rhamnopyra‐nosyl‐(1–2)‐[α‐L‐arabinofuranosyl‐(1–3)]‐4‐O‐acetyl‐β‐D‐fucopyranoside (2), 3‐O‐β‐D‐galactopyranosyl‐(1–2)‐β‐D‐glucuronopyranosyl quillaic add 28‐O‐α‐L‐arabinopyranosyl‐(1–3)‐α‐L‐rhamnopyranosyl‐(1–2)‐[α‐L‐arabinofuranosyl‐(1–3)]‐4‐O‐acetyl‐β‐D‐fucopyranoside (3), 3‐O‐β‐D‐galacto‐pyranosyl‐(1–2)‐[β‐D‐xytopyranosyl‐(1–3)]‐β‐D‐glucurono‐pyranosyl quillaic add 28‐O‐β‐D‐xylopyranosyl‐(1–3)‐α‐L‐rhamnopyranosyl‐(1–2)‐[α‐L‐arabinofuranosyl‐(1–3)]‐4‐O‐acetyl‐β‐D‐fucopyranoside (4), respectively.     

Two Triterpenoid Saponins from Lonicera Japonica

The flowers of Lonicera japonica Thunb are a Chinese traditional medicine and have thefunctions such as anti-bacteria, anti-virus and hepato-protective. A new triterpenoidsaponin 2, together with a known saponin l, was obtained ftom its flowers. This papermainly discussed the structure elucidation of these two saponins.Acid hydrolysis ofsaponin 1 and 2 yielded the same aglycon. By comparing 1 H and13C NMR data, the aglycon was determined to be hederageninl. This result was alsoconfirmed by…     

A New Triterpenoid Glycoside from Dichotomanthes tristaniaecarpa

Dichotomanthes tristaniaecarp ( Kurz.) belongs to the family Rosaceae. Its root bark is used as Chinese folk medicine for treatment of flu, cough, sore throat and nosebleed. Chemical constituents of this species have not been reported previously. Compound 1 was obtained as colorless needles, mp. 213-215 °C. The molecular formula was determined as C36H58O11 by its negative-ion FAB MS ([M]- at m/z 665) and 13C NMR DEPT spectrum. The analysis of 13C NMR spectrum showed 30 signals for …     

Triterpenoid Saponins from Luculia pincia Hook

Two new triterpenoid saponins, cincholic acid-3-O-β-D-xylopyranoside, 28-O-β-D-glucopyranosyl ester (I), quinovic acid28-O-β-D-glucopyranosyl ester (4), and a new phenolic glucoside, 4-[4‘‘-O-( 2‘‘, 3‘‘, 5‘‘, 6‘‘-tetrahydroxy phenyl)-β-D-glucoside]-l-butene (2), along with five known triterpenoid saponins and one phenolic glucoside were isolated from the n-butanol fraction of the stems of Luculia pinciana Hook. Their structures were established by means of spectroscopic methods.