A new iridoid glycoside from Paederia scandens

<正>A new glycoside named 6β-O-β-D-glucosylpaederosidic acid(1) was isolated from Paederia scandens and its structure was elucidated on the basis of spectroscopic and chemical evidence,together with four known iridoids,paederoside(2),paederosidic acid(3),paederosidic acid methyl ester(4),and deacetyl asperulosidic acid methyl ester(5).Compound 5 was isolated from this plant for the first time.     

A new triterpenoid saponin from Abrus precatorius Linn

A new triterpenoid saponin, 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl subprogenin D (1), together with six known triterpenoids: subprogenin D (2), abrusgenic acid (3), triptotriterpenic acid B (4), abruslactone A (5), abrusogenin (6) and abrusoside C (7) were isolated from the leaves and stems of Abrus precatorius. Their structures were elucidated on the basis of physical and NMR analysis, respectively. Compounds 5 and 6 showed moderate cytotoxicity against MCF-7, SW1990, Hela, and Du-145 cell lines. Compounds 1, 2 and 4 were isolated from this plant for the first time.     

A new labdanic norditerpene from Pinus sylvestris

A new labdanic norditerpene and six known labdanic diterpenes were isolated from the petroleum ether extract of the needles of Pinus sylvestris. By spectroscopic methods, the isolated compounds were determined as 15-norpinifolic acid (1), pinifolic acid (2), 4-eplimbricataloic acid (3), monomethyl pinifolate (4), 18α-acetoxylabd-8(17)-en-15-oic acid (5), 2-pentenoic acid (6) and 3β-hydroxy-8(17),E-13-labdadien-15-oic acid (7), respectively. Compound 1 showed significant anti-tumour activity.     

Platycoside O, a new triterpenoid saponin from the roots of Platycodon grandiflorum

A new unusual minor triterpenoid saponin, platycoside O (1), was isolated from the 75% EtOH extract obtained from the roots of Platycodon grandiflorum, together with four known saponins: platycoside M-3 (2), platycoside J (3), platycoside F (4) and platycoside B (5). The structure of 1 was determined as 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-24-methoxyl, 24-oxo-28-oic acid 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside on the basis of spectral analysis and chemical evidence.     

Phenolic compounds from Scorzonera latifolia (Fisch. & Mey.) DC

A new 3-benzylphthalide, scorzoveratrin 4'-O-β-glucoside (1), together with the known 3-benzylphthalides, scorzoveratrin (2) and scorzoveratrozit (3), the caffeoyl derivatives, chlorogenic acid methyl ester (4), 4,5-dicaffeoylquinic acid (5), 4,5-dicaffeoylquinic acid methyl ester (6), 3,5-dicaffeoylquinic acid (7) and caffeic acid (8) were isolated from the subaerial parts of Scorzonera latifolia (Fisch. & Mey.) DC. All secondary metabolites were assigned using physicochemical and spectroscopic data. The known compounds 2-8 were isolated for the first time from this species.     

Platycoside N: a new oleanane-type triterpenoid saponin from the roots of Platycodon grandiflorum

A new oleanane-type triterpenoid saponin, named platycoside N (1), together with six known saponins, was isolated from the roots of Platycodon grandiflorum. On the basis of acid hydrolysis, comprehensive spectroscopic data analyses and comparison with the spectral data of the known compounds, its structure was elucidated as 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-β-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside. The six known compounds were platycodin D (2), deapioplatycodin D (3), platycodin D3 (4), deapioplatycodin D3 (5), platycoside E (6) and deapioplatycoside E (7).     

Terpene glycosides from the roots of Sanguisorba officinalis L. and their hemostatic activities

Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (1), geraniol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (2), geraniol-1-O-α-Larabinopyranosyl-(1→6)-β-D-glucopyranoside (3), 3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (4), 3β-[(α-L-arabinopyranosyl)-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (ziyu-glycoside I, 5), 3β,19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (6) and 3β,19α-dihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (7). Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 1–7 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5) showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside Ι has strong hemostatic activity.     

Phenolic compounds from the aerial parts of Diplomorpha canescens

One new C-methyl flavanone glucoside, farrerol 4'-O-β-D-glucopyranoside (1) was isolated from the aerial parts of Diplomorpha canescens (MEISN.) C. A. MEYER. Fourteen known phenolic compounds such as farrerol (2), luteolin 7-methyl ether 5-O-β-D-glucopyranoside (3), (-)-pinoresinol (4), (-)-lariciresinol (5), (-)-dihydrosesamin (6), (±)-dehydrodiconiferyl alcohol (7), rutarensin (8), umbelliferone (9), coniferyl aldehyde (10), sinapyl aldehyde (11), p-coumaric acid methyl ester (12), p-hydroxybenzaldehyde (13), p-hydroxyacetophenone (14) and syringaldehyde (15) were also isolated for the first time from this plant. Structure of 1 was determined on the basis of spectroscopic data including two dimensional (2D)-NMR, circular dichroism (CD) and by the application of Klyne's rule.     

Steroids and an oxylipin from an algicolous isolate of Aspergillus flavus

A new oxylipin, (8E,12Z)-10,11-dihydroxyoctadeca-8,12-dienoic acid (1), a new steroid, 3β,4α-dihydroxy-26-methoxyergosta-7,24(28)-dien-6-one (2), and four known steroids, episterol (3), (22E,24R)-ergosta-7,22-dien-3β,5α,6α-triol (4), (22E,24R)-ergosta-5,22-dien-3β-ol (5), and (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (6), were isolated from the cultures of Aspergillus flavus, an endophytic fungus isolated from the marine red alga Corallina officinalis. Their structures and relative stereochemistry were elucidated by 1D, 2D NMR and mass spectroscopic techniques. 1 and 2 exhibited low activity to inhibit acetylcholinesterase and no activity against plant pathogenic fungi Colletotrichum lagenarium and Fusarium oxysporum.     

Inhibitory effects of constituents from Euphorbia lunulata on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells

A new flavonol galactopyranoside, myricetin 3-O-(2',3'-digalloyl)-β-D-galactopyranoide (1), and 23 known constituents, including myricetin 3-O-(2'-galloyl)-β-D-galactopyranoide (2), myricitrin (3), myricetin (4), quercetin 3-O-(2', 3'-digalloyl)-β-D-galactopyranoide (5), quercetin 3-O-(2'-galloyl)-β-D-galactopyranoide (6), hyperin (7), isoquercetrin (8), quercetin (9), kaempferol (10), apigenin (11), luteolin (12), 3-O-methylquercetin (13), 5,7,2',5'-tetrahydroxyflavone (14), 1,3,4,6-tetra-O-galloyl-β-D-glucose (15), 1,2,6-tri-O-galloyl-β-D-glucose (16), 1,3,6-tri-O-galloyl-β-D-glucose (17), gallic acid (18), protocatechuic acid (19), 3,4,5-trimethoxybenzoic acid (20), 2,6-dihydroxyacetophenone (21), 3,3'-di-O-methylellagic acid (22), ellagic acid (23) and esculetin (24) were isolated from Euphorbia lunulata Bge. Their structures were determined by spectroscopic analysis. Isolated hydrolysable tannins, flavonoids, and flavonol galactopyranoside gallates showed significant inhibition of the differentiation of 3T3-L1 preadipocytes and triglyceride accumulation in maturing adipocytes, and nitric oxide production in RAW 264.7 cells.     

Isoprenoids and Flavonoids with Antimicrobial Activity from Ficus conraui Warburg (Moraceae)

A new triterpene, conrauidienol ( 1 ), and a new dihydroflavonol, conrauiflavonol ( 2 ), along with β‐amyrin acetate ( 3 ), betulinic acid ( 4 ), ursolic acid ( 5 ), 6β‐hydroxystigmasta‐4,22‐dien‐3‐one ( 6 ), 8‐prenylapigenin ( 7 ), β‐sitosterol glucoside ( 8 ), and 3,4′,5‐trihydroxy‐6″,6″‐dimethylpyrano[2,3‐g]flavone ( 9 ) were isolated from the stem barks of Ficus conraui Warburg (Moraceae). Their structures were elucidated by spectroscopic analysis. The hexane, AcOEt, and MeOH extracts, as well as the new isolated compounds exhibited selective antimicrobial activities varying from weak to moderate.     

日香桂根的化学成分研究（III）

利用柱层析法（硅胶,C18）从日香桂根的乙酸乙酯提取物中分离出8个单体化合物［女贞苷(1),连翘苷（2）,(+)-羟基松脂醇-1-O-β-D-葡萄糖(3),(+) 环橄榄树脂素(4), 2α,3β-二羟基乌苏-12-烯-28酸(5),对羟基苯乙醇(6),(-) 橄榄脂素(7)和橄榄树脂素-4-O-β-D-葡萄糖苷(8)］,其结构经₁H NMR和¹³C NMR确证。5为首次在木犀科植物中发现,4为首次在木犀属植物中发现,2, 3, 7和8为首次在日香桂植物中发现。     

A new polyoxygenated triterpene and two new aeginetic acid quinovosides from the roots of Rehmannia glutinosa

A new minor polyoxygenated triterpene named glutinolic acid (1) and two new aeginetic acid quinovosides (2, 3) were isolated from the roots of Rehmannia glutinosa LIBOSCH. (Scrophulariaceae) cultivated in Gunwi-gun, Korea. The structures of these compounds were established as 3α,19α,20β,24,30-pentahydroxyurs-12-en-28-oic acid (1, glutinolic acid), aeginetic acid 5-O-β-D-quinovoside (2) and aeginetoyl ajugol 5″-O-β-D-quinovoside (3) on the basis of chemical and spectroscopic evidence.     

Antioxidant, anti-glycation and anti-inflammatory activities of phenolic constituents from Cordia sinensis

Nine compounds have been isolated from the ethyl acetate soluble fraction of C. sinensis, namely protocatechuic acid (1), trans-caffeic acid (2), methyl rosmarinate (3), rosmarinic acid (4), kaempferide-3-O-β-D-glucopyranoside (5), kaempferol-3-O-β-D-glucopyranoside (6), quercetin-3-O-β-D-glucopyranoside (7), kaempferide-3-O-α-L-rhamnopyranosyl (1→6)-β-D-glucopyranoside (8) and kaempferol-3-O-α-L-rhamno-pyranosyl (1→6)-β-D-glucopyranoside (9), all reported for the first time from this species. The structures of these compounds were deduced on the basis of spectroscopic studies, including 1D and 2D NMR techniques. Compounds 1-9 were investigated for biological activity and showed significant anti-inflammatory activity in the carrageen induced rat paw edema test. The antioxidant activities of isolated compounds 1-9 were evaluated by the DPPH radical scavenging test, and compounds 1, 2, 4 and 7-9 exhibited marked scavenging activity compared to the standard BHA. These compounds were further studied for their anti-glycation properties and some compounds showed significant anti-glycation inhibitory activity. The purity of compounds 2-5, 8 and 9 was confirmed by HPLC. The implications of these results for the chemotaxonomic studies of the genus Cordia have also been discussed.     

A new butanolide compound from the aerial part of Lindera akoensis with anti-inflammatory activity

A new butanolide, 3β-((E)-dodec-1-enyl)-4β-hydroxy-5β-methyldihydrofuran-2-one (1) and four known butanolides: Akolactone A (2), (3Z,4α,5β)-3-(dodec-11-enylidene)-4-hydroxy-5-methylbutalactone (3), (3E,4α,5β)-3-(dodec-11-enylidene)-4-hydroxy-5-methylbutalactone (4) and dihydroisoobtusilactone (5), were isolated from the aerial parts of Lindera akoensis. These butanolides showed in vitro anti-inflammatory activity decrease the LPS-stimulated production of nitrite in RAW264.7 cell, with IC?? values of 1.4-179.9 μM.     

A new isorhamnetin glycoside and other phenolic compounds from Callianthemum taipaicum

A new flavonol glycoside together with five known phenolic compounds were isolated from the whole herb of Callianthemum taipaicum. The compounds were identified as isorhamnetin-3-O-α-L-arabinoside-7-O-β-D-glucoside (1), isorhamnetin-3-O-β-D-glucoside (2), dibutyl phthalate (3), (+)-1-hydroxylpinoresinol-4'-β-D-glucoside (4), pinoresinol-4'-O-β-D-glucoside (5) and 2-phenylethyl-β-primeveroside (6). Compound 1 was identified as a new flavonol glycoside. The compound 6 was isolated for the first time as natural product. All compounds were isolated for the first time from the Callianthemum genus. Furthermore, the 2D-NMR data of the four known compounds 2-5 are given for the first time in this paper. All the structures were identified on the basis of detailed spectral analysis. The compounds 1 and 4 exhibited certain antifungal activity.     

Oxygenated hexylitaconates from a marine sponge-derived fungus Penicillium sp

In the course of our search for bioactive metabolites from marine organisms, new hexylitaconic acid derivatives (1-4), along with (3S)-hexylitaconic acid (5), were isolated from a sponge-derived fungus Penicillium sp. Based on the NMR and MS data, the structures of compounds 1-4 were defined as α,β-dicarboxylic acid derivatives, such as hexylitaconic acid and tensyuic acids which were previously reported as metabolite of Aspergillus niger, Penicillium striatisporum, or Apiospora montagnei. The isolated compounds were evaluated for cytotoxicity against a panel of five human solid tumor cell lines, and for anti-inflammatory activity gauged by their inhibitory effects on the production of major pro-inflammatory mediators (nitric oxide (NO), interleukin (IL)-6, tumor necrosis factor (TNF)-α, and IL-1β) in murine macrophage cells. Compounds 1 and 4 showed weak inhibition of IL-1β production at the concentration of 200 μM.     

藿香的化学成分分析

从藿香茎叶的乙醇提取物中共分离鉴定出5个化合物:异鼠李素-3-O-β-D-半乳糖苷(1)、金丝桃苷(2)、3,5,8,3,′4′-五羟基-7-甲氧基黄酮-3-O-β-D-吡喃葡萄糖苷(3)、尼泊尔鸢尾异黄酮-7-O-α-L-吡喃鼠李糖苷(4)和正三十烷酸(5).其中化合物3和4为首次从该属植物中分离得到.     

Benzyl 2-β-glucopyranosyloxybenzoate, a new phenolic acid glycoside from Sarcandra glabra

From the whole plant of Sarcandra glabra, a new phenolic acid glycoside, benzyl 2-β-glucopyranosyloxybenzoate (1), together with seven known compounds including eleutheroside B? (2), 5-O-caffeoylshikimic acid (3), (-)-(7S, 8R)-dihydrodehydrodiconiferyl alcohol (4), (-)-(7S, 8R)-dihydrodehydrodiconiferyl alcohol 9-, 9′- and 4-O-α-D-glucopyranoside (5-7), and (-)-(7S, 8R)-5-methoxydihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (8) was isolated. Their structures were elucidated by spectral analysis including 1D-, 2D-NMR and HR-ESI-MS. Compound 2 was found to exhibit potent cytotoxic activity against BGC-823 and A2780 cancer cell lines using MTT method with IC?? value of 2.53 and 1.85 μM, respectively.     

Inhibitory effects of constituents from Morus alba var. multicaulis on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells

A new arylbenzofuran, 3',5'-dihydroxy-6-methoxy-7-prenyl-2-arylbenzofuran (1), and 25 known compounds, including moracin R (2), moracin C (3), moracin O (4), moracin P (5), artoindonesianin O (6), moracin D (7), alabafuran A (8), mulberrofuran L (9), mulberrofuran Y (10), kuwanon A (11), kuwanon C (12), kuwanon T (13), morusin (14), kuwanon E (15), sanggenon F (16), betulinic acid (17), uvaol (18), ursolic acid (19), β-sitosterol (20), oxyresveratrol 2-O-β-D-glucopyranoside (21), mulberroside A (22), mulberroside B (23), 5,7-dihydroxycoumarin 7-O-β-D-glucopyranoside (24), 5,7-dihydroxycoumarin 7-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranoside (25) and adenosine (26), were isolated from Morus alba var. multicaulis Perro. (Moraceae). Their structures were determined by spectroscopic methods. The prenyl-flavonoids 11-14, 16, triterpenoids 17,18 and 20 showed significant inhibitory activity towards the differentiation of 3T3-L1 adipocytes. The arylbenzofurans 1-10 and prenyl-flavonoids 11-16 also showed significant nitric oxide (NO) production inhibitory effects in RAW264.7 cells.