In the last decade, along with the development of taxonomy research in marine-derived actinobacteria, more and more halogenated natural products were discovered from marine actinobacteria. Most of them showed good biological activity and unique structure compared to those from land. The special halogenation mechanism in some compounds' biosynthesis has drawn great attention. So in this review, we focus on the halogenated natural products from marine actinobacteria and their halogenation mechanisms.

The crude extracts of the fermentation broth from a marine sediment-derived actinomycete strain, Saccharothrix sp. 10-10, showed significant antibacterial activities against drug-resistant pathogens. A genome-mining PCR-based experiment targeting the genes encoding key enzymes involved in the biosynthesis of secondary metabolites indicated that the strain 10-10 showed the potential to produce tetracenomycin-like compounds. Further chemical investigation of the cultures of this strain led to the identification of two antibiotics, including a tetracenomycin (Tcm) analogs, Tcm X (1), and a tomaymycin derivative, oxotomaymycin (2). Their structures were identified by spectroscopic data analysis, including UV, 1D-NMR, 2D-NMR and MS spectra. Tcm X (1) showed moderate antibacterial activities against a number of drug-resistant pathogens, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE) pathogens, with the MIC values in the range of 32-64 microg x mL(-1). In addition, 1 also displayed significant cytotoxic activities against human cancer cell lines, including HL60 (leukemia), HepG2 (liver), and MCF-7 (breast) with the IC 50 values of 5.1, 9.7 and 18.0 micromol x L(-1), respectively. Guided by the PCR-based gene sequence analysis, Tcm X (1) and oxotomaymycin (2) were identified from the genus of Saccharothrix and their 13C NMR data were correctly assigned on the basis of 2D NMR spectroscopic data analysis for the first time.

OBJECTIVETo investigate chemical constituents of Iodes cirrhosa.

METHODConstituents were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic and chemical methods.

RESULTTwenty-four compounds were obtained from a H2O-soluble portion of an ethanolic extract of the root of lodes cirrhosa Turcz. Structures of the isolates were identified as (-)-(7R,8S,7'E) -4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8,4'-oxyneolign-7'-ene-9'-O-beta-D-glucopyra-noside (1), (-)-(7S,8S,7'E)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8,4'-oxyneolign-7'-ene-9'-O-beta-D-glucopyranoside(2), (+)-(7S,8S)-syringylglycerol 8-O-beta-D-glucopyranoside (3), (+)-(7S, 8S)-guaiacylglycerol 8-O-P-D-glucopyranoside (4), (-)-(7S, 8S)-4,7,9, 9'-tetrahydroxy-3,3'-dimethoxy-8,4'-oxyneolignan-7-O-beta-D-glucopyranoside (5),(-)-alaschanisoside A (6), (-)-(2R)-1-O-beta-D-glucopyranosyl-2-(2-methoxy-4-[1-(E)-propen-3-ol] phenoxyl propane-3-ol(7), (-)-(2R)-1-O-beta-D-glucopyranosyl-2-{2,6-dimethoxy-4-[1-(E)-propen-3-ol] phenoxyl} propane-3-ol(8), (-)-liriodendrin(9), (-)-(7S, 8R)-guaiacylglycerol 9-O-beta-D-glucopyranoside(10), (-)-(7R, 8R)-guaiacylglycerol 9-O-beta-D-glucopyranoside(11),(-)-(7R,8R)-syringylglycerol 9-O-beta-D-glucopyranoside(12), (-)-(7R,8R)-guaiacylglycerol 7-O-beta-D-glucopyranoside(13), (-)-11,13-dihydrodeacylcynaropicrin 3-O-beta-D-glucopyranoside(14), (-)-sweroside (15), (-)-2-hydroxy-5-(2-hydroxyethyl) phenyl beta-D-glucopyranoside(16), (-)-(1'R)-1'-(3-hydroxy-4-methoxyphenyl) ethane-1',2'-diol-3-O-beta-D-glucopyranoside(17), (-)-tachioside(18), (-)-3,5-dimethoxy-4-hydroxyphenyl beta-D-glucopyranoside(19), (-)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone-3-O-beta-D-glucopy ranoside(20), (-)-2-methoxy4-(1-propionyl) phenyl beta-D-glucopyranoside(21), (-)-4-propionyl-3, 5-dimethoxyphenyl beta-D-glucopyranoside(22), erigeside C(23), and scopoletin beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside(24).

CONCLUSIONCompounds 1-24 were obtained from the genus for the first time.

Drugs, Chinese Herbal ; analysis ; Ethanol ; chemistry ; Glucosides ; analysis ; Isomerism ; Magnoliopsida ; chemistry ; Plant Roots ; chemistry ; Solubility ; Water ; chemistry

To study chemical constituents contained in ethanol extracts from roots of Machilus yaoshansis. Fifteen compounds were separated from the roots of M. yaoshansis by using various chromatographic techniques. Their structures were identified on the basis of their physicochemical properties and spectral data as twelve lignans(+)-guaiacin (1), kadsuralignan C (2), (+)-isolariciresinol (3), 5'-methoxy-(+)-isolariciresinol (4), (7'S, 8R, 8'R)-lyoniresinol (5), meso-secoisolariciresinol (6), isolariciresinol-9'-O-beta-D-xylopyranoside (7), 5'-methoxy-isolariciresinol-9'-O-beta-D-xylopyranoside (8), lyoniresinol-9'-O-beta-D-xylopyranoside (9), (2R, 3R) -2, 3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran (10), 3, 5'-dimethoxy-4', 7-epoxy-8, 3'-neolignan-4, 9, 9'-triol (11), nectandrin B (12), and three flavanes(+)-catechin (13), (-)-epicatechin (14), and bis-8, 8'-catechinylmethane (15). All of the compounds 1-15 were separated from M. yaoshansis for the first time.
Butylene Glycols ; chemistry ; Catechin ; chemistry ; Lauraceae ; chemistry ; Lignans ; chemistry ; Lignin ; chemistry ; Naphthols ; chemistry ; Plant Roots ; chemistry

OBJECTIVETo investigate chemical constituents of the stems and branches of Adina polycephala and their pharmacological activities.

METHODThe constituents were isolated by a combination of various chromatographic techniques including column chromatography on silica gel, Sephadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic data analysis. In vitro cytotoxic, anti-inflammatory, anti-oxidant, anti-HIV, neuroprotective and anti-diabetic activities were screened by using cell-based models.

RESULTTwenty-eight constituents were isolated. Their structures were identified as clemochinenoside B (1), kelampayoside A (2), osmanthuside H (3), 4-hydroxy-3-methoxyphenol-beta-D-[6-O-(4-hydroxy-3,5-dimethoxylbenzoate)]-glucopyranoside (4), and syringic acid beta-D-glucopyranosyl ester (5). Ten iridoidal glycosides: geniposidic acid (6), geniposide (7), 6beta-hydroxygeniposide (8), 6beta-hydroxygeniposide (9), ixoside (10), ixoside 11-methyl ester (11), 11-methyl forsythide (12), 7beta-hydroxysplendoside (13), gardoside (14) and mussaenosidic acid (15), (+) -pinoresinol (16), (+) -medioresinol (17), (+) -syringaresinol (18), (-)-lariciresinol (19), evofolin-B (20), alpha-hydroxyacetovaillone (21), syringic acid (22), vanillin (23), 3, 4, 5-trimethoxyphenol (24), and 2,6-dimethoxy-1, 4-benzoquinone (25), beta-sitosterol (26), mannitol (27), and daucosterol (28). At a concentration of 1.0 x 10(-5) mol x L(-1), these compounds were inactive in the assays, including cytotoxicity against human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549 and A2780), anti-inflammatory activity against the release of beta-glucuronidase in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF), antioxidant activity in Fe(2+)-cystine-induced rat liver microsomal lipid peroxidation, anti-HIV activity against HIV-1 replication, neuroprotective activity against serum deprivation or glutamate induced neurotoxicity in cultures of PC12 cells, and the inhibitory activity against protein tyrosine phosphatase 1B (PTP1B).

CONCLUSIONCompounds 1-20 were obtained from the genus Adina for the first time. The 13C-NMR data of compounds 10 and 11 were reassigned. A further evaluation of pharmacological activity of these compounds is expected.

Animals ; Cell Line, Tumor ; Cell Proliferation ; drug effects ; Humans ; Molecular Structure ; Plant Extracts ; chemistry ; pharmacology ; Plant Stems ; chemistry ; Rats ; Rubiaceae ; chemistry

OBJECTIVETo study the chemical constituents of Iodes cirrhosa and evaluate their bioactivity.

METHODThe compounds were isolated and purified by various kinds of column chromatography methods and their structures were determined by spectroscopic data analysis. Neuroprotective assay against serum deprivation induced SH-SYSY-JNK3 cell apoptosis was evaluated by MTr method while potassium channel-blocking activity was assayed in both non-specific and specific K+ channel-regulator screening models.

RESULTTwenty-one compounds were obtained from an EtOAc portion of an ethanolic extract of the root of I. cirrhosa. Their structures were elucidated as 1beta, 3beta-dihydroxyurs-9(11),12-diene(1), bauerenyl acetate(2),3beta-hydroxy-11-oxo-olean-12-enyl palmitate(3), 3beta-acetoxy-urs-12-ene-11-one(4), betulinic acid(5), stigmasta-5, 22-diene-3beta-ol(6), 7beta-hydroxystigmasterol(7), stigmasta-5, 22diene-3beta-ol3-O-beta-D-glucopyranoside(8),scopoletin(9),scopolin(10),clovamide(11),methyl 3,5-di-O-caffeoylquinate(12),3,5-dicaffeoylquinic acid(13),2,6-dimethoxy-1,4-benzoquinone(14), protocatechualdehyde(15), vanillin(16), protocatechuic acid(17), vanillic acid(18),caffeic acid(19),azelaic acid(20),and succinic acid(21). Compound 3,4,6,9,10,14,15,18 and 20 showed neuroprotective activities against serum deprivation induced SH-SYSY-JNK3 cell apoptosis at a concentration of 1.0 x 10(6) mol x L(1) with relative protection rates of 177%, 144%, 137%, 137%, 143%, 145%, 137%, 189%, 130%, respectivley. Compound 16 could increase DiBAC4(3) fluorescence response in both non-specific and specific K+ channel-regulator screening models at the concentration of 1.0 x 10(-5) mol x L(-1).

CONCLUSIONCompound 1 was a new compound and all compounds were isolated from this genus for the first time. Compounds 3,4,6,9,10,14,15,18 and 20 showed neuroprotective activities while 16 exhibited K+ channel-blocking activity.

Apoptosis ; drug effects ; Cell Line, Tumor ; Humans ; Magnoliopsida ; chemistry ; Neuroprotective Agents ; chemistry ; pharmacology ; Plant Extracts ; chemistry ; pharmacology ; Potassium Channels ; drug effects