Lanostanoids Isolated from Ganoderma lucidum Mycelium Cultured by Submerged Fermentation

Three new lanostane triterpene acids, 3‐O‐acetylganoderic acid B ( 1 ), 8β,9α‐dihydroganoderic acid C ( 3 ), and 3‐O‐acetylganoderic acid K ( 4 ), as well as two new lanostane triterpene acid ethyl esters, ethyl 3‐O‐acetylganoderate B ( 2 ) and ethyl ganoderate J ( 5 ), were isolated and characterized from Ganoderma lucidum mycelia which was cultured by submerged fermentation method. Their structures were elucidated on the basis of spectroscopic methods. In addition, the identification of two known lanostane triterpene acid methyl esters, methyl O‐acetyl ganoderate C and methyl 3,7,11,15,23‐pentaoxo‐lanost‐8‐en‐26‐oate were identified by comparison of the NMR data with those reported in the literature.     

A New 18(13 → 12β)‐abeo‐Lanostadiene Triterpenoid from Ganoderma fornicatum

A new triterpenoid, fornicatin C (= (3β)‐3‐hydroxy‐18(13 → 12β)‐abeo‐lanosta‐13(17),24‐dien‐18‐oic acid; 1 ), was isolated from the fruiting bodies of Ganoderma fornicatum, together with the known compounds fornicatin A ( 2 ) and fornicatin B ( 3 ), among other constituents. The structure of 1 was elucidated by means of spectroscopic techniques, and those of 2 and 3 were identified by comparing their spectroscopic data with those reported in the literature.     

Highly oxygenated lanostane triterpenoids from the fungus Ganoderma applanatum

Two new highly oxygenated lanostane triterpenoids, ganoderic acid AP2 (1) and ganoderic acid AP3 (2), were isolated from the fruiting bodies of the fungus Ganoderma applanatum (Ganodermataceae), along with four known analogues, ganoderenic acids A, B, D and G (3-6). The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis.     

Triterpenoids from the Stems of Schisandra glaucescens

Two new lanostane triterpenoids, schiglauzic acid ( 1 ) and schiglaucyclozic acid ( 2 ), together with two known ones, anwuweizic acid ( 3 ) and manwuweizic acid ( 4 ), were isolated from the stems of Schisandra glaucescens. Their structures were determined on the basis of extensive spectroscopic methods, including two‐dimensional NMR techniques, and were further confirmed by X‐ray crystallographic analysis.     

Triterpenoids from Eugenia grandis: structure elucidation by NMR spectroscopy

A new pentacyclic triterpenoid, 2alpha,3beta-dihydroxylup-12-en-28-oic acid (1) and a rarely encountered pentacyclic triterpenoid, 3beta-hydroxylup-12-en-28-oic acid (2), together with five known compounds, friedelin (3), 3beta-friedelinol (4), betulinic acid (5), oleanolic acid (6) and beta-sitosterol (7) were isolated from the chloroform extract of stem bark of Eugenia grandis (Syn: Syzygium grande). The structure and stereochemistry of the new compound (1) and the rarely encountered compound (2) were established by 1D and 2D NMR spectroscopic techniques. All the above isolated compounds from this plant are reported for the first time.     

New triterpenoids from the leaves of Abrus precatorius

Three new (1-3) triterpenoids and one known (4) triterpenoid were isolated from an acid hydrolyzed methanol-soluble extract of the leaves of Abrus precatorius. Their structures were identified as (20S,22S)-3beta,22-dihydroxycucurbita-5(10),24-diene-26,29-dioic acid delta-lactone (1), 3-O-[6'-methyl-beta-D-glucuronopyranosyl]-3beta,22beta-dihydroxyolean-12-en-29-oic acid methyl ester (2), 3-O-beta-D-glucuronopyranosylsophoradiol methyl ester (3), and sophoradiol (4) by spectroscopic techniques including 2D NMR.     

Two new lanostane triterpenoids from Abies sachalinensis

The continuous chemical investigation on the ethyl acetate (EtOAc) soluble fraction of the MeOH extract afforded two new lanostane triterpenoid derivatives including one with a rearranged lanostane skeleton. They were identified as 3,4-seco-8-(14→,13R)abeo-17,13-friedo-9β-lanosta-4(28), 7,14(30),24-tetraen-26,23-olide-23-hydroxy-3-oic acid (1) and 7,14-mariesa-dien-3a-hydroxy-25-methoxy-26-oic acid (2). Structural determination of these compounds were carried out by the spectral studies especially by the two digital (2D)-NMR and high-resolution MS experiences.     

New lanostane-type triterpene acids from wolfiporia extensa

ABSTRACT: BACKGROUD: Dried sclerotia of Wolfiporia extensa (Polyporaceae) is used to invigorate the spleen and to tranquilize the mind in Chinese herbal medicine. Lanostane-type triterpene acids were regard as major secondary metabolites from dried sclerotia of W. extensa. RESULTS: Three new lanostane-type triterpene acids, 3-epi-benzoyloxyl-dehydrotumulosic acid (1), 3-epi-(3'-O-methyl malonyloxy)-dehydrotumulosic acid (2) and 3-epi-(3'-hydroxy-3'-methylglutaryloxyl)-dehydrotumulosic acid (3), were isolated from the sclerotia of W. extensa, together with 3 known lanostane derivatives (4-6). Their structures were elucidated on the basis of spectroscopic analysis, including 1D and 2D-NMR techniques. CONCLUSION: Six lanostane derivatives including three new triterpene acids and three known compounds were reported from the sclerotia of W. extensa in this paper.     

Chemical constituents of Jordanian propolis

Seventeen compounds, including a new lanostane triterpenoid, 24(Z)-1β-3β-dihydroxyeupha-7,24-dien-26-oic acid, have been isolated from the methanolic extracts of two samples of Jordanian propolis collected from two different places with different dominant flora. The structures of the isolated compounds were elucidated by spectral methods including IR, UV, MS and 1- and 2-D NMR.     

Constituents of Kenyan Gardenia volkensii

A new triterpenoid, 3-oxo-22alpha-hydroxy-olean-12-en-28-oic acid (1), oleanolic acid (2) and a known iridoid, 10-hydroxy-1-oxo-7-iriden-11-oic acid methyl ester (3) have been isolated from the dichloromethane extract of the dried seeds of Gardenia volkensii. Their structures were established by 1D and 2D NMR spectroscopic and MS methods.     

Studies on Triterpenoid Glycosides from Rhizomes of Panacis majoris and Their Antiplatelet Aggregation Activity

A new triterpenoid glycoside(1) and seven known triterpenoid glycosides, pseudoginsenoside RT2(2), yesanchinoside R2(3), vinaginsenoside R13(4), vinaginsenoside R8(5), notoginsenoside E(6), 6'-O-acetylginsenoside Re(7), 6"-O-acetylginsenoside Rb₁(8), were isolated from the rhizomes of Panacis majoris. The new triterpenoid glycoside was elucidated as 3-O-[β-D-glucopyranosyl-(1→2)-β-D-(6'-O-ethyl)-glucuronopyranosyl]-oleanolic acid-28-O-β-D-glucopyranoside by extensive spectroscopic and phytochemical methods. Compounds 2-8 were obtained from the plant for the first time. Compounds 3 and 4 displayed good activities against adenosine diphosphate (ADP)-induced platelet aggregation, and compounds 1, 5, 6 and 8 showed moderate activities. Compound 6 exhibited moderate antiplatelet aggregation activity induced by arachidonic acid(AA).     

Two triterpenoid saponins from Neonauclea sessilifolia

From the dried roots of Neonauclea sessilifolia (Rubiaceae), two new triterpenoid saponins, 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-quinovopyranosyl quinovic acid (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-quinovopyranosyl pyrocincholic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (2), were isolated, together with five known saponins. The structures of the new saponins were determined by spectroscopic and chemical means.     

Renchanglactone A, a new triterpenoid lactone from Kadsura renchangiana

From the stems of Kadsura rechangiana, a new triterpenoid lactone named renchanglactone A (1), was isolated together with four known triterpenoids, kadsulactone A, mawuweizic acid, ganwuweizic acid and kadsuric acid. Their structures were determined by spectroscopic methods including 2D-NMR techniques.     

Two new lanostane triterpenoids from Abies sachalinensis

The continuous chemical investigation on the ethyl acetate （EtOAc） soluble fraction of the MeOH extract afforded two new lanostane triterpenoid derivatives including one with a rearranged lanostane skeleton. They were identified as 3,4-seco-8-（14→13R）abeo-17,13-friedo-9β-lanosta-4（28）, 7,14（30）,24-tetraen-26,23-olide-23-hydroxy-3-oic acid （1） and 7,14-mariesa- dien-3oL-hydroxy-25-methoxy-26-oic acid （2）. Structural determination of these compounds were carried out by the spectral studies especially by the two digital （2D）-NMR and high-resolution MS experiences.     

Platycoside N: a new oleanane-type triterpenoid saponin from the roots of Platycodon grandiflorum

A new oleanane-type triterpenoid saponin, named platycoside N (1), together with six known saponins, was isolated from the roots of Platycodon grandiflorum. On the basis of acid hydrolysis, comprehensive spectroscopic data analyses and comparison with the spectral data of the known compounds, its structure was elucidated as 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-β-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside. The six known compounds were platycodin D (2), deapioplatycodin D (3), platycodin D3 (4), deapioplatycodin D3 (5), platycoside E (6) and deapioplatycoside E (7).     

Lanostane Triterpenes from Ceriporia lacerate HS‐ZJUT‐C13A,a Fungal Endophyte of Huperzia serrata

Two new lanostane triterpenes, 3β‐acetoxy‐15α‐hydroxylanosta‐8,24‐dien‐21‐oic acid ( 1 ) and 3β‐acetoxylanosta‐7,9(11),24‐trien‐21‐oic acid ( 2 ), along with the four known analogs, 3 – 6 , were isolated from the culture broth of Ceriporia lacerate HS‐ZJUT‐C13A, a fungal endophyte residing in the stems of the traditional Chinese herb Huperzia serrata. The structures of the new compounds 1 and 2 were established by spectroscopic methods, including UV, IR, HR‐ESI‐MS, and extensive 1D‐ and 2D‐NMR techniques. To the best of our knowledge, this is the first report on triterpene metabolites from the genus Ceriporia.     

Triterpenoids and phenolics from the fruiting bodies of Inonotus hispidus and their activations of melanogenesis and tyrosinase

Two new 24-methyl lanostane triterpenoids,hispindic acids A and B(1 and 2),and a new phenolic compound,hispinine(7),along with nine known compounds(3-6,and 8-12),were isolated from the fruiting bodies of Inonotus hispidus.Their structures were elucidated based on the extensive analysis of spectroscopic data(NMR and HRMS).Hispindic acid A(1) possesses an unusual formyl group at C-30.Compounds 1,3-4,and 8 showed stronger activate abilities of melanogenesis and tyrosinase in B16 melanoma cells than those of positive control,8-methoxypsoralen,at 50 μmol/L     

New triterpenoid saponins from leaves of Panax japonicus (3). Saponins of the specimens collected in Miyazaki prefecture

Two new dammarane-type triterpenoid saponins, chikusetsusaponin LM1 (1), chikusetsusaponin LM2 (2), and three known triterpenoid saponins, ginsenoside Re (3), ginsenoside Rg1 (4), ginsenoside F3 (5), were isolated from the leaves of P. japonicus C. A. Meyer collected in Miyazaki prefecture, Japan. The structures of new chikusetsusaponins were elucidated on the basis of spectroscopic and physicochemical evidences.     

A new triterpenoid from the roots of Tripterygium Wilfordii

<正>A new triterpenoid 3,4,6-trihydroxy-2-oxo-1(10),3,5,7-tetraen-23,24-nor-D:A-friedooleana-29-oic acid,as well as twelve known terpenes were isolated from the roots of Tripterygium wilfordii.Its structure was established on the basis of spectroscopic methods.     

A new triterpenoid saponin from the roots of Silene viscidula

A new triterpenoid saponin, silenoviscoside F (1), was isolated from the roots of Silene viscidula, together with three known saponins, dianchinenoside D (2), sinocrassuloside I (3) and sinocrassuloside II (4). The structure of compound 1 was elucidated by spectroscopic data, GC-MS and chemical methods. The structures of compounds 2-4 were determined on the basis of spectroscopic data comparison with the literature values, which were isolated from the genus Silene for the first time.