Sesquiterpenoids from the resinous exudates of Commiphora myrrha and their neuroprotective effects

Ten new furanosesquiterpenoids, myrrhterpenoids A-J (1- 10), together with eight known analogues (11- 18), were isolated from the resinous exudates of COMMIPHORA MYRRHA. Their structures and relative configurations were elucidated by spectroscopic methods (IR, ESIMS, HRESIMS, 1D and 2D NMR) and by the ChemDraw 3D modeling using MM2. All isolated furanosesquiterpenes showed neuroprotective effects against MPP (+)-induced neuronal cell death in SH-SY5Y cells.     

Phenolic acid derivatives with neuroprotective effect from the aqueous extract of Clerodendranthus spicatus

Two new phenolic acid helisterculins C (1) and D (2) were isolated from the whole plant of Clerodendranthus spicatus. Their structures were elucidated on the basis of 1D and 2D NMR, MS, and CD analysis. Compound 1 possesses an unusual bicyclol [2. 2. 2] octane moiety which is rare in the previously isolated phenolic acid derivatives. The two compounds were tested in vitro for neuroprotective activities against 6-OHDA-induced cell death in SH-SY5Y cells, and the result showed that compounds 1 and 2 displayed moderate neuroprotective activity with the IC₅₀ values of 17.4 and 21.3 μM, respectively.     

Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination

ABSTRACT: The chemical constituents and biological activities of the terrestrial Aspergillus flavipes MM2 isolated from Egyptian rice hulls are reported. Seven bioactive compounds were obtained, of which one sterol: ergosterol (1), four butyrolactones: butyrolactone I (2), aspulvinone H (3), butyrolactone-V (6) and 4,4'-diydroxypulvinone (7), along with 6-methylsalicylic acid (4) and the cyclopentenone analogue; terrien (5). Structures of the isolated compounds were deduced by intensive studies of their 1D & 2D NMR, MS data and comparison with related structures. The strain extract and the isolated compounds (1-7) were biologically studied against number of microbial strains, and brine shrimp for cytotoxicity. In this article, the taxonomical characterization of A. flavipes MM2 along with its upscale fermentation, isolation and structural assignment of the obtained bioactive metabolites, and evaluate their antimicrobial and cytotoxic activities were described.     

南海细薄星芒海绵抗肿瘤活性成分研究(Ⅱ)

目的研究细薄星芒海绵Stelletta tenuisLindgren的抗肿瘤活性成分。方法利用溶酶萃取和多种层析手段,以体外细胞毒模型跟踪筛选,对南海细薄星芒海绵的抗肿瘤活性成分进行追踪分离,应用波谱技术,并结合文献对照,对所分离得到的化合物进行结构鉴定。结果得到8个异玛拉巴烷(isomalabaricane)型三萜类化合物,其结构分别鉴定为:stellettin B(1),C(2),D(3),E(4),rhabdastrellic acid A(5),stellettin H(6),22,23-dihydrostellettin B(7),geoditin A(8)。结论化合物1-8均系首次从中国南海海绵Stelletta ten-uisLindgren中获得,并归属了它们的1H NMR和13C NMR数据。     

Triterpenoids from pyrethrum tatsienense

Two novel and eight known triterpenoids were isolated from alcoholic extract of the whole plant of Pyrethrum tatsienense. The structures of new compounds were elucidated as olean-12-en-3beta,11alpha,16beta-triol-3-O-palmitate (1), ursa-12-en-3beta,11beta,16beta-triol-3-O-palmitate (2) by spectroscopic methods including intensive 2D NMR techniques (H1-H1 COSY, gHMQC, gHMBC) and FAB-MS, and the known compounds were identified on the basis of comparing their NMR data with those of corresponding compounds in the literature.     

Ferulates, amurenlactone A and amurenamide A from traditional Chinese medicine cortex Phellodendri Amurensis

Two new ferulate compounds, amurenlactone A (1) and amurenamide A (2), along with 11 known compounds have been isolated from the cortex of Phellodendron amurense. The structures of the new compounds were established based on 1D, 2D NMR and mass spectral analyzes. The known compounds were identified by comparison with authentic samples.     

Two new norbisabolane sesquiterpenoid glycosides from Glochidion coccineum

Two new norbisabolane sesquiterpenoid glycosides, glochicoccinosides A (1) and B (2), together with two known compounds, have been isolated from the rhizomes of Glochidion coccineum. Their structures were elucidated by the combination of 1D NMR, 2D NMR, and MS spectral analysis, as well as chemical evidence. Cytotoxic activities and the antioxidant effect of these compounds were evaluated, but none of them showed activity.     

Triterpenoids from Gouania ulmifolia

Two new triterpenoids, named gouanic acid A (1) and gouanic acid B (2), were isolated from the aerial parts of Gouania ulmifolia, along with six known compounds. The structures of the new compounds were determined by spectroscopic methods, mainly NMR (1D and 2D) and mass spectrometry. The new compounds did not show significant antimicrobial activities.     

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 3β,19α-dihydroxy-12α-ethoxy-urs-13(18)-ene-28,20β-lactone-3-O-[β-D-glucopyranosyl(1 → 3)]-[α-L-rhamnopyranosyl(1 → 2)]-α-L-arabinopyranoside (1) and 3β,19α-dihydroxy-12α-methoxy-urs-13(18)-ene-28,20β-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 flavonol glycoside and activity of compounds from the flower of Nymphaea candida

A new compound, kaempferol 3-O-(2'-O-galloylrutinoside) (1), was isolated from the white flower of Nymphaea candida, together with nine known flavonol glycosides, kaempferol (2), kaempferol 3-O-beta-D-glucopyranoside (3), kaempferol 3-O-alpha-l-rhamnopyranoside (4), kaempferol 3-O-alpha-l-rhamnopyranosylglucopyranoside (5), kaempferol 7-O-beta-D-glucopyranoside 3-(O-alpha-l-rhamnopyranosylglucopyranoside) (6), quercetin (7), quercetin 3-O-beta-D-xylopyranoside (8), myricetin (9), myricetin 3'-O-beta-D-xylopyranoside (10). The structure of 1 was established on the basis of the analysis of its 1D and 2D NMR spectral data. Compounds 1-7 and 9 exhibited moderate to significant antioxidant activities, which were evaluated by measurement of low-density lipoprotein (LDL) and malondialdehyde (MDA) levels in vitro. Compounds 1, 3, 4, 6 and 9 exhibited promising neuroprotective effects on ischemic injury model of cultured rat cortical neurons treated with sodium dithionite in glucose-free medium. Furthermore, compounds 1, 5, and 9 had distinct cytotoxicity to adrenal gland pheochromocytoma, PC12 cells, being treated by the same way.     

Neolignan and lignan glycosides from branch bark of Davidia involucrata

Two new neolignan glycosides, davidioside A (1) and davidioside B (2), have been isolated along with six known compounds from the branch bark of Davidia involucrata. Identification of their structures was achieved by 1D and 2D NMR experiments, including (1)H-(1)H COSY, NOESY, HMQC, and HMBC methods as well as FAB mass spectral data.     

Lignans from Pilea cavaleriei Levl subsp. cavaleriei

A new lignan glycoside, named (7S,8R,8′R)-(−)-lariciresinol-9-O-α-L-rhamnopyranosyl (1→2) β-D-glucopyranoside (1),was isolated from the ethanol extract of Pilea cavaleriei Levl subsp. cavaleriei, together with 17 known lignans (2−18). The structures of these compounds were elucidated by extensive spectroscopic analysis, including 1D NMR, 2D NMR and HR-ESI-MS. All the compounds were obtained from the genus Pilea for the first time.     

Triterpene saponins from Lysimachia christinae

Seven triterpene saponins were isolated from Lysimachia christinae and identified as lysichriside A (1), lysichriside B (2), primulanin (3), lysikokianoside 1 (4), anagallisin C (5), ardisiacrispin A (6), and ardisicrenoside B (7). Compounds 1 and 2 are new triterpene saponins, compounds 3, 5, and 7 were isolated from this genus, and compounds 4 and 6 were isolated from this species for the first time. Their structures were elucidated by means of 1D and 2D NMR experiments.     

Phenolic compounds from Nicotiana tabacum and their biological activities

Three new phenolic compounds, nicotphenols A-C (1-3), together with 14 known phenols (4-17), were isolated from the leaves of Nicotiana tabacum. Their structures were established by means of spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1-3 were tested for their anti-HIV-1 activities and cytotoxicities. They all showed significant cytotoxic abilities and modest anti-HIV-1 activities, respectively.     

Himalomycin A and B: isolation and structure elucidation of new fridamycin type antibiotics from a marine Streptomyces isolate

In our screening of marine Streptomycetes for bioactive compounds, in addition to the known metabolites rabelomycin (1), fridamycin D (2b), N-benzylacetamide and N-(2'-phenylethyl)acetamide, two new anthracycline antibiotics designated as himalomycin A (2c) and B (2d) were isolated from the culture broth of the marine Streptomyces sp. isolate B6921. The structure of the new antibiotics was determined by comparison of the NMR data with those of fridamycin D (2b) and by detailed interpretation of mass, 1D and 2D NMR spectra.     

Two new lanostane triterpenoids from Poria cocos

Two new lanostane triterpenoids, 29-hydroxypolyporenic acid C (4) and 25-hydroxypachymic acid (5), together with three known compounds, ergosta-7,22-dien-3beta-ol (1), polyporenic acid C (2) and pachymic acid (3), were isolated from the 95% ethanolic extract of the sclerotium of Poria cocos (Schw.) Wolf. Their structures were determined by extensive spectroscopic analyses, including IR, UV, ESITOF-MS, HRESI-MS, 1D and 2D NMR data (1H NMR, 13C NMR, 1H-1H COSY, NOESY, HSQC and HMBC).     

Two new norbisabolane sesquiterpenoid glycosides from Glochidion coccineum

Two new norbisabolane sesquiterpenoid glycosides, glochicoccinosides A (1) and B (2), together with two known compounds, have been isolated from the rhizomes of Glochidion coccineum. Their structures were elucidated by the combination of 1D NMR, 2D NMR, and MS spectral analysis, as well as chemical evidence. Cytotoxic activities and the antioxidant effect of these compounds were evaluated, but none of them showed activity.     

Constituents from Hoya parasitica and their cell growth inhibitory activity

An androstanoid, hoyasterone (1), a sesquiterpene, 15-bulnesolic acid (2), and a phenolic compound, 1-(4-hydroxy-3-methoxyphenyl)-1-methoxypropan-2-ol (3), together with a known triterpene, dihydrocanaric acid, were isolated from Hoya parasitica. Structures were elucidated by 1 D and 2 D NMR and mass spectroscopic analysis. Among the isolated compounds, only dihydrocanaric acid exhibited growth inhibitory activity against both HeLa and SW480 cells.     

Cichorins B and C: two new benzo-isochromenes from Cichorium intybus

Two new benzo-isochromenes, named cichorins B (1) and C (2), were isolated from Cichorium intybus. The structures of the new compounds were elucidated by detailed spectroscopic analysis such as 1H, 13C NMR, COSY, HMQC, HMBC, and HR-EI-MS. Relative configurations of asymmetric centers of cichorins B and C were determined by the analysis of the 1H NMR coupling constants together with the 2D NOESY and 1D NOE experiments as well as from [α]2?(D) value.     

Water-soluble constituents from the leaves of Ilex oblonga

Four new water-soluble constituents, oblongaroside A (1), oblongar ester A (2), oblongaroside B (3), and oblongaroside C (4), were isolated along with four known compounds: 4-O-beta-D-glucopyranosyl-3-hydroxybenzalcohol (5), 7-methoxyl-4-O-beta-D-glucopyranosyl-3-hydroxybenzalcohol (6), 4-O-beta-D-glucopyranosyl-3-hydroxybenzoic acid (7), and 3,4-dihydroxybenzoic acid (8) from the leaves of Ilex oblonga. Identification of their structures was achieved by 1D and 2D NMR experiments, including (1)H-(1)H COSY, NOESY, HMQC, and HMBC methods and FAB mass spectral data.