Six New Steroidal Saponins from Helleborus thibetanus

Six steroidal saponins, including five spirostanol glycosides, 1 – 5 , and one furostanol glycoside 1‐sulfonate, 6 , previously unknown in nature, together with three known compounds, 7 – 9 , were isolated from dried roots and rhizomes of Helleborus thibetanus. Their structures were elucidated by extensive 1D‐ and 2D‐NMR experiments, along with IR and HR‐ESI‐MS data, as well as the results of acid hydrolysis. Compounds 1 – 5 possessed a C(25)?C(27) bond and were glycosylated at HO? C(1), which was unusual in steroidal saponins.     

Two New Cytotoxic Spirostane‐Steroidal Saponins from the Roots of Bletilla striata

Two new spirostane‐steroidal saponins, bletilnoside A ( 1 ) and bletilnoside B ( 2 ), together with five known compounds, 3 – 7 , were isolated from the roots of Bletilla striata (Thunb .) Reichb . F. The structures of the new compounds were determined based on their 1D‐ and 2D‐NMR spectral data. The isolated compounds 1 – 7 were tested for cytotoxicity against four human tumor cells (A549, SK‐OV‐3, SK‐MEL‐2, and HCT15) in vitro using a sulforhodamin B bioassay, and compounds 1, 2 , and 5 showed significant cytotoxicities against all tested tumor cell lines with IC₅₀ values ranging from 3.98±0.16 to 12.10±0.40 μM .     

Optimization of the Ultrasonic-Assisted Extraction Technology of Steroidal Saponins from Polygonatum kingianum Collett & Hemsl and Evaluating Its Quality Planted in Different Areas

Polygonatum kingianum Collett & Hemsl is one of the famous traditional Chinese herbs with satisfactory therapeutic effects on invigorating Qi, nourishing Yin and moistening lungs, in which steroidal saponins are one class of important active substances. The main purpose is to determine the optimal extraction technology of steroidal saponins and evaluate the quality of P. kingianum planted in five different areas. The optimal ultrasonic-assisted extraction (UAE) technology was established by using single-factor experiments and the response surface methodology (RSM), and the determination method of high-performance liquid chromatography (HPLC) for dioscin and diosgenin, two primary types of acid-hydrolyzed steroidal saponins, was constructed with good linear range and precision. The results showed that UAE was an efficient extraction method for steroidal saponins, and the extraction yield was significantly affected by the liquid-solid ratio. The optimal extraction technology was generated following a liquid-solid ratio of 10:1 (mL/g), an ethanol concentration of 85% (v/v), an extraction time of 75 min, an extraction temperature of 50 °C and three extractions, of which these parameters were in line with the predicted values calculated by RSM. Considering only dioscin and diosgenin, the quality of P. kingianum planted at five sample plots presented non-significant difference. However, the content of diosgenin in Pingbian Prefecture (PB) was higher than that of the other four areas with a value of 0.46 mg/g. Taken together, the optimal UAE technology for P. kingianum steroidal saponins was determined via RSM. The quality evaluation revealed that there was a non-significant difference among P. kingianum planted in different areas based on the contents of the sum of dioscin and diosgenin. This work has important reference value for the exploitation and utilization of P. kingianum.     

Two New Spirostanol Saponins from Reineckia carnea

Two new spirostanol saponins, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐(β‐D ‐xylopyranoside) ( 1 ) and (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranoside] ( 2 ), along with two known compounds, (1β,3β,5β,25S)‐spirostan‐1,3‐diol 1‐[α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐xylopyranoside] ( 3 ) and (1β,3β,4β,5β,25S)‐spirostan‐1,3,4,5‐tetrol 5‐(β‐D ‐glucopyranoside) ( 4 ) were isolated from the whole plant of Reineckia carnea. The structures of the new steroids were determined by detailed analysis of their 1D‐ and 2D‐NMR spectra and chemical methods, and by comparison with spectral data of known compounds. Compounds 3 and 4 were isolated from the genus Reineckia for the first time.     

New Steroidal Saponins from the Leaves of Yucca elephantipes

Two new spirostanol saponins, namely elephanosides G and H ( 1 and 2 , resp.) were isolated from the leaves of Yucca elephantipes (Agavaceae), together with the two known furostanol saponins 3 and 4 and the six known flavonoid O‐ and C‐glycosides 5 – 10 . The new structures were elucidated as (3β,25S)‐spirost‐5‐en‐3‐yl O‐β‐D ‐glucopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 1 ) and (3β,5β,25R)‐3‐[(2‐O‐β‐D ‐glucopyranosyl‐β‐D ‐galactopyranosyl)oxy]spirostan‐12‐one ( 2 ) on the basis of detailed spectroscopic analysis and acidic hydrolysis.     

Two New Steroidal Saponins from Tacca plantaginea

Two new C27 steroidal glycosides, named taccaoside A(1) and B(2), were isolated from the traditional Chinese herb Tacca plantaginea. The spectroscopic and chemical evidences revealed their structures to be 26-O-β-D-glucopyranosyl-(25R)-3β,26-dihydroxy furost-5,20-diene-3-O-[α-L-rhamnopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→3)]-β-D-glucopyranoside(1) and 26-O-β-D-glucopyranosyl-(25R)-3β,26-dihydroxy furost-5,20-diene-3-O-[α-L-rhamnopyranosyl-(1→2)]-[β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→3)]-β-D-glucopyranoside(2),respectively.     

Two New Acylated Tridesmosidic Saponins from Astragalus armatus

Two new tridesmosidic glycosides of (3β,6α,16β,20R,24S)‐20,24‐epoxycycloartane‐3,6,16,25‐tetrol (=cycloastragenol), armatosides I and II ( 1 and 2 , resp.), were isolated from the roots of Astragalus armatus (Fabaceae) as well as the known bidesmosidic glycosides of cycloastragenol, trigonoside II ( 3 ) and trojanoside H ( 4 ). Their structures were elucidated as (3β,6α,16β,20R,24S)‐3‐O‐(2,3‐di‐O‐acetyl‐β‐D ‐xylopyranosyl)‐20,24‐epoxy‐25‐O‐β‐D ‐glucopyranosyl‐6‐O‐β‐D ‐xylopyranosylcycloartane‐3,6,16,25‐tetrol ( 1 ), and (3β,6α,16β,20R,24S)‐3‐O‐(2‐O‐acetyl‐β‐D ‐xylopyranosyl)‐20,24‐epoxy‐25‐O‐β‐D ‐glucopyranosyl‐6‐O‐β‐D ‐xylopyranosylcycloartane‐3,6,16,25‐tetrol ( 2 ). These structures were established by extensive NMR and MS analyses and by comparison with literature data.     

Investigation of chemical changes in Polygonatum kingianum after traditional processing by multiple fingerprint profiles in combination with multivariate methods

Polygonati Rhizoma (Huangjing) is traditional medicine in China, which can only be used as medicine after being processed. However, there is a limited theoretical basis for analyzing the changes in chemical components after traditional processing. In this study, analytical techniques including Fourier transform infrared spectroscopy, high-performance gel permeation chromatography–evaporative light scattering detection, and HPLC–diode array detection were proposed to perform multiple fingerprint analyses of the changes in the processed materials; the total sugar was also determined. Moreover, the chemometric studies, including hierarchical cluster analysis and principal component analysis, were used to visualize the discrimination of raw and processed materials. The results revealed that the chemical constituents had been profoundly changed following sample processing. In conclusion, these methods could be successfully used to compare raw and processed materials of Polygonatum kingianum, which could be used to elaborate the rationality of processing from the perspective of chemical composition.     

Steroidal Saponins from the Rhizomes of Smilacina henryi

Five steroidal saponins, namely henryiosides A–E ( 1 – 5 ), were isolated from the EtOH extract of the rhizomes of Smilacina henryi. Their structures were elucidated by the extensive use of 1D‐ and 2D‐NMR experiments, along with HR‐MALDI‐MS analysis and the results of acid hydrolysis. The aglycones of henryiosides A–E possess a C(7)?C(8) or C(9)?C(11) bond and were not previously found in saponins.     

Two New Steroidal Saponins from Diuranthera inarticulata

There are only three species in the genus Diuranthera (Liliaceae), which is endemic in the southwest of China1. Four steroidal saponins, diuranthosides A-C and chloromalo-side A were isolated from the fresh roots of D. major. This paper deals with the structure elucidation of two new steroidal saponins, diuranthosides D and E, which were isolated from the methanolic extract of whole plant of D. inarticulata Wang et K. Y. Lang.Diuranthoside D (1), [(]-38 (c 0.08, pyridine), afforded galac…     

地奥心血康中的两个新甾体皂苷

通过正相和反相硅胶柱层析, 从地奥心血康药粉的正丁醇萃取物中分离纯化出2个微量的新甾体皂苷, 通过MS和NMR(包括HMQC, HMBC和NOESY)等波谱解析, 结合化学降解分析将其结构鉴定为3β,26-二醇-25(R)-Δ^5,20(22)-二烯-呋甾-26-O-β-D-吡喃葡萄糖苷(1)和26-O-β-D-吡喃葡萄糖基-3β,20α,26-三醇-25(R)-Δ^5,22-二烯-呋甾-3-O-α-L-吡喃鼠李糖基(1→2)-[α-L-吡喃鼠李糖基(1→4)]-β-D-吡喃葡萄糖苷(2).     

Two New Triterpene Saponins from Acanthophyllum laxiusculum

Two new triterpene glycosides, 1 and 2 , together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman ‐Czeika . The structures of the new compounds were established by extensive 1D‐ and 2D‐NMR spectroscopic experiments and MS analyses as 23‐O‐β‐D ‐galactopyranosylgypsogenic acid 28‐O‐{β‐D ‐glucopyranosyl‐(1→2)‐6‐O‐[4‐carboxy‐3‐hydroxy‐3‐methyl‐1‐oxobutyl]‐β‐D ‐glucopyranosyl‐(1→6)}‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranosyl ester ( 1 ) and gypsogenic acid 28‐O‐{β‐D ‐glucopyranosyl‐(1→2)‐6‐O‐[4‐carboxy‐3‐hydroxy‐3‐methyl‐1‐oxobutyl]‐β‐D ‐glucopyranosyl‐(1→6)}‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranosyl ester ( 2 ).     

Two New Steroidal Saponins from the Fresh Leaves of Agave sisalana

A new furostanol saponin, sisalasaponin C ( 1 ), and a new spirostanol saponin, sisalasaponin D ( 2 ), were isolated from the fresh leaves of Agave sisalana, along with three other known steroidal saponins and two stilbenes. Their structures were identified as (3β,5α,6α,22α,25R)‐3,26‐bis[(β‐D ‐glucopyrano‐ syl)oxy]‐22‐hydroxyfurostan‐6‐yl β‐D ‐glucopyranoside ( 1 ), (3β,5α,25R)‐12‐oxospirostan‐3‐yl 6‐deoxy‐α‐L ‐mannopyranosyl‐(1→4)‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 2 ), (3β,5α,6α,22α,25R)‐22‐methoxyfurostane‐3,6,26‐triyl tris‐β‐D ‐glucopyranoside, cantalasaponin‐1, polianthoside D, (E)‐ and (Z)‐2,3,4′,5‐tetrahydroxystilbene 2‐O‐β‐D ‐glucopyranosides. The last three known compounds were isolated from the fresh leaves of Agavaceae for the first time. The structures of the new compounds were elucidated by detailed spectroscopic analysis, including 1D‐ and 2D‐NMR experiments, and chemical techniques.     

Two New Triterpene Saponins from Cyclamen africanum Boiss. & Reuter

Two new oleanane‐type triterpene saponins, afrocyclamins A and B ( 1 and 2 , resp.), were isolated from a MeOH extract of the roots of Cyclamen africanum Boiss . & Reuter , together with three known triterpenoid saponins, lysikokianoside, deglucocyclamin I, and its dicrotalic acid derivative. The structures were elucidated, on the basis of 1D‐ and 2D‐NMR experiments and mass spectrometry as (3β,20β)‐13,28‐epoxy‐16‐oxo‐3‐{O‐β‐D ‐xylopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}oxy}oleanan‐29‐al ( 1 ) and (3β,16α,20β)‐16,28,29‐trihydroxy‐olean‐12‐en‐3‐yl O‐4‐O‐(4‐carboxy‐3‐hydroxy‐3‐methyl‐1‐oxobutyl)‐β‐D ‐xylopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranoside ( 2 ).     

南海短足软珊瑚Cladiella sp.中两个新孕甾醇苷的分离

从短足软珊瑚Cladiella sp．中,分离得到3个甾类化合物：孕甾-5,20-二烯-3β-醇-3-O-α-L-吡喃岩藻糖苷(1)、孕甾-5,20-二烯-3β-醇-3-O-β-D-吡喃木糖苷(2)和(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(3),其中1和2为新化合物．孕甾醇苷具有抗早孕和抑制肿瘤细胞生长活性．     

Two New Triterpenoid Saponins from Stauntonia obovatifoliola Hayata ssp. intermedia

Two new hederagenin‐type saponins, staunoside G ( 1 ) and staunoside H ( 2 ), along with twelve known triterpenoid saponins, were isolated from stems of Stauntonia obovatifoliola Hayata ssp. intermedia. Their structures were determined by analysis of HR‐EI‐MS, and 1D‐ and 2D‐NMR data, and comparison with those in literature. The two new compounds showed moderate cytotoxicities against three tumor cells, i.e., A549 (lung carcinoma), 4T1 (mammary carcinoma), and HeLa (cervical carcinoma).     

Two New Saponins from Lysimachia davurica

Two new saponins named davuricoside I (1) and davuricoside E (2) were isolated from the whole plants ofLysimachia davurica. Their structures were determined by 1D and 2D NMR, FAB-MS techniques, and chemical methods.     

Two New Triterpene Saponins from the Seed Residue of Hippophae rhamnoides L.

Two new triterpene saponins, named hippophosides E and F ( 1 and 2 , resp.), together with two known compounds, were isolated from the seed residue of Hippophae rhamnoides L. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D‐ and 2D‐NMR and HR‐MS experiments, and by comparison with literature data.