Five New Steroidal Glycosides from Caralluma dalzielii

Five new pregnane glycosides, caradalzielosides A–E ( 1 – 5 ), were isolated from the aerial parts of Caralluma dalzielii. Their structures were elucidated by extensive 1D‐ and 2D‐NMR spectroscopic analysis as well as by HR‐FAB‐MS experiments.     

Ypsilactosides A and B,Two New C22‐Steroidal Lactone Glycosides from Ypsilandra thibetica

Two new C₂₂‐steroidal lactone glycosides, ypsilactosides A ( 1 ) and B ( 2 ), were isolated from the EtOH extract of the whole plant of Ypsilandra thibetica. Their structures were established as (3β,5α,16β,20S)‐3,16‐dihydroxy‐6‐oxopregnane‐20‐carboxylic acid γ‐lactone 3‐(β‐D ‐glucopyranoside) ( 1 ) and (3β,16β)‐3,16‐dihydroxypregna‐5,20‐diene‐20‐carboxylic acid γ‐lactone 3‐{O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside} ( 2 ) on the basis of extensive spectroscopic analyses and chemical degradations.     

Two New Secoiridoid Glycosides from Tripterospermum chinense

Two new secoiridoid glycosides, tripterospermumcin A ( 1 ) and B ( 2 ), were isolated from the EtOH extract of the aerial parts of Tripterospermum chinense (Migo ) H. Smith , along with three known compounds, secologanin, secologanol, and sweroside. Their structures were established on the basis of UV, IR, MS, and extensive 1D‐ and 2D‐NMR analyses, as well as by literature comparison of spectroscopic data.     

New Glycosidic Constituents of Abutilon pakistanicum

Pakisides A and B ( 1 and 2 , resp.), new catalpol‐type iridoid glycosides, and a new glycoside, 3 , of scutellarein have been isolated from the AcOEt‐soluble fraction of the whole plant of Abutilon pakistanicum, along with buddlejoside and lapachol. The structures of new compounds were elucidated by spectroscopic techniques including ¹H‐and ¹³C‐NMR (DEPT), and 2D‐NMR experiments.     

Two New Phenylethanoid Glycosides from Callicarpa longissima

Two new phenylethanoid glycosides, longissimosides A and B ( 1 and 2 , resp.), together with eight structurally related known compounds, were isolated from the EtOH extract of leaves and stems of Callicarpa longissima (Hemsl .) Merr . The structures of 1 and 2 were elucidated as 2‐(3,4‐dihydroxyphenyl)ethyl O‐(α‐L ‐rhamnopyranosyl)‐(1→3)‐O‐(2‐O‐syringoyl‐β‐D ‐xylopyranosyl)‐(1→6)‐ 4‐O‐[(E)‐caffeoyl]‐β‐D ‐glucopyranoside ( 1 ) and 2‐(3‐hydroxy‐4‐methoxyphenyl)ethyl O‐(α‐L ‐rhamnopyranosyl)‐(1→3)‐O‐(β‐D ‐apiofuranosyl)‐(1→6)‐4‐O‐[(E)‐isoferuloyl]‐β‐D ‐glucopyranoside ( 2 ) on the basis of spectroscopic data and acid hydrolysis.     

New Secondary Metabolites from Asphodelus tenuifolius

Asphorins A and B ( 1 and 2 , resp.), two new triterpene glycosides, have been isolated along with a new chromone, 3 , from the AcOEt subfraction of the MeOH extract of the whole plant of Asphodelus tenuifolius. Their structures were elucidated by spectral analysis including 2D‐NMR spectroscopic experiments.     

A New Triterpene and Phenolic Compounds from the Roots of Pteroxygonum giraldii

A chemical investigation of the roots of Pteroxygonum giraldii led to the isolation of a new arborane‐type triterpene, pteroxygonumnol A ( 1 ), a new myricetin glycoside, myricetin 3‐O‐β‐D ‐galactopyranoside 3′‐O‐β‐D ‐xylopyranoside ( 2 ), and a group of phenolic lipids, 3 – 6 , along with four known phenolic compounds, (?)‐epigallocatechin, (?)‐epigallocatechin gallate, gallic acid, and 2‐(4‐hydroxyphenyl)acetic acid. Their structures were elucidated on the basis of extensive spectroscopic analyses.     

A New Lignan and Four New Lignan Glycosides from Mananthes patentiflora

A new lignan, 5‐hydroxyjusticidin A (= 9‐(1,3‐benzodioxol‐5‐yl)‐5‐hydroxy‐4,6,7‐trimethoxynaphtho[2,3‐c]furan‐1(3H)‐one; 1 ), and four new diphyllin‐type lignan glycosides, mananthosides C–F ( 2 – 5 ), containing glucosyl (Glc), arabinosyl (Ara), galactosyl (Gal), and/or apiosyl residues, have been isolated from Mananthes patentiflora, together with five known compounds. Their structures and configurations were elucidated by in‐depth 1D‐ and 2D‐NMR experiments, as well as MS analysis.     

Six New C21 Steroidal Glycosides from Cynanchum bungei Decne

Six new C₂₁ steroidal glycosides 1 – 6 were isolated from the stem parts of Cynanchum bungei Decne . The structures of the new glycosides were determined on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR and HR‐ESI‐MS techniques as well as by comparison of their spectral data with those of related compounds.     

New Triterpenoid and Ergostane Glycosides from the Leaves of Hydrocotyle umbellata L.

Two new triterpenoid glycosides, together with two new ergostane glycosides, umbellatosides A–D ( 1 – 4 , resp.), have been isolated from the leaves of Hydrocotyle umbellata L. Their structures were established by 2D‐NMR spectroscopic techniques (¹H,¹H‐COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry as 3β,22β‐dihydroxy‐3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucuronopyranosyl]olean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐glucopyranosyl ester ( 1 ), 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucuronopyranosyl]oleanolic acid 28‐O‐β‐D ‐glucopyranosyl ester ( 2 ), (3β,11α,26)‐ergosta‐5,24(28)‐diene‐3,11,26‐triol 3‐O‐(β‐D ‐glucopyranosyl)‐11‐O‐(α‐L ‐rhamnopyranosyl)‐26‐O‐β‐D ‐glucopyranoside ( 3 ), and (3β,11α,21,26)‐ergosta‐5,24(28)‐diene‐3,11,21,26‐tetrol 3‐O‐(β‐D ‐glucopyranosyl)‐11‐O‐(α‐L ‐rhamnopyranosyl)‐26‐O‐β‐D ‐glucopyranoside ( 4 ).     

Two New Cytotoxic Nonsulfated Pentasaccharide Holostane (=20‐Hydroxylanostan‐18‐oic Acid γ‐Lactone) Glycosides from the Sea Cucumber Holothuria grisea

Two new lanostane‐type nonsulfated pentasaccharide triterpene glycosides, 17‐dehydroxyholothurinoside A ( 1 ) and griseaside A ( 2 ), were isolated from the sea cucumber Holothuria grisea. Their structures were elucidated by spectroscopic methods, including 2D‐NMR and MS experiments, as well as chemical evidence. Compounds 1 and 2 possess the same pentasaccharide moieties but differ slightly in their side chains of the holostane‐type triterpene aglycone. The structures of the two new glycosides were established as (3β,12α)‐22,25‐epoxy‐3‐{(O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[O‐3‐O‐methyl‐β‐D ‐glucopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐6‐deoxy‐β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐xylopyranosyl)oxy}‐12,20‐dihydroxylanost‐9(11)‐en‐18‐oic acid γ‐lactone ( 1 ) and (3β,12α)‐3‐{(O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[O‐3‐O‐methyl‐β‐D ‐glucopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐6‐deoxy‐β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐xylopyranosyl)oxy}‐12,20,22‐trihydroxylanost‐9(11)‐en‐18‐oic acid γ‐lactone ( 2 ). The 17‐dehydroxyholothurinoside A ( 1 ) and griseaside A ( 2 ) exhibited significant cytotoxicity against HL‐60, BEL‐7402, Molt‐4, and A‐549 cancer cell lines.     

Structure Elucidation of Two New Diterpenoids from Isodon phyllostachys: Phyllostacins A and B

Two new ent‐kaurane‐derived diterpene derivatives, phyllostacins A ( 1 ) and B ( 2 ), were isolated from the aerial parts of Isodon phyllostachys, together with two known compounds, irroratin A ( 3 ) and serrin B ( 4 ). Both 1 and 2 were found to be present as diastereoisomers. In the case of 1 , the corresponding diastereoisomeric diacetates 5 and 6 were prepared and separated. The structures of the new compounds were elucidated by extensive 1D‐ and 2D‐NMR spectroscopic methods, in combination with MS experiments. In (D₅)pyridine solution, the two epimers of 1 are present in equal amounts, but in CDCl₃ or CD₃OD, the (S)‐epimer predominates in the mixture of hemiacetals.     

New Secondary Metabolites from Allium victorialis

Allumines A and B ( 1 and 2 , resp.), two new steroidal alkaloids, and a new cyclopentene derivative, 3 , were isolated from the CHCl₃‐soluble fraction of the whole plant of Allium victorialis. Their structures were elucidated by spectroscopic techniques, including 1D‐ and 2D‐NMR spectroscopy.     

A New Prenylated Isoflavone and a New Flavonol Glycoside from Flemingia philippinensis

A new prenylated isoflavonoid, flemiphilippinin G ( 1 ), and a new flavonol glycoside, flemiphilippininside ( 2 ), along with eleven known isoflavonoids were obtained from the roots of Flemingia philippinensis (Merr. et Rolfe) Li . Their structures were elucidated on the basis of spectroscopic data. The in vitro cytotoxicities of compounds 1 – 13 against MCF‐7, A549, and Hep‐G2 cell lines were determined by using the MTT (=3‐(4,5‐dimethylthazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide) colorimetric assay, and their antioxidant activities were evaluated by ferric‐reducing antioxidant power (FRAP) method. Compound 1 exhibited significant cytotoxicity against all the tested cell lines with IC₅₀ values of 4.8–7.3 μM , and compound 2 was found to be inactive. Both compounds 1 and 2 showed weak antioxidant activities with FRAP values of 110±15 and 124±16 μmol/g, respectively.     

New C19－Diterpenoid Alkaloids from the Roots of Delphinium Giraldii

Three new C19-diterpenoid alkaloids, giraldines A (1), B (3) and C (4), were isolated from the roots of Delphinium giraldii Diels, together with three known C19-diterpenoid alkaloids, dihydrogadesine (5), tatsiensine (6) and siwanine A (7), as well as their structures were elucidated by chemical evidence and spectral analyses, including IR, MS, 1D NMR and 2D NMR.     

A New Tetracyclic Diterpene from Jatropha curcas

Jatrophodione A ( 1 ), a new diterpene with four rings, together with nine known compounds, caniojane ( 2 ), jatropholone A ( 3 ), jatropholone B ( 4 ), jatrogrossidione ( 5 ), 2‐epijatrogrossidione ( 6 ), heudelotinone ( 7 ), gossweilone ( 8 ), (3α)‐3‐hydroxy‐ent‐pimara‐8(14),15‐dien‐12‐one ( 9 ), and 12‐hydroxy‐13‐methylpodocarpa‐8,11,13‐trien‐3‐one ( 10 ), was isolated from the aerial parts of Jatropha curcas. Compounds 5, 6, 9 , and 10 were found for the first time in this plant. Their structures were established by spectroscopic analysis, including 2D‐NMR spectroscopic techniques. Cytotoxicities of compounds 1, 2, 7, 8 , and 9 were tested on the three cancer cell lines A549, Hela, and SMMC‐7721. Results showed that 7 exhibited cytotoxicity against SMMC‐7721 with an IC₅₀ value of 21.68 μM , whereas 7 and 8 were active against A549 with the IC₅₀ values of 16.04 and 20.47 μM , and against Hela with the IC₅₀ values of 10.67 and 22.83 μM , respectively.     

Two New Kaempferol Glycosides from Androsace umbellata

Two new kaempferol glycosides, 5‐hydroxy‐2‐(4‐hydroxyphenyl)‐4‐oxo‐7‐(α‐L ‐rhamnopyranosyloxy)‐4H‐chromen‐3‐yl 2‐O‐acetyl‐3‐O‐β‐D ‐glucopyranosyl‐α‐L ‐rhamnopyranoside ( 1 ) and 5‐hydroxy‐2‐(4‐hydroxyphenyl)‐4‐oxo‐7‐(α‐L ‐rhamnopyranosyloxy)‐4H‐chromen‐3‐yl β‐D ‐glucopyranosyl‐(1→2)‐6‐O‐[(2E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranoside ( 2 ), along with ten known compounds, were isolated from the 95% EtOH extract of the whole plant of Androsace umbellata. The structures of the new glycosides were determined on the basis of detailed spectroscopic analyses, including 1D‐ and 2D‐NMR, MS, and chemical methods.     

Seven New Acyl Glycosides from Erycibe obtusifolia

Seven new acyl glycosides, benzyl 5‐O‐vanilloyl‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 1 ), 4‐hydroxy‐3‐methoxyphenyl 5‐O‐syringoyl‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 2 ), isopentyl 5‐O‐syringoyl‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 3 ), 3,4,5‐trimethoxyphenyl 5‐O‐sinapoyl‐β‐d ‐apiofuranosyl‐(1→6)‐β‐d ‐glucopyranoside ( 4 ), 6‐methoxy‐7‐[(6‐O‐sinapoyl‐β‐d ‐glucopyranosyl)oxy]coumarin ( 5 ), 6‐methoxy‐7‐[(2‐O‐sinapoyl‐β‐d ‐glucopyranosyl)oxy]coumarin ( 6 ), and isopentyl β‐d ‐apiofuranosyl‐(1→6)‐[5‐O‐syringoyl‐β‐d ‐apiofuranosyl‐(1→2)]‐β‐d ‐glucopyranoside ( 7 ), were isolated from Chinese folk herb Erycibe obtusifolia. Their structures were elucidated on the basis of extensive spectroscopic analysis, including UV, IR, MS, and 1D‐ and 2D‐NMR techniques. Further, these compounds were evaluated against HCT‐8 (human colon carcinoma), Bel‐7402 (human liver carcinoma), BGC‐823 (human stomach carcinoma), A549 (human lung carcinoma), and A2780 (human ovarian carcinoma) cell lines, however, none of them exhibited a significant bioactivity (IC₅₀ > 10 μm ).     

Anthraquinones and Lignans from Cassia occidentalis

One new anthraquinone glycoside, 6‐O‐(α‐L ‐rhamnopyranosyl‐(1→6)‐β‐d‐ glucopyranosyl)emodin ( 1 ), and two new sesquilignans, seslignanoccidentaliols A ( 2 ) and B ( 3 ), were isolated from the whole plant of Cassia occidentalis. The structures of the new compounds were established by means of spectroscopic methods, especially 2D‐NMR data (¹H,¹H‐COSY, HMQC, HMBC, and ROESY), as well as HR‐ESI‐MS analysis. One previously reported sesquilignan, erythro‐guaiacylglycerol‐β‐O‐4′‐(5′)‐methoxylariciresinol, was revised to be seslignanoccidentaliol A ( 2 ). The 6‐O‐(α‐L ‐rhamnopyranosyl‐(1→6)‐β‐d‐ glucopyranosyl)emodin ( 1 ) exhibited moderate anti‐HIV‐1 activity with an EC₅₀ value of 2.90 μg/ml and a therapeutic‐index (TI) value of 260.     

New Antifungal Terpenoid Glycosides from Alibertia edulis (Rubiaceae)

Phytochemical investigation from the stems of Alibertia edulis led to the isolation and identification of a new iridoid 6β‐hydroxy‐7‐epigardoside methyl ester ( 1 ) and a new saponin 3β‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranosyl]‐28‐O‐β‐D ‐glucopyranoside pomolate ( 2 ), along with three known compounds, shanzhiside methyl ester ( 3 ), ixoside ( 4 ), and 3,4,5‐trimethoxyphenyl 1‐O‐β‐D ‐apiofuranosyl‐(1→6)‐O‐β‐D ‐glucopyranoside ( 5 ). The structures of 1 and 2 were established on the basis of their spectroscopic data. Iridoid 1 and saponin 2 exhibited moderate inhibitory activities against Candida albicans and C. krusei in a dilution assay.