A new epimeric pair of mono-THF annonaceous acetogenins from Goniothalamus gardneri

From the roots of Goniothalamus gardneri Hook f. et. Thoms (Annonaceae), we have isolated a novel epimeric pair, gardnerinin ( 1) and 34- EPI-gardnerinin ( 1'), characterized by the presence of a gamma-hydroxymethyl-gamma-lactone moiety. These compounds represent an unusual type of mono-THF Annonaceous acetogenins, bearing one flanking hydroxy group on the hydrocarbon side, and another hydroxy group on the lactone side, that is only one carbon away from the THF ring.     

Leiocyclocin C and D, two cyclopeptides from Goniothalamus leiocarpus

Two new cyclopeptides, leiocyclocin C (1) and D (2), were isolated from the seeds of Goniothalamus leiocarpus (Annonaceae). Their structures were determined as cyclo-(Gly1-Ser-Pro2-Tyr2-Gly2-Tyr1-Pro1-Pro3) and cyclo-(Gly1-Leu-Pro1-Gly2-Phe-Tyr-Pro2), respectively, by means of spectral and chemical methods.     

Constituents from the stems of Goniothalamus griffithii

A new cyclopeptide, grifficyclocin A (1), and a new aporphine alkaloid, griffinin (2) were isolated together with two known styryllactones from the stems of Goniothalamus griffithii. Their structures were identified spectroscopically and chemically. Among them, the griffinin (2) was isolated as the enol form in two tautomers, and the two known styryllactones, goniothalamin (3) and 8- O-acetylgoniotriol (4), showed selective in vitro antitumor activities.     

Styryllactones from the rhizomes of Goniothalamus griffithii

Three new styryl-lactones 8-acetylgoniofufurone(1), 7-acetylgonio-pypyrone(3), and 5-acetylgoniopypyrone(4), along with ten known compounds, goniofufurone(2), goniopypyrone(5), goniothalamin, goniothalenol, (+)-isoaltholactone, goniodiol, 7-acetylgoniodiol, goniotriol, 8-acetylgoniotriol, 9-deoxygoniopypyrone were isolated from the rhizomes of Goniothalamus griffithii Hook f. et. Thoms. Their structures were elucidated by IR, MS, NMR spectra and chemical evidence. All compounds showed cytotoxic activities against human cancer cell lines.     

Brachystemols A–C,three new furan derivatives from Brachystemma calycinum

Three new furan derivatives, brachystemols A–C (1–3), and 13 known compounds (4–15) were isolated from the EtOH extract of Brachystemma calycinum. Their structures were identified by means of spectroscopic methods. Compounds 4–13 were isolated from this plant for the first time.     

Brachystemols A-C, three new furan derivatives from Brachystemma calycinum

Three new furan derivatives, brachystemols A-C (1-3), and 13 known compounds (4-15) were isolated from the EtOH extract of Brachystemma calycinum. Their structures were identified by means of spectroscopic methods. Compounds 4-13 were isolated from this plant for the first time.     

Nobilisides A - C, three new triterpene glycosides from the sea cucumber Holothuria nobilis

Three new triterpene glycosides, named nobilisides A ( 1), B ( 2) and C ( 3), were isolated from the sea cucumber Holothuria nobilis Selenka. Their structures were deduced by extensive spectral analysis and chemical evidence. Compounds 1 and 3 are non-sulfated monoglycosides while 2 is a sulfated diglycoside. The presence of two conjugated double bonds [22 E,24-diene and 7,9(11)-diene] in the aglycone of 1 is a rare structural feature among sea cucumber glycosides, while 2 and 3 possess the same 22,25-epoxy moiety as their side chains. All three glycosides exhibited significant cytotoxicity against human tumor cell lines.     

Two epimeric pairs of C-4-acetyl annonaceous acetogenins from Goniothalamus donnaiensis

Further studies on the roots of Goniothalamus donnaiensis Finet et Gagnap (Annonaceae) led to the isolation of two pairs of Annonaceous acetogenins, donnaienin C ( 1) and 34- EPI-donnaienin C ( 1'), donnaienin D ( 2) and 34- EPI-donnaienin D ( 2'), containing a rare gamma-hydroxymethyl-gamma-lactone moiety and a C-4-acetoxy group. Their structures were elucidated by spectral data and chemical derivatization. Preliminary pharmacological tests showed that the mixture of donnaienin C( 1) and 34- EPI-donnaienin C ( 1') inhibited human hepatoma (Bel) cell lines in vitro (IC (50), 7.1 microg/ml).     

Structures of three new flavone derivatives, brosimones G, H, and I, from Brosimopsis oblongifolia

From the roots of BROSIMOPSIS OBLONGIFOLIA three new flavone derivatives, named brosimone G ( 3), H ( 4), and I ( 5) together with the known albanin A ( 1) and E ( 2), were isolated. Antimicrobial activity of the compounds is also reported.     

Irisdichotins A–C,three new flavonoid glycosides from the rhizomes of Iris dichotoma Pall.

Three new compounds including one flavonol glycoside, irisdichotin A (1), and two flavanonol glycosides, irisdichotins B (2) and C (3), were isolated from the rhizomes of Iris dichotoma Pall. Their structures were elucidated on the basis of spectroscopic methods.     

Lobophylins F-H: three new cembrene diterpenoids from soft coral Lobophytum crassum

Three new cembrenoids, lobophylins F-H (1–3), along with three known ones, lobophylins A-C (4–6), were isolated from the ethyl acetate extract of the Taiwan water soft coral Lobophytum crassum. The structures of isolated cembrenoids were elucidated on the basis of extensive spectroscopic methods such as IR, 1D, 2D NMR and HR–ESI–MS.     

Mururins A-C,three new lignoids from Brosimum acutifolium and their protein kinase inhibitory activity

Two new flavonolignans, mururins A and B ( 1 and 2), and a new lignan, mururin C ( 3), were isolated from the bark of Brosimum acutifolium Huber together with three known lignans. Their structures were elucidated by spectroscopic means and chemical modifications. They were tested for protein kinase A (PKA) and protein kinase C (PKC) inhibitory activity. Mururin A showed 3 % and 63 % inhibition to PKA and PKC, respectively, at 20 microM. Mururin B showed 58 % and 38 % inhibition, respectively. Mururin C did not have significant activity.     

Two new bislabdane-type diterpenoids and three new diterpenoids from the roots of Cunninghamia lanceolata

Two new bislabdane-type diterpenoids lanceolatin (1), lancelatol (2) and three new diterpenoids 15-nor-14-oxo-8(17),12-labdanien-14,18-dionic acid (3), 8(17),12,14-labdantrien-18-oic acid (4) and 8(17),12,14-labdantrien-18-ol (5), together with 7 known diterpenoids were isolated from the roots of Cunninghamia lanceolata. Their structures were determined by spectroscopic and chemical methods. All of these compounds were isolated from the species for the first time. One of the isolated compounds showed a significant inhibition effect on mouse hind-paw edema induced by carrageenan.     

Isolation, structural elucidation, and cytotoxicity of three new ent-kaurane diterpenoids from Isodon japonica var. glaucocalyx

Three new ENT-kaurane diterpenoids, glaucocalyxin H ( 1), glaucocalyxin I ( 2), and glaucocalyxin J ( 3), together with four known diterpenoids ( 4- 7), were isolated from the leaves of Isodon japonica Hara var. glaucocalyx. Their structures were elucidated by spectroscopic analysis, and the structures of compounds 2 and 3 were further confirmed by X-ray crystallographic analysis. Compounds 1, 4, and 5 were evaluated for their cytotoxicity IN VITRO against CE-1, U87, A-549, MCF-7, Hela, K-562, and HepG-2 human tumor cell lines. Compound 1 showed potent inhibitory activities against six tumor cell lines with IC (50) values ranging from 1.86-10.95 μM, and compounds 4 and 5 exhibited significant selective cytotoxicity on seven tumor cell lines.     

Irisdichotins A-C, three new flavonoid glycosides from the rhizomes of Iris dichotoma Pall

Three new compounds including one flavonol glycoside, irisdichotin A (1), and two flavanonol glycosides, irisdichotins B (2) and C (3), were isolated from the rhizomes of Iris dichotoma Pall. Their structures were elucidated on the basis of spectroscopic methods.     

A new diepoxy-ent-kauranoid,rugosinin, from Isodon rugosus

A new diterpenoid, rugosinin (1), isolated from Isodon rugosus, with absolute configuration was proved by single-crystal X-ray diffraction analysis, to be the member of a rare class of C-20/C-7 and C-20/C-14 diepoxy- ent-kauranoids. Effusanin A (2), effusanin B (3), effusanin E (4), lasiokaurin (5) and oridonin (6) were found as known constituents of the genus Isodon with C-20/C-7 epoxy function. These compounds have exhibited DNA-damaging activity in assay which employed DNA-repair deficient (RAD 52Y) and repair proficient (RAD +) yeast strains.     

Salvicins A and B,new lignans from Salvia santolinifolia

Phytochemical investigation on the CHCl₃ soluble fraction of the ethanolic extract from the whole plants of Salvia santolinifolia led to two new lignans salvicins A (1) and B (2). Their structures were elucidated on the basis of spectral data.     

Isolation and identification of three new flavones from Achillea millefolium L.

Column chromatography on silica gel of a petroleum ether extract of the flowering heads of Achillea millefolium L. allowed three flavones to be separated and identified. Spectral studies (PMR, mass spectrometry, and UV) and a comparison with data for compounds reported in the literature established the flavones as 5-hydroxy-3,6,7,4'-tetramethoxyflavone, artemetin, and casticin. These compounds have not been reported previously as constituents of A. millefolium.