A new norisoprenoid from the leaves of Ficus pumila

One new norisoprenoid 3,9-dihydroxy dihydro actinidiolide (1), together with eleven known compounds (2–12), were isolated from ethanol extract of the leaves of Ficus pumila collected in Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. Compounds 1, 2, 4, 5, 8 and 10–12 were isolated from the F. pumila for the first time. All compounds were evaluated for their cytotoxic activity. Compounds 3 and 9 showed weak cytotoxic activity against Hela, MCF-7 and A549 cell lines.     

New furoquinoline alkaloid and flavanone glycoside derivatives from the leaves of Oricia suaveolens and Oricia renieri (Rutaceae)

Fractionation of the methanol extract of the leaves of Oricia renieri and Oricia suaveolens (Rutaceae) led to the isolation of 13 compounds including the hitherto unknown furoquinoline alkaloid named 6,7-methylenedioxy-5-hydroxy-8-methoxy-dictamnine (1) and a flavanone glycoside named 5-hydroxy-4′-methoxy-7-O-[α-l-rhamnopyranosyl(1?→5″)-β-d-apiofuranosyl]-flavanoside (2), together with 11 known compounds (3–13). The structures of the compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral data and comparison. All compounds isolated were examined for their activity against human carcinoma cell lines. The alkaloids 1, 5, 12, 13 and the phenolic 2, 8, 11 tested compounds exhibited non-selective moderate cytotoxic activity with IC₅₀ 8.7–15.9 μM whereas compounds 3, 4, 6, 7, 9 and 10 showed low activity.     

Two new prenylated isoflavones from Maclura cochinchinensis collected in Hoa Binh province Vietnam

Two new prenylisoflavones, 3′,4′,5-trihydroxy-8-prenyl-dihydrofuran[2″,3″:7,6]isoflavone (1) and 4′,5-dihydroxy-8-prenyl-dihydrofuran[2″,3″:7,6]isoflavone (2), along with five known prenylisoflavones (3–7), benzylalcohol-4-O-β-d-glucoside (8) and two cinnamic acid esters (9, 10) were isolated from the leaves of Maclura cochinchinensis (Cudrania cochinchinensis). Their structures were elucidated by analysis of NMR (¹H-, ¹³C-NMR, HSQC, HMBC), MS spectra and comparison with the published data. Compounds 4–10 were the first time isolated from this species. Prenylisoflavones 1–4 and 6–7 were evaluated for their in vitro cytotoxic activity on KB and HepG2 cancer cell lines. Compound 4 showed cytotoxic activity against both cancer cell lines with IC₅₀ values of 26.99 and 19.95 μM, respectively. The other compounds were considered as inactive.     

New transformation pathway and cytotoxic derivatives from the acid hydrolysis of timosaponin B III

Timosaponin B III is a major bioactive steroidal saponin isolated from Anemarrhena asphodeloides Bge. To potentially discover derivatives with better biological activity, timosaponin B III was structurally modified via acid hydrolysis to yield one new (2, timopregnane A I) C₂₁ steroidal glycoside and seven known compounds. Their structures were elucidated on the basis of NMR spectroscopy and mass spectrometry. All eight compounds were evaluated for cytotoxic activity against MCF7, SW480, HepG2, and SGC7901 cell lines in vitro. As a result, compounds 6 and 7 showed significant activity (IC₅₀ 2.94–12.2?μM) against all tested cell lines. Structure–activity relationships of these compounds were investigated and the preliminary conclusions were provided. Moreover, a new transformation pathway was discovered in the acid hydrolysis of timosaponin B III for the first time.     

New isolates from leaves of Nicotiana tabacum and their biological activities

Three new isolates (1?3) including one new sterol and two new flavonoids together with three known sterols (4?6) were isolated from the leaves of Nicotiana tabacum. Their structures were determined mainly by spectroscopic methods, including extensive 1D and 2D NMR techniques. All compounds were evaluated for their anti-tobacco mosaic virus and cytotoxic activities. The results showed that compounds 2 and 3 exhibited high anti-TMV activity with inhibition rate of 34.2 and 33.4%, respectively, which were roughly equivalent to that of positive control. The cytotoxicities of compounds 1 and 4–6 against five human tumour cell lines were also tested, and tested compounds showed weak inhibitory activities against some tested human tumour cell lines.     

A new cytotoxic biflavonoid from the rhizome of Wikstroemia indica

One new chalcone-flavone biflavonoid, 3′-hydroxydaphnodorin A (1), together with 12 known biflavonoids (2–13), was isolated from the rhizome of Wikstroemia indica. Their structures were established on the basis of extensive spectroscopic methods. Eight isolated compounds 1–3, 6, 7, 9, 12 and 13 were evaluated for their cytotoxic activities against cancer-derived cell lines Hep3B, HepG2 and CNE2, and 1 was found to possess moderate cytotoxicity against HepG2 and CNE2 cell lines, with IC₅₀ values of 65.5 ± 11.4 and 53.6 ± 10.1 μM, respectively.     

New cytotoxic and anti-inflammatory compounds isolated from Morus alba L.

Six Diels–Alder adducts (1–6) and nine prenylated flavanones (7–15) were isolated from the root bark of Morus alba L. Among them, soroceal B (1) and sanggenol Q (7) were new compounds. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D and 2D NMR techniques. Compounds 1–3, 9, 10, 12, 13 and 15 exhibited cytotoxic activity against five human tumour lines and compound 2 inhibited significantly selective cytotoxic activities towards HL-60 and AGS cells with IC₅₀ of 3.4 and 3.6 μM. Compounds 3, 5, 9 and 12 exhibited moderate inhibitory activity against nitric oxide production in LPS-activated RAW264.7.     

A new phenolic compound from Phedimus middendorffianus with antiproliferative activity

Abstract

A new phenolic compound (1) and together with 12 known compounds–eight flavonoids (2?～?9), two phenolic compounds (10 and 11) and two benzoic acid (12 and 13)–were isolated from Phedimus middendorffianus (Maxim.). The structures of all compound were determined on the basis of spectroscopic (MS and NMR) analyses. Compounds 4, 5, 7 and 11?～?13 were showed anti-proliferative activities against MCF-7 than PC-3 cell line. Also compound 12 and 13 showed the significant cytotoxic activities against two cancer cell lines, PC-3 and MCF-7.     

A new furostanol saponin from Dendrobium chrysanthum Lindl. with cytotoxic activity

A new furostanol saponin, (25R)-26-O-(α-d-glucopyranosyl)-(1→2)-α-l-rhamnopyranosyl-furost-5-ene-3β, 22α, 26-triol-3-O-α-d-glucopyranoside (1), together with four known compounds 2–5 were isolated from the ethanolic extract of the stems of Dendrobium chrysanthum Lindl. The structures of these new compounds were identified by extensive spectroscopic analysis including 1D and 2D NMR and HR-ESI-MS, as well as chemical methods. Compounds 1–3 were isolated from D. chrysanthum for the first time. Furthermore, the inhibitory effects of the compounds on tumor cells were evaluated, and compounds 1–2 exhibited significant cytotoxic activities potentially against SPC-A1, MCF-7 and HeLa human cancer cell lines. Compounds 3–5 showed inhibitory activity against the SPC-A1 and MCF-7.     

New lignan from the rattan stems of Schisandra chinensis

A new lignan named schilignan F (1), together with twelve known ones (2–13), were isolated from the rattan stems of Schisandra chinensis. Their chemical structures were elucidated by spectroscopic methods including one and two-dimensional NMR spectra referring to the literatures as well as high-resolution mass spectrometric analysis. All compounds were evaluated for their cytotoxicities against human Hela cancer cell lines in vitro. The results showed that compounds 2, 6 and 8 exhibited weak cytotoxic activity with IC₅₀ values of 30.6, 86.3 and 41.0 μM, and cisplatin showed cytotoxic activity with IC₅₀ value of 27.3 μM.     

One new berberine from the branches and leaves of Polyalthia obliqua Hook.f. & Thomson

One new alkaloid consanguine B (1), together with 10 known alkaloids (2–11), were isolated from ethanol extract of the branches and leaves of Polyalthia obliqua Hook.f. & Thomson collected in the Hainan Province, China. Their structures were elucidated by the detailed analysis of comprehensive spectroscopic data. All compounds were evaluated for their cytotoxic activities. Compound 1 showed weak cytotoxic activities against Hela and MCF-7 human cancer cell lines.     

Markhacanasin C,cycloartane triterpenoid from the leaves of Markhamia stipulata var. canaense V.S. Dang

One new cycloartane triterpenoid, named markhacanasin C (1), together with three known triterpenoids, oleanolic acid (2), ursolic acid (3) and 6β,19α-dihydroxyursolic acid (4) were isolated by various chromatographic methods from the most cytotoxic fraction of the ethyl acetate extract of Markhamia stipulata var. canaense V.S. Dang leaves. Among them, 4 was reported for the first time from the genus Markhamia, while 2 and 3 were found for the first time from this species. Their structures were elucidated by IR, UV, HR-ESI-MS and NMR experiments. The cytotoxicity of isolated compounds (3 and 4) against three human cancer cell lines (HeLa, HepG2, and MCF-7) were evaluated. At the concentration of 100 μg/mL, 3 exhibited significant cytotoxic activity (86.36 ± 3.69%).     

Study on chemical constituents of an edible mushroom Volvariella volvacea and their antitumor activity in vitro

Abstract

Phytochemical investigation of the fruiting body of Volvariella volvacea led to the isolation of a new furanone, 2(5H)-furanone-4-propionic acid named volvafuranone A (1), together with twelve known compounds (2–13). Compounds 2–7, 9–11 were isolated from this mushroom for the first time. The isolated compounds were assessed for their cytotoxicity against four human tumour lines (SGC-7901, PC-3M, MCF-7, HepG-2), and the results showed that compound 2, 3, 12, 13 have significant cytotoxicity with IC₅₀ values of 5.90?μM (HepG-2), 20.72?μM (HepG-2), 27.98?μM (PC-3M) and 23.15?μM (PC-3M), respectively.     

Cytotoxic triquinane-type sesquiterpenoids from the endophytic fungus Cerrena sp. A593

Abstract

The culture broth of Cerrena sp. A593, which was isolated from Pogostemon cablin, showed potent cytotoxicity against several human tumor cell lines. The following chemical study resulted in the isolation of two new triquinane-type sesquiterpenoids, named cerrenins D (1) and E (2), along with two known compounds plerocybellone A (3) and chloriolin B (4). Their structures were fully assigned with the aid of extensive spectroscopic analysis (¹H and ¹³C NMR, HSQC, HMBC, ¹H-¹H COSY, HRESIMS, and IR) and data from the literature. Moreover, cytotoxic activity in vitro of compounds 1–4 were evaluated against SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. The new compound 1 exhibited weak growth inhibitory activity against all the four tumor cell lines with IC₅₀ values of 41.01, 14.43, 29.67, 44.32?μM.     

Dapson in Heterocyclic Chemistry,Part I: Novel Synthesis of Sulfone Biscompounds for Antimicrobial and Antitumor Activities

This article describes the synthesis of some novel sulfone bis-compounds bearing the biologically active thioether 3–6 ; thioureido 7, 8, 15, 16; triazole 10, 11; thiosemicarbazido 9, 12, 13; and 1,3,4-thiadiazole 14, 17 moieties starting with 4,4′-diisothiocyanato-1,1-diphenylsulfone 2. The structures of newly synthesized compounds were confirmed by elemental analysis, IR, ¹ H-NMR and mass spectral data. Compound 3 was found to be the most active compound against Escherichia coli. Also, compound 15 acted as potent cytotoxic agent.     

Chemical constituents and biological activities from branches of Colubrina asiatica

Sixteen compounds were isolated from a Thai medicinal plant, Colubrina asiatica. The isolated compounds were elucidated on the basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene acids (1–6), five steroids (7–11), one benzoic acid derivative (12), two peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin (16). Compounds 3 and 10 showed antimalarial activity against Plasmodium falciparum. Compound 5 showed antimycobacterial activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak cytotoxicity against cancer cell lines. Compounds 1–15 have been isolated for the first time from this plant.     

Isolation and purification of diterpenoids from the aerial parts of Isodon excisoides target-guided by UPLC-LTQ-Orbitrap-MS

Cytotoxic diterpenoids were enriched and orientation prepared from the aerial parts of Isodon excisoides target-guided by UPLC-LTQ-Orbitrap-MS. Four diterpenoids were obtained, including a novel compound: 1α-acetoxy-7α, 14β, 20α-trihydroxy-ent-kaur-16-en-15-one (1); together with three known compounds kamebakaurin (2), lasiokaurin (3), enmenol-1-β-glucoside (4). Their structures were elucidated on the basis of spectroscopic methods in conjunction with published data for their analogues. All compounds were tested for their cytotoxic effects against five human cancer cell lines HCT-116, HepG2, A2780, NCI-H1650 and BGC-823, respectively. Compounds 1 and 2 showed obviously cytotoxic activity against the five cancer cell lines with IC₅₀ ranging from 1.06 to 3.60 μM. Compounds 3 and 4 showed selective cytotoxic activity.     

A new monoterpene glucoside and complete assignments of dihydroflavonols of Pulicaria jaubertii: potential cytotoxic and blood pressure lowering activity

One new monoterpene glucoside and five dihydroflavonols were isolated for the first time from the aerial parts of Pulicaria jaubertii and identified as p-menthane-2-O-β-D-glucopyranoside [1], dihydroquercetin (taxifolin) [2], 7,3′-di-O-methyltaxifolin [3], 3′-O-methyltaxifolin [4], 7-O-methyltaxifolin (padmatin) [5] and 7-O-methyl-dihydrokampferol (7-O-methylaromadenderin) [6]. The structures of these compounds were unambiguously assigned on the basis of NMR spectroscopic data (¹H, ¹³C, DEPT, HSQC, HMBC) and MS analysis. 2D-NMR methods required revision of assignments of H-6 and H-8 for dihydroflavonol compounds. Possible cytotoxic activity as well as blood pressure (BP) lowering activity were tested. The alcoholic extract showed cytotoxic activity against prostate carcinoma (PC-3), breast carcinoma (MCF-7) and hepatocellular carcinoma (HepG-2) human cell lines with IC₅₀ 19.1, 20.0 and 24.1 μg, respectively. The higher dose levels of the alcoholic extract significantly reduced normal BP of rats in a dose-dependent manner.     

Two new flavans from the trunk and leaves of Horsfieldia glabra

Two new flavans, (2R, 4R)-4′-hydroxy-3′,5′-methyl-6,7-methylenedioxy-4-O-2′-cycloflavan (1), and (2R, 4R)-4′-hydroxy-3′-methyl-6,7-methylenedioxy-4-O-2′-cycloflavan (2), along with six known compounds were isolated from the trunk and leaves of Horsfieldia glabra. Their structures were elucidated by means of extensive spectroscopic analysis. Compounds 1 and 2, together with 4–7 were assessed for their cytotoxicity against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that they had no activity.     

Polyketides with different post-modifications from desert endophytic fungus Paraphoma sp.

Three new polyketides 4,6,8-trihydroxy-5-methyl-3,4-dihydronaphthalen-1(2H)-one (1), 5,7-dihydroxy-3-(1-hydroxyethyl)-3,4-dimethylisobenzofuran-1(3H)-one (2) and 1-(4-hydroxy-6-methoxy-1,7-dimethyl-3-oxo-1,3-dihydroisobenzofuran-1-yl) ethyl acetate (3) together with seven known analogues (4–10) were isolated from desert endophytic fungus Paraphoma sp. The structures of these compounds were elucidated by analysis of NMR data. The absolute configuration of (1–3) was established on the basis of CD experiments. The possible biosynthetic pathway of compounds (1–10) was suggested, which implied that these secondary metabolites might be originated from polyketide biosynthesis with different post-modification reactions. Compounds 2, and 5–8 were evaluated for bioactivities against plant pathogen A. solani, whereas none of them displayed any biological effects. In addition, compounds 1, 2 and 5–10 were also tested for cytotoxic activities against three human cancer cell lines (HepG2 cells, MCF-7 cells and Hela cells) without biological effects.