Triterpenes from Tripterygium wilfordii Hook

Two new friedelane-type triterpenes, tripterfrielanons A (1) and B (2), along with six known triterpenoids, friedelin (3), canophyllal (4), canophyllalic acid (5), 3-oxo-29-hydroxyfriedelane (6), wilforlide A (7), wilforlide B (8), have been isolated from the EtOH extract of the roots of Tripterygium wilfordii Hook.f. Compounds 4, 5, 6 were isolated for the first time from this plant. The new triterpenes 1 and 2 exhibited mild cytotoxic activity against human Hela cell lines in vitro. The assay showed the IC₅₀ of 1 and 2 were 8.5 and 25 μg/mL, respectively.     

Annonaceous Acetogenins of the Seeds from Annona Muricata

Muricatenol (1) is a new C₃₇ non-THF ring acetogenin with four hydroxyls and one isolated double bond in the long aliphatic chain. 2,4-cis-Gigantetrocinone (2) and 2,4-trans-gigantetrocinone (3) have been isolated as their acetates by preparative TLC. 2,4-trans-Isoannonacin-10-one (4) and 2,4-trans-isoannonacin (5) have been isolated as only 2,4-trans-form for the first time (no cis-form). Also four known acetogenins, gigantetrocin-A (6), gigantetrocin-B (7), annomontacin (8), gigantetronenin (9) and a mixture of N-fatty acyl tryptamines have been isolated (10). Their structures have been established on the basis of spectral analyses. The CHCl₃ fraction of the seeds showed strong antitumor activities.     

A New Bicoumarin from Stellera Chamaejasme L

Thirteen compounds were isolated from roots of Stellera chamaejasme L. (Thymelaeaceae). They are β-sitosterol (2), simplexin (3), pimelea factor P2 (4), daucosterol (5), (+)-3-hydroxy-1,5-diphenyl-1-pentanone (6), 4-ethoxy-benzoic acid (7), 2,4,6-Trimethoxy-benzoic acid (8), (+)-afzelechin (9), fumaric acid (10), N,N-dimethyl-L-aspartic acid (11), umbelliferone (12), daphniretin (13) and a novel bicoumarin named bicoumastechamin (1). Among the known compounds, 7, 8, 9, 10 and 11 were first isolated from this plant, and 6 was first isolated from the natural resources. Their structures have been elucidated on the basis of spectral data. In vitro bioassays showed that 4 inhibited cancer cell growth, 13 exhibited immunomodulatory activity, and 6 exhibited both immunomodulatory and anti-tumor activity.     

Furostanoside from Asparagus filicinus

A new furostanoside, named aspafilioside D (1), together with the five known compounds officinalisnin-II (2), Asp-IV' (3), (+)-4'-O-methyl-nyasol (4), (+)-nyasol (5) and tormentic acid (6), have been isolated from the roots of Asparagus filicinus. The structure of 1 has been elucidated on the basis of spectral data.     

Two new triterpenoids from Picria fel-terrae

Two new triterpenoids, picfeltarraegenin VII (1) and picfeltarraenin X (2), have been isolated from Picria fel-terrae Lour., along with three known ones, picfeltarraegenin VI (3), picfeltarraenins VI (4) and VII (5). Their structures have been elucidated by means of spectroscopic methods.     

3-Oxo-axisonitrile-3, a new sesquiterpene isocyanide from the Chinese marine sponge Acanthella sp

A new sesquiterpene isocyanide, 3-oxo-axisonitrile-3 (1), with a spiro [5,6] decane skeleton (spiroaxane) together with a known related sesquiterpene isonitrile (2), sesquiterpene isothiocyanates (3-8) and two diterpene isonitriles (9, 10) have been isolated from the Chinese marine sponge Acanthella sp. The structure of 1 has been determined on the basis of spectroscopic analysis.     

Anthraquinones from Gladiolus gandavensis

Five new anthraquinones have been obtained from the ethanolic extracts of the subterranean corms of Gladiolus gandavensis Van Houtt. Their structures were elucidated as 3,8-dihydroxy-6-methoxy-1-methyl-anthraquinone (gandavensin D, 1), methyl 3,8-dihydroxy-6,7-methylenedioxy-1-methyl-anthraquinone- 2-carboxylate (gandavensin E, 2), 2,3,8-trihydroxy-6-methoxy-1-methoxymethyl-anthraquinone (gandavensin F, 3), 8-hydroxy-3,6-dimethoxy-1-methyl-anthraquinone-2-carboxylic acid (gandavensin G, 4) and 1,7-dihydroxy-3,6-dimethoxy-anthraquinone (gandavensin H, 5) on the basis of spectral data. The known compounds isolated for the first time from this plant have been determined to be methyl 3,6,8-trihydroxy-7-methoxy-1-methyl-anthraquinone-2-carboxylate (6), methyl 3,6,8-trihydroxy-1-methyl-anthraquinone-2-carboxylate (7), 3,8-dihydroxy-6-methoxy-1-methyl-anthraquinone-2-carboxylic acid (8), 3,6,8-trihydroxy-1-methyl-anthraquinone-2-carboxylic acid (9), 6,8-dihydroxy-3-methoxy-1-methyl-anthraquinone-2-carboxylic acid (10), methyl 3,8-dihydroxy-6-methoxy-1-methyl-anthraquinone-2-carboxylate (11) and methyl 3,7,8-trihydroxy-1-methyl-anthraquinone-2-carboxylate (12).     

Two new phenylpropanoid esters of rhamnose from Lagotis yunnanensis

Two new phenylpropanoid esters of rhamnose, lagotoside B (1) and lagotoside C (2), together with three known compounds (3-5), were isolated from Lagotis yunnanensis. The structures of 1 and 2 were elucidated by spectroscopic methods. Compounds 3-5 have been obtained from this species for the first time.     

Three new norlignans from Curculigo capitulata

From the ethanolic extract of the rhizomes of Curculigo capitulata have been isolated, and structurally elucidated by spectral evidences and chemical methods, three new norlignans, capituloside (1), a mixture of curculigenin (2) and isocurculigenin (3), along with four known compounds (4-7), a mixture of 1-O-methylcurculigine (4) and 1-O-methylisocurculigine (5) and a mixture of curculigine (6) and isocurculigine (7).     

A new cucurbitacin from Picria fel-terrae

A new cucurbitacin, picfeltarraenone II (1) as well as four known cucurbitacins, picfeltarraegenin I (2), picfeltarraenin IA (3), picfeltarraenin IB (4), and picfeltarraenin IV (5), have been isolated and characterized from the whole plant of Picria fel-terrae. The purity of picfeltarraenin IA has been determined by TLC and HPLC.     

Microbial hydroxylation of cinobufagin by Mucor spinosus

Mucor spinosus has been employed for the biotransformation of cinobufagin (1) to afford three metabolites. On the basis of their physico-chemical data, the structures of the transformation products have been characterized as 1β-hydroxy-cinobufagin (2), 12β-hydroxy-cinobufagin (3) and 1β,12β-dihydroxy-cinobufagin (4), of which metabolites 2 and 4 are new compounds. In vitro cytotoxic activities of the biotransformation products and the substrate-cinobufagin have been assayed against four tumor cell lines of Bel 7420, BGC 823, HeLa and HL 60; they all showed cytotoxic activities.     

Pregnane glycosides from the stems of Marsdenia tenacissima

Four new pregnane glycosides, named marstenacissides A (1), B (2), C (3), and D (4), have been isolated from the stems of Marsdenia tenacissima. Their structures were established on the basis of chemical and spectral methods.     

Ether-soluble resin glycosides from the roots of Ipomoea batatas

Two new resin glycosides, batataosides I (1) and II (2), and five known compounds, friedelin (3), scopoletin (4), octadecyl caffeate (5), β-sistosterol (6) and daucosterol (7), were isolated from the roots of Ipomoea batatas. Their structures have been determined based on the chemical and spectral data. Batataosides I and II have novel structures because the core simonic acid B was esterised with cinnamic acid for the first time, and three different substituent esterification groups in one resin glycoside is scarce. The absolute configuration of the aglycone was elucidated to be S by Mosher's method.     

Further flavonol and iridoid glycosides from Ajuga remota aerial parts

Five new iridoid glycosides characterised as 6-keto-8-acetylharpagide (1), 6,7-dehydro-8-acetylharpagide (2), 7,8-dehydroharpagide (3), 8-acetylharpagide-6-O-β-glucoside (4), harpagide-6-O-β-glucoside (5) together with three flavonol glycosides, myricetin 3-O-rutinoside-4'-O-rutinoside (6), myricetin 3-O-rutinoside-3'-O-rutinoside (7) and isorhamnetin 3-O-rutinoside-7-O-rutinoside-4'-O-β-glucoside (8) have been isolated from the aerial parts of Ajuga remota. Also isolated were two known compounds ajugarin IV and ajugarin V. Their structures were established using spectroscopic methods including UV, IR, FAB-MS, HR-MS, 1D and 2D NMR techniques.     

Chemical study on Cyathula officinalis Kuan

Four new compounds, 4-[(1-ethoxy-2-hydroxy)ethyl]phenol (1), 2,3-isopropylidene cyasterone (2), 24-hydroxycyasterone (3) and 2,3-isopropylidene isocyasterone (4), together with fourteen known compounds, have been isolated from the roots of Cyathula officinalis Kuan. Their structures have been elucidated predominantly by spectroscopic methods.     

Structural elucidation of fritillahupehin from bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia

A novel diterpenoid ester, fritillahupehin (1) and three known fatty acids, palmitic acid (2), lignoceric acid (3) and azelaric acid (4), have been isolated from the bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia. The structure of fritillahupehin has been established to be ent-kauran-16β-yl lignocerate by means of spectroscopic and chemical evidence. Compounds 2-4 were isolated from Fritillaria sp. for the first time.     

New anthraquinones from Gladiolus gandavensis

Two new anthraquinones, methyl 8-hydroxy-3-methoxy-6,7-methylenedioxy-1-methylanthraquinone-2-carboxylate (gandavensin A, 1) and methyl 8-hydroxy-3,6,7-trimethoxy-1-methylanthraquinone-2-carboxylate (gandavensin B, 2), have been isolated from the light petroleum extract of the subterranean corm of Gladiolus gandavensis Van Houtt., along with methyl 8-hydroxy-3,6-dimethoxy-1-methylanthraquinone-2-carboxylate (3), methyl trans-p-methoxycinnamate (4), 5,7-dimethoxy-2-methylchromone (5), and 5-hydroxy-2-hydroxymethyl-7-methoxychromone (6). Their structures were elucidated on the basis of spectral data.     

Bowdichine, a new diaza-adamantane alkaloid from Bowdichia virgilioides

A novel alkaloid named bowdichine (1), only the third with a diaza-adamantane skeleton containing an unusual N-acetyl enamine moiety, and the known alkaloids acosmine (2), ormosanine (3) and podopetaline (4) have been isolated from the stem bark of Bowdichia virgilioides. The structures were elucidated on the basis of spectral data, mainly 1D and 2D NMR of the diaza-adamantane alkaloids 1 and 2.     

Seven new meroditerpenoids, from the marine sponge Strongylophora strongylata, that inhibited the maturation of starfish oocytes

Seven new meroditerpenoids, strongylophorines 13-19 (1-7), have been isolated together with the four known strongylophorines 2 (8), 3 (9), 4 (10), and 8 (11) by a screening method using oocytes of the starfish Asterina pectinifera from a marine sponge Strongylophora strongylata collected at Iriomote Island, Okinawa, Japan. The structures were assigned according to their spectral data. Ten strongylophorines inhibited the maturation of starfish oocytes in the range 1.1-37.6 μM (IC₅₀), while strongylophorine 4 (10) was not active at 250 μM.     

New tetracyclic diterpenoid and new ceramides from the soft coral Sinularia conferta

The new tetracyclic diterpenoid confertdiate (1) and two new ceramides, (2) and (3), have been isolated from the soft coral Sinularia conferta, collected from Sanya Bay, Hainan Island, China. Their structures have been elucidated by spectroscopic analysis, and comparison of the ¹³C NMR data with those of the known diterpenoid isomandapamate confirmed the structure of 1.