New chalcanonol glycoside from the seeds of saw palmetto: antiproliferative and antioxidant effects

A new chalcanonol glycoside dimer, bis-O-[(I-4′) → (II-6′)]-α-hydroxyphloretin-2′-O-β-glucoside (1), in addition to six known compounds, namely ( ? )-epicatechin (2) and ( ? )-epiafzelechin (3), 4-hydroxybenzoic acid (4), protocatechuic acid (5), methylgallate (6), β-sitosterol (7) and β-sitosterol-3-O-glucoside (8), was isolated from the seeds of saw palmetto. The structures of the isolated compounds were established from the analysis of their MS and 1D and 2D NMR spectroscopic data. The antiproliferative activities of the isolated compounds towards PC3, the human prostate cancer cells were investigated. Amongst the isolated compounds, the new compound and the sterolic derivatives showed antiproliferative effects. Screening of the antioxidant effects of the isolated compounds by 2,2′-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid radical assay revealed that the isolated phenolics were active free radical scavengers.     

Cytotoxic constituents from Vicia monantha subsp. monantha seeds

Chemical investigation of Vicia monantha subsp. monantha Retz. revealed isolation of one new hydroxy- fatty acid (6) identified as (6-Z, 10-E)-9-hydroxy henicosa-6,10-dienoic acid in addition to six known metabolites; hexadecanoic acid (1), β-sitosterol (2), β-amyrin (3), β-sitosterol-glucoside (4), 2,3-dihydroxypropyl tetradecanoate (5) and (Z)-9-hydroxypentadec-6-enoic acid (7). The cytotoxic effect of the isolated compounds was assessed by MTT assay using lung cancer A-549, prostate cancer PC3, breast cancer MCF-7, colon cancer HCT-116 and liver cancer HepG2 cell lines. Only compounds 1, 2, and 4 showed cytotoxic effect on HCT-116 cells where compound 2 was the most active with IC₅₀ value of 22.61 μg/mL. In addition, compounds 1, 2, 3, and 4 showed promising cytotoxic effect on MCF-7 cells with IC₅₀ values of 21.03, 15.42, 10.089, and 11.34 μg/mL, respectively.     

Sassarandainol: a new neolignan and anti-inflammatory constituents from the stem of Sassafras randaiense

A new neolignan, (R)-( ? )-sassarandainol (1), together with 10 known compounds (2–11), was isolated from the stem of Sassafras randaiense. The structures were determined by spectroscopic techniques. Among these isolates, γ-tocopherol (5), subamolide B (7) and β-sitosterone (9) exhibited moderate iNOS inhibitory activity on nitrite production induced (%) value of 30.51, 28.68 and 16.96, respectively.     

A new isoflavone glycoside from Pueraria alopecuroides

A new isoflavone glycoside, (?)-tuberosin-3-O-β-D-glucopyranoside (1), along with 10 known compounds 1a-10, was isolated from Pueraria alopecuroides. Their structures were determined on the basis of spectral data including 1D and 2D NMR and HREIMS. These compounds were isolated from this plant for the first time.     

A new tigliane-type diterpene from Euphorbia dracunculoides Lam

One new tigliane-type diterpene, 4-deoxy-4(β)H-8-hydroperoxyphorbol-12-benzoate-13-isobutyrate (1), together with two known diterpenoids, 3-acetyl-5,8-dibenzoyl-14α-propanoyl-13,17-epoxy-7-myrsinaone diterpene with C9–C10 cyclised to form an additional lactone ring (2), Euphodendriane A (3) have been isolated from the whole plants of Euphorbia dracunculoides Lam. Their structures were elucidated by means of extensive spectroscopic analysis (NMR and HR-ESI-MS) and comparison with data reported in the literature. This is the first isolation of 8-hydroperoxy tigliane diterpene (1) from the genus of Euphorbia. All compounds were evaluated for their antifungal activities.     

Trichocitrin,a new fusicoccane diterpene from the marine brown alga-endophytic fungus Trichoderma citrinoviride cf-27

One new diterpene, trichocitrin (1), and four known secondary metabolites, nafuredin (2), 5-hydroxy-2,3-dimethyl-7-methoxychromone (3), 24-methylenecycloartanol (4) and citrostadienol (5), were isolated from the culture of marine brown alga-endophytic Trichoderma citrinoviride cf-27. Trichocitrin (1) represents the first Trichoderma-derived and furan-bearing fusicoccane diterpene, and its structure and relative configuration were identified by analysis of 1D/2D NMR and mass spectroscopic data. Compounds 1 and 2 exhibited 8.0- and 9.5-mm inhibition zones, respectively, against Escherichia coli at 20 μg/disc and 54.1 and 36.7% growth inhibition, respectively, of Prorocentrum donghaiense at 80 μg/mL.     

Two new diterpene and sesquiterpene from Pteris dispar

A new diterpene and a new sesquiterpene were isolated from Pteris dispar and identified on the basis of spectral data including 2D NMR.Compounds 1 and 2 showed potent cytotoxic activity against KB cell.     

Two new labdane-type diterpenoids cinnamate from Croton decalvatus Esser

Two new labdane diterpene derivatives, crotondecalvatin A (1) and crotondecalvatin B (2) were obtained from the leaves and twigs of Croton decalvatus. The structures of compounds were established on the basis of extensive spectroscopic data.     

Chemical constituents of the mangrove-associated fungus Capnodium sp. SZ-F22. A new eremophilane sesquiterpene

A new eremophilane sesquiterpene, capnodiumone (1), along with five known eremophilane sesquiterpenes (2–6) and eight other compounds (7–14), have been isolated from a mangrove-associated fungus Capnodium sp. SZ-F22. The chemical structures were elucidated on the basis of extensive spectroscopic analysis. The broth extract of the fungus exhibited a good inhibitory effect on the mycelium growth against Fusarium graminearum at 100 μg/mL, however, all the 14 compounds showed no expected antifungal activity. The probable reasons were discussed.     

A new ent-kaurane diterpene derivative from the stems of Eurya chinensis R.Br

One new ent-kaurane diterpene derivative (1), along with four known diterpenes, was isolated from the stems of Eurya chinensis R.Br. The structure of the new compound was established by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. Compound 1 showed moderate anti-inflammatory activities with IC₅₀ value of 8.12 μM. This is the first example of diterpenoids with 4-hydroxy-4-(2-hydroxyethyl)-1-hydroxyl-cyclohexanoyl substituent.     

A new tigliane-type diterpene ester from <Emphasis Type="Italic">Wikstroemia scytophylla</Emphasis>

A new tigliane-type diterpene ester, wiksphyllamin B (1), and one known compound, 12-O-benzoylphorbol 13-octanoate (2), were isolated from the stems of Wikstroemia scytophylla Diels. Their structures were identified using spectroscopic methods. The incorrect assignment of ¹³C NMR data of compound 2 in the literature was revised according to the 2D NMR spectra.     

A new dolabellane diterpene and a new polyacetylene from the soft coral Clavularia viridis

A new dolabellane diterpene (1) and a new polyacetylene (2) were isolated from the soft coral Clavularia viridis. The structures of 1 and 2 were elucidated by spectroscopic analyses including 1D and 2DNMR experiments and HRESIMS data. The absolute configuration of 1 was determined by the modified Mosher’s method and 2 by ECD calculations. Compound 1 exhibited moderate cytotoxicities against MCF-7 and A549 cell lines with IC₅₀ values of 10.5 and 12.6 µM, respectively.     

Supramolecular inclusion of a pillared double-layered host by an anion-directed second-sphere coordination

In this paper, we have illustrated the utilisation of a second-sphere coordination approach to construct supramolecular inclusion solids with varieties of guest molecules. A flexible molecule N,N,N′,N′-tetra-p-methylbenzyl-ethylenediamine (L1) bearing doubly protonated H-bond donors was designed, capable of forming N–H…Cl hydrogen bonds with a crystallographically unique chloride anion, to construct an anion-directed ligand. The pillared double-layered host framework was constructed by an anion-directed ligand and primary coordination sphere [CoCl₄]^2 ?  through weak C–H…Cl hydrogen-bonding interactions. A variety of guest molecules, such as p-anisaldehyde, 1,4-dimethoxy-2,5-bis(methoxymethyl)benzene, can be included, leading to the formation of novel supramolecular inclusion solids: [L1]·4[H]⁺·[CoCl₄]^2 ? ·2Cl^? ·1.5[C₈H₈O₂]·0.25[CH₃OH] (1) and [L1]·4[H]⁺·[CoCl₄]^2 ? ·2Cl^? ·1.5[C₁₂H₂₀O₄]·0.5[CH₃OH] (2).

We have presented herein the utilisation of a second-sphere coordination approach to construct supramolecular inclusion solids with a variety of guest molecules. A novel type of a pillared double-layered host framework was constructed by a second-sphere coordination between the anion-directed ligand (L1 = N,N,N′,N′-tetra-p-methylbenzyl-ethylenediamine) and [CoCl₄]^2 ?  through weak C–H…Cl hydrogen-bonding interaction, and a variety of guest molecules, such as p-anisaldehyde, 1,4-dimethoxy-2,5-bis(methoxymethyl)benzene, can be included, leading to the formation of supramolecular inclusion solids: [L1]·4[H]⁺·[CoCl₄]^2 ? ·2Cl^? ·1.5[C₈H₈O₂]·0.25[CH₃OH] (1) and [L1]·4[H]⁺·[CoCl₄]^2 ? ·2Cl^? ·1.5[C₁₂H₂₀O₄]·0.5[CH₃OH] (2)

     

A new labdane diterpene from the rhizomes of Alpinia officinarum

A new labdane diterpene, (Z)-12,14-labdadien-15(16)-olide-17-oic acid (1), and a new natural cadinane sesquiterpene, 4-isopropyl-6-methyl-1-naphthalenemethanol (2), were isolated from the ethanolic extract of the rhizomes of Alpinia officinarum, together with three other products, galangin (3), kaempferol (4) and quercetin (5). Their structures were elucidated by using extensive spectroscopic methods. Compounds 1 and 2 showed no remarkable cytotoxic activity against HeLa and HepG2 cancer cell lines with IC₅₀>50 μg mL^? 1.     

Two new spongian diterpene analogues isolated from the marine sponge Acanthodendrilla sp

Abstract

Two new marine natural compounds, 3β-acetoxy-15-hydroxyspongia-12-en (1) and 3-methylspongia-3,12-dien-16-one (2), were isolated from the marine sponge Acanthodendrilla sp., collected in Pulau-Pulau. Compounds 1 and 2 represent new chemical entities of the known spongian diterpene family. Compound 1 is a new 3-acetoxyspongia and compound 2 presents an unreported rearranged 3-methylspongia-3-en. Their structures, including relative configurations, were fully elucidated based on 1D and 2D NMR analyses, as well as HRESTOFMS experiments. No significant bioactivities were found for these compounds. This work reports two new chemical structures, compounds 1 and 2, together with the first isolation of spongian diterpenes from Acanthodendrilla genus.     

A new triterpenoid saponin and a diterpene glucoside from the seeds of Orychophragmus violaceus

One new triterpenoid saponin orychoside A (1) and one new diterpene glucoside orychoside B (12), together with eleven known compounds, were isolated from the seeds of Orychophragmus violaceus. The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The known compounds were identified by comparison with data reported in the literature. All compounds were tested for their cytotoxic activities against the HepG2 and A549 cell lines in vitro. The new compound 1 exhibited potent cytotoxicity against the two cell lines with IC₅₀ values of 7.13 and 8.77 μM, respectively. Compounds 2, 5, 8 and 9 were found to possess obvious cytotoxicity.     

Bioactivity-guided isolation of new antiproliferative compounds from Juniperus foetidissima Willd.

Based on a literature survey on cytotoxic medicinal plants, Juniper species were identified as interesting source of antitumor compounds. Using bioassay-guided fractionation against Caov-4 cancer cells on acetone extract of leaves and branchlets of Juniperus foetidissima led to the isolation of a new 3H-benzofuaran-2-one: 4-methyl-3-methoxy-3H-benzofuaran-2-one (1), a new sesquiterpene: 4,9(α)-dihydroxy-nardosin-6-en (2) and an already known labdane-type diterpene: 15-hydroxy-8(17),13(E)-labdadiene-19-carboxilic acid (3). Compounds 1–3 exhibited cytotoxic effects, with moderate cytotoxicity against the EJ-138 bladder and CAOV-4 ovary cancer cell lines.     

A new highly oxygenated daphnane diterpene esters from the flower buds of Daphne genkwa

The phytochemical investigation of the flower buds of Daphne genkwa yielded eight highly oxygenated daphnane-type diterpene esters, including a new one, genkwanine N 20-palmitate (1) and seven known ones (2–8). The molecular structures of the isolated compounds were elucidated on the basis of extensive spectroscopic analysis, including UV, IR, NMR, and MS, and comparison with literature data. Furthermore, compound 1 showed potential cytotoxic activity in vitro, against A549 and Hep G2 tumour cell lines.     

Penicindopene A,a new indole diterpene from the deep-sea fungus Penicillium sp. YPCMAC1

A new indole diterpene, named penicindopene A (1), together with seven known compounds (2?–?8), was isolated from the deep-sea fungus Penicillium sp. YPCMAC1. The structure of penicindopene A was elucidated by extensive spectroscopic analyses (1?D and 2?D NMR, and HRESIMS data), in addition to the ECD calculations for the assignments of its absolute configuration. Penicindopene A represented the first example of indole diterpenes possessing a 3-hydroxyl-2-indolone moiety, and it exhibited moderate cytotoxicities against A549 and HeLa cell lines with IC₅₀ values of 15.2 and 20.5?µM, respectively.     

Structure elucidation and NMR assignments of a new dihydrochalcone from Empetrum nigrum subsp. asiaticum (Nakai ex H.Ito) Kuvaev

Abstract

A new dihydrochalcone, namely 2',5'-dimethyl-3'-methoxy-4',6'-dihydroxyl-dihydrochalcone (1) together with five known compounds were isolated from the CHCl₃ extract from Empetrum nigrum L. var. japonicum K. Koch (E. nigrum). The structures of 1 was elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques.