Limonoids from Citrus sudachi

Four new limonoid derivatives, 1-O-methylichangensin (1), sudachinoid A (2), B (3), and C (4) were isolated from the seeds of Citrus sudachi, together with the known compounds ichangensin, obacunone, obacunoic acid and limonin, and the structures of the new compounds were elucidated based on spectroscopic and chemical evidence.     

A new diphenyl ether from Phoma sp. strain, SHZK-2

A new diphenyl ether methyl 2-(2-formyl-3-hydroxy-5-methylphenoxy)-5-hydroxy-3-methoxybenzoate (3), together with four known compounds, asterric acid (1), methyl asterrate (2), 9(Z),12(Z)-nonadecadienoic acid (4) and orsellinic acid (5), were isolated from the Phoma sp. strain SHZK-2, which was isolated from a polluted environment in southern China. The structures of these compounds were determined by spectroscopic methods. Cytotoxicities of compounds against HEPG2 cell and Raji cell lines were preliminarily evaluated by the MTT method.     

New galloyl derivative from winged sumac (Rhus copallinum) fruit

Twelve compounds were isolated from Winged Sumac (Rhus copallinum) fruit and their structures were elucidated on the basis of NMR and mass spectral data. The isolates included a new galloyl derivative, (R)-galloyl malic acid dimethyl ester (1), and eleven known compounds, gallic acid (2), methyl gallate (3), glucogallin (4), methyl m-digallate (5), methyl p-digallate (6), quercetin (7), myricetin (8), rhamnazin (9), kaempferol (10), betulinic acid (11), and oleanolic acid (12). All of the compounds were evaluated for antiproliferative effects against human colon tumorigenic (HCT-116, Caco-2) and nontumorigenic (CCD18-Co) cell lines.     

Antioxidative phenols and phenolic glycosides from Curculigo orchioides

A new orcinol glucoside, orcinol-1-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3), was isolated from the rhizomes of Curculigo orchioides GAERTN., together with seven known compounds: orcinol glucoside (1), orcinol-1-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (2), curculigoside (4), curculigoside B (5), curculigoside C (6), 2,6-dimethoxyl benzoic acid (7), and syringic acid (8). The structures of these compounds were elucidated using spectroscopic methods. The antioxidant activities of these isolated compounds were evaluated by colorimetric methods based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. All the compounds showed potent antioxidative activities and the structure-activity relationship is discussed.     

New triterpenoids isolated from the root bark of Ulmus pumila L

Three new triterpenoids, 1-3, were isolated from the dried root bark of Ulmus pumila. Along with the three new compounds, six known triterpenoids, epifriedelanol (4), friedelin (5), oleanolic acid (6), maslinic acid (7), camaldulenic acid (8), and arjunolic acid (9) were also isolated. The structures of new compounds were established as ulmudiol (bauer-7-ene-1alpha,3beta-diol, 1), dehydroulmudiol [bauer-7,9(11)-diene-1alpha,3beta-diol, 2], and ulmuestone [3alpha-hydroxy-11alpha-(4'-hydroxy-3'-methoxy)benzoyloxybauer-1-one, 3], on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. In addition, the cytotoxic activities of these compounds are also reported.     

Seimatoric acid and colletonoic acid:Two new compounds from the endophytic fungi,Seimatosporium sp.and Colletotrichum sp.

A new metabolite,named seimatoric acid(1),representing a new oxobutanoic acid derivative has been isolated from Seimatosporium sp., in addition to four known compounds viz.,2-hydroxymethyl-4β,5α,6β-trihydroxycyclohex-2-enone(2),(-)-phyllostine(3),(+)-epiepoxydon(4) and(+)-epoxydon monoacetate(5).Similarly one new benzoic acid derivative,named colletonoic acid(6) was isolated from the ethyl acetate fraction of Colletotrichum sp.The structures of the new compounds were elucidated by detailed ~1 H NMR,~(13)C NMR,COSY,HMQC.HMBC spectroscopic analysis,and HR-E1-MS.Seimatoric acid(1)was also isolated from another taxonomical unidentified fungal strain 4295 in ourgroup.The structures of the known compounds were elucidated by their spectral data comparison to literature data.Preliminary studies showed that colletonoic acid(6) showed good antibacterial,antifungal,and antialgal activities.     

Cytotoxicity of triterpenes isolated from Aceriphyllum rossii

Bioassay-guided fractionation of a MeOH extract of the whole plant of Aceriphyllum rossii (Saxifragaceae) led to the isolation of two new triterpenes, 3alpha,23-isopropylidenedioxyolean-12-en-27-oic acid (1) and 23-hydroxy-3-oxoolean-12-en-27-oic acid (2), together with six known triterpenes, 3-oxoolean-12-en-27-oic acid (3), 3alpha-hydroxyolean-12-en-27-oic acid (4), beta-peltoboykinolic acid (5), aceriphyllic acid A (6), oleanolic acid (7), and gypsogenic acid (8). The structures of these compounds were elucidated on the basis of physicochemical and spectroscopic analyses. These compounds were evaluated for in vitro cytotoxicity against the K562 and HL-60 cell lines. Olean-12-en-27-oic acid derivatives (1-6) exhibited considerable cytotoxicity against K562 and HL-60 cell lines with IC(50) values ranging from 12.2 to 28.7 microM and from 12.1 to 25.8 microM, respectively.     

A Highly Rearranged Pentaprenylxanthonoid from the Resin of Garcinia hanburyi

Gamboketanol ( 1 ), a highly rearranged pentaprenylated xanthonoid, two new caged pentaprenylated xanthonoids, gambogefic acid A ( 2 ) and gambogellic acid A ( 3 ), together with two known compounds, were isolated from the acetone extract of the resin of Garcinia hanburyi. Their structures were established on the basis of extensive spectroscopic and mass‐spectrometric analyses. The cytotoxicity of compounds 1 – 3 against HeLa tumor cell line was evaluated, with all of them being modestly active.     

大叶鱼骨木茎的化学成分研究

Chemical constituents of the stems of Canthium simile were studied.Seven compounds were isolated from ethyl acetate extract of the stem,and their structures were elucidated by various spectroscopic methods.They were identified as syringic acid (Ⅰ),isovanillic acid (Ⅱ),Caruilignan D (Ⅲ),(3β)-28-Norlup-20(29)-ene-3,17-diol(Ⅳ),3,4-dimethoxy-2,4-hexadienedioic acid (Ⅴ),dibutyl phthalate (Ⅵ) and diisobutyl phthalate(Ⅶ).The seven compounds were isolated from this genus for the first time.     

Chromanone Derivatives from the Pericarps of Calophyllum polyanthum

Three new chromanone derivatives, calopolyanic acid ( 1 ), isocalopolyanic acid ( 2 ), and isorecedensic acid ( 3 ), were isolated from the pericarps of Calophyllum polyanthum Wall . ex Choisy , along with seven known compounds, apetalic acid, blancoic acid, chapelieric acid, methyl isoapetalate, isoapetalic acid, isocalolongic acid, and recedensic acid. All of these compounds were reported from C. polyanthum for the first time. The structures of 1 – 3 were elucidated by spectroscopic methods.     

New 3,4-seco-ent-kaurene dimers from Croton micans

From the stems of Croton micans Sw., five new 3,4-seco-ent-kaurene dimers: micansinoic acid (1), isomicansinoic acid (2), and the dimethyl (3), monomethyl (4) and monoethyl ester (5) of micansinoic acid were isolated. The structures of the new compounds were elucidated by spectroscopic data interpretation, mainly 1D and 2D NMR experiments and MS. These compounds are the first 3,4-seco-ent-kaurene dimers from a Croton species.     

New Triterpenoid Fatty Acid Esters from the Small Twigs of Viburnum Odoratissimum

α‐Amyrin margarate ( 1 ), moretenyl margarate ( 2 ) and moretenyl palmitate ( 3 ), three triterpenoid fatty acid esters, have been isolated from the acetone extract of the small twigs of Viburnum odoratissimum in addition to the three known compounds, α‐amyrin palmitate ( 4 ), ursolic acid ( 7 ) and vibsanin‐K ( 8 ). The structures of compounds 1–3 were elucidated based on extensive spectroscopic analysis and alkaline hydrolysis. Preliminary pharmacological studies revealed that vibsanin‐K and ursolic acid exhibited significant cytotoxicity against human gastric (NUGC) and oral epidermoid (HONE‐1) tumor cells at a concentration of 50 μg/mL while compounds 1–3 were inactive.     

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.     

Constituents from the stems of Hibiscus taiwanensis

Five new compounds, hibicuslide A (1), hibicuslide B (2), hibicuslide C (3), hibicutaiwanin (4), hibicusin (5), and fifty-one known compounds have been isolated from the stems of Hibiscus taiwanensis. The structures of these compounds were determined by spectroscopic and chemical transformation methods. Among them, mansonone H (19) and uncarinic acid A (30) inhibited HIV replication in H9 lymphocyte cells. The 9,9'-O-feruloyl-(-)-secoisolaricinresinol (12), myriceric acid C (29), and uncarinic acid A (30) showed cytotoxic activity against human lung carcinoma and breast carcinoma.     

Two new terpenoids from fruits of Ziziphus jujuba

One new ceanothane-type triterpene and one new sesquiterpene,together with two known triterpenes were isolated from the fruits of Ziziphus jujuba Mill.(Rhamnaceae).Based on the spectral analyses,the structures of two new compounds were elucidated as 2α-aldehydo-A(1)-norlup-20(29)-en-27,28-dioic acid(zizyberanal acid)(1),and zizyberanone(2).While the two known triterpenes were identified as zizyberanalic acid(3)and ursofic acid(4).     

Two new lupene-type triterpenoids from the roots of Liquidambar formosana

Two new lupene-type triterpenoids, 3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (1) and 2α-acetoxyl-3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (2), along with 18 known compounds, were isolated from Liquidambar formosana. The structures were elucidated on the basis of spectroscopic methods, including UV, IR, ESIMS, 1D- and 2D-NMR experiments, as well as by comparison of the spectral data with those of related compounds.     

A new dibenzofuran and other constituents from Ligularia caloxantha, a Chinese medicinal plant

A new dibenzofuran named 1,2,4-trimethyl-7,8-dimethoxy-dibenzofuran (1), together with seven known compounds, euparin (2), 2,5-diacetyl-6-hydroxy-benzofuran (3), 2-acetyl-5,6-dimethoxy-benzofuran (4), gummosogenin (5), lupeol (6), stigmasterol (7) and (E)-2,5-dihydroxy-cinnamic acid (8), were isolated from the roots of Ligularia caloxantha, a Chinese medicinal plant. The structures of the compounds were elucidated by spectroscopic methods.     

Two New Triterpene Esters from Daphniphyllum oldhami

Two new triterpene esters,2-O-eaffeoylalphitolic acid(1)and methyl 2-O-eaffeoyl-alphitolate(2),together with two known triterpenes were isolated from the shrub Daphniphyllum oldnami.The structures of new compounds were elucidated on the basis of detailed spectroscopic analysis and compared with related compound.     

藤黄酸氰基衍生物的合成及抗肿瘤活性

以藤黄酸为原料,经过酯化反应或酰胺化反应,在C-30位的羧基上引入不同的烷氰基或芳香氰基,设计合成了7个藤黄酸氰基衍生物,其中6个为新化合物,其结构经MS和¹H NMR确证。 采用四氮唑蓝(MTT)法测试了合成化合物对肝癌细胞(HepG2)、结肠腺癌细胞(RKO)和卵巢腺癌细胞(OVCAR-3)的体外抗肿瘤活性,结果表明,所合成的化合物均具有一定的抗肿瘤活性,其中化合物4和6的抗肿瘤活性明显优于阳性对照物藤黄酸。     

Constituents of Salvia microphylla

A new phenolic ester 2-( p-hydroxyphenyl)ethyl eicosaheptanoic acid ester (1) and a known one hexacosylferulate (2) were isolated from the acetone extract of Salvia microphylla. In addition, two sesquiterpenes beta-eudesmol (3) and 8alpha-hydroxy-beta-eudesmol (4), a diterpene carnosic acid 12-methyl ether (12-methoxycarnosic acid) (5), three triterpenes erithrodiol 3-acetate, oleanolic acid, lupeol and beta-sitosterol were obtained as known compounds from this plant extract. The structures of the isolated compounds were elucidated by spectroscopic methods, including one- and two- dimensional 1H- and 13C-NMR and MS spectroscopies. The selected compounds were tested for antimicrobial activity against standard bacterial strains, and only carnosic acid 12-methyl ether showed antimicrobial activity against S. aureus at 78 microg mL(-1).