A new triterpene from the leaves of Craibiodendron yunnanense

A new triterpene, taraxast-20(30)-en-3β,12β-diol (1), and eight known compounds were isolated from the leaves of Craibiodendron yunnanense. Their structures were established on the basis of spectral evidence. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 35–37, January–February, 2008.     

Chemical Constituents of Polyalthia nemoralis

Three new natural products, the taraxastane‐type triterpenoid 1 , the azafluorene‐based constituent 2‐hydroxyonychine ( 2 ), and the diterpenoid nemoralisin ( 3 ) were isolated from the EtOH extract of Polyalthia nemoralis, along with five known compounds. The structures of the new compounds were established by in‐depth spectroscopic and mass‐spectrometric analyses, as well as by chemical transformation.     

Two New Polyoxygenated Triterpenoids from Actinidia valvata

Two new polyoxygenated triterpenoids, (2β,3α,6α)‐2,3,6,20,23,30‐hexahydroxyurs‐12‐en‐28‐oic acid ( 1 ) and (2β,3α)‐2,3,20,23,24,30‐hexahydroxyurs‐12‐en‐28‐oic acid O‐β‐D ‐glucopyranosyl ester ( 2 ) were isolated from the roots of Actinidia valvata Dunn . Their structures were elucidated by means of extensive spectroscopic studies. Both compounds showed moderate cytotoxic activity in vitro against the BEL‐7402 and SMMC‐7721 tumor cell lines.     

New Cytotoxic Triterpenoids from the Aerial Parts of Euphorbia sieboldiana

Phytochemical investigation of the EtOH extract of Euphorbia sieboldiana led to the isolation of four new oleanane‐type triterpenoids, (1β,2α,3β,19β)‐1,2,3,19‐tetrahydroxyolean‐12‐en‐28‐oic acid, (1β,3β,19β)‐1,3,19‐trihydroxyolean‐12‐en‐28‐oic acid, (1β,2α,3β,16β,19β)‐1,2,3,16,19‐pentahydroxyolean‐12‐en‐28‐oic acid, and (1β,2α,3β,19β,23)‐1,2,3,19,23‐pentahydroxyolean‐12‐en‐28‐oic acid, along with 16 known compounds. Their structures were established by extensive 1D‐ and 2D‐NMR, as well as other spectral analyses. Biological evaluation of the four new triterpenoids revealed potent cytotoxic activities against HeLa and Hep‐G2 cells.     

Chemical Constituents from the Roots of Patrinia Rupestris

Phytochemical investigation of the roots of Patrinia rupestris afforded a new triterpenoid patrirupin A ( 1 ) and a new iridoid patrirupin B ( 2 ), as well as three known triterpenoids: 3‐oxo‐olean‐12‐en‐28‐oic acid ( 3 ), ursolic acid ( 4 ), α‐amyrin ( 5 ), three known iridoids: isovaltratum ( 6 ), 11‐ethoxyviburtinal ( 7 ), homobaldrinal ( 8 ), five known steroids: ergosterol ( 9 ), ergost‐6,22‐diene‐3β,5α,8α‐triol ( 10 ), 6‐hydroxenone ( 11 ), β‐sitosterol ( 12 ), daucosterol ( 13 ), and two known flavones: 1‐hydroxy‐5‐methoxy xanthen‐9‐one ( 14 ), 3′,4′,5,7‐tetrahydroxyflavanone ( 15 ). The new compounds were characterized by means of spectroscopic methods including UV, IR, 1D, 2D NMR and HRESIMS, and the known ones were established on the basis of comparing their NMR data with those of the corresponding compounds in the literature.     

Triterpenoids from the Roots of Camellia oleifera C.Abel and Their Cytotoxic Activities

Three new triterpenoids, 21β,22α‐diangeloyloxy‐3β,15α,16α,28‐tetrahydroxyolean‐12‐en‐23‐al ( 1 ), 21β‐angeloyloxy‐3β,15α,16α,28‐tetrahydroxy‐22α‐(2‐methylbutanoyloxy)olean‐12‐en‐23‐al ( 2 ), and 21β‐angeloyloxy‐3β,16α,28‐trihydroxy‐22α‐(2‐methylbutanoyloxy)olean‐12‐en‐23‐al ( 3 ), along with six known triterpenoids, were isolated from the roots of Camellia oleifera C.Abel . The structures of compounds 1 – 3 were elucidated on the basis of spectroscopic analyses. Moreover, all compounds isolated were evaluated for their cytotoxic activities by MTT (=3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide) assay.     

Two new triterpenoids from the fungus Diplodia cupressi

Abstract

One new pentanortriterpenoid, 23,24,25,26,27-pentanorlanost-7,9(11)-dien-3β,22-diol (1), one new triterpenoid, lanost-8-en-3β,22S,23S-triol (2), together with the known triterpenoid, 23,24,25,26,27-pentanorlanost-8-en-3β,22-diol (3), were obtained from culture of the fungus Diplodia cupressi associated with the moss Polytrichum commune. The structures of the new compounds were elucidated by extensive spectroscopic techniques including HR-ESIMS and 1?D and 2?D NMR experiments. The cytotoxicity of these compounds against human cancer cell lines (A549, Hep G2, Hepa 1c1c7, and Hela) was evaluated and compound 2 exhibited weak inhibitory activity with IC₅₀ value of 35.0?±?2.3?μM against the proliferation of the Hepa 1c1c7 cells.     

Diterpenoid Alkaloids from Delphinium yunnanense

Three new diterpenoid alkaloids, along with eleven known alkaloids, were isolated from the whole herbs of Delphinium yunnanense. The new alkaloids include a rearranged‐type C₁₉‐diterpenoid alkaloid, named yunnanenseine A ( 1 ), and two hetisine‐type C₂₀‐diterpenoid alkaloids, named yunnanenseine B and C ( 2 and 3 , resp.). Their structures were elucidated by detailed NMR‐spectroscopic studies.     

Yunnandaphninines F and G,New C30 Alkaloids from Daphniphyllum yunnanense

Eight C₃₀ Daphniphyllum alkaloids, including two new ones, yunnandaphninines F and G ( 1 and 2 , resp.), were isolated from the leaves and stems of Daphniphyllum yunnanense. Their structures were elucidated on the basis of the spectroscopic data.     

Chemical Constituents of the Leaves of Desmos cochinchinensis var. fulvescens Ban

A phytochemical investigation of MeOH extract of Desmos cochinchinensis var. fulvescens Ban afforded two new compounds, 1β,7α‐dihydroxyeudesman‐4‐one ( 1 ) and 5αH‐megastigm‐7‐ene‐3α,4α,6β,9‐tetrol ( 2 ), together with nine known terpenoids. The structures of the new compounds were elucidated by 1D‐ and 2D‐NMR spectroscopic analysis. Their relative configurations were assigned by NOESY experiments.     

Triterpenoids and Iridoid Glycosides from Gentiana dahurica

One new and six known pentacyclic triterpenoids, 1 and 4 – 9 , resp., along with two new and three known iridoid glycosides, 2 and 3 , and 10 – 12 , resp., were isolated from the roots of Gentiana dahurica (‘Qin‐Jiao’). The new structures were elucidated by means of spectroscopic and chemical methods as 1β,2α,3α,24‐tetrahydroxyursa‐12,20(30)‐dien‐28‐oic acid ( 1 ), 6′‐O‐acetylgentiopicroside ( 2 ), and 3′‐acetylgentiopicroside ( 3 ). Isolated compounds were tested for their cytotoxicity against the MCF‐7 human breast cancer cell line using the MTT assay. Among them, triterpenoids 2α,3β,24‐trihydroxyurs‐12‐en‐28‐oic acid ( 6 ) and 3β,24‐dihydroxyurs‐12‐en‐28‐oic acid ( 9 ) were found to have moderate cytotoxic effects with IC₅₀ values of 20.9 and 21.7 μg/ml, respectively. Additionally, the chemotaxonomic significance of the identified secondary metabolites is briefly discussed.     

Chemical Constituents from Fruits and Stem Bark of Celtis australis L.

Four triterpenoids named (9β,31R)‐9,25‐cyclo‐30‐propylhopan‐31‐ol ( 1 ), (3β)‐3‐hydroxy‐30‐propylhopan‐31‐one ( 2 ), (3β)‐oleanan‐3‐ol ( 3 ), and (3β,9β)‐9,25‐cycloolean‐12‐en‐3‐yl β‐D ‐glucofuranoside ( 4 ), a steroid named (3β,9β,14β)‐14‐hydroxy‐9,19‐cyclocholan‐3‐yl β‐D ‐glucopyranoside ( 5 ), and an anthraquinone named 6‐hydroxy‐5,7,8‐trimethoxy‐9,10‐dioxo‐9,10‐dihydroanthracen‐2‐yl acetate ( 6 ) have been isolated from the fruits and bark of Celtis australis (Ulmaceae), along with apigenin, quercetin, and its glucoside. Their structures were elucidated by means of chemical and spectral analysis including COSY, NOESY, and HMBC experiments.     

New Polyoxygenated Triterpenoids from Stachyurus himalaicus var. himalaicus

Two new polyoxygenated triterpenoids, stachlic acid A (= (2α,3β)‐2,3,23,29‐tetrahydroxyolean‐12‐en‐28‐oic acid; 1 ) and stachlic acid B (= (2α,3α)‐2,29‐dihydroxy‐3,23‐[(1,1‐dimethylmethylene)dioxy]olean‐12‐ene‐28‐oic acid; 2 ), were isolated from Stachyurus himalaicus var. himalaicus. Their structures were established by means of extensive spectroscopic studies and chemical evidence. The purified product 1 was found to have moderate in vitro cytotoxic activity against human Hela cells.     

Two New Pentacyclic Triterpenoids from Centella asiatica

Two new pentacyclic triterpenoids, named centelloside D ( 1 ) and centelloside E ( 9 ), together with the seven known compounds 2 – 8 , were isolated from the whole plants of Centella asiatica. Compound 5 was reported for the first time from this genus. 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. Compounds 1 – 4, 6 , and 8 did not show any cytotoxicity against L929 (mouse embryonic fibroblast).     

A Hydroxylated Lupeol‐Based Triterpenoid Ester Isolated from the Scurrula parasitica Parasitic on Nerium indicum

(3β,7β)‐7‐Hydroxylup‐20(29)‐en‐3‐yl hexadecanoate ( 1 ), a new lupeol‐based triterpenoid ester, along with sixteen known compounds, 7β,15α‐dihydroxylup‐20(29)‐ene‐3β‐O‐palmitate ( 2 ), lupeol palmitate ( 3 ), lupeol ( 4 ), 3‐oxolup‐20(29)‐ene ( 5 ), ursolic acid ( 6 ), cycloeucalenol ( 7 ), stigmasterol ( 8 ), β‐sitosterol ( 9 ), β‐daucosterol ( 10 ), quercetin ( 11 ), quercetin 3‐O‐α‐L ‐arabinoside ( 12 ), quercetin 3‐O‐α‐L ‐rhamnoside ( 13 ), catechin ( 14 ), gitoxigenin 3‐O‐α‐L ‐rhamnoside ( 15 ), gitoxigenin 3‐O‐α‐D ‐glucoside ( 16 ), and digitoxigenin 3‐O‐α‐L ‐rhamnoside ( 17 ), was isolated from the leaves of the Southern China mistletoe, Scurrula parasitica Linn parasitic on Nerium indicum Mill . Their structures were elucidated by spectroscopic analyses, including 2D‐NMR techniques. Cytotoxic activities of compounds 1 – 7 and 11 – 17 were evaluated against three cancer cell lines, PANC‐1, HL‐60, and SGC‐7901, revealing that compounds 4, 6, 11 , and 15 – 17 exhibited effective cytotoxicities, while others were inactive. A structure? activity relationship study of compounds 1 – 5 indicated that the 3‐OH group in lupeol‐based triterpenoids is essential for antitumor activity.     

New Labdane diterpenes from Hedychium yunnanense with cytotoxicity and inhibitory effects on nitric oxide production

Two new labdane diterpenes, hedychenoids A (1) and B (2), were isolated from the rhizomes of Hedychium yunnanense, together with four known ones hedychenone (3), forrestin A (4), villosin (5) and calcaratarin C (6). Their structures were determined on the basis of NMR (1D and 2D) and mass spectroscopic analysis. Compounds 2, 3 and 5 exhibited cytotoxicity against SGC-7901 with IC₅₀ values of 14.88 ± 0.52, 7.08 ± 0.21 and 7.76 ± 0.21 μg/ml, 3 and 5 against HeLa with IC₅₀ values of 9.76 ± 0.48 and 13.24 ± 0.63 μg/ml, respectively. Compounds 2, 5 showed inhibitory effects against nitric oxide production in LPS and IFN-γ-induced RAW 264.7 murine macrophages with IC₅₀ values of 6.57 ± 0.88 and 5.99 ± 1.20 μg/ml, respectively.     

Study on the Constituents of Roots of Aceriphyllum rossii

A new stereoisomer of a tetrahydrofuranoid lignan, acerifuranoid A ( 1 ), and two new oleanane‐type triterpenoids, aceriphyllic acids J and K ( 2 and 3 ), were isolated from the roots of Aceriphyllum rossii. Their structures were elucidated on the basis of spectroscopic analyses and chemical evidence. These isolated compounds exhibited weak cytotoxic activity against various cancer cell lines with IC₅₀>150 μM .     

滇姜花新二萜成分的研究

从滇姜花中分离并鉴定了５个二萜成分，其中新化合物滇姜花素Ａ，Ｂ的结构经光谱及化学方法推定。     

Two New Constituents from Torricellia tiliifolia Stem Barks

A new iridoid, torrilliolide ( 1 ), and a new pyridine alkaloid, torricelline ( 2 ), were isolated from the stem barks of Torricellia tiliifolia. Their structures were determined by analysis of their spectroscopic data. Both compounds exhibited cytotoxicity against Spodoptera litura cell line.