Complete assignments of 1H and 13C NMR spectral data for three sesquiterpenoids from Inula helenium

The complete assignments of all the (1)H and (13)C NMR signals of three sesquiterpene lactones, 4-oxo-5(6),11-eudesmadiene-8,12-olide (1), 4-oxo-11-eudesmaene-8,12-olide (2) and (1(10)E)-5beta-Hydroxygermacra-1(10),4(15),11-trien-8, 12-olide (3), were carried out by various 2D NMR experiments. Compounds 1-3 were isolated from the roots of Inula helenium for the first time. Among them, 1 was identified as a new nor-sesquiterpene lactone, and 2 was isolated from a natural source for the first time. The (13)C-NMR data of compound 3 was also reported for the first time.     

Three new phenolic glycosides from the caulis of Millettia speciosa

Three new phenolic glycosides, millettiaspecosides A--C (1-3), were isolated from the caulis of Millettia speciosa along with three known phenolic glycosides, khaephuoside B (4), seguinoside K (5), albibrissinoside B (6). Their structures were established by spectroscopic methods. The spectral analysis permitted correct assignments for (1)H and (13)C NMR data of compounds 4 and 5.     

兴安柴胡化学成分研究（Ⅱ）

从兴安柴胡根部乙醚提取部分通过层析方法分得5种化合物,经光谱方法鉴定为6,7,3′,8′-双藁本内酯(B_1),6,7,3a′,6′-双藁本内酯(B_2),顺-6,7-二羟基藁本内酯(B_3),孕甾烯醇酮(B_4),香草醛(B_5),其中B_1为新化合物。     

Chemical constituents from the roots of Xanthium sibiricum

Xanthium sibiricum patrin ex Widder (Compositae) is an annual herb which grows all around China. Chemical investigations of its roots resulted in the identification of 15 compounds: stigmast-4-en-6β-ol-3-one (1), β-sitostenone (2), β-sitosterol (3), nonadecanoic acid (4), 5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol (5), scopoletin (6), Jatrocin B (7), (±)syringaresinol (8), 9,9'-O-di-(E)-feruloyl-(-)-secoisolariciresinol (9), cleomiscosin A (10), cleomiscosin C (11), N-trans-feruloyl tyramine (12), daucosterol (13), 5-methyluracil (14) and uracil (15). Structures were elucidated by spectroscopic (NMR and MS) methods and confirmed by comparing with reference samples and literature data. Compounds 1-2, 4-12, 14, and 15 were isolated from this genus for the first time, while this is the first report of coumarinolignoids in the Compositae family, and coumarinoligoids could be considered as valuable chemotaxonomic markers for the plant.     

Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa

Thirteen curcuminoids (1–13) were isolated from the rhizomes of Curcuma longa. Among them, 1,5‐dihydroxy‐1,7‐bis(4‐hydroxyphenyl)‐4,6‐heptadiene‐3‐one (1), 1,5‐dihydroxy‐1‐(4‐hydroxy‐3‐methoxyphenyl)‐7‐(4‐hydroxyphenyl)‐4,6‐heptadiene‐3‐one (2), 1,5‐dihydroxy‐1‐(4‐hydroxyphenyl)‐7‐(4‐hydroxy‐3‐methoxyphenyl)‐4,6‐heptadiene‐3‐one (3), and 3‐hydroxy‐1,7‐bis‐(4‐hydroxyphenyl)‐6‐heptene‐1,5‐dione (4) are new compounds, and 1‐(4‐hydroxyphenyl)‐7‐(3, 4‐dihydroxyphenyl)‐1, 6‐heptadiene‐3, 5‐dione (5) is isolated from natural sources for the first time. The structures of these compounds were elucidated by extensive spectroscopic analyses, especially 1D and 2D NMR spectroscopy. The ¹³C NMR data and complete ¹H and ¹³C NMR assignments of some known compounds are reported for the first time. In addition, the errors of ¹H and ¹³C assignments reported in the literature were corrected. Copyright © 2009 John Wiley & Sons, Ltd.     

Three new and antitumor anthraquinone glycosides from Lasianthus acuminatissimus MERR

Three new anthraquinone glycosides, lasianthuoside A (1), B (2), and C (3), were isolated from the root of Lasianthus acuminatissimus MERR., The structural elucidation of these anthraquinones was mainly established on the basis of 1D and 2D NMR and HR-MS spectroscopic analysis. Ten known compounds, damnacanthol (4), damnacanthol 11-methyl ether (5), damnacanthol-3-O-beta-D-primeveroside (6), asperuloside (7), asperulosidic acid (8), deacetyl asperulosidic acid (9), a nonglycosidic iridoid (10), 2,6-dimethoxy-4-hydroxyphenol-1-O-beta-D-glucopyranoside (11), tachioside (methoxyhydroquinone-4-O-beta-D-glucopyranoside) (12), and isotachioside (methoxyhydroquinone-1-O-beta-D-glucopyranoside) (13) were also identified for the first time from this plant in the course of the phytochemical and spectroscopic investigation. In addition to this report, a preliminary evaluation of 13 compounds in treating rheumatoid arthritis and antitumor effects of six anthraquinones are presented.     

南海软珊瑚Sarcophyton molle化学成分的研究

从中国南海软肉芝软珊瑚(Sarcophyton molle)中分离到七个化合物, 经紫外光谱(UV), 红外光谱(IR), 质谱(MS)和核磁共振光谱(1H NMR, 13C NMR)分析, 确定了其化学结构。它们是: 异新西松烯(1), (E, E, E)-7, 8-环氧-1-异丙基-4, 8, 12-三甲基-十四环-1,3, 11-三烯(2), 正十八烷酸(3), 鲨肝醇(4), 神经酰胺(5), 胸腺嘧啶(6), 胸腺嘧啶脱氧核苷(7)。其中化合物(2)为新化合物。本文是第一次报道软珊瑚Sarcophyton molle的化学成分。     

Complete assignments of 1H and 13C NMR data for three new arylnaphthalene lignan from Justicia procumbens

Three new arylnaphthalene lignans, named neojusticin C (1), procumbenoside C (2) and procumbenoside D (3), have been isolated from the whole plant of Justicia procumbens, together with three known ones, justicidinoside B (4), justicidinoside C (5), and diphyllin-1-O-beta-D-apiofuranoside (6). The complete assignments of 1H and 13C NMR data for three new lignans were first obtained by means of 2D NMR techniques, including HSQC and HMBC.     

Aurasperone F--a new member of the naphtho-gamma-pyrone class isolated from a cultured microfungus, Aspergillus niger C-433

A novel dimeric naphtho-gamma-pyrone, named aurasperone F (1), was isolated from the fermentation broth of the culture extracts of Aspergillus niger C-433, isolated from grapes, along with the known compounds fonsecin (2), aurasperone B (3), aurasperone C (4), aurasperone D (5) and aurasperone E (6). The chemical structure of the new natural product was established by extensive one- and two-dimensional NMR spectroscopic studies (1H, 13C, COSY, HMQC, 1D NOE spectra), as well as on the UV, MS and IR spectral analysis.     

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。     

New flavonoids from Oxytropis myriophylla

Eight compounds were isolated from Oxytropis myriophylla. On the basis of spectral analyses, their structures were elucidated to be (6R,9R)-roseoside (1), (6R,9S)-roseoside (2), adenosine (3), myriophylloside B (4), myriophylloside C (5), myriophylloside D (6), myriophylloside E (7), and myriophylloside F (8). Five flavonoids (4-8) were new compounds, and the three known compounds were isolated from this plant for the first time.     

A New p‐Terphenyl Derivative from the Mushroom Thelephora vialis

One novel p‐terphenyl compound, named vialisyl A ( 1 ), was isolated from the fruiting bodies of Thelephora vialis, together with six known compounds, ganbajunin B ( 2 ), phenylacetic acid ( 3 ), a mixture of ganbajunins D ( 4 ) and E ( 5 ), and vialinins A ( 6 ) and B ( 7 ). Their structures were established by extensive analysis of spectroscopic data (including ¹H‐ and ¹³C‐NMR, HSQC, HMBC, 2D‐INADEQUATE) as well as by comparison with literature reports.     

南海中华小尖柳珊瑚Muricella sinensis化学成分的研究

从采自中国南海的中华小尖柳珊瑚(Muricella sinensis)中分离得到了1个新的Eunicellane型二萜, 命名为sinensin (1), 和6个已知化合物: 13-去乙酰氧基calicophirin B (2), calicophirin B (3), calicophirin C (4), astrogorgin (5), calicoferol E (6)和calicoferol B (7), 这些化合物的结构是经波谱学实验(1H NMR, 13C NMR, HMQC, HMBC, COSY和NOESY)并与文献报道的数据对照而确定的.     

Complete assignments of 1H and 13C NMR data for seven arylnaphthalide lignans from Justicia procumbens

Three new arylnaphthalide lignans named 6'-hydroxy justicidin A (1), 6'-hydroxy justicidin B (2) and 6'-hydroxy justicidin C (3) have been isolated from the whole plant of Justicia procumbens, together with four known ones, neojusticin A (4), chinensinaphthol methyl ester (5), isodiphyllin (6) and taiwanin C (7). The complete assignments of 1H and 13C NMR chemical shifts for the new lignans and the 13C NMR chemical shifts for the known lignans were obtained for the first time by means of 2D NMR techniques, including HSQC and HMBC.     

Sesquiterpenoids from Curcuma wenyujin dreg and their biological activities

Four new sesquiterpenoids,4,8-dioxo-6β-hydroxyl-7β,1 1-epoxycarabrane(1),4,8-dioxo-6β-hydroxyl-7,1 1-epoxycarabrane(2),wenyujinins Q and R(3-4),and nine known sesquiterpenoids(5-13) were isolated from the Curcuma wenyujin(C wenyujin) dreg.Their structures and relative configurations were elucidated using 1D,2D NMR,and HR-ESI-MS data.All the compounds were isolated for the first time from the C.wenyujin dreg and evaluated for their antibacterial and antifungal activities.Compounds 3,5-8 exhibited strong broad-spectrum antifungal activities against tested nine pathogenic fungi.     

Terpenoid-related metabolites from a formosan soft coral Nephthea chabrolii

Two new sesquiterpenoidal natural products chabrolidiones A and B (1 and 2), two C(18) terpenoid-related carboxylic acids, ketochabrolic acid (3) and isoketochabrolic acid (4), and one naphthoquinone derivative chabrolonaphthoquinone C (5), along with two known compounds (+)-aristolone (6) and teuhetenone A (7) were isolated from a Formosan soft coral Nephthea chabrolii. The structures of the new metabolites were determined on the basis of extensive spectroscopic analysis and by comparison of NMR data with those of related metabolites. Metabolite 1 has been synthesized previously, but was isolated for the first time from natural sources. Cytotoxic activity of metabolites 1-3 and 5-7 against a limited panel of cancer cell lines is also described.     

Novel,Complex Flavonoids from Mallotus philippensis (Kamala Tree)

One new flavanone, 4′‐hydroxyisorottlerin ( 2 ), and two new chalcone derivatives, kamalachalcones C ( 3 ) and D ( 4 ), were isolated from Mallotus philippensis (kamala tree). The largest compound ( 4 ; M_r 1098 g/mol) was shown to possess a unique, fused‐ring system made of two hydroxy‐chalcone units, giving rise to eight fused benzene/pyran units. From the same plant, the following six known compounds were also isolated: kamalachalcone A ( 5 ) and B ( 6 ), isoallorottlerin ( 7 ), isorottlerin ( 8 ), 5,7‐dihydroxy‐8‐methyl‐6‐prenylflavanone ( 9 ); 6,6‐dimethylpyrano(2″,3″: 7,6)‐5‐hydroxy‐8‐methylflavanone ( 10 ), and rottlerin ( 1 ). The structures of the new compounds were confirmed by in‐depth spectral analyses, including 2D‐NMR techniques, and the full ¹³C‐NMR assignments of the known flavanones 1 and 7 – 10 are published for the first time.     

The anti-HBsAg (human type B hepatitis, surface antigen) and anti-HBeAg (human type B hepatitis, e antigen) C18 dibenzocyclooctadiene lignans from Kadsura matsudai and Schizandra arisanensis

The C(18) dibenzocyclooctadiene lignans including three novel schizanrin F (1), G (2), H (3), along with the known kadsurarin (4), were isolated from Kadsura matsudai. A new C(19) homolignan named schiarisanrin E (5), together with the known C(18) lignans, gomisin B (6), G (7) and (+)-gomisin K(3) (8) were obtained from Schizandra arisanensis. Gomisin B, G and (+)-gomisin K(3) showed moderate to strong activity for antihepatitis in anti-HBsAg (human type B hepatitis, surface antigen) and/or anti-HBeAg (human type B hepatitis, e antigen) tests. The structural elucidations of new compounds 1-3 and 5 were based on two-dimensional (2D) NMR techniques including COSY, HMQC, HMBC, NOESY and CD spectra. Preliminary structure-activity relationship studies for these isolated lignans are also discussed.     

Fusaroside, a unique glycolipid from Fusarium sp., an endophytic fungus isolated from Melia azedarach

Fusaroside (1), a unique trehalose-containing glycolipid composed of the 4-hydroxyl group of a trehalose unit attached to the carboxylic carbon of a long-chain fatty acid, was isolated from the organic extract of fermentation broths of an endophytic fungus, Fusarium sp. LN-11 isolated from the leaves of Melia azedarach. Six known compounds, phalluside (2), (9R*,10R*,7E)-6, 9,10-trihydroxyoctadec-7-enoic acid (3), porrigenic acid (4), (9Z)-2,3-dihydroxypropyl octadeca-9-enoate (5), cerevisterol (6) and ergokonin B (7), were also isolated from this fungus. The glycolipid contains a rare branched long-chain fatty acid (C(20:4)) with a conjugated diene moiety and a conjugated ketone moiety. The structure of the new compound 1 was elucidated by spectroscopic methods (1D and 2D NMR experiments, MS) and chemical degradations. The metabolites 1-5 were shown to have moderate to weak active against the brine shrimp larvae. To our knowledge, this is the first report of isolation of the first representative of a new family of glycolipids from natural sources.     

Resveratrol derivatives from Upuna borneensis

Four new resveratrol derivatives, upunaphenols B (1), C (4), D (5) (resveratrol tetramer) and E (6, resveratrol dimer with a C6-C1 unit), together with nine known resveratrol oligomers and resveratrol were isolated from an acetone soluble part of stem of Upuna borneensis (Dipterocarpaceae). The structures of new compounds were determined by spectral analysis including 1D and 2D NMR experiments.