Carboxylic Acids from <Emphasis Type="Italic">Phyllanthus urinaria</Emphasis>

Five compounds, terephthalic acid mono-[2-(4-carboxy-phenoxycarbonyl)-vinyl] ester (1), (E)-3-(5′-hydroperoxy-2,2′-dihydroxy[1,1′-biphenyl]-4-yl)-2-propenoic acid (2), 3,4,5-trihydroxybenzoic acid (3), succinic acid (or butanedioic acid) (4), and 2,3,4,5,6-pentahydroxybenzoic acid (5), were isolated from Phyllanthus urinaria. The structures of these compounds were elucidated by means of spectral techniques including IR, MS, and 1D/2D NMR. 1 and 2 are new compounds.__________Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 14–17, January–February, 2005.     

Itosides A – I,New Phenolic Glycosides from Itoa orientalis

Eight new benzoylated gentisyl alcohol (=2‐(hydroxymethyl)benzene‐1,4‐diol) glucosides, itosides A–H ( 1 – 8 ), together with the new pyrocatechol (=benzene‐1,2‐diol) glycoside itoside I ( 9 ) were isolated from the bark and twigs of Itoa orientalis (Flacourtiaceae). In itosides B–D ( 2 – 4 ), the gentisyl alcohol moiety was esterified by 1‐hydroxy‐6‐oxocyclohex‐2‐ene‐1‐carboxylic acid, while itosides E–H ( 5 – 8 ) contained instead an additional 2‐hydroxybenzoic acid moiety. The compounds were accompanied by the known derivatives 4‐hydroxytremulacin ( 10 ), poliothyrsoside ( 11 ), poliothyrsin ( 12 ), homaloside D ( 13 ), tremulacin, and pyrocatechol β‐D ‐glucopyranoside. The structures of the new compounds were elucidated by spectral and chemical methods.     

New Acetylcholinesterase‐Inhibitory Pregnane Glycosides of Cynanchum atratum Roots

Three new pregnane glycosides, cynatroside A ( 1 ), cynatroside B ( 2 ), and cynatroside C ( 3 ), isolated from the roots of Cynanchum atratum (Asclepiadaceae), were characterized as 7β‐{[O‐α‐L ‐cymaropyranosyl‐(1→4)‐O‐β‐D ‐digitoxopyranosyl‐(1→4)‐β‐D ‐oleandropyranosyl]oxy}‐3,4,4a,4b,5,6,7,8,10,10a‐decahydro‐6α‐hydroxy‐4b‐ methyl‐2‐(2‐methyl‐3‐furyl)phenanthren‐1(2H)‐one ( 1 ), 7β‐{[O‐β‐D ‐cymaropyranosyl‐(1→4)‐O‐α‐L ‐diginopyranosyl‐(1→4)‐β‐D ‐cymaropyranosyl]oxy}‐3,4,4a,4b,5,6,7,8,10,10a‐decahydro‐2,6α‐dihydroxy‐4b‐methyl‐2‐(2‐methyl‐3‐furyl)phenanthren‐1(2H)‐one ( 2 ), and 7β‐{[O‐α‐L ‐cymaropyranosyl‐(1→4)‐O‐β‐D ‐digitoxopyranosyl‐(1→4)‐β‐L ‐cymaropyranosyl]oxy}‐3,4,4a,4b,5,6,7,8,10,10a‐decahydro‐2,6α‐dihydroxy‐4b‐methyl‐2‐(2‐methyl‐3‐furyl)phenanthren‐1(2H)‐one ( 3 ), respectively. In addition, ten known constituents were identified, i.e., cynascyroside D ( 4 ), glaucoside C ( 5 ), glaucoside D ( 6 ), atratoside A ( 7 ), 2,4‐dihydroxyacetophenone ( 8 ), 4‐hydroxyacetophenone ( 9 ), syringic acid ( 10 ), azelaic acid ( 11 ), suberic acid ( 12 ), and succinic acid ( 13 ). Among these compounds, 1 – 4 significantly inhibit acetylcholinesterase activity.     

Iridoid Glycosides and Phenolic Compounds from the Flowers of Vitex agnus‐castus

A new and rare type of iridoid glycoside, agnusoside ( 1 ), a new caffeoylquinic acid derivative, castusic acid ( 2 ), and a new sugar ester, 1,2‐di‐(4‐hydroxybenzoyl)‐β‐glucopyranose ( 3 ), along with ten known compounds belonging to iridoid glycosides (agnuside, trans‐eurostoside), caffeoylquinic acid derivatives (chlorogenic acid and isochlorogenic acid A), flavonoids (isoorientin, isovitexin, kaempferol 3‐O‐sophoroside, luteolin 6‐C‐(2′′‐O‐trans‐caffeoyl)glucopyranoside, and simple phenolic acids (4‐hydroxybenzoic acid, 3,4‐dihydroxybenzoic acid), chemical classes were isolated from the flowers of Vitex agnus‐castus. The structures of the isolates were established by extensive 1D‐ and 2D‐NMR spectroscopic analysis as well as HR‐ESI‐MS. Agnusoside ( 1 ) represents an unusual type of iridoid glycoside with its 6‐keto C(4) nonsubstituted aglycone.     

Water‐Soluble Constituents from the Liverwort Marchantia polymorpha

Four new glycosides, the bibenzyl glycoside α,β‐dihydrostilbene‐2,4′,5‐triol 2,5‐di‐(β‐D ‐glucopyranoside) ( 1 ), the shikimic acid glycoside shikimic acid 4‐(β‐D ‐xylopyranoside) ( 2 ), and two phenylethanoid glycosides 2‐(3,4‐dihydroxyphenyl)ethyl O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐allopyranoside ( 3 ) and 2‐(3,4‐dihydroxyphenyl)ethyl O‐β‐D ‐xylopyranosyl‐(1→6)‐β‐D ‐allopyranoside ( 4 ), together with three known aromatic glycosides were isolated from the H₂O‐soluble fraction of the EtOH extract of the liverwort Marchantia polymorpha. Their structures were elucidated on the basis of chemical and spectroscopic evidences.     

Tetrapterosides A and B,two new oleanane‐type saponins from Tetrapleura tetraptera

From the stem bark of Tetrapleura tetraptera, two new oleanane‐type saponins, tetrapteroside A 3‐O‐{6‐O‐[(2E,6S)‐2,6‐dimethyl‐6‐hydroxyocta‐2,7‐dienoyl]‐β‐D ‐glucopyranosyl‐(1 → 2)‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐(1 → 4)‐[β‐D ‐glucopyranosyl‐(1 → 2)]‐β‐D ‐glucopyranosyl}‐3,27‐dihydroxyoleanolic acid (1), and tetrapteroside B 3‐O‐{ β‐D ‐glucopyranosyl‐(1 → 2)‐6‐O‐[(E)‐feruloyl]‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐(1 → 4)‐[β‐D ‐glucopyranosyl‐(1 → 2)]‐β‐D ‐glucopyranosyl}‐3,27‐dihydroxyoleanolic acid (2), were isolated. Further extractions from the roots led to the isolation of four known oleanane‐type saponins. Their structures were elucidated by the combination of mass spectrometry (MS), one and two‐dimensional NMR experiments. Copyright © 2009 John Wiley & Sons, Ltd.     

Assembly,Structures, and Properties of a Series of Metal‐Organic Coordination Polymers Derived from a Semi‐rigid Bis‐pyridyl‐bis‐amide Ligand

Four metal‐organic coordination polymers [Cd(4‐bpcb)_1.5Cl₂(H₂O)] ( 1 ), [Cd(4‐bpcb)_0.5(mip)(H₂O)₂] · 3H₂O ( 2 ), [Co(4‐bpcb)(oba)(H₂O)₂] ( 3 ), and [Ni(4‐bpcb)(oba)(H₂O)₂] ( 4 ) [4‐bpcb = N,N′‐bis(4‐pyridinecarboxamide)‐1, 4‐benzene, H₂mip = 5‐methylisophthalic acid, and H₂oba = 4, 4′‐oxybis(benzoic acid)] were synthesized under hydrothermal conditions and characterized by single‐crystal X‐ray diffraction, elemental analyses, IR spectroscopy, powder X‐ray diffraction, and TG analysis. In complex 1 , two Cl^– anions serve as bridges to connect two Cd‐(μ₁‐4‐bpcb) subunits forming a dinuclear unit, which are further linked by μ₂‐bridging 4‐bpcb to generate 1D zigzag chain. Complex 2 shows a 2D 6³ network constructed by [Cd‐mip]_n zigzag chains and μ₂‐bridging 4‐bpcb ligands. Complexes 3 and 4 are isostructural 2D (4, 4) grid networks derived from [M‐oba]_n (M = Co, Ni) zigzag chains and [M‐(4‐bpcb)]_n linear chains. The 1D chains for 1 and the 2D networks for 2 – 4 are finally extended into 3D supramolecular architectures by hydrogen bonding interactions. The roles of dicarboxylates and central metal ions on the assembly and structures of the target compounds were discussed. Moreover, the thermal stabilities, photoluminescent properties, and photocatalytic activities of complexes 1 – 4 and the electrochemical properties of complexes 3 and 4 were investigated.     

Syntheses,Structures, and Electrochemical Properties of Two Bis‐triazole‐bis‐amide‐based Copper(II) Pyridine‐2,3‐dicarboxylate Coordination Polymers

Abstract. Two bis‐triazole‐bis‐amide‐based copper(II) pyridine‐2,3‐dicarboxylate coordination polymers (CPs), [Cu(2,3‐pydc)(dtb)_0.5(DMF)] · 2H₂O ( 1 ) and [Cu(2,3‐pydc)(dth)_0.5(DMF)] · 2H₂O ( 2 ) (2,3‐H₂pydc = pyridine‐2,3‐dicarboxylic acid, dtb = N,N′‐bis(4H‐1,2,4‐triazole)butanamide, and dth = N,N′‐bis(4H‐1,2,4‐triazole)hexanamide), were synthesized under solvothermal conditions. CPs 1 and 2 show similar two‐dimensional (2D) structures. In 1 , the 2,3‐pydc anions bridge the Cu^II ions into a one‐dimensional (1D) chain. Such 1D chains are linked by the dtb ligands to form a 2D layer. The adjacent 2D layers are extended into a three‐dimensional (3D) supramolecular architecture by hydrogen‐bonding interactions. The electrochemical properties of 1 and 2 were investigated.     

Syntheses,Structures, and Photoluminescent and Magnetic Properties of Four Novel Complexes Constructed from 2,4,5‐Tri(4‐pyridyl)‐imidazole and Benzene‐1,3,5‐tricarboxylic Acid

Four novel 2D complexes M₂(Hptim)₂(HBTC)₂ [M = Co ( 1 ), Cd ( 2 ), Zn ( 3 ), Mn ( 4 ); Hptim = 2,4,5‐tri(4‐pyridyl)‐imidazole; HBTC^2– = Benzene‐1,3,5‐tricarboxylic acid] were synthesized under solvothermal conditions. The four complexes are isomorphous and present a unique structure with a 1D ladder of [Co₂(HBTC)₂]_n. The 2D network structure of 1 is achieved through bridging Hptim groups, which coordinate to the metal atoms of two adjacent 1D [Co₂(HBTC)₂]_n ladders. Magnetic measurements reveal that dominant antiferromagnetic coupling was observed in compounds 1 and 4 . Compounds 2 and 3 both exhibit strong fluorescent emissions in the solid state and may be suitable candidates for fluorescent materials.     

Chemical Constituents of the Endophytic Fungal Strain Phomopsis sp. NXZ‐05 of Camptotheca acuminata

From the endophytic fungal strain Phomopsis sp. NXZ‐05 of Camptotheca acuminata Decne . (Nyssaceae), six new compounds were isolated, including the ten‐membered macrolides 1 – 4 and their (known) parent compound multiplolide A ( 7 ), as well as a new unsaturated fatty acid, (4E)‐6,7,9‐trihydroxydec‐4‐enoic acid ( 5 ) and its methyl ester 6 . Their structures were elucidated by spectroscopic and mass‐spectrometric analyses, including 1D‐ and 2D‐NMR experiments and HR‐ESI‐MS, and their biological activities were elucidated.     

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 new acacic acid‐type saponins from Albizia coriaria

Three new acacic acid derivatives, named coriariosides C, D, and E ( 1–3 ) were isolated from the roots of Albizia coriaria. Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR studies and mass spectrometry as 3‐O‐[β‐D ‐xylopyranosyl‐(1 → 2)‐β‐D ‐fucopyranosyl‐(1 → 6)‐2‐(acetamido)‐2‐deoxy‐β‐D ‐glucopyranosyl]‐21‐O‐{(2E,6S)‐6‐O‐{4‐O‐[(2E,6S)‐2,6‐dimethyl‐ 6‐O‐(β‐D ‐quinovopyranosyl)octa‐2,7‐dienoyl]‐4‐O‐[(2E,6S)‐2,6‐dimethyl‐6‐O‐(β‐D ‐quinovopyranosyl)octa‐2,7‐dienoyl]‐β‐D ‐quinovopyranosyl}‐2,6‐dimethylocta‐2,7‐dienoyl}acacic acid 28‐O‐β‐D ‐xylopyranosyl‐(1 → 4)‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐β‐D ‐glucopyranosyl ester ( 1 ), 3‐O‐{β‐D ‐fucopyranosyl‐(1 → 6)‐[β‐D ‐glucopyranosyl‐(1 → 2)]‐β‐D ‐glucopyranosyl}‐21‐O‐{(2E,6S)‐6‐O‐{4‐O‐[(2E,6S)‐2,6‐dimethyl‐6‐O‐(β‐D ‐quinovopyranosyl)octa‐2,7‐dienoyl]‐4‐O‐[(2E,6S)‐2,6‐dimethyl‐6‐O‐(β‐D ‐quinovopyranosyl)octa‐2,7‐dienoyl]‐β‐D ‐quinovopyranosyl}‐2,6‐dimethylocta‐2,7‐dienoyl}acacic acid 28‐O‐α‐L ‐rhamno pyranosyl‐(1 → 2)‐β‐D ‐glucopyranosyl ester ( 2 ), and 3‐O‐[β‐D ‐fucopyranosyl‐(1 → 6)‐β‐D ‐glucopyranosyl]‐21‐O‐{(2E,6S)‐6‐O‐{4‐O‐[(2E,6S)‐2,6‐dimethyl‐6‐O‐(β‐D ‐quinovopyranosyl)octa‐2,7‐dienoyl)‐β‐D ‐quinovopyranosyl]octa‐2,7‐dienoyl}acacic acid 28‐O‐β‐D ‐glucopyranosyl ester ( 3 ). Copyright © 2010 John Wiley & Sons, Ltd.     

Four new ursane‐type saponins from Morina nepalensis var. alba

Four new ursane‐type saponins, monepalosides C–F, together with a known saponin, mazusaponin II, were isolated from Morina nepalensis var. alba Hand.‐Mazz. Their structures were determined to be 3‐O‐α‐L ‐arabinopyranosyl‐(1 → 3)‐&[alpha;‐L ‐rhamnopyranosyl‐(1 → 2)]‐α‐L ‐arabinopyranosylpomolic acid 28‐O‐β‐D ‐glucopyranosyl‐(1 → 6)‐β‐D ‐glucopyranoside (monepaloside C, 1 ), 3‐O‐α‐L ‐arabinopyranosyl‐(1 → 3)‐&[alpha;‐L ‐rhamnopyranosyl‐(1 → 2)]‐β‐D ‐xylopyranosylpomolic acid 28‐O‐β‐D ‐glucopyranosyl‐(1 → 6)‐β‐D ‐glucopyranoside (monepaloside D, 2 ), 3‐O‐α‐L ‐arabinopyranosyl‐(1 → 3)‐&[beta;‐D ‐glucopyranosy‐(1 → 2)]‐α‐L ‐arabinopyranosylpomolic acid 28‐O‐β‐D ‐glucopyranosyl‐(1 → 6)‐β‐D ‐glucopyranoside (monepaloside E, 3 ) and 3‐O‐β‐D ‐xylopyranosylpomolic acid 28‐O‐β‐D ‐glucopyranoside (monepaloside F, 4 ) on the basis of chemical and spectroscopic evidence. 2D NMR techniques, including ¹H–¹H COSY, HMQC, 2D HMQC‐TOCSY, HMBC and ROESY, and selective excitation experiments, including SELTOCSY and SELNOESY, were utilized in the structure elucidation and complete assignments of ¹H and ¹³C NMR spectra. Copyright © 2002 John Wiley & Sons, Ltd.     

Cytotoxic metabolites of <Emphasis Type="Italic">Streptimonospora salina</Emphasis>

Streptimonospora salina gen. nov., sp. nov. was found to produce three phenoxazinone antibiotics, 2-amino-3H-phenoxazin-3-one (1), 2-methylamino-3H-phenoxazin-3-one (2), 2-acetylamino-3H-phenoxazin-3-one (3), and one phenazine antibiotic, phenazine-1-carboxylic acid (4). The chemical structures of the compounds were determined using 1D and 2D NMR spectrometry and electrospray mass spectrometry (ESMS). Compounds 1-4 exhibited modest cytotoxicity against a human renal carcinoma cell line ACHN with IC₅₀ values of 35.4, 12.4, 65.4, and 82.9 μM, respectively. Compound 2 was discovered for the first time from a biological origin. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 405–406, July–August, 2008     

Two Zinc(II) Coordination Polymers Based on the Ligand 1, 4‐Bis[(2‐methyl‐imidazol‐1‐yl)methyl]benzene: Syntheses,Crystal Structures and Properties

Two coordination polymers (CPs), {[Zn₂(BMB)(5‐AIPA)₂] · 2H₂O}_n( 1 ) and [Zn(BMB)(5‐NIPA)]_n( 2 ) {BMB = 1, 4‐bis[(2‐methyl‐imidazol‐1‐yl)methyl]benzene, 5‐AIPA = 5‐aminoisophthalic acid, 5‐NIPA = 5‐nitroisophthalic acid}, were synthesized under hydrothermal conditions. Compound 1 displays a 2D double‐layer structure, which is packed into a 3D supramolecule by interlayer hydrogen bonds and π–π stacking interactions. Compound 2 displays a threefold interpenetrating 3D network, which is composed of left‐handed helical chains and two types of meso‐helical chains along different directions.     

Two Coordination Polymers Constructed from 5‐(4‐Pyridyl)‐1H‐tetrazole Ligands with Different Organic Carboxylates: Structure and Luminescence Properties

Two coordination polymers (CPs), namely, [Cu(Hptz)₂(Hhba)₂]_n ( 1 ) [Hptz = 5‐(4‐pyridyl)‐1H‐tetrazole, H₂hba = 2‐hydroxybenzoic acid] and [Zn₃(ptz)₂(hpa)₂]_n ( 2 ) (H2hpa = 2‐hydroxy‐2‐phenylacetic acid), were synthesized by solvothermal reactions. Both complexes were characterized by elemental analysis, infrared spectroscopy, powder X‐ray diffraction, thermogravimetric analysis, and single‐crystal X‐ray diffraction analysis. Compound 1 exhibits a 2D (4,4) network, where each layer connects to four adjacent layers to construct a 3D supramolecular framework. Compound 2 has a 3D framework structure composed of 1D SUBs, which are formed by both carboxyl and tetrazole groups. The complexes represent two rare examples of CPs constructed from Hptz and organic carboxyl acid ligands. Complex 2 exhibits intense, red‐shifted emissions in the visible region at room temperature.     

Unusual p‐Coumarates from the Stems of Vaccinium myrtillus

The two previously unreported esters 1 and 2 of pentane‐2,4‐diol and p‐coumaric acid (=3‐(4‐hydroxyphenyl)prop‐2‐enoic acid) along with 13 known compounds including 6 oleanane‐ and ursane‐type triterpenoids were isolated from MeOH extracts of the stems of Vaccinium myrtillus. The structures of the new compounds were assigned as (2S,4R)‐4‐(β‐D ‐glucopyranosyloxy)pentan‐2‐yl (2E)‐p‐coumarate ( 1 ) and its aglycone 2 on the basis of 1D‐ and 2D‐NMR spectroscopic analyses of the isolated and synthesized compounds and molecular modelling experiments. This is the first report on the occurrence of a chiral pentane‐2,4‐diol linker between the phenol‐derived acid and a glycoside part in natural products.     

A new cerebrogalactoside from <Emphasis Type="Italic">Juglans mandshurica</Emphasis>

A new cerebrogalactoside, Juglans cerebroside A (1), together with five known compounds, quercetin-3-O-β-D-galactopyranoside (2), myricetin-3-O-β-D-galactopyranoside (3), 2″E-quercetin-3-O-β-D-(6″″-O-[3″(4′″-hydroxyphenyl) propylene acyl]) glucopyranoside (4), gallic acid (5), and 2-methyl-1-hexadecanol (6) were isolated from the leaves of Juglans mandshurica Maxim. The structures of these compounds were determined by 1D, 2D NMR, and MS techniques.     

Two New 7‐Dehydrobrefeldin A Acids from Cylindrocarpon obtusisporum,an Endophytic Fungus of Trewia nudiflora

Two new 7‐dehydrobrefeldin A acids, (2E,4R*)‐4‐hydroxy‐4‐{(1R*,2S*)‐4‐oxo‐2‐[(1E)‐6‐oxohept‐1‐en‐1‐yl]cyclopentyl}but‐2‐enoic acid ( 3 ) and (2E,4R*)‐4‐hydroxy‐4‐{(1R*,2S*)‐2‐[(1E,6S*)‐6‐hydroxyhept‐1‐en‐1‐yl]‐4‐oxocyclopentyl}but‐2‐enoic acid ( 4 ), were isolated from the endophytic fungal strain Cylindrocarpon obtusisporum (Cooke & Harkness ) Wollenw . of Trewia nudiflora, together with two known compounds, 7‐dehydrobrefeldin A ( 2 ) and brefeldin A ( 1 ). Their structures were determined on the basis of extensive 1D‐ and 2D‐NMR‐spectral analysis.     

Foetidissimosides C–F,Novel Glycosides from the Roots of Cucurbita foetidissima

Two novel echinocystic acid (=(3β,16α)‐3,16‐dihydroxyolean‐12‐en‐28‐oic acid) glycosides, foetidissimosides C ( 1 ), and D ( 2 ), along with new cucurbitane glycosides, i.e., foetidissimosides E/F ( 3 / 4 ) as an 1 : 1 mixture of the (24R)/(24S) epimers, were obtained from the roots of Cucurbita foetidissima. Their structures were elucidated by means of a combination of homo‐ and heteronuclear 2D‐NMR techniques (COSY, TOCSY, NOESY, ROESY, HSQC, and HMBC), and by FAB‐MS. The new compounds were characterized as (3β,16α)‐28‐{[O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl]oxy}‐16‐hydroxy‐28‐oxoolean ‐12‐en‐3‐yl β‐D ‐glucopyranosiduronic acid ( 1 ), (3β,16α)‐16‐hydroxy‐28‐oxo‐28‐{{O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐[β‐D ‐xylopyranosyl‐(1→4)]‐O‐6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl}oxy}olean‐12‐en‐3‐yl β‐D ‐glucopyranosiduronic acid ( 2 ), and (3β,9β,10α,11α,24R)‐ and (3β,9β,10α,11α,24S)‐25‐(β‐D ‐glucopyranosyloxy)‐9‐methyl‐19‐norlanost‐5‐en‐3‐yl 2‐O‐β‐D ‐glucopyranosyl‐β‐D ‐glucopyranoside ( 3 and 4 , resp.).