Four New 13,28‐Epoxyoleanane Saponins from Lysimachia lobelioides

Four new oleanane saponins, lobelioidosides A–D ( 1 – 4 , resp.), all endowed with 16‐oxo and a 23‐OH group, as well as with a 13,28‐epoxy bridge as a common moiety, have been isolated from the 75% EtOH extract of the whole plant of Lysimachia lobelioides. Their structures were elucidated on the bases of MS, ¹H‐ and ¹³C‐NMR, HMQC, HMBC, and ¹H,¹H‐COSY data analysis.     

New Triterpenoidal Saponins from Gypsophila repens

Six new triterpene glycosides, repensosides A–F ( 1 – 6 , resp.), were isolated from the roots of Gypsophila repens L. Their structures, established by extensive 1D‐ and 2D‐NMR spectroscopic experiments as well as MS analyses, were found to be based on gypsogenic acid (or gypsogenin) as aglycone, with three to nine branched or unbranched sugar moieties.     

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.     

Triterpene Saponins from the Leaves of Ilex pernyi

Eight new triterpene saponins, ilexpernosides C–J ( 1 – 8 , resp.), and eight known triterpene saponins were isolated from the 70% EtOH extract of the leaves of Ilex pernyi. The structures of the new compounds were elucidated by spectroscopic data and chemical degradation.     

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.     

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.     

Asterolaurins G – J,New Xenicane Diterpenoids from the Taiwanese Soft Coral Asterospicularia laurae

Four new xenicane diterpenoids, asterolaurins G–J ( 1 – 4 , resp.) have been isolated from the Taiwanese soft coral Asterospicularia laurae. Their structures were determined by extensive spectroscopic analyses (UV, CD, IR, ¹H‐ and ¹³C‐NMR, ¹H,¹H‐COSY, HMBC, and NOESY). The cytotoxic activities of all compounds were evaluated.     

Furostane‐Type Steroidal Saponins from the Roots of Chlorophytum borivilianum

Four new furostanol steroid saponins, borivilianosides A–D ( 1 – 4 , resp.), corresponding to (3β,5α,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐hydroxyfurostan‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐galactopyranoside ( 1 ), (3β,5α,22R,25R)‐ 26‐(β‐D ‐glucopyranosyloxy)‐22‐methoxyfurostan‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐galactopyranoside ( 2 ), (3β,5α,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐methoxyfurostan‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 3 ), and (3β,5α,25R)‐26‐(β‐D ‐glucopyranosyloxy)furost‐20(22)‐en‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 4 ), together with the known tribuluside A and (3β,5α,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐methoxyfurostan‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→2)‐O‐[β‐D ‐xylopyranosyl‐(1→3)]‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐galactopyranoside were isolated from the dried roots of Chlorophytum borivilianum Sant and Fern . Their structures were elucidated by 2D ‐NMR analyses (COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry.     

Medicinal Flowers. Part 29. Acylated Oleanane‐Type Triterpene Bisdesmosides: Perennisaponins G,H, I,J, K,L, and M with Pancreatic Lipase Inhibitory Activity from the Flowers of Bellis perennis

The MeOH extract from the flowers of Bellis perennis was found to show pancreatic‐lipase inhibitory activity (IC₅₀ 455 μg/ml). From the extract, seven new triterpene saponins named perennisaponins G ( 1 ; IC₅₀ 163 μM ), H ( 2 ; 137 μM ), I ( 3 ; 147 μM ), J ( 4 ; 148 μM ), K ( 5 ; 223 μM ), L ( 6 ; 81.4 μM ), and M ( 7 ; 195 μM ) were isolated as pancreatic lipase inhibitors. The stereostructures of 1 – 7 were elucidated on the basis of chemical and spectroscopic evidence.     

Four New Alkaloids,Brevianamides O – R,from the Fungus Aspergillus versicolor

Four new alkaloids, brevianamides O–R ( 1 – 4 , resp.), were isolated from the AcOEt extract of the solid‐state fermented rice culture of the fungus Aspergillus versicolor. Their structures were elucidated on the basis of spectroscopic analyses.     

Phochinenins A – F,Dimeric 9,10‐Dihydrophenanthrene Derivatives,from Pholidota chinensis

Six new compounds, phochinenins A–F ( 1 – 6 ), dimerized from 9,10‐dihydrophenanthrene and dihydrostilbene through direct coupling or an oxygen bridge, along with eight known compounds, were isolated from the whole plants of Pholidota chinensis. Their structures were elucidated on the basis of extensive spectroscopic investigations (1D‐, 2D‐NMR, and HR‐EI‐MS).     

Three Escin‐Like Triterpene Saponins: Assamicins VI,VII, and VIII from the Seeds of Aesculus assamica Griff

Three new escin‐like triterpene saponins, assamicins VI ( 1 ), VII ( 2 ), and VIII ( 3 ), were isolated from the seeds of A. assamica, together with a known saponin, isoescin Ib ( 4 ). Their structures were established as 28‐O‐acetyl‐21‐O‐(3,4‐di‐O‐angeloyl‐6‐deoxy‐β‐glucopyranosyl)‐3‐O‐{O‐β‐glucopyranosyl‐(1→2)‐O‐[β‐glucopyranosyl‐(1→4)]‐β‐glucopyranuronosyl}protoaescigenin ( 1 ), 21‐O‐angeloyl‐3‐O‐{O‐α‐rhamnopyranosyl‐(1→2)‐O‐[β‐glucopyranosyl‐(1→3)]‐β‐glucopyranuronosyl}protoaescigenin ( 2 ), and 21‐O‐angeloyl‐3‐O‐{O‐[β‐glucopyranosyl‐(1→3)]‐β‐glucopyranuronosyl}protoaescigenin ( 3 ) on the basis of spectroscopic analysis (protoaescigenin=(3β,4β,16α,21β,22α)‐olean‐12‐ene‐3,16,21,22,23,28‐hexol; angelic acid=(2Z)‐2‐methylbut‐2‐enoic acid).     

Unusual Nortriterpenoid Saponins from Stauntonia chinensis

Four new saponins, yemuosides YM₁₇–YM₂₀ ( 1 – 4 , resp.), were isolated from the rattan of Stauntonia chinensis DC. (Lardizabalaceae) along with a known saponin, nipponoside D ( 5 ). Their structures were elucidated by spectroscopic analysis and chemical evidence as 20,30‐dihydroxy‐29‐noroleanolic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 1 ), 20,29‐dihydroxy‐30‐noroleanolic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 2 ), 29‐hydroxy‐30‐norolean‐20(21)‐enolic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 3 ), 29‐hydroxyoleanolic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 4 ), and 23,29‐dihydroxyoleanolic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 5 ). Yemuoside YM₁₇–YM₁₉ ( 1 – 3 , resp.) contain novel unusual nortriterpene aglycones.     

Three New Xanthones from the Fungus Penicillium sp. NH‐7‐1

Three new xanthones, drimiopsins G–I ( 1 – 3 , resp.), and two known congeners, griseoxanthone C ( 4 ) and norlichexanthone ( 5 ), were isolated from a fungal isolate, Penicillium sp. NH‐7‐1. The structures of all compounds were determined on the basis of extensive spectroscopic analyses, as well as by comparison with literature reports, and the structure of compound 1 was further confirmed by single‐crystal X‐ray diffraction.     

Triterpene Saponins from Entada phaseoloides

Four oleanane‐type triterpene saponins, phaseoloideside A–D ( 1 – 4 ), were isolated from the seed kernels of Entada phaseoloides, along with rheediinoside B. The structures of the four new compounds were established by 2D‐NMR spectroscopic methods, HR‐ESI‐MS analysis, and chemical degradation. Phaseoloideside D ( 4 ) showed cytotoxic activity against the Eca‐109 cell line with an IC₅₀ value of 28.0 μM .     

Chlojaponilactones B – E,Four New Lindenane Sesquiterpenoid Lactones from Chloranthus japonicus

Reinvestigation of the AcOEt‐soluble part of the EtOH extract of whole plants of Chloranthus japonicus afforded four new lindenane‐type sesquiterpenoid lactones, chlojaponilactones B–E ( 1 – 4 , resp.), together with nine known sesquiterpenoids. Their structures and relative configurations were established on the basis of extensive spectroscopic data and by comparison with the relevant literature.     

Glycopentosides D – F,Three New Phenolic Glycosides from Glycosmis pentaphylla

A phytochemical investigation of the BuOH‐soluble fraction of the EtOH extract from the stems of Glycosmis pentaphylla resulted in the isolation of three new phenolic glycosides, glycopentosides D–F ( 1 – 3 , resp.). Their structures were determined by using spectroscopic analysis including UV, ¹H‐ and ¹³C‐NMR, DEPT, COSY, ROESY, HMBC, HSQC, HR‐ESI‐MS, and acid hydrolysis.     

Three New Alkaloids,Paxiphyllines C – E,from Daphniphyllum paxianum

Nine Daphniphyllum alkaloids, including three new ones, paxiphyllines C–E ( 1 – 3 , resp.), were isolated from the twigs and the leaves of Daphniphyllum paxianum. Paxiphylline C ( 1 ) represents the first example of Daphniphyllum alkaloids with a carbonyldioxy group. Their structures were elucidated on the basis of spectroscopic data.