New lignan glycosides from Justicia procumbens

Four new lignan glycosides (1–4), named procumbenosides I, K, L, and M, together with cleistanthin B (5) reported for the first time in the genus Justicia, and 5 other known arylnaphthalene lignan glycosides (6–10) were isolated from the whole plant of Justicia procumbens. The structures of the new compounds were elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. Procumbenoside M (4) was a rare sesquilignan glycoside never previously reported in the species of Justicia. The paper also provided insight into the conformational equilibria existing in the lignan glycosides of the plant.     

Two new arylnaphthalide lignans and antiplatelet constituents from Justicia procumbens

Two new arylnaphthalide lignans, procumphthalide A (1) and 4-O-beta-D-glucopyranosyl-(1"'-->2")-beta-D-apiofuranosyldiphyllin, named procumbenoside B (2), along with cilinaphthalide B (3) and several other known compounds were isolated from the methanolic extracts of Justicia procumbens. By using NMR and other spectral methods, the structures of 1 and 2 were elucidated. Cilinaphthalide B (3), justicidin A (4), and taiwan E methyl ether (5) were shown to have an antiplatelet effect in human plateletrich plasma. In human citrated PRP, 5 showed a strong inhibitory effect on platelet aggregation induced by adrenaline in a concentration-dependent manner, with an IC(50) value of about 27.6 microM.     

A new lignan glycoside from Trigonostemon heterophyllus

Phytochemical investigation on the stems of Trigonostemonheterophyllus led to the isolation of a new lariciresinol-based lignan glycoside, trigonoheteran (1), together with a known lignan glycoside, aviculin (2). Their structures were elucidated by spectroscopic methods including 1D and 2D NMR (HMQC, ¹H–¹H COSY, HMBC, and NOESY).     

爵床中一个新的木脂体苷——爵床苷E

用硅胶柱色谱和Sephadex LH-20柱色谱对安徽产爵床(Justicia procumbens L.)全草乙醇提取物的乙酸乙酯和正丁醇部位进行分离纯化,得到6个单体化合物,通过IR、NMR等波谱技术以及一些化学方法推测化合物结构,分别为爵床脂素A(1)、新爵床脂素B(2)、爵床脂素B(3)、爵床苷B(4)、尿嘧啶(5)和爵床苷E(6),其中6为新的木脂体苷类化合物。     

Justicia lignans VI--prostalidin D, a new arylnaphthalide lignan from Justicia diffusa var. prostrata C.B. Clarke

A new arylnaphthalide lignan, prostalidin D (6) was isolated as a minor metabolite from Justicia diffusa var. prostrata. 6 contains a rare catechol unit and its structure was confirmed by total synthesis. In addition, seven known lignans, namely, justicidin E (7), helioxanthin (8), justicidin A (9), medioresinol dimethyl ether (10), medioresinol (11), lariciresinol (12) and 8-methoxyisolariciresinol (13) have also been isolated from the same source and identified by direct comparison with authentic samples.     

Xylopyrine-C,a new cyclopeptide alkaloid from Zizyphus xylopyra

Xylopyrine-C, a new 14-membered ring cyclopeptide alkaloid, has been isolated from the root bark of Zizyphus xylopyra together with a known alkaloid scutianine-C, and their structures were established by chemical and spectral evidences.     

Three new lignan glycosides from the fruits of Forsythia suspense

Two new lignan glycosides forsythiayanoside A (1) and forsythiayanoside B (2), one new stereoisomer of lignan glycoside (+)-8-hydroxyepipinoresinol-4-O-β-d-glucopyranoside (3), together with seven known compounds (4–10), were isolated from the fruits of Forsythia suspense (Thunb.) Vahl. Compounds 4 and 10 were isolated from this species for the first time. The structures of 1–3 were elucidated on the basis of chemical and spectral analyses, including 1D and 2D NMR data and HR-ESI-MS. The absolute configurations were determined by the circular dichroism method. All isolates were tested for their cytotoxicities against five human cancer cell lines (A549, Colo-205, Hep-3B, HL60, and KB). In particular, compound 3 showed significant cytotoxicity with IC₅₀ values of 9.48, 7.75, 0.59, 4.06, and 38.38 μM, respectively.     

海洋来源真菌Trichoderma citrinoviride中的1个新生物碱类化合物

目的 对1株分离自福建沿海的橘绿木霉Trichoderma citrinoviride NM-035所发酵产生的抗肿瘤活性成分进行研究。方法 将纯化得到的菌株在28摄氏度下静置培养30天,发酵液经乙酸乙酯萃取得到总浸膏;先后利用硅胶柱层析、凝胶柱层析以及半制备型高效液相等色谱手段,对总浸膏进行分离纯化;通过核磁共振和高分辨电喷雾质谱方法并结合文献,对产物的结构进行解析并最终对其活性进行初步评价。结果 从该菌株中分离得到了1个新的tetramic acid型生物碱,并命名为penicillenol F (1)。该化合物对人恶性黑色素瘤和肝癌细胞具有一定的抑制活性。 结论 从橘绿木霉Trichoderma citrinoviride NM-035中发现1个新的具有抑制人恶性黑色素瘤和肝癌细胞活性的生物碱类化合物penicillenol F(1)。     

New sesquiterpenoid glycoside and phenylpropanoid glycosides from the tuber of Ophiopogon japonicus

A new sesquiterpenoid glycoside, cryptomeridiol 11-O-β-d-xylopyranosyl-(1→6)-β-d- glucopyranoside (1), two new phenylpropanoid glycosides, 3,4-dihydroxy-allylbenzene 3-O-β-d-glucopyranosyl-4-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside (2), and 3,4,5-trihydroxy-allylbenzene 3-O-β-d-glucopyranosyl-4-O-β-d-glucopyranoside (3), along with four known phenylpropanoid glycosides (4–7), were isolated from the tuber of Ophiopogon japonicus. Compounds 4–7 were obtained from the genus Ophiopogon for the first time. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR and HR-ESI-MS.     

A new cyclolignan glycoside from the tubers of Pinellia ternata

A new 2,7′-type cyclolignan glycoside, cyclolignanyingoside A (1), together with six known compounds (2–7) were isolated from the tubers of Pinellia ternata (Thunb.) Breit. The structure of 1 was elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses, HR-ESI-MS, and CD spectrometry. The cytotoxic, antioxidant and tyrosinase-inhibiting activities of all the isolates were determined. However, all the isolates exhibited no activity on the selected cell lines (Hep-3B, Bcap-37, and MCF-7). In addition, compounds 1–3 and 7 exhibited strong 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, and compounds 2 and 4 showed a moderate mushroom tyrsinase inhibitory activity.     

胆木茎中一个新的吲哚生物碱苷

目的研究中药胆木水溶性部位的化学成分。方法采用大孔吸附树脂，硅胶柱色谱和Sephadex LH20凝胶柱色谱分离纯化，通过光谱分析鉴定化合物的结构。结果从胆木水溶性部位中分离得到7个化合物，分别鉴定为： naucleamide A-10-O-β-D-glucopyranoside (I)， 5-β-carboxystrictosidin (II)， 獐牙菜苷(III)， 番木鳖苷A(IV)， 3,4-dimethoxyphenyl-β-D-glucopyranoside (V)， 3,4,5-trimethoxyphenyl-β-D-glucopyranoside (VI)， 2-phenethylrutinoside (VII)。结论化合物I为新的吲哚类生物碱苷，化合物I～VII均为首次从该植物中分得。     

A new lignan and anti-inflammatory flavonoids from Kerria japonica

A new lignan named kerinol (1) as well as 12 known compounds were isolated from the twigs of Kerria japonica (L.) DC (Rosaceae). Their structures were elucidated on the basis of spectroscopic analysis. Linariin (3) and isolinariin B (4), two major flavonoids of K. japonica, were found to exhibit significant anti-inflammatory activities in mice in vivo with an inhibitory rate of 25.5% (p < 0.001) and 13.1% (p < 0.05), respectively.     

Indole alkaloid glycosides with a 1′-(phenyl)ethyl unit from Isatis indigotica leaves

Seven indole alkaloid glycosides containing a 1′-(4″-hydroxy-3″,5″-dimethoxyphenyl)ethyl unit (1–7) were isolated from an aqueous extract of Isatis indigotica leaves (da qing ye). Their structures were determined by spectroscopic data analysis combined with enzymatic hydrolysis as well as comparison of their experimental CD (circular dichroism) and calculated ECD (electrostatic circular dichroism) spectra. Based on analysis of ${\left[\alpha \right]}_{\text{D}}^{20}$ and/or Cotton effect (CE) data of 1–7, two simple roles to assign location and/or configuration of β-glycopyranosyloxy and 1′-(phenyl)ethyl units in the indole alkaloid glycosides are proposed. Stereoselectivity in plausible biosynthetic pathways of 1–7 is discussed. Compounds 3 and 4 and their mixture in a 3:2 ratio showed activity against KCNQ2 in CHO cells. The mixture of 5 and 6 (3:2) exhibited antiviral activity against influenza virus H1N1 PR8 with IC₅₀ 64.7 μmol/L (ribavirin, IC₅₀ 54.3 μmol/L), however, the individual 5 or 6 was inactive. Preliminary structure–activity relationships were observed.     

A new pregnane glycoside and oligosaccharide from Parabarium huaitingii

Two new compounds, along with two known compounds, were isolated from the barks of Parabarium huaitingii, and their structures were determined as 5α-pregn-6-ene-3β,17α,20(S)-triol-20-O-β-d-digitoxopyranoside (1), cymaropyranurolactone 4-O-β-d-digitalopyranosyl-(1 → 4)-O-β-d-cymaropyranosyl-(1 → 4)-O-β-d-oleandropyranosyl-(1 → 4)-O-β-d-cymaropyranoside (2), 3β,17α,20(S)-trihydroxy-5α-pregn-6-ene (3), and 5α-pregn-6-ene-3β,17α,20(S)-triol-3-O-β-d-digitalopyranoside (4) by spectroscopic methods.     

A new phenylpropanoid and a new isoflavone glycoside from Shenqi Fuzheng Injection

A new phenylpropanoid and a new isoflavone glycoside were isolated from Shenqi Fuzheng Injection. Their structures were elucidated as (αS)-α-ethenyl-4-hydroxy-3-methoxy-benzenemethanol (1) and calycosin 7-O-[α-d-glucopyranosyl (1 → 4)]-β-d-glucopyranoside (2) by means of spectroscopic methods including UV, IR, HR-ESI-MS, and NMR. The absolute configurations of 1 and 2 were confirmed by quantum chemical calculation and acid hydrolysis.     

何首乌中二苯乙烯苷的药效学和药动学研究进展

二苯乙烯苷类成分是何首乌中的特有成分,具有广泛的药理学活性.本文综述了二苯乙烯苷(2,3,5,4’-四羟基二苯乙烯-2-O-β-D-葡萄糖苷)在抗氧化、心血管系统、中枢神经系统和抗肿瘤等药效学方面的作用,探讨了其可能的作用机制及应用前景.同时对其吸收和代谢等药动学方面的最新研究进展进行了总结,以期为进一步深入研究二苯乙烯苷类成分的药学特点和药物研发方向提供思路.     

A new phenolic glycoside and cytotoxic constituents from Celosia argentea

A new phenolic glycoside, 4-O-β-D-apifuranosyl-(1 → 2)-β-D-glucopyranosyl-2-hydroxy-6-methoxyacetophenone (2) and 11 known compounds were isolated from the MeOH extract of the plant Celosia argentea. The structures of the compounds were elucidated on the basis of spectroscopic analysis and chemical methods. Among the isolated compounds, stigmasterol (10) showed moderate inhibitory activities against SGC-7901 and BEL-7404 cells.     

A new furofuran lignan with antioxidant and antiseizure activities from the leaves ofPetasites japonicus

A new furofuran lignan (1) was isolated from the n-butanol fraction of the methanolic extract of the leaves of Petasites japonicus (Sieb. et Zucc.) Maxim. (Compositae). The structure of compound 1 was determined to be 2alpha-(4'-hydroxy-3'-methoxyphenyl)-6alpha-(4"-hydroxy-3"-methoxyphenyl)-8alpha-hydroxy-3,7-dioxabicyclo[3.3.0octane 4'-O-(beta-D-glucopyranoside) by spectroscopic methods including 2D-NMR. In further studies, it was found that the compound 1 expressed an antioxidant activity in DPPH radical scavenging assay, and moreover, ameliorated the seizure in kainic acid-treated mice.     

Cytisine-type alkaloids and flavonoids from the rhizomes of Sophora tonkinensis

A new cytisine-type alkaloid, (?)-N-hexanoylcytisine (1), and a new isoflavan, (3S, 4R)-4-hydroxy-7,4′-dimethoxyisoflavan 3′-O-β-d-glucopyranoside (2), along with 10 known compounds, were isolated from the rhizomes of Sophora tonkinensis. Their structures were determined by spectroscopic methods, chemical evidence, and ECD data analysis. All of the isolates were evaluated for their cytotoxic activities against four human tumor cell lines.     

北刘寄奴中苯乙醇苷类成分的分离与鉴定

目的研究中药北刘寄奴(Siphonostegia chinensis Benth.)的化学成分。方法采用正相硅胶、反相ODS、Sephadex LH-20等柱色谱及高效液相色谱等手段进行分离纯化,并通过理化性质与光谱分析鉴定化合物的结构。结果从北刘寄奴体积分数为95%的乙醇提取物中分离了6个苯乙醇苷类单体成分,分别鉴定为去咖啡酰基类叶升麻苷(decaffeoylverbascoside,1)、acteoside(2)、isoacte-oside(3)、crenatoside(4)、β-oxoacteoside(5)和syringalide A 3'-α-L-rhamnopyranoside(6)。结论其中化合物1、3～6为首次从阴行草属中分离得到。