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.     

Flavonol Glycosides and Cytotoxic Triterpenoids from Alphitonia Philippinensis

Three new flavonol glycosides, namely, isorhamnetin 3‐O‐(6″‐O‐(Z)‐p‐coumaroyl)‐β‐D ‐glucopyranoside ( 1 ), quercetin 3‐O‐α‐L ‐rhamnopyranosyl(1 → 2)‐α‐L ‐arabinopyranosyl(1 → 2)‐α‐L ‐rhamnopyranoside ( 2 ), and quercetin 3‐O‐α‐L ‐arabinopyranosyl(1 → 2)‐α‐L ‐rhamnopyranoside ( 3 ), were isolated from the stems of Alphitonia philippinensis. Their structures were established by spectral analysis. In addition, NMR data were assigned for ceanothenic acid ( 11 ). Some of the isolated triterpenoids and flavonoid glycosides showed cytotoxicity against human PC‐3 cells and hepatoma HA22T cells, and inhibition of replication on herpes simplex virus type‐1.     

Flavonol Glycosides from the Leaves of Embelia Keniensis

Five new flavonol glycosides characterized as syringetin 3‐O‐α‐rhamnoside‐7‐O‐β‐glucoside, syringetin 3‐O‐α‐rhamnoside‐7,4′‐di‐O‐β‐glucoside, quercetin‐7‐O‐β‐galactosyl (1→3)‐β‐galactoside, myricetin 3‐O‐α‐rhamnosyl (1→4)‐β‐galactoside and myricetin 3‐O‐β‐glucosyl (1→2)‐β‐glucoside‐7‐O‐β‐glucosyl‐(1→4)‐α‐rhamnoside have been isolated from a methanolic extract of Embelia keniensis leaves. Known flavonols isolated from the same extract included myricetin, quercetin, kaempferol, myricetin 3‐O‐α‐rhamnoside, myricetin 3‐O‐β‐glucoside, quercetin 3‐O‐α‐rhamnoside, quercetin 3‐O‐β‐glucoside, quercetin 3‐O‐β‐xyloside, isorhamnetin 3‐O‐α‐rhamnoside and myricetin 3‐O‐rutinoside. Their structures were established from extensive spectroscopic and chemical studies and by comparison with authentic samples.     

Two new acylated flavonoid glycosides from Morina nepalensis var. alba Hand.‐Mazz.

From the whole plant of Morina nepalensis var. alba Hand.‐Mazz., two new acylated flavonoid glycosides ( 1 and 2 ), together with four known flavonoid glycosides ( 3–6 ), were isolated. Their structures were determined to be quercetin 3‐O‐[2″′‐O‐(E)‐caffeoyl]‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐galactopyranoside (monepalin A, 1 ), quercetin 3‐O‐[2″′‐O‐(E)‐caffeoyl]‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐glucopyranoside (monepalin B, 2 ), quercetin 3‐O‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐galactopyranoside (rumarin, 3 ), quercetin 3‐O‐β‐D ‐galactopyranoside ( 4 ), quercetin 3‐O‐β‐D ‐glucopyranoside ( 5 ) and apigenin 4^′‐O‐β‐D ‐glucopyranoside ( 6 ). Their structures were determined on the basis of chemical and spectroscopic evidence. Complete assignments of the ¹H and ¹³C NMR spectra of all compounds were achieved from the 2D NMR spectra, including H–H COSY, HMQC, HMBC and 2D HMQC‐TOCSY spectra. Copyright © 2002 John Wiley & Sons, Ltd.     

Polar Constituents from Sageretia Thea Leaf Characterized by HPLC‐SPE‐NMR Assisted Approaches

Nine glycosides ( 1–9 ) were characterized from the n‐butanol‐soluble fraction of the ethanolic extract of the leaves of Sageretia thea by the general approach. Among these, Compounds 6 and 7 were identified as a mixture. Application of HPLC‐SPE‐NMR in two selected fractions led to the separation of this mixture and the characterization of three additional minors ( 10–12 ). Among these, 7‐O‐methylmyricetin 3‐O‐α‐l ‐arabinofuranoside ( 8 ) is a new natural product and eight compounds, i.e. glucofragulin A ( 1 ), quercetin‐3‐O‐α‐l ‐arabinopyranoside ( 5 ), 3‐O‐β‐d ‐galactopyranoside ( 6 ), 3‐O‐β‐d ‐glucopyranoside ( 7 ), and 3‐O‐α‐l ‐arabinofuranoside ( 11 ), myricetin‐3‐O‐α‐l ‐arabinofuranoside ( 9 ) and 3‐O‐β‐d‐glucopyranoside ( 10 ), and quercetrin ( 12 ), are found for the first time from the title plant.     

Diversity of Chemical Constituents from Saxifraga Montana H.

A thorough phytochemical investigation of the whole plant of Saxifraga montana H. afforded a new glucoside, methyl 6″‐O‐(E)‐p‐hydroxycinnamoxyl‐glucosyringate ( 1 ), and seventeen known natural products, 3‐methyl‐6‐methoxy‐3,4‐dihydroisocoumarin‐8‐O‐β‐D‐glucospyranoside ( 2 ), gallic acid ( 3 ), glucosyringic acid ( 4 ), daphnoretin ( 5 ), chamaejasmoside ( 6 ), myricetin ( 7 ), quercetin ( 8 ), quercetin‐3‐O‐β‐D‐galactopyranoside ( 9 ), quercetin‐3‐O‐α‐L‐arabinoside ( 10 ), quercetin‐3‐O‐β‐D‐glucospyranoside ( 11 ), rutin ( 12 ), quercetin‐3‐O‐β‐D‐glucopyranosyl (6‐1) glucopyranoside ( 13 ), ursolic acid ( 14 ), 5,28‐stigmastadien‐3β‐ol ( 15 ), β‐sitosterol ( 16 ), β‐daucosterin ( 17 ), 6′‐palmitoxyl‐β‐daucosterin ( 18 ). On the basis of various spectroscopic methods, especially intensive 2D‐NMR (COSY, HMQC and HMBC), FAB‐MS and HR‐ESI‐MS techniques, their structures were elucidated.     

Flavonoid Glycosides from the Leaves of Machilus philippinensis

Thirteen flavonoid glycosides ( 1‐7 , 11‐13 , 15 , 17 , and 18 ) were isolated from the EtOH extract of the leaves of Machilus philippinensis. Of these, kaempferol 3‐O‐(2‐O‐β‐D ‐apiofuranosyl)‐α‐L ‐rhamnopyranoside ( 1 ) and kaempferol 3‐O‐(2‐O‐β‐D ‐apiofuranosyl)‐a‐L ‐arabinofuranoside ( 2 ) are new natural products. By application of HPLC‐SPE‐NMR hyphenated technique, five additional flavonol glycosides were characterized ( 8‐10 , 14 , and 16 ). Their structures were elucidated based on spectroscopic analysis. Of these, quercetin 3‐O‐(6‐O‐α‐L ‐rhamnopyranosyl)‐β‐D ‐galactopyranoside ( 5 ) and kaempferol 3‐O‐α‐L ‐arabinopyranoside ( 15 ) showed moderate inhibitory activity against α‐glucosidase type IV from Bacillus stearothermophilus with the IC₅₀ values of 19.5 and 19.0 μM, respectively.     

DOSY NMR applied to analysis of flavonoid glycosides from Bidens sulphurea

2D DOSY ¹H NMR has proved to be a useful technique in the identification of the molecular skeleton of the four major compounds of ethyl acetate extract of aerial parts of Bidens sulphurea (Asteraceae). The combination of this technique with HPLC, mass spectrometry and other NMR techniques enabled the identification of four flavonoid glycosides: quercetin‐3‐O‐β‐D ‐galactopyranoside, quercetin‐3‐O‐β‐D ‐glycopyranoside, quercetin‐3‐O‐α‐L ‐arabinofuranoside and quercetin‐3‐O‐β‐D ‐rhamnopyranoside. Copyright © 2009 John Wiley & Sons, Ltd.     

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 saponins from Sechium mexicanum

The chemical study of Sechium mexicanum roots led to the isolation of the two new saponins {3‐O‐β‐D ‐glucopyranosyl (1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (1) and {3‐O‐β‐D ‐glucopyranosyl (1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐[β‐D ‐apiosyl‐(1 → 3)]‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (2), together with the known compounds {3‐O‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,6β,16α,23‐pentahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (3), tacacosides A₁ (4) and B₃ (5). The structures of saponins 1 and 2 were elucidated using a combination of ¹H and ¹³C 1D‐NMR, COSY, TOCSY, gHMBC and gHSQC 2D‐NMR, and FABMS of the natural compounds and their peracetylated derivates, as well as by chemical degradation. Compounds 1–3 are the first examples of saponins containing polygalacic and 16‐hydroxyprotobasic acids found in the genus Sechium, while 4 and 5, which had been characterized partially by NMR, are now characterized in detail. Copyright © 2009 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.     

Chemical Components of Anaphalis Sinica Hance

Twenty components (including a new flavanone) were isolated and identified from the whole plant of Anaphalis sinica Hance. Their structures were determined on the basis of spectral analysis and chemical transformation. These components are 6‐[(5‐methyl‐6‐ethyl‐4‐hydroxy‐pyrone‐3‐yl)‐methylene]glabranine ( 1 ), kaempferol ( 2 ), tiliroside ( 3 ), quercetin ( 4 ), quercetin‐3‐O‐β‐D‐glucoside ( 5 ), scutellarin ( 6 ), 5,7‐dihydroxy‐8‐methoxyflavone ( 7 ), 5,7‐dihydroxy‐4′‐methoxy‐flavone‐7‐O‐α‐L‐rhamnopyranosyl(1→6)‐β‐D‐glucopyranoside ( 8 ), helipyrone ( 9 ), 4′‐hydroxydehydrokawain ( 10 ), panamin ( 11 ), ursolic acid ( 12 ), pomolic acid ( 13 ), 3‐acetyloleanolic acid ( 14 ), a mixture of N‐(2‐hydroxy‐acyl)‐4‐hydroxy‐8(E)‐ene‐sphingenine ( 15 ), O‐methyl‐D‐inositol ( 16 ), a mixture of β‐sitosterol ( 17 ) and stigmasterol ( 18 ) and a mixture of daucosterol ( 19 ) and stigmasterol‐β‐D‐glucoside ( 20 ). Among them, 6‐[(5‐methyl‐6‐ethyl‐4‐hydroxy‐pyrone‐3‐yl)‐methylene]glabranine ( 1 ) is a new compound, and ¹³C NMR data of panamin ( 11 ) is reported for the first time.     

Brauhenefloroside E and F; acylated flavonol glycosides from Stocksia brauhica Linn

Two new acylated flavonol glycosides, 3‐O‐{[2‐O‐β‐D ‐glucopyranosyl]‐3‐[O‐β‐D ‐glucopyranosyl]‐4‐[(6‐O‐p‐coumaroyl)‐O‐β‐D ‐glucopyranosyl]}‐α‐L ‐rhamnopyranosyl‐kaempferol 7‐O‐α‐L ‐rhamnopyranoside and 3‐O‐{2‐[(6‐O‐p‐coumaroyl)‐O‐β‐D ‐glucopyranosyl]‐3‐[O‐β‐D ‐glucopyranosyl]‐4‐[(6‐O‐p‐coumaroyl)‐O‐β‐D ‐glucopyranosyl]}‐α‐L ‐rhamnopyranosyl‐kaempferol 7‐O‐α‐L ‐rhamnopyranoside, trivially named as brauhenefloroside E (1) and F (2), respectively, were isolated from the fruits of Stocksia brauhica and their structures were elucidated using spectroscopic methods, including 2D NMR experiments. Copyright © 2010 John Wiley & Sons, Ltd.     

Xanthone O‐Glycosides from the Roots of Pteris Multifida

Two new xanthone glycosides and six known compounds were isolated from the roots of Pteris multifida. Based on spectroscopic and chemical methods, the structures of the new compounds were elucidated as 1‐hydroxy‐4,7‐dimethoxy‐8‐(3‐methyl‐2‐butenyl)‐6‐O‐α‐L‐rhamnopyranosyl‐(1→2)‐[β‐D‐glucopyranosyl‐(1→3)]‐β‐D‐glucopyranosylxanthone ( 1 ), and 1,3‐dihydroxy‐7‐methoxy‐8‐(3‐methyl‐2‐butenyl)‐6‐O‐α‐L‐rhamnopyranosyl‐(1 →2)‐[β‐D‐glucopyranosyl‐(1→3)]‐β‐D‐glucopyranosylxanthone ( 2 ), respectively.     

Systematic characterization of flavonoids from Siraitia grosvenorii leaf extract using an integrated strategy of high‐speed counter‐current chromatography combined with ultra high performance liquid chromatography and electrospray ionization quadrupole time‐of‐flight mass spectrometry

The chemical constituents of the Siraitia grosvenorii leaf extract were studied. Firstly, high‐speed counter‐current chromatography was applied to the one‐step separation of four compounds from S. grosvenorii leaf extract with the solvent system composed of 0.01% acetic acid water/n‐butanol/n‐hexane/methanol (5:3:1:1, v/v/v/v). In this work, 270 mg of crude sample yielded four compounds, a new kaempferol O‐glycoside derivative, kaempferol 3‐O‐α‐L‐[4‐O‐(4‐carboxy‐3‐hydroxy‐3‐methylbutanoyl)]‐rhamnopyranoside‐7‐O‐α‐L‐rhamnopyranoside, named kaempferitrin A (2.1 mg, 90%), and three known compounds, grosvenorine (3.4 mg, 93%), kaempferitrin (14.4 mg, 99%) and afzelin (4 mg, 98%), and the structures of these compounds were identified by NMR spectroscopy and mass spectrometry. Then, ultra high performance liquid chromatography with electrospray ionization quadrupole time‐of‐flight mass spectrometry was used to illustrate the dominant flavonoids in S. grosvenorii leaf extract. 34 flavonoids including 19 kaempferol O‐glycosides, 4 quercetin O‐glycosides, 6 flavanone derivatives, and 5 polymethoxyflavones, were accurately or tentatively identified by carefully comparing their retention times, UV data, precise masses, the typical fragments of the standards and literature data. Most of these compounds were reported for the first time. This study establishes a foundation for the further development and utilization of S. grosvenorii leaves in future.     

Two new complex triterpenoid saponins from Gledistsia dolavayi Franch.

Two new triterpenoid saponins, gledistside A ( 1 ) and gledistside B ( 2 ), isolated from the fruits of Gledistsia dolavayi Franch., were characterized as the 3,28‐O‐bisdesmoside of echinocystic acid acylated with monoterpene carboxylic acids. On the basis of spectroscopic and chemical evidence, their structures were elucidated as 3‐O‐β‐D ‐xylopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl‐28‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→4)‐[β‐D ‐galactopyranosyl‐(1→2)]‐α‐L ‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2,6‐dimethyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D ‐glucopyranosylechinocystic acid ( 1 ) and 3‐O‐β‐D ‐xylopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl‐28‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→4)‐[β‐D ‐galactopyranosyl‐(1→2)]‐α‐L ‐rhamnopyranosyl‐(1→2)‐{6‐O‐[2‐hydroxymethyl‐6‐methyl‐6(S)‐hydroxy‐2‐trans‐2,7‐octadienoyl]}‐β‐D ‐glucopyranosylechinocystic acid ( 2 ). The complete ¹H and ¹³C assignments of saponins 1 and 2 were achieved on the basis of 2D NMR spectra including HMQC‐TOCSY, TOCSY, ¹H–¹H COSY, HMBC, ROESY and HMQC spectra. Copyright © 2002 John Wiley & Sons, Ltd.     

Flavonol Glycoside from Psorospermum androsaemifolium

A new flavonol glycoside, 3′‐(4′''‐(3′''',4′'''‐dihydroxyphenoxy)‐2′''‐hydroxyphenoxy)acanthophorin B ( 1a ) together with 3′‐(2′'',4′''‐dihydroxyphenoxy)acanthophorin B ( 1 ), acanthophorin B ( 2 ), vismiaquinone ( 3 ), rheochrysidin ( 3a ), lupeol acetate and fatty acid were isolated from the chloroform extract of the stem bark of Psorospermum androsaemifolium Baker (Clusiaceae). The structure of 1a was determined on the basis of detailed spectroscopic analysis and comparison with the literature. Compounds 1a and 3a showed moderate antimicrobial activity.     

HPLC with quadrupole TOF‐MS and chemometrics analysis for the characterization of Folium Turpiniae from different regions

Folium Turpiniae has been used as a traditional Chinese medicine for the treatment of abscesses, fevers, gastric ulcers, and inflammations. This paper describes a strategy of combining HPLC with photodiode array detection and quadrupole TOF‐MS, as well as phytochemical and chemometrics analysis for the characterization, isolation, and simultaneous quantification of the chemical constituents of Folium Turpiniae. 19 constituents were identified, namely, 11 flavonoids, seven gallic acid derivates, and quinic acid. Among them, 15 compounds were identified in this herbal medicine for the first time; compound 10 appears to be novel and was isolated and confirmed as ellagic acid‐3‐O‐α‐l ‐rhamnopyranoside by NMR spectroscopy and MS. In addition, nine marker compounds, namely gallic acid ( 2 ), ellagic acid‐3‐O‐α‐l ‐rhamnopyranoside ( 10 ), apigenin‐7‐O‐(2′′‐rhamnosyl)gentiobioside ( 11 ), ellagic acid ( 12 ), luteolin‐7‐O‐β‐d ‐neohesperidoside ( 13 ), ligustroflavone ( 14 ), 4′‐O‐methylellagic acid‐3‐O‐α‐l ‐rhamnopyranoside ( 16 ), rhoifolin ( 17 ), and neobudofficide ( 18 ), were quantified simultaneously in ten batches of Folium Turpiniae collected from different regions. Moreover, hierarchical clustering analysis and principal component analysis indicated that both samples from Hubei ( S1 ) and Guangxi ( S3 ) provinces showed apparent differences from the others. Samples from Jiangxi province ( S2 , S4 , and S7–10 ) possessed similar properties and therefore belong to the same group.     

Periplocain A,a New Naphthalene Derivative from Periploca aphylla Growing in Saudi Arabia

Periplocain A ( 2 ), a new naphthalene derivative together with four known compounds: 2‐ethylhexyl benzoate ( 1 ), quercetin‐3‐O‐α‐l ‐rhamnopyranoside ( 3 ), quercetin‐3‐O‐β‐d ‐glucopyranoside ( 4 ), and quercetin‐3‐(6‐O‐α‐l ‐rhamnopyranosyl‐β‐d ‐glucopyranoside) ( 5 ) were isolated from the AcOEt fraction of the aerial parts of Periploca aphylla (Asclepiadaceae). Their structures were established by multiple spectroscopic methods in addition to HR‐ESI‐MS and by comparison with literature data.     

中药枸骨叶中三萜皂苷和黄酮苷类成分研究

A new triterpene glycoside, pomolic acid 3-O-6″-methyl-β-D-glucuronopyranosyl-（1→3）-α-L-arabino- pyranoside, and a new flavonol glycoside, quercetin 3-O-β-D-glucopyranosyl-（1→2）-α-L-arabinopyranoside together with three known triterpene saponins and two flavonol glycosides, were isolated from the leaves of Ilex cornuta. Their structures were established on the basis of spectroscopic analysis.