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…     

Two New Steroidal Glycosides from Ophiopogon japonicus

The tuber of Ophiopogon japonicus Ker-Gawl. is recorded to have various functions, such as against cardiovascular diseases and anti-bacteria, and used as a potent drug to treat different diseases, especially heart diseases1. Since the first steriodal glycoside was isolated from the plant by Japanese scholars2, much attention has been paid to the studies of the chemical components of O. japonicus in recent decades. Steroidal glycosides as the major glycosides with the aglycones of ruscogenin …     

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).     

New Steroidal Saponins Isolated from the Rhizomes of Paris mairei

The genus Paris is an excellent source of steroidal saponins that exhibit various bioactivities. Paris mairei is a unique species and has been widely used as folk medicine in Southwest China for a long time. With the help of chemical methods and modern spectra analysis, five new steroidal saponins, pamaiosides A–E (1–5), along with five known steroidal saponins 6–10, were isolated from the rhizomes of Paris mairei. The cytotoxicity of all the new saponins was evaluated against human pancreatic adenocarcinoma PANC-1 and BxPC3 cell lines.     

Two New Steroidal Glycosides from Caryopteris terniflora

Two new steroidal glycosides were isolated from the Chinese medicinal plant Caryopteris terniflora. The spectroscopic and chemical evidences revealed that their structures tobe 6-(β-sitosteroyl-3-O-β-glucopyranosidyl) hexacosanate 1 and 6‘-(stigmasteroyl-3-O-β-glucopy-ranosidyl) linolenate 2, respectively.     

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.     

Three New Triterpene Saponins from Bolbostemma paniculatum

Two novel noroleanane saponins, tubeimoside A ( 1 ) and tubeimoside B ( 2 ), and a new dammarane triterpene saponin, tubeimoside C ( 3 ), together with two known compounds, 4 and 5 , were isolated from the bulbs of Bolbostemma paniculatum (Maxim .) Franquet . Compound 4 was found in this genus for the first time. Based on spectroscopic methods, including IR, NMR (DEPT, COSY, HMQC, HMBC, and TOCSY), and MS experiments, and chemical reactions, the structures of the new compounds were elucidated as 3β‐[β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyloxy]‐2β,23‐dihydroxy‐28‐norolean‐12‐en‐16‐one ( 1 ), 3β‐[β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyloxy]‐2β,23‐dihydroxy‐28‐norolean‐12‐en‐22‐one ( 2 ), (3β,7β)‐7,18,20‐trihydroxydammar‐24‐en‐3‐yl 2‐O‐α‐L ‐arabinopyranosyl‐β‐D ‐glucopyranoside ( 3 ).     

Two New Steroidal Glycosides from Fermented Leaves of Agave americana

Two new spirostanol glycosides named agamenoside A and B, ere isolated from the fermented leaves of Agave americana. Their structures were elucidated as (23S,25R)-5α-spirostan-3β,6α，23－triol 3-O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(1) and (25R)-5α-spiro-stan-3β,6α-diol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyra-nosyl-(1→4)-β-D-galactopyranoside(2) by a combination of chemical and spectral methods.     

粗糙菝葜中甾体皂甙

粗糙菝基(Smilax lebrunii Lévl)为百合科菝葜属植物,主要分布在我国甘肃、四川、湖南等地,其化学成分迄今未见报道.前文报道了防已叶菝葜植物甾体皂甙的研究工作,本文介绍从粗糙菝葜根茎中分得的2个新的甾体皂甙.用70％乙醇提取粗糙菝葜根粉(500g),将乙醇提取物经常法脱脂和除糖后,采取多次硅胶柱层析,最后用Sephadex LH-20柱纯化,甲醇洗脱分别得到甙1(50mg)和甙2(10mg).     

Structures and Bioactivities of Steroidal Saponins Isolated from the Genera Dracaena and Sansevieria

The species Dracaena and Sansevieria, that are well-known for different uses in traditional medicines and as indoor ornamental plants with air purifying property, are rich sources of bioactive secondary metabolites. In fact, a wide variety of phytochemical constituents have been isolated so far from about seventeen species. This paper has reviewed the literature of about 180 steroidal saponins, isolated from Dracaena and Sansevieria species, as a basis for further studies. Saponins are among the most characteristic metabolites isolated from the two genera. They show a great variety in structural motifs and a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-proliferative effects and, in most case, remarkable cytotoxic properties.     

Two New Steroidal Saponins from the Processed Polygonatum kingianum

Two new spirostanol saponins, kingianoside I ( 1 ) and kingianoside K ( 2 ), corresponding to (3β,23S,25R)‐23‐hydroxy‐12‐oxospirost‐5‐en‐3‐yl 4‐O‐β‐D ‐glucopyranosyl‐β‐D ‐galactopyranoside ( 1 ) and (3β,25R)‐7‐oxospirost‐5‐en‐3‐yl α‐L ‐arabinofuranosyl‐(1→4)‐[6‐deoxy‐α‐L ‐mannopyranosyl‐(1→2)]‐β‐D ‐glucopyranoside ( 2 ), along with 13 known compounds, daucosterol, (25R)‐kingianoside G, (25RS)‐kingianoside A, pratioside D₁, (25RS)‐pratioside D₁, (25S)‐kingianoside C, kingianoside C, ginsenoside Rb₁, saponins Tb and Pb, dioscin, gracillin, and saponin Pa, were isolated from the processed rhizomes of Polygonatum kingianum. The structures of the new compounds were elucidated by detailed spectroscopic analyses, including 1D‐ and 2D‐NMR techniques, and chemical methods. Compound 2 contains a novel unusual spirostanol saponin aglycone. Ginsenoside Rb₁ and saponin Tb were isolated for the first time from the genus Polygonatum. The 13 known compounds were detected for the first time in the processed Polygonatum kingianum.     

Two New Steroidal Glycosides from Liriope muscari

Liriope muscari (Decn.) Bailey (Liliaceae) is a folk medicinal plant used as a substitute of Ophiopogon japonicus (Thunb.) Ker-Gawl., mainly distributing in Quanzhou, Fujian Province, China1. Previously, we reported the isolation and identification of two…     

Two New Spirostanol Steroidal Sapogenins from Fermented Leaves of Agave americana

The genus Agave is well known as rich sources of steroidal saponins and sapogenins 1. More than ten steroidal sapogenins have been isolated from Agave americana L.2-4 In this paper, we describe the structural determination of two new steroidal sapogenins from fermented leaves of A. americana L. The methanolic extracts of dried residues of fermented leaves of A. americana L. produced in Ruili County of Yunnan Province at January 2000, were subjected to repeated column chromatography of …     

Natural Deep Eutectic Solvents for the Extraction of Bioactive Steroidal Saponins from Dioscoreae Nipponicae Rhizoma

In the present study, a simple and environmentally friendly extraction method based on natural deep eutectic solvents (NADESs) was established to extract four bioactive steroidal saponins from Dioscoreae Nipponicae Rhizoma (DNR). A total of twenty-one types of choline chloride, betaine, and L-proline based NADESs were tailored, and the NADES composed of 1:1 molar ratio of choline chloride and malonic acid showed the best extraction efficiency for the four steroidal saponins compared with other NADESs. Then, the extraction parameters for extraction of steroidal saponins by selected tailor-made NADES were optimized using response surface methodology and the optimal extraction conditions are extraction time, 23.5 min; liquid–solid ratio, 57.5 mL/g; and water content, 54%. The microstructure of the DNR powder before and after ultrasonic extraction by conventional solvents (water and methanol) and the selected NADES were observed using field emission scanning electron microscope. In addition, the four steroidal saponins were recovered from NADESs by D101 macroporous resin with a satisfactory recovery yield between 67.27% and 79.90%. The present research demonstrates that NADESs are a suitable green media for the extraction of the bioactive steroidal saponins from DNR, and have a great potential as possible alternatives to organic solvents for efficiently extracting bioactive compounds from natural products.     

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 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.     

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 ).     

Two New Taccalonolides from Tropic Plant Tacca subflaellata

Two new steroidal bitter principles,taccolanolide O,P have been isolated from Tacca subflaellata and their structures were established by spectroscopic methods.     

Dracaenoside A and B, New C-22 Steroidal Lactone Glycosides from the Stem of Dracaena cochinchinensis

Two new C-22 steroidal lactone glycosides, named dracaenoside A and B were isolated from the methanol extract of the fresh stem of Dracaena cochinchinensis. Their structures were established as (20S)3β,14α,16β-trihydroxy pregn-5-ene-22-carboxylic acid (22,16)-lactone 3-O-α-L-rhamnopyranosyl (1→2)[ α-L-rhamnopyranosyl (l→4)]-β-D-glucopyranoside and (20S)3β, 14α,16β-trihydroxy pregn-5-ene-22-carboxylic acid (22,16)-lactone 3-O-α-L-rhamnopyranosyl (1→2)[β-D-glucopyranosyl(1→3)]-β-D-glucopyranoside by means of 2D NMR spectral and chemical methods. It is the first time that steroidal lactone glycosides were isolated from the genus Dracaena.