Three new triterpenes from the roots of Rhus javanica L. var. roxburghiana

Three new triterpenes, lantabetulal (1), lantanolal (2), and lantanolol (3) along with lantabetulic acid (4) and lantanolic acid (5) were isolated from the roots of Rhus javanica L. var. roxburghiana. The structural assignments of all these compounds were carried out by their spectroscopic analysis.     

A new bisabolane sesquiterpenoid from Euphorbia chrysocoma

The new sesquiterpenoid (6R)-2-chloro-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (1), together with ten known compounds, (6R)-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (2), bauerenol acetate (3), lupenone (4), α-amyrenone (5), β-sitosterol (6), stigmasterol (7), β-amyrin (8), ursolic acid (9), betulinic acid (10), scopolin (11), have been isolated from the roots of Euphorbia chrysocoma Lévl. et Vant. Their structures have been elucidated by spectroscopic data.     

A new kaempferol trioside from <Emphasis Type="Italic">Solidago altissima</Emphasis> L.

A new kaempferol trioside [kaempferol 3-O-rutinoside 7-O-β-d-apiofuranoside, (1)] was isolated together with nine phenolic compounds, trans-tiliroside (2), caffeic acid (3), chlorogenic acid (4), 3-O-caffeoylquinic acid (5), 4-O-caffeoylquinic acid (6), 3-O-coumaroylquinic acid (7), 4-O-coumaroylquinic acid (8), 3,5-di-O-caffeoylquinic acid (9) and 4,5-dicaffeoylquinic acid (10) from the leaves of Solidago altissima L. The structure elucidations of the compounds were based on the analyses of spectroscopic data.     

New sterol esters from the flowers of Punica granatum Linn.

Two new β-sitosterol esters have been isolated from the flowers of Punica granatum Linn. (Punicaceae) along with the known compounds n-tricosane (3), n-heptacosanyl n-hexanoate (4), olean-5,12-dien-3β-ol-28-oic acid (5), and olean-12-en-3β-ol-28-oic acid (6). The structures of the new phytosterols have been elucidated as stigmast-5-en-3β-ol-3β-dodecanoate (β-sitosterol laurate, 1) and stigmast-5-en-3β-ol-3β-tetradecanoate (β-sitosterol myristate, 2) on the basis of spectral data and chemical analyses.     

Aspergchromones A and B,two new polyketides from the marine sponge-associated fungus Aspergillus sp. SCSIO XWS03F03

Two new polyketides, aspergchromones A (1) and B (2), together with five known compounds, secalonic acid D (3), noreugenin (4), (3S)-5-hydroxymellein (5), (4S)-6-hydroxyisosclerone (6), and (-)-regiolone (7), were isolated from the ethyl acetate extract of marine sponge-derived fungus Aspergillus sp. SCSIO XWS03F03. Their structures were elucidated by means of spectroscopic techniques (1D and 2D NMR, MS, UV, and IR). The absolute configurations of the new compounds were established by ECD calculations. Compound 3 showed moderate antimicrobial activity.     

Sinapic acid derivatives from the seeds of Raphanus nussatirus L.

A new disulfide glycoside, raphthioglucoside (1), and a new sinapic acid derivative, sinapic acid 5-hydroxymethylfurfural ester (2), together with sinapic acid (3) have been isolated from the seeds of Raphanus nussatirus L. The structures of compounds 1-3 were determined based on chemical analysis and spectroscopic methods (UV, 1D and 2D NMR, HRFABMS, HREIMS and elemental analysis).     

A new lignan glycoside from <Emphasis Type="Italic">Juniperus rigida</Emphasis>

A new lignan glycoside, named juniperigiside (1) was isolated from the CHCl₃ soluble fraction of the MeOH extract of stems and leaves of Juniperus rigida S.et Z. Compound 1 was identified by 1D- and 2D-NMR spectroscopy as well as CD analysis as (2R,3S)-2,3-dihydro-7-methoxy-2-(4′-hydroxy-3′-methoxyphenyl)-3-hydroxymethyl-5-benzofuranpropanol 4′-O-(3-O-methyl)-α-L-rhamnopyranoside. Five known lignans, icariside E4 (2), desoxypodophyllotoxin (3), savinin (4), thujastandin (5), and (−)-nortrachelogenin (6) in addition to five known labdane diterpenes including trans-communic acid (7), 13-epi-torulosal (8), 13-epi-cupressic acid (9), imbricatoric acid (10), and isocupressic acid (11) were also isolated and their structures were characterized by comparing their spectroscopic data with those in the literature. All compounds were isolated for the first time from this plant, and 5 and 6 were first reported from the genus Juniperus. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay. Compounds 3, 4, 7, and 8 showed considerable cytotoxicity against four human cancer cell lines in vitro.     

Biotransformation of diethenylbenzenes. III: Identification of metabolites of 1,3-diethenylbenzene in rat

1. Biotransformation of 1,3-diethenylbenzene (1) in rat gave four major metabolites, namely, 3-ethenylphenylglyoxylic acid (2), 3-ethenylmandelic acid (3), N-acetyl-S-[2-(3-ethenylphenyl)-2-hydroxyethyl]-L-cysteine (4) and N-acetyl-S-[1-(3-ethenylphenyl)-2-hydroxyethyl]-L-cysteine (5) were isolated from urine and identified by n.m.r. and mass spectrometry.

2. Four minor metabolites, 3-ethenylbenzoic acid (6), 3-ethenylphenylacetic acid (7), 3-ethenylbenzoylglycine (8) and 2-(3-ethenylphenyl)ethanol (9) were identified by g.l.c.-mass spectrometric analysis of urine extract derivatized in two different ways.

3. All identified metabolites are derived from 3-ethenylphenyloxirane (10), a reactive metabolic intermediate. No product of any metabolic transformation of second ethenyl group has been identified. However, several minor unidentified metabolites were detected by g.l.c.-mass spectrometry.

4. Total thioether excretion in 24h urine after a single i.p. dose of 1 amounted to 28·3±3·5 dose (mean±SD). No significant differences in the thioether fraction were observed in the dose range 100-300mg/kg.

5. Thioether metabolites consisted mainly of mercapturic acids 4 and 5. The ratio of metabolites 5 to 4 was 62:38. Each mercapturic acid consisted of two diastereomers. Their ratio, as determined by quantitative ¹³C-n.m.r. measurement was 95:5 and 79:21 for mercapturic acids 4 and 5, respectively.     

New flavonoids and other constituents from Lespedeza cuneata

Two new flavonoids, 6,8,3′,4′-tetrahydroxy-2′-methoxy-7-methylisoflavanone (1) and 6,8,3′,4′-tetrahydroxy-2′-methoxy-6′-(1,1-dimethylallyl)-isoflavone (2), were isolated from the 95% ethanolic extract of the dried roots of Lespedeza cuneata together with betulinic acid (3), β-sitosterol (4), hexacosanoic acid 2,3-dihydroxy-propyl ester (5), which were isolated from this plant for the first time. Their structures were elucidated by spectral analysis.     

Caragasinin C: a new oligostilbene from the roots of Caragana sinica

A new oligostilbene, caragasinin C (1), and seven known compounds, betulinic acid (2), 4-hydroxybenzaldehyde (3), (?)-medicarpin (4), wistin (5), (2E,4S)-4-hydroxy-2-nonenoic acid (6), pallidol (7), and (+)-α-viniferin (8), were isolated from the roots of Caragana sinica. The structure of caragasinin C was established on the basis of spectroscopic techniques, including HRESIMS, 1D and 2D-NMR.     

Four lanostane-type triterpenes from the fruiting bodies of mushroom Laetiporus sulphureus var. miniatus

Two new 3,4-seco-lanostane-type triterpenes, named as 15α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid (1), 5α-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid 3-methyl ester (2), and one new lanostane triterpene 15α-acetoxylhydroxytrametenolic acid (3) together with a known one versisponic acid D (4) were isolated from the fruiting bodies of Laetiporus sulphureus var. miniatus. Their structures were determined on the basis of extensive spectroscopic methods and comparison with reported data. All four compounds were evaluated for their cytotoxicities against five human cancer cell lines; however, none exhibited inhibitory effects.     

群海绵Agelas sp.的化学成分研究

目的 研究海绵Agelas sp.的化学成分。方法 运用乙醇提取、硅胶、Sephadex-LH₂₀色谱柱、HPLC等多种方法进行分离和纯化,根据理化性质和波谱数据进行结构鉴定。结果 分离得到9个化合物,经结构鉴定分别为4,5-二溴吡咯-2-甲酰胺（1）、4,5-二溴吡咯-2-甲酸（2）、4,5-二溴吡咯-2-甲酸甲酯（3）、N-（4,5-二溴-2-吡咯甲酰基）甘氨酸甲酯（4）、1-（4,5-二溴-2-吡咯甲酰胺基）丙酸甲酯（5）、1-（4,5-二溴-2-吡咯甲酰胺基）丙酸乙酯（6）、异吲哚-1,3-二酮（7）、2（3H）-苯并噻唑酮（8）和manzacidin C（9）。结论 化合物4~9为首次从该属海绵中分离得到,其中化合物4~6为新天然产物。     

Two new phenolic compounds and antitumor activities of asparinin A from Asparagus officinalis

Two new phenolic acid compounds, asparoffin C (1) and asparoffin D (2), together with four known compounds, asparenyol (3), gobicusin B (4), 1-methoxy-2-hydroxy-4-[5-(4-hydroxyphenoxy)-3-penten-1-ynyl] phenol (5), and asparinin A (6), have been isolated from the stems of Asparagus officinalis. The structures were established by extensive spectroscopic methods (MS and 1D and 2D NMR). Compound 6 has obvious antitumor activities both in vitro and in vivo.     

A New Bicoumarin from Stellera Chamaejasme L

Abstract

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.     

A new drimane sesquiterpenoid and a new triterpene lactone from fungus of Fomes officinalis

A new sesquiterpenoid fomeffic acid (1) and a new triterpene lactone fomefficinin (2) were isolated from the fungus Fomes officinalis, together with another six known compounds fomitopsin C (3), dehydrosulfurenic acid (4), dehydroeburiconic acid (5), dehydroeburicoic acid (6), 3-keto-dehydrosulfurenic acid (7), and laricinolic acid (8). The structures and stereochemistry of 1 and 2 were determined by NMR and X-ray diffraction analyses. The sesquiterpenoid and five triterpenes were tested for cytotoxicity against HL-60, Bel-7402, and KB cancer lines in vitro, and they appeared to be modestly active.     

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.     

Chemical constituents of Citrus sinensis var. Shukri from Pakistan

The variety ‘Shukri’ is a new hybrid of Citrus sinensis and is frequently grown for its sweet edible fruits in the southern part of Pakistan. The leaves of this hybrid variety have been investigated in search of secondary metabolites for the first time. As a result of chromatographic analysis of the methanolic extract, a new ceramide along with a flavonone glycoside and two steroids has been isolated, which were spectroscopically characterized as (E)-N-(1,3,4,5-tetrahydroxyhexadecan-2-yl)dec-4-enamide (1), atripliside B (2), β-sitosterol (3), and β-sitosterol-3-O-β-D-glucopyranoside (4), respectively. Compound 1 was found to be a new addition in the list of natural products, whereas, to the best of our knowledge, compounds 2–4 have been isolated for the first time from this source.     

Chemical Constituents from the roots of Ranunculus ternatus

Two new glycosides named as ternatoside A (1) and ternatoside B (2), with four known constituents sternbin (3), methylparaben (4), 4-O-d-glucopyranosyl-p-coumaric acid (5) and linocaffein (6) were isolated from the roots of Ranunculus ternatus, The structures of new compounds were determined by 1D and 2D NMR, MS techniques, and chemical methods.     

Three new polyunsaturated lipids from a Guangxi marine sponge Haliclona sp.

Three new polyunsaturated lipids, (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraen-3-one (1), (6Z,9Z,12Z,15Z)-1-bromooctadeca-6,9,12,15-tetraen-3-one (2), and (Z)-ethyl docos-5-enoate (3), together with two known polyunsaturated lipids, 4(Z),7(Z),10(Z)-tridecatrienoic acid (4) and (6Z,9Z,12Z,15Z)-octadeca-1,6,9,12,15-pentaen-3-one (5), were isolated from the marine sponge Haliclona sp., which was collected from Guangxi, using HSCCC and HPLC methods. Chemical structures of the five compounds were elucidated by spectroscopic techniques.     

Aromatic acid derivatives from the lateral roots of Aconitum carmichaelii

Seven new aromatic acid derivatives (1–7), together with five known analogs, were isolated from the lateral roots of Aconitum carmichaelii. Structures of the new compounds were determined by spectroscopic and chemical methods as 4-methyl ( ? )-(R)-hydroxyeucomate (1), 4-butyl ( ? )-(R)-hydroxyeucomate (2), 4-butyl-1-methyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (3), 1-butyl-4-methyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (4), dimethyl (+)-(R)-2-O-(4′-hydroxy-3′-methoxybenzoyl)malate (5), dimethyl (+)-(R)-2-O-(4′-hydroxybenzoyl)malate (6), and methyl ( ± )-3-(4′-hydroxy-3′-methoxyphenyl)-3-sulfopropionate (7), respectively. Compounds 1 and 2 are 2-benzylmalates (eucomate derivatives), 3–6 belong to 2-O-benzoylmalates, and 7 is a rare phenylpropionate containing a sulfonic acid group. The absolute configurations of eucomate derivatives were confirmed by X-ray crystallographic analysis of 4-methyl eucomate (11).