Sesquiterpene constituents from the liverwort Bazzania japonica

The hydrodistillation products of the liverwort Bazzania japonica were separated by preparative gas chromatography (GC) and investigated by spectroscopic methods. Seven unknown compounds were isolated and identified by GC-MS and NMR. Four of them, the norsesquiterpene hydrocarbons 4-epi-11-nor-aristola-1(10),11-diene (1), 4-epi-11-nor-aristola-1,9,11-triene (2), 4-epi-11-nor-aristola-9,11-diene (3), and one oxygenated sesquiterpene, (-)-aristol-1(10)-en-12-ol (5) are new natural compounds, and one, (+)-himachala-2,4-diene (7), has for the first time been isolated from liverworts. The absolute configurations of 5 and 7 were derived by chemical correlation reactions and/or enantioselective GC using cyclodextrin phases. 1, 2 and 3 have identical absolute configuration.     

Phytotoxicity of constituents of glandular trichomes and the leaf surface of camphorweed, Heterotheca subaxillaris

Camphorweed, Heterotheca subaxillaris (Lam.) Britt. & Rusby, has a camphor-like odor, and its leaf surfaces contain glandular trichomes of the type shown to contain high levels of isoprenoids in other species. Borneol (1), the phytotoxic calamenene-type sesquiterpenes (2-5, 9-11), and methylated flavones (12-15) were isolated from the dichloromethane rinsate of camphorweed aerial tissues. The strongest plant growth inhibitor against Agrostis stolonifera and Lactuca sativa seedlings, as well as duckweed (Lemna pausicostata), was 2-methoxy-calamenene-14-carboxylic acid (2). Esterification of calamenene carboxylic acids decreased their biological activity.     

广东紫珠中的萜类化合物及其抗炎活性

对岭南药材广东紫珠(Callicarpa kwangtungensis)地上部分进行化学成分研究,得到11个萜类化合物,分别鉴定为sambucunlin A(1)、2α-羟基羽扇豆醇(2)、swinhoeic acid(3)、3β-羟基-乌苏烷-11-烯-13β,28-内酯(4)、蔷薇酸(5)、2α,3β,6β,18β,23-pentahydroxy-olean-12-en-28-oic acid(6)、rel-5-(3S,8S-dihydroxy-1R,5S-dimethyl-7-oxa-6-oxobicyclo-oct-8-yl)-3-methyl-2Z,4E-pentadienoic acid(7)、salvionoside B(8)、齐墩果酸(9)、白桦脂酸(10)和α-香树脂醇(11)。其中,化合物1～4和6～8为首次从该属植物中分离得到。在化学成分分离基础上,进一步选择脂多糖(LPS)诱导的RAW 264.7小鼠巨噬细胞炎症模型进行萜类化合物抗炎活性测试。结果表明:化合物3和9具有显著的抗炎活性,对比结构发现,三萜类化合物(3～6、9和11)抗炎活性优于倍半萜类化合物(7和...     

Flavonol tetraglycosides and other constituents from leaves of Styphnolobium japonicum (Leguminosae) and related taxa

Two flavonol tetraglycosides comprising a trisaccharide at C-3 and a monosaccharide at C-7 were isolated from the leaves of Styphnolobium japonicum (L.) Schott and characterised as the 3-O-alpha-rhamnopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-glucopyranoside-7-O-alpha-rhamnopyranosides of quercetin and kaempferol. The 3-O-alpha-rhamnopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-galactopyranoside-7-O-alpha-rhamnopyranoside of kaempferol, the 3-O-alpha-rhamnopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-glucopyranosides of kaempferol and quercetin and the 3-O-alpha-rhamnopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-galactopyranoside of kaempferol were also obtained from this species for the first time. Some or all of these flavonol tetra- and triglycosides were detected in 17 of 18 specimens of S. japonicum examined from living and herbarium material, although the most abundant flavonoid in the leaves was generally quercetin 3-O-alpha-rhamnopyranosyl(1-->6)-beta-glucopyranoside (rutin). The triglycosides, but not the tetraglycosides, were detected in herbarium specimens of Styphnolobium burseroides M. Sousa, Rudd & Medrano and Styphnolobium monteviridis M. Sousa & Rudd, but specimens of Styphnolobium affine (Torrey & A. Gray) Walp. contained a different profile of flavonol glycosides. The flavonol tetra- and triglycosides of S. japonicum were also present in leaves of Cladrastis kentukea (Dum. Cours.) Rudd, a representative of a genus placed close to Styphnolobium in current molecular phylogenies. An additional constituent obtained from leaves of Styphnolobium japonicum was identified as the maltol derivative, 3-hydroxy-2-methyl-4H-pyran-4-one 3-O-(4'-O-p-coumaroyl-6'-O-(3-hydroxy-3-methylglutaroyl))-beta-glucopyranoside.     

A flavonol tetraglycoside from Sophora japonica seeds

A flavonol tetraglycoside, kaempferol 3-O-alpha-L-rhamnopyranosyl(1-->6)-beta-D-glucopyranosyl(1-->2)- beta-D-glucopyranoside-7-O-alpha-L rhamnopyranoside, together with nine known compounds were isolated from the seeds of Sophora japonica L. Their structures were elucidated on the basis of spectral and chemical evidence.     

Antioxidant phenylpropanoid glycosides from the leaves of Wasabia japonica

From the MeOH extract of the leaves of W. japonica, seven phenylpropanoid gentiobiosides (1-7) were isolated along with eight known phenylpropanoids (8-15). Structures of 1-7 were determined based on spectroscopic data and chemical evidence. The activity of compounds 1-15 to scavenge superoxide anion radicals was investigated using an electron spin resonance (ESR) method.     

Fragments of acylated 6-O-α- -rhamnopyranosylcatalpol from leaves of Premna japonica

Five monoacyl rhamnopyranoses were isolated from leaves of Premna japonica. The structures were determined to be 2- and 3-O-trans-isoferuloylrhamnopyranoses, 2- and 3-O-trans-p-methoxycinnamoylrhamnopyranoses and 2-O-cis-p-methoxycinnamoylrhamnopyranose.     

Chemical composition and antibacterial activities of the essential oils of Lippia chevalieri and Lippia multiflora from Burkina Faso

The chemical composition of the essential oils of Lippia chevalieri and Lippia multiflora obtained from the air-dried leaves by hydrodistillation were analysed using GC and GC-MS. L. chevalieri and L. multiflora belonged to thymol/p-cymene/2-phenyl ethyl propionate and thymol/p-cymene/thymyl acetate chemotypes, respectively. The essential oils were also tested against 09 strains using a broth microdilution method. The Gram-negative bacteria were the most sensitive. The essential oil of L. multiflora was the most active.     

Biflavonoids from Lonicera japonica

Two biflavonoids, 3'-O-methyl loniflavone [5,5',7,7'-tetrahydroxy 3'-methoxy 4',4'-biflavonyl ether (1)] and loniflavone [5,5',7,7',3'-pentahydroxy 4',4'-biflavonyl ether (2)] along with luteolin (3) and chrysin (4) were isolated from the leaves of Lonicera japonica. The structures were established on the basis of UV/vis, 1D, 2D NMR (HMQC and HMBC) and ESI-QTOF-MS/MS spectroscopic methods and chemical evidences.     

Furostanol saponins from the rhizomes of Dioscorea japonica and their effects on NGF induction

The rhizome of Dioscorea japonica is a food and medicinal source known as ‘San Yak’ in Korea. Two new furostanol saponins, coreajaponins A (1) and B (2), together with 10 known compounds (3-12) were isolated from the rhizomes of D. japonica. Their structures were determined by spectroscopic methods, including 1D and 2D NMR techniques, HRMS, and chemical methods. Nerve growth factor (NGF), a crucial factor for neuronal survival and differentiation, can potentially improve neurodegenerative diseases and diabetic polyneuropathy. We evaluated the effects of isolates (1-12) on NGF induction in a C6 rat glioma cell line. Coreajaponin B (2) upregulated NGF content without significant cell toxicity, as did 6, 8, 9, and 11.     

Cardiovascular effects of the essential oil of Croton zehntneri leaves and its main constituents, anethole and estragole, in normotensive conscious rats

Cardiovascular effects of the essential oil of Croton zehntneri (EOCZ) were investigated in conscious rats. In these preparations, intravenous (i.v.) injections of EOCZ (1-20 mg kg(-1)) and its main constituents anethole and estragole (both at 1-10 mg kg(-1)) elicited brief and dose-dependent hypotension and bradycardia (phase I) that were followed by a significant pressor effect associated with a delayed bradycardia (phase II). The initial hypotension and bradycardia (phase I) of EOCZ were unchanged by atenolol (1.5 mg kg(-1), i.v.) or L-NAME (20 mg kg(-1), i.v.) pretreatment, but were respectively reversed into pressor and tachycardic effects by methylatropine (1 mg kg(-1), i.v.) pretreatment. The subsequent pressor effect and the delayed bradycardia (phase II) remained unaffected by atenolol, but were abolished by L-NAME and methylatropine pretreatment, respectively. In rat endothelium-containing aorta preparations, the vasoconstrictor responses to phenylephrine were enhanced and reduced, respectively, by the lower (1-30 microg mL(-1)) and higher (300-1000 microg mL(-1)) concentrations of EOCZ. Only the enhancement of phenylephrine-induced contraction was abolished by either the incubation with L-NAME (50 microM) or in the absence of the endothelium. These data show, for the first time, that i.v. administration EOCZ induces an initial hypotension followed by a pressor response, two effects that appear mainly attributed to the actions of anethole and estragole. The EOCZ-induced hypotension (phase I) is mediated by a cholinergic mechanism and seems to result mainly from the concomitant bradycardia. The pressor response of EOCZ (phase II) seems to be caused by an indirect vasoconstrictive action of EOCZ most likely through inhibition of endothelial nitric oxide production.     

A diterpene quinone from the bark of Cryptomeria japonica

A diterpene, cryptoquinone, was isolated from the bark of Cryptomeria japonica, the structure, 7,11,14-trioxoabieta-8,12-diene, was established by spectral analyses and X-ray crystallography. This diterpene quinone showed moderate antifungal activities against Pyricularia orizae and Alternaria alternata, and cytotoxic activity against mouse lymphoid neoplasm (P388) cells with an IC(50) of 0.26 microg/ml.     

Oligosaccharide polyester and triterpenoid saponins from the roots of Polygala japonica

An oligosaccharide polyester, 1-O-(E)-p-coumaroyl-(3-O-benzoyl)-beta-D-fructofuranosyl-(2-->1)-[6-O-(E)-feruloyl-beta-D-glucopyranosyl-(1-->2)]-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)-(4-O-acetyl)-beta-D-glucopyranosyl-(1-->3)]-4-O-[4-O-alpha-L-rhamnopyranosyl-(E)-p-coumaroyl]-alpha-D-glucopyranoside (polygalajaponicose I), and four triterpenoid saponins, 3beta, 23, 27-trihydroxy-29-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-olean-12-en-28-oic acid (polygalasaponin XLVII), 3-O-beta-D-glucopyranosyl presenegenin 28-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (polygalasaponin XLVIII), 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl-(1-->5)-beta-D-apiofuranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester (polygalasaponin XLIX) and 2beta, 27-dihydroxy-3-O-beta-D-glucopyranosyl 11-oxo-olean-12-en-23, 28-dioic acid 28-O-beta-D-galactopyranosyl-(1-->5)-beta-D-apiofuranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (polygalasaponin L), in addition to five known compounds have been isolated from the roots of Polygala japonica.     

Emission of floral volatiles from Mahonia japonica (Berberidaceae)

Flowering Mahonia japonica plants were subjected to controlled environments and the floral volatiles emitted from whole racemes (laterals) were trapped by Porapak Q adsorbent and analysed by GC-FID. An experiment with photoperiods of 6 and 9 h at constant temperature (10+/-1 degrees C) demonstrated that photoperiod was the stimulus for enhanced emission of most volatiles. Small quantitative differences in emitted fragrance composition were observed between light and dark periods and between plants acclimatised to different photoperiods. Maximum rates of emission occurred in the middle of the light period; aromatic compounds (benzaldehyde, benzyl alcohol and indole) displayed a more rapid increase and subsequent decline compared with monoterpenes (cis- and trans-ocimene and linalool). When the photoperiod was extended from 6 to 9 h, maximum rates of emission continued throughout the additional 3 h. Total emission (microg/h) of volatiles was 2-fold greater in the day-time (DT) (39.7 microg/h) compared with the night-time (NT) (19.8 microgg/h) under a 6 h photoperiod and was not significantly different from total emission under a 9 h photoperiod.     

Diterpene constituents of leaves from Juniperus brevifolia

The dichloromethane extract from leaves of Juniperus brevifolia, through chromatographic fractionations yield six compounds: 3beta-hydroxy-abieta-8,11,13-trien-7-one, 18-hydroxy-sandaracopimara-8(14),15-dien-7-one, sandaracopimara-8(14),15-dien-18-yl formate; and the first examples of sandaracopimaranes and abieta-8,11,13-triene diterpenoids with a large aliphatic chain on C-18, abieta-8,11,13-trien-18-yl hexadecanoate, 7-oxoabieta-8,11,13-trien-18-yl hexadecanoate, sandaracopimara-8(14),15-dien-18-yl hexadecanoate. Moreover fifteen known compounds were also isolated, some of them for the first time identified on Juniperus genus. The compound abieta-8,11,13-trien-18-yl formate is reported for the first time as a natural product. All the structures were established by spectroscopic methods. 2D NMR techniques have allowed the revision of certain previously reported (13)C NMR assignments. Studies on the isolated new compounds showed those possessing a diterpenol ester of a long-chain fatty acid present lipophilicity very distinct from other diterpenoid compounds.     

Fermentative hydrogen production from Laminaria japonica and optimization of thermal pretreatment conditions

As a sustainable biofuel feedstock, marine algae have superior aspects to terrestrial biomass such as less energy and water requirement for cultivation, higher CO₂ capture capacity, and negligible lignin content. In this study, various marine algae were tested for fermentative hydrogen production (FHP). Among them, Laminaria japonica exhibited the best performance, showing the highest H₂ yield of 69.1 mL H₂/g COD_added. It was attributed to its high carbohydrate content and main constituents of polysaccharides, laminarin and alginate, which were found to posses higher H₂ production potential than agar and carrageenan. To enhance the H₂ production from L. japonica, thermal pretreatment was applied at various conditions. At 170 °C and 20 min, H₂ yield was maximized to 109.6 mL H₂/g COD_added. The experimental results suggested that marine algae, especially L. japonica, could be used for FHP, and future works would be focused on gaining more energy from the H₂ fermentation effluent.