Three New Triterpene Saponins from Hemsleya chinensis

Three new triterpenoid saponins, xuedanglycosides A–C ( 1 – 3 , resp.), along with six known ones, were isolated from the rhizomes of Hemsleya chinensis. By detailed analysis of the NMR spectra, by chemical methods, and by comparison with spectral data of known compounds, the structures of new compounds were determined to be 16α,23α‐epoxy‐2β,3α,20β‐trihydroxy‐10α,23α‐cucurbita‐5,24‐dien‐11‐on‐2‐yl β‐D ‐glucopyranoside ( 1 ), 2β,3α,16α,20β‐tetrahydroxycucurbita‐5,25‐diene‐11,22‐dion‐2‐yl β‐D ‐glucopyranoside ( 2 ), and oleanolic acid 28‐O‐β‐xylopyranosyl‐(1→6)‐O‐β‐glucopyranoside ( 3 ). In addition, hemslecin A 2‐O‐β‐D ‐glucopyranoside ( 6 ), hemsamabilinin B ( 7 ), and hemslonin A ( 9 ) were obtained for the first time from this plant.     

Cucurbitane Triterpenoids from the Fruit Pulp of Momordica charantia and Their Cytotoxic Activity

Two new cucurbitane‐type triterpenes, 25‐methoxycucurbita‐5,23(E)‐diene‐3β,19‐diol ( 1 ) and 7β‐ethoxy‐3β‐hydroxy‐25‐methoxycucurbita‐5,23(E)‐dien‐19‐al ( 2 ), together with three known cucurbitane‐type triterpenes, 3β,7β,25‐trihydroxycucurbita‐5,23(E)‐dien‐19‐al ( 3 ), (23E)‐3β‐hydroxy‐7β,25‐dimethoxycucurbita‐5,23‐dien‐19‐al ( 4 ), and 3β‐hydroxy‐25‐methoxycucurbita‐6,23(E)‐dien‐19,5β‐olide ( 5 ), were isolated from the fruit pulp of Momordica charantia. The structures of two new compounds were elucidated on the basis of 1D and 2D NMR, MS, IR, optical rotation. Among these isolates, compounds 1 , 2 , and 5 showed slight cytotoxic activity against the SK‐Hep 1 cell line with IC₅₀ values of 33.1, 24.3, and 38.7 μM, respectively.     

Huangqiyenins G – J,Four New 9,10‐Secocycloartane (=9,19‐Cyclo‐9,10‐secolanostane) Triterpenoidal Saponins from Astragalus membranaceus Bunge Leaves

Four new 9,10‐secocycloartane (=9,19‐cyclo‐9,10‐secolanostane) triterpenoidal saponins, named huangqiyenins G–J ( 1 – 4 , resp.), were isolated from Astragalus membranaceus Bunge leaves. The acid hydrolysis of 1 – 4 with 1M aqueous HCl yielded D ‐glucose, which was identified by GC analysis after treatment with L ‐cysteine methyl ester hydrochloride. The structures of 1 – 4 were established by detailed spectroscopic analysis as (3β,6α,10α,16β,24E)‐3,6‐bis(acetyloxy)‐10,16‐dihydroxy‐12‐oxo‐9,19‐cyclo‐9,10‐secolanosta‐9(11),24‐dien‐26‐yl β‐D ‐glucopyranoside ( 1 ), (3β,6a,10α,24E)‐3,6‐bis(acetyloxy)‐10‐hydroxy‐12,16‐dioxo‐9,19‐cyclo‐9,10‐secolanosta‐9(11),24‐dien‐26‐yl β‐D ‐glucopyranoside ( 2 ), (3β,6α,9α,10α,16β,24E)‐3,6‐bis(acetyloxy)‐9,10,16‐trihydroxy‐9,19‐cyclo‐9,10‐secolanosta‐11,24‐dien‐26‐yl β‐D ‐glucopyranoside ( 3 ), and (3β,6α,10α,24E)‐3,6‐bis(acetyloxy)‐10‐hydroxy‐16‐oxo‐9,19‐cyclo‐9,10‐secolanosta‐9(11),24‐dien‐26‐yl β‐D ‐glucopyranoside ( 4 ).     

Eight New Cucurbitane Glycosides,Kuguaglycosides A – H,from the Root of Momordica charantia L.

Eight new cucurbitane glycosides, kuguaglycosides A–H ( 1 – 8 , resp.), together with five known analogues, 3β,23‐dihydroxycucurbita‐5,24‐dien‐7β‐yl β‐D ‐glucopyranoside ( 9 ), karaviloside III ( 10 ), karaviloside V ( 11 ), karaviloside XI ( 12 ), and momordicoside K ( 13 ), were isolated from the root of Momordica charantia L. The structures of the new compounds were determined on the basis of spectroscopic and chemical methods.     

Baimantuoluosides A – C,Three New Withanolide Glucosides from the Flower of Datura metel L.

In search for bioactive compounds from the flower of Datura metel L., three new withanolide glucosides, namely baimantuoluosides A, B, and C ( 1 – 3 , resp.) were isolated. Enzymatic hydrolysis of 1 – 3 afforded the corresponding aglycones 1a, 2a , and 3a , respectively. The structures of the new compounds were elucidated as (5α,6α,7α,12β,22R)‐5,12‐dihydroxy‐1,26‐dioxo‐6,7 : 22,26‐diepoxyergosta‐2,24‐dien‐27‐yl β‐D ‐glucopyranoside ( 1 ), (5α,6α,7α,12α,22R)‐5,12‐dihydroxy‐1,26‐dioxo‐6,7 : 22,26‐diepoxyergosta‐2,24‐dien‐27‐yl β‐D ‐glucopyranoside ( 2 ), (5α,6α,7α,22R)‐5‐hydroxy‐1,26‐dioxo‐6,7 : 22,26‐diepoxyergosta‐2,24‐dien‐27‐yl β‐D ‐glucopyranoside ( 3 ) on the basis of chemical and physicochemical evidence, and are further confirmed by the structure determination by X‐ray diffraction of withanolide aglycone 1a .     

Triterpenoids from the Mangrove Plant Hibiscus tiliaceus

Three new triterpenoids with the rarely occurring nigrum skeleton, namely (20E)‐22‐hydroxynigrum‐20‐en‐3‐one ( 1 ), 21β‐hydroxynigrum‐22(29)‐en‐3‐one ( 2 ), and 21α‐hydroxynigrum‐22(29)‐en‐3‐one ( 3 ), were isolated from the mangrove plant Hibiscus tiliaceus. Additionally, five known triterpenoids including friedelin ( 4 ), 12‐oleanen‐3β‐ol ( 5 ), 3β‐hydroxy‐12‐oleanen‐28‐oic acid ( 6 ), 20(29)‐lupen‐3β,28‐diol ( 7 ), and cucurbita‐5,23‐dien‐3β,25‐diol ( 8 ) were also isolated and identified. The latter structures were elucidated by a detailed NMR and MS analyses, as well as by comparison with reported literature data.     

Clintoniosides A – C,New Polyhydroxylated Spirostanol Glycosides from the Rhizomes of Clintonia udensis

Phytochemical analyses were carried out on the rhizomes of Clintonia udensis (Liliaceae) with particular attention paid to the steroidal glycoside constituents, resulting in the isolation of three new polyhydroxylated spirostanol glycosides, named clintonioside A ( 1 ), B ( 2 ), and C ( 3 ). On the basis of their spectroscopic data, including 2D‐NMR spectroscopy, in combination with acetylation and hydrolytic cleavage, the structures of 1 – 3 were determined to be (1β,3β,23S,24S,25R)‐1,23,24‐trihydroxyspirost‐5‐en‐3‐yl O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside ( 1 ), (1β,3β,23S,24S)‐3,21,23,24‐tetrahydroxyspirosta‐5,25(27)‐dien‐1‐yl O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucopyranoside ( 2 ), and (1β,3β,23S,24S)‐21‐(acetyloxy)‐24‐[(6‐deoxy‐β‐D ‐gulopyranosyl)oxy]‐3,23‐dihydroxyspirosta‐5,25(27)‐dien‐1‐yl O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucopyranoside ( 3 ).     

Two New Cucurbitane Triterpenoids from Immature Fruits of Momordica charantia

Two new cucurbitane triterpenoids, kuguacin X ( 1 ) and kuguaglycoside I ( 2 ), together with three known analogs, were isolated from immature fruits of Momordica charantia. By detailed analysis of IR, NMR, and MS data, acid hydrolysis, and comparison with spectroscopic data of known compounds, the new compounds were determined to be (23E)‐5β,19‐epoxycucurbita‐6,23‐diene‐3β,22ξ,25‐triol ( 1 ) and (23E)‐5β,19‐epoxycucurbita‐6,23‐dien‐19‐on‐3β,25‐diol 3‐O‐β‐D ‐allopyranoside ( 2 ).     

Ergostane Steroids from Dysoxylum lukii

Phytochemical investigation of the 70% EtOH extract from the stem bark of Dysoxylum lukii led to the isolation of three new ergostane steroids, (3β)‐3,20‐dihydroxyergosta‐5,24(28)‐dien‐7‐one ( 1 ), (3β,4β,7α)‐ergosta‐5,24(28)‐diene‐3,4,7‐triol ( 2 ), and (3β,7α)‐3,20‐dihydroxyergosta‐5,24(28)‐dien‐7‐yl acetate ( 3 ), together with the known compound (3β,4β)‐ergosta‐5,24(28)‐diene‐3,4,20‐triol ( 4 ). Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR (COSY, HMQC, HMBC, and NOESY) analyses.     

Noroleanane Triterpenoids from the Aerial Parts of Lantana camara

Two novel triterpenoids, lantadienone ( 1 ) and camaradienone ( 2 ), were isolated from the aerial parts of Lantana camara, along with seven known compounds, lantadene A, lantadene B, β‐sitosterol 3‐(β‐D ‐glucopyranoside), camaric acid, lantanilic acid, lantanolic acid, and camangeloyl acid. Their structures were elucidated as (3β,22β)‐3,25‐epoxy‐3‐hydroxy‐22‐{[(2Z)‐2‐methyl‐1‐oxobut‐2‐enyl]oxy}‐28‐noroleana‐12,17‐dien‐11‐one ( 1 ) and (3β)‐3,25‐epoxy‐3‐hydroxy‐28‐noroleana‐12,17‐dien‐11‐one ( 2 ), respectively, by means of spectral studies. The triterpenoids 1 and 2 represent 28‐noroleananes oxidized at C(11) and C(22) or at C(11), reported for the first time.     

Scyphiphorins A and B,Two New Iridoid Glycosides from the Stem Bark of a Chinese Mangrove Scyphiphora hydrophyllacea

Two new iridoid glycosides, named scyphiphorins A ( 1 ) and B ( 2 ), together with four known compounds, geniposidic acid (=(1S,4aS,7aS)‐1‐(β‐D ‐glucopyranosyloxy)‐1,4a,5,7a‐tetrahydro‐7‐(hydroxymethyl)cyclopenta[c]pyran‐4‐carboxylic acid; 3 ), 4‐(4‐hydroxy‐3‐methoxybenzyl)butan‐2‐one, oleanolic acid (=(3β)‐3‐hydroxyolean‐12‐en‐28‐oic acid), and stigmasterol β‐D ‐glucoside (=(3β,22E)‐stigmasta‐5,22‐dien‐3‐yl β‐D ‐glucopyranoside), were isolated for the first time from the stem bark of a Chinese mangrove, Scyphiphora hydrophyllacea Gaertn . f. The structures of compounds 1 and 2 were determined as 10‐O‐benzoylgeniposidic acid and 10‐O‐[(2E,6R)‐8‐hydroxy‐2,6‐dimethyl‐1‐oxooct‐2‐en‐1‐yl]geniposidic acid, respectively, on the basis of spectroscopic data and chemical methods, including 2D NMR techniques.     

Three New Triterpene Saponins from Gynostemma pentaphyllum

Three new dammarane‐type triterpene saponins, 1 – 3 , together with three known compounds, 4 – 6 , were isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino . By means of chemical and spectroscopic methods, their structures were established as (20S)‐3β,20,21‐trihydroxydammara‐23,25‐diene 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)] [β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucopyranosyl‐21‐O‐β‐D ‐glucopyranoside ( 1 ), (20R,23R)‐3β,20‐dihydroxy‐19‐oxodammar‐24‐en‐21‐oic acid 21,23‐lactone 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)] [β‐D ‐xylopyranosyl‐(1→3)]‐α‐L ‐arabinopyranoside ( 2 ), and (21S,23S)‐3β,20ξ,21,26‐tetrahydroxy‐19‐oxo‐21,23‐epoxydammar‐24‐ene 3‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)] [β‐D ‐xylopyranosyl‐(1→3)]‐α‐L ‐arabinopyranoside ( 3 ).     

Terpenoids from Two Dicranopteris Species

Two new compounds, (6S,13S)‐6‐{[β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}cleroda‐3,14‐dien‐13‐ol ( 1 ) and kadsuric acid 3‐methyl ester ( 2 ), together with nine known compounds, (6S,13E)‐6‐{[β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}cleroda‐3,13‐dien‐15‐ol ( 3 ), (6S,13S)‐6‐[6‐O‐acetyl‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}‐13‐{[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐fucopyranosyl]oxy}cleroda‐3,14‐diene ( 4 ), (6S,13S)‐6‐{[6‐O‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐rhamnopyranosyl]oxy}‐13‐{[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐fucopyranosyl]oxy}cleroda‐3,14‐diene ( 5 ), 15‐hydroxydehydroabietic acid ( 6 ), 15‐hydroxylabd‐8(17)‐en‐19‐oic acid ( 7 ), junicedric acid ( 8 ), (4β)‐kaur‐16‐en‐18‐oic acid ( 9 ), (4β)‐16‐hydroxykauran‐18‐oic acid ( 10 ), and (4β,16β)‐16‐hydroxykauran‐18‐oic acid ( 11 ) were isolated from the fronds of Dicranopteris linearis or D. ampla. Their structures were established by extensive 1D‐ and 2D‐NMR spectroscopy. Compounds 1 and 3 – 8 showed no anti‐HIV activities.     

Phenyl and Phenylethyl Glycosides from Picrorhiza scrophulariiflora

Three new phenyl glycosides, scrophenoside A ( 1 ), B ( 2 ), and C ( 3 ), and two new phenylethyl glycosides, scroside D ( 4 ) and scroside E ( 5 ), were isolated from the stem of Picrorhiza scrophulariiflora Pennell (Scrophularlaceae), besides five known compounds. On the basis of spectroscopic evidence, the structures of the new compounds were elucidated as 4‐acetyl‐2‐methoxyphenyl 6‐O‐[4‐(β‐D ‐glucopyranosyloxy)vanilloyl]‐β‐D ‐glucopyranoside ( 1 ), 4‐acetylphenyl 6‐O‐[(E)‐p‐coumaroyl]‐β‐D ‐glucopyranoside ( 2 ), 4‐[(1R)‐ and (1S)‐1‐hydroxyethyl]‐2‐methoxyphenyl β‐D ‐glucopyranoside ( 3a and 3b , resp.), 2‐(3,4‐dihydroxyphenyl)ethyl O‐β‐D ‐glucopyranosyl‐(1→3)‐4‐O‐[(E)‐feruloyl]‐β‐D ‐glucopyranoside ( 4 ), and 2‐(3,4‐dihydroxyphenyl)ethyl O‐β‐D ‐glucopyranosyl‐(1→3)‐6‐O‐[(E)‐feruloyl]‐β‐D ‐glucopyranoside ( 5 ).     

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 ).     

Sulfated Triterpenes from Lemon Balm

The hydroalcoholic (EtOH/H₂O) extract of matured leaf margins of lemon balm (Melissa officinalis L.) afforded a new 3,23‐disulfate of 2α,3β‐23,29‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐glucopyranoside ( 1 ) and a new 23‐monosulfate of 2α,23‐dihydroxyurs‐12‐en‐28‐oic acid 3‐O‐β‐D ‐glucopyranoside ( 2 ), along with six known compounds, i.e., 23‐monosulfate of 2α,3β,19α,23‐tetrahydroxyurs‐12‐ene‐28‐oic acid 28‐O‐β‐D ‐glucopyranoside ( 3 ), 3,5,6‐trihydroxydehydro‐α‐ionol 9‐O‐β‐D ‐glucopyranoside ( 4 ), quadranoside III ( 5 ), rosmarinic acid ( 6 ), caffeic acid ( 7 ), and luteolin ( 8 ). All the isolated compounds were evaluated for their antioxidant, antimicrobial, antimalarial, and cytotoxic activities. Only rosmarinic acid exhibited substantial antioxidant and antimicrobial activities, whereas sulfated terpenes showed considerably lower or no antimicrobial activity.     

New Minor Spirostane Glycosides from Ypsilandra thibetica

A further phytochemical investigation on the whole plants of Ypsilandra thibetica yielded three new spirostane glycosides, named ypsilandrosides M–O ( 1 – 3 ). Their structures were established as (3β,11α,25R)‐3,11‐dihydroxyspirost‐5‐en‐12‐one 3‐{O‐α‐L ‐rhanmopyranosyl‐(1→4)‐O‐L ‐rhanmopyranosyl‐(1→4)‐O‐[α‐L ‐rhanmopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside} ( 1 ), (3β,7β,25R)‐spirost‐5‐ene‐3,7‐diol 3‐{O‐α‐L ‐rhanmopyranosyl‐(1→4)‐O‐α‐L ‐rhanmopyranosyl‐(1→4)‐O‐[α‐L ‐rhanmopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside} ( 2 ), and (3β,7α,25R)‐spirost‐5‐ene‐3,7,17‐triol 3‐{O‐α‐L ‐rhanmopyranosyl‐(1→4)‐O‐α‐L ‐rhanmopyranosyl‐(1→4)‐O‐[α‐L ‐rhanmopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside} ( 3 ) by means of a combination of MS, 1D‐ and 2D‐NMR spectroscopic methods, and chemical degradation. Among them, compound 3 is the first pennogenin (=(3β,25R)‐spirost‐5‐ene‐3,17‐diol) saponin whose aglycone contains an OH group at C(7). Compounds 1 – 3 were evaluated for the inhibition of the growth of five tumor cell lines, but all of them proved to be inactive.     

New Dammarane Monodesmosides from the Acidic Deglycosylation of Notoginseng‐Leaf Saponins

Three new dammarane monodesmosides, named notoginsenosides Ft₁ ( 1 ), Ft₂ ( 2 ), and Ft₃ ( 3 ), together with three known ginsenosides, were obtained from a mild acidic hydrolysis of the saponins from notoginseng (Panax notoginseng (Burk .) F. H. Chen ) leaves. Their structures were elucidated to be (3β,12β,20R)‐12,20‐dihydroxydammar‐24‐en‐3‐yl O‐β‐D ‐xylopyranosyl‐(1 → 2)‐O‐β‐D ‐glucopyranosyl‐(1 → 2)‐β‐D ‐glucopyranoside ( 1 ), (3β,12β)‐12,20,25‐trihydroxydammaran‐3‐yl O‐β‐D ‐xylopyranosyl‐(1 → 2)‐O‐β‐D ‐glucopyranosyl‐(1 → 2)‐β‐D ‐glucopyranoside ( 2 ), and (3β,12β,24ξ)‐12,20,24‐trihydroxydammar‐25‐en‐3‐yl O‐β‐D ‐xylopyranosyl‐(1 → 2)‐O‐β‐D ‐glucopyranosyl‐(1 → 2)‐β‐D ‐glucopyranoside ( 3 ), by means of spectroscopic evidences. The known ginsenosides Rh₂ and Rg₃ 4 – 6 were obtained as the major products from this acidic deglycosylation.     

Four New Cycloartane (=9,19‐Cyclolanostane) Saponins from the Aerial Parts of Thalictrum fortunei

The four new cycloartane (=9,19‐cyclolanostane) glycosides 1 – 4 were isolated from the aerial parts of Thalictrum fortunei (Ranunculaceae). The structures of these new glycosides were elucidated as (3β,16β,24S)‐cycloartane‐3,16,24,25,30‐pentol 3,25‐di‐β‐D ‐glucopyranoside ( 1 ), (3β,16β,24S)‐24‐(acetyloxy)cycloartane‐3,16,25,30‐tetrol 3,25‐di‐β‐D ‐glucopyranoside ( 2 ), (3β,16β,24S)‐24‐(acetyloxy)‐3‐(β‐D ‐glucopyranosyloxy)cycloartane‐16,25,30‐triol 25‐[β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranoside] ( 3 ), and (3β,16β,24S)‐24‐(acetyloxy)‐3‐(β‐D ‐glucopyranosyloxy)cycloartane‐16,25,30‐triol 25‐[β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐glucopyranoside] ( 4 ). The structure elucidations were accomplished by 1D ‐ and 2D‐NMR methods, HR‐ESI‐MS, and hydrolysis.     

Phenylethyl Glycosides from Digitalis lanata

Three new phenylethyl glycosides, 3′′′′‐O‐methylmaxoside (=2‐(3,4‐dihydroxyphenyl)ethyl O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐[β‐D ‐glucopyranosyl‐(1→6)]‐4‐O‐(E)‐feruloyl‐β‐D ‐glucopyranoside; 1 ), digilanatosides A (=2‐(3,4‐dihydroxyphenyl)ethyl O‐6‐O‐(E)‐sinapoyl‐β‐D ‐glucopyranosyl‐(1→3)‐4‐O‐(E)‐caffeoyl‐β‐D ‐glucopyranoside; 2 ), and digilanatoside B (=2‐(3,4‐dihydroxyphenyl)ethyl O‐6‐O‐(E)‐p‐coumaroyl‐β‐D ‐glucopyranosyl‐(1→3)‐4‐O‐(E)‐caffeoyl‐β‐D ‐glucopyranoside; 3 ) were isolated from the aerial parts of Digitalis lanata, along with two known phenylethyl glycosides, purpureaside A and maxoside, a phenylpropanoid glucose ester, 1‐O‐(E)‐feruloyl‐β‐glucopyranose, a benzoquinolethanoid glucoside, cornoside, a cardenolide, lanatoside C, a furostane‐type steroidal saponin, purpureagitoside, and a disaccharide, sucrose. Their structures were elucidated on the basis of spectroscopic evidence (1D‐ and 2D‐NMR, and HR‐MALDI‐MS).