[Cembranoids and their bioactivities in soft coral Sarcophyton glaucum].

Chemical constituents in soft coral Sarcophyton glaucum were separated and purified by various chromatographic methods. Based on the spectral data, physicochemical properties, and comparison with the data reported in the literature, nine cembranoids, including a new cembranoid named sefsarcophinolide(1) together with eight known cembranoids, namely(+)-isosarcophine(2), sarcomilitatin D(3), sarcophytonolide J(4),(1S,3E,7E,13S)-11,12-epoxycembra-3,7,15-triene-13-ol(5), sarcophytonin B(6),(-)-eunicenone(7), lobophytin B(8), and arbolide C(9), were identified. As revealed by biological activity experiment results, compounds 2-6 had weak acetylcholinesterase inhibitory activity, and compound 5 displayed weak cytotoxicity against K562 tumor cell line.

Two new triterpenoid saponins from Bupleurum marginatum Wall. ex DC.

Two new triterpenoid saponins (1 and 2), together with two known saponins (3 and 4) were isolated from Bupleurum marginatum Wall. ex DC. Their structures were elucidated by the comprehensive spectroscopic analysis. Compounds 1 and 2 represented the rare example of an oleanane-type triterpenoid with two sugar moieties at C-3 and C-28. The cytotoxic activity of four compounds was evaluated against normal heptocell BRL-3A in vitro.

A New Monoterpenoid and a New Flavonoid Glycoside from the Peels of Clausena lansium.

One new monoterpenoid, nerol oxide-8-carboxylic acid (1), and one new flavonoid glycoside, claulansoside A (2), together with six known compounds, clausenamide (3), quercetin (4), isorhamnetin (5), dihydromyric (6), 2",3"-dihydroxyanisolactone (7) and (E,E)-8-(7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)psoralen (8), have been isolated from the peels of Clausena lansium (Lour.) Skeels. Their structures were determined using a combination of 1D, and 2D NMR (HMQC, HMBC, COSY and NOESY) techniques, and HR-ESI-MS analyses. Compounds 1 and 7 exhibited antibacterial activity against Staphylococcus aureus with the diameter of inhibition zones of 11.5 mm and 14.2 mm. Compounds 3 and 6 showed α-glucosidase inhibitory activity in vitro.

A New Degraded Sesquiterpene from the Twigs of Trigonostemon lutescens.

A new degraded sesquiterpene, tectoionol C (1), together with five known compounds wilsonol F (2), heterodendrin (3), epi-heterodendrin (4), 7-deoxogeayine (5), and 1H-indole-3-carboxylicacid, methyl ester (6), was isolated from the twigs of Trigonostemon lutescens. Their structures were determined by spectroscopic methods including 1D and 2D NMR techniques, as well as by comparison with published data.

A new dolabellane diterpenoid and a sesquilignan from Aglaia odorata var. microphyllina.

One new diterpenoid, 11alpha,12betaH-dolabella-4,8(17)-dien-3alpha,7beta,18-triol (1) and one new sesquilignan, 9-methoxy-7',8'-cis-7",8"-cis-buddlenol B (2), together with three known compounds, (+)-diasyringaresinol (3), N-methyl-5- hydroxy-delta3-pyrrolin-2-one (4) and marmin (5), have been isolated from Aglaia odorata var. microphyllina. Their structures were determined using 1D and 2D NMR spectroscopy. Compound 1 exhibited cytotoxic activity against the K562 cell line with an IC50 value of 12.5 microg/mL.

Characterization and determination of 2-(2-phenylethyl)chromones in agarwood by GC-MS.

Agarwood is the fragrant resinous heartwood obtained from certain trees in the genus Aquilaria belonging to the family Thymelaeaceae. 2-(2-Phenylethyl)chromones and characteristic sesquiterpenes are the main classes of aromatic compounds isolated from agarwood. Although there are many sesquiterpenes, relatively few 2-(2-phenylethyl)chromones have been determined in agarwood by GC-MS. After analysis of the MS spectra of eighteen 2-(2-phenylethyl)chromone derivatives isolated from agarwood and identified by NMR spectroscopy, together with the reported MS data and characteristic of structures of 2-(2-phenylethyl)chromones, the MS characterization, fragmentation patterns and characteristic fragment peaks for the compounds were deduced and a table summarizing MS characterization of 2-(2-phenylethyl)chromones in agarwood is presented. All the 2-(2-phenylethyl)chromones previously reported in agarwood are substituted by methoxy or/and hydroxy groups, except for one compound. Due to the fact they all possess the same basic skeleton (molecular weight: 250) and similar substituent groups (methoxy or hydroxy groups), a formula (30m + 16n = MW - 250) is provided to calculate the number of methoxy (m) or hydroxy (n) groups according to molecular ion peak or molecular weight (MW). We deduced that the characteristic fragmentation behaviors of the 2-(2-phenylethyl)chromones are the cleavages of the CH2-CH2 bond between chromone moiety and phenyl moiety. Thus, characteristic fragment ions, such as m/z 91 [C7H7], 107 [C7H6+OH], 121 [C7H6+OCH3], 137 [C7H5+OH+OCH3] are formed by different substituted benzyl moieties, while characteristic fragment ions such as m/z 160 [C10H8O2], 176 [C10H7O2+OH], 190 [C10H7O2+OCH3], 220 [C10H6O2+OCH3×2] are formed by different substituted chromone moieties. Furthermore, rules regarding to the relationship between the positions of hydroxy or methoxy groups and the relative abundances of benzyl and chromone fragment ions have been deduced. Elucidation of how the positions of hydroxy or methoxy groups affect the relative abundances of benzyl and chromone fragment peaks is also provided. Fifteen unidentified compounds of an artificial agarwood sample analyzed by GC-MS, were preliminary determined as 2-(2-phenylethyl)chromones by analysis of their MS characterization and by comparison of their MS spectra with those of 18 standard compounds or 2-(2-phenylethyl)chromones reported in literature according to the above-mentioned methods and rules. This report will be helpful for the analysis and structural elucidation of 2-(2-phenylethyl)chromones in agarwood by GC-MS, and provides fast and reliable characterization of the quality of agarwood.

2-(2-phenylethyl)chromone derivatives in Chinese agarwood "Qi-Nan" from Aquilaria sinensis.

Five new 2-(2-phenylethyl)chromone derivatives, qinanones A-E (1-5), together with eight known 2-(2-phenylethyl)chromone derivatives (6-13), were isolated from the Et2O extract of high-quality Chinese agarwood "Qi-Nan" originating from Aquilaria sinensis. The structures of the new 2-(2-phenylethyl)chromones were elucidated by spectroscopic techniques (UV, IR, 1D and 2D NMR) and MS analyses. In the bioassay for acetylcholinesterase inhibitors, compounds 1-6, 10, and 12 exhibited weak inhibitory activities (inhibition percentage ranged from 10 % to 24 % at the concentration of 50 µg/mL). Compared with other agarwoods, "Qi-Nan" was different in containing 2-(2-phenylethyl)chromones with unsubstituted chromone rings.

Two new acridone alkaloids from the branch of Atalantia buxifolia and their biological activity.

Two new acridone alkaloids, 3-methoxy-1,4,5-trihydroxy-10-methylacridone (1) and 2,3-dimethoxy-1,4,5-trihydroxy-10-methylacridone (2), were isolated from the ethanol extract of the branch of Atalantia buxifolia. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR. Compounds 1 and 2 exhibited significant antibacterial activity against Staphylococcus aureus and weak inhibitory effect on acetylcholinesterase.

A new antibacterial denitroaristolochic acid from the tubers of Stephania succifera.

A new denitroaristolochic acid, demethylaristofolin C (1), together with six known alkaloids, crebanine N-oxide (2), (-)-sukhodianine-ß-N-oxide (3), palmatine (4), corydalmine (5), dehydrocorydalmine (6), and corynoxidine (7), was isolated from the tubers of Stephania succifera. The structure of demethylaristofolin C was elucidated by spectroscopic techniques (UV, IR, 1D, and 2D NMR) and HR-ESI-MS analyses. These compounds exhibited antibacterial activities against Staphylococcus aureus and methicillin-resistant S. aureus strains in different degrees.

A new sesquiterpene lactone from Elephantopus tomentosus.

A new sesquiterpene lactone, named tomenphantopin H (1), together with two known germacranolides, 2ß-methoxy-2-deethoxy-8-O-deacylphantomolin-8-O-tiglinate (2) and 2-deethoxy-2-hydroxyphantomolin (3), was isolated from the whole plant of Elephantopus tomentosus Linn. The new compound was completely elucidated using a combination of 1D and 2D NMR techniques (COSY, HMQC, and HMBC) and HR-ESI-MS analyses. All compounds exhibited antibacterial activity.

A new tetranortriterpenoid from the roots of Atalantia buxifolia.

A new tetranortriterpenoid, named 6-deacetyl-severinolide, together with six known tetranortriterpenoids severinolide, acetyl-isoepiatalantin, 7-isovaleroylcycloepiatalantin, cycloepiatalantin, 7-isovaleroylcycloseverinolide, and atalantin, was isolated from the ethanol extract of the roots of Atalantia buxifolia collected in Hainan. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR (HMQC, ¹H-¹H COSY, HMBC, and NOESY).

Two new triterpenoid saponins from the leaves of Ilex kudingcha.

Two new triterpene saponins, ilekudinchosides F (1) and G (2), along with three known saponins were isolated from the leaves of Ilex kudingcha C. J. Tseng. The new compounds were characterized as 3ß,19α-dihydroxy-12α-ethoxy-urs-13(18)-ene-28,20ß-lactone-3-O-[ß-D-glucopyranosyl(1 → 3)]-[α-L-rhamnopyranosyl(1 → 2)]-α-L-arabinopyranoside (1) and 3ß,19α-dihydroxy-12α-methoxy-urs-13(18)-ene-28,20ß-lactone-3-O-[α-L-rhamnopyranosyl(1 → 2)]-α-L-arabinopyranoside (2). The new structures were elucidated by spectroscopic methods including 1D and 2D NMR, HR-TOF-MS, and CD spectrometry, and the known compounds were identified by the comparison of their NMR and HR-TOF-MS data with those reported in the literature.

A new diterpene from the stems of Manihot esculenta.

A new diterpene, named yucalexin P-23 (1), together with three known compounds, yucalexin P-15 (2), protocatechuic acid (3), and catalpinic acid (4), was isolated from the stems of Manihot esculenta. Their structures were determined by means of physicochemical evidence and spectral analysis. Compounds 3 and 4 exhibited antimicrobial activity.

Cytotoxic and antibacterial flavonoids from dragon's blood of Dracaena cambodiana.

Chemical studies on the constituents from the dragon's blood of Dracaena cambodiana led to the discovery of three new flavonoid derivatives (1- 3) and six known compounds (4- 9). The structures of the three new compounds were elucidated by NMR and MS spectroscopic analyses. All compounds were evaluated for their growth inhibitory activity against human cell lines K-562, SMMC-7721, and SGC-7901, as well as antibacterial activities against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA). As a result, compounds 1, 2, 5, 7, and 9 showed cytotoxicity against K-562, SMMC-7721, and SGC-7901 cell lines. All these compounds were observed to exhibit antibacterial activities against S. aureus, and compounds 1- 4, 6, 8, and 9 were observed to exhibit antibacterial activity against MRSA.

A new drimane sesquiterpenoid glycoside from the seeds of Antiaris toxicaria.

A new drimane sesquiterpenoid glycoside, named 7-drimen-3ß,11-diol 3-O-ß-d-glucopyranoside, was isolated from the 95% EtOH extract of the seeds of Antiaris toxicaria (Pers.) Lesch. The chemical structure was completely elucidated using a combination of 1D and 2D NMR techniques (COSY, HMQC, HMBC, and ROESY) and HR-ESI-MS analysis. The compound showed inhibitory activities toward methicillin-resistant Staphylococcus aureus (MRSA), chronic myelogenous leukemia (K562), and human hepatoma (SMMC-7721) cell lines.

Cytotoxic cardenolide glycosides from the seeds of Antiaris toxicaria.

Bioassay-guided fractionation of the ethanolic extract from the seeds of Antiaris toxicaria led to the isolation of three new cardiac glycosides named toxicarioside J, toxicarioside K, and toxicarioside L, together with a known glucostrophalloside. The structures of the new compounds were elucidated by spectroscopic methods including HRESIMS, UV, IR, and 1D, 2D NMR techniques. The cytotoxic activities of these cardiac glycosides against human gastric (SGC-7901) and human hepatoma (SMMC-7721) cell lines were evaluated, and all of them exhibited significant cytotoxicity.

A new prenylated xanthone from the branches of Calophyllum inophyllum.

The investigation of chemical constituents from the branches of Calophyllum inophyllum Linn led to the isolation of a new prenylated xanthone, named caloxanthone Q (1), together with three known compounds, 2-deprenylrheediaxanthone B (2), jacareubin (3), and 6-deoxyjacareubin (4). Their structures were completely elucidated on the basis of spectroscopic methods (UV, IR, HR-ESI-MS, 1D NMR, and 2D NMR).

Two new 2-(2-phenylethyl)chromones from Chinese eaglewood.

Two new 2-(2-phenylethyl)chromones, (5S(*),6R(*),7S(*))-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (1) and (5S(*),6R(*),7R(*))-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (2), were isolated from the Chinese eaglewood of Aquilaria sinensis (Lour.) Gilg. Their structures were established by detailed MS and NMR spectroscopic analysis, as well as comparison with the literature data.

Scyphiphin C, a new iridoid from Scyphiphora hydrophyllacea.

Chemical investigation of the ethanol extract of the aerial parts of Scyphiphora hydrophyllacea Gaertn.collected in Hainan Province of China resulted in the isolation of a new iridoid, scyphiphin C (1) and a known iridoid glycoside, shanzhiside methyl ester (2). Their structures were elucidated by a study of their physical and spectral data.

[GC-MS analysis of volatile constituents from five different kinds of Chinese eaglewood].

Volatile oils of five different kinds of Chinese eaglewood were extracted with aether at room temperature. The chemical constituents and relative contents of the volatile oils were analysed by GC-MS. It showed that all the five volatile oils were mainly composed of sesquiterpenes, aromatic constituents and fatty acids. Several sesquiterpenes, such as hinesol, nootkatone, valerenic acid, velleral, guaiol, gamma-gurjunene, gamma-selinene, viridiflorol, isoaromadendrene epoxide, valencene, alpha-costol et. al., together with several aromatic constituents, 2,4-di-tert-butylphenol,4-methyl-2,6-di-tert-butylphenol, phenylpropionic acid, 1-(benzyloxy)-8-naphthol, anisylacetone, et. al. were found in the volatile oils of Chinese eaglewood for the first time. The samilarities and differences of the volatile oils from the five kinds of Chinese eaglewood were compared. It suggested that the quality of Chinese eaglewood could be evaluated by GC-MS analyse of the volatile oil.