1.Bioactive sesquineolignans from the twigs of Litsea cubeba.
Huan XIA ; Gui-Yang XIA ; Ling-Yan WANG ; Min WANG ; Ya-Nan WANG ; Peng-Cheng LIN ; Sheng LIN
Chinese Journal of Natural Medicines (English Ed.) 2021;19(10):796-800
In a continuing search for biological natural products with structure diversity from traditional Chinese herbs, five new sesquineolignans (1-5) were isolated from an ethyl acetate extract of the twigs of Litsea cubeba. Their structures were elucidated based on MS, 1D and 2D NMR spectroscopic data, as well as experimental electronic circular dichroism (ECD) spectra. Compounds 1-5 showed moderate inhibitory effects against LPS-induced NO production in RAW264.7 macrophages, with IC
Litsea
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Macrophages
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Molecular Structure
3.New homoisoflavanones from Polygonatum odoratum (Mill.) Druce.
Li-Hong LI ; Feng-Zhi REN ; Shu-Hong CHEN ; Yue-Qi GAO
Acta Pharmaceutica Sinica 2009;44(7):764-767
To study chemical constituents of Polygonatum odoratum (Mill.) Druce, the compounds were separated with column chromatography and HPLC. On the basis of physicochemical properties and spectral data, their structures were confirmed. Nine compounds were isolated and identified as 5,7-dihydroxy-6-methoxyl-8-methyl-3-(2',4'-dihydroxybenzyl)chroman-4-one (1), 5,7-dihydroxy-6-methyl-3-(2',4'-dihydroxybenzyl)chroman-4-one (2), 5,7-dihydroxy-6-methoxyl-8-methyl-3-(4'-methoxybenzyl)chroman-4-one (3), disporopsin (4), chrysoeriol (5), 5,4'-dihydroxy-7-methoxy-6-methylflavone (6), N-trans-feruloyltyramine (7), N-trans-feruloyloctopamine (8), and (+)-syringaresinol (9). Compounds 1-3 are new homoisoflavanones. Compounds 4-9 are isolated from this plant for the first time.
Isoflavones
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isolation & purification
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Molecular Structure
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Polygonatum
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chemistry
4.Chemistry research on natural product derivatives of dihydro-β-agarofuran sesquiterpenoids.
Ruo-Nan NING ; Jia-Qi XU ; Yi-Xin XU
China Journal of Chinese Materia Medica 2020;45(23):5712-5721
Dihydro-β-agarofuran sesquiterpenoids possess chemical diversity and biodiversity. A dihydro-β-agarofuran sesquiterpenoid with only hydroxyl groups has been prepared by basic hydrolysis of crude extract of Euonymus bungeanus with 0.4% yield. Twelve derivatives were available in esterification, oxidation, decarboxylation, etc. Extensive ~1H-NMR,~(13)C-NMR, MS spectroscopic analyses and single-crystal X-ray diffraction analysis with Cu Kα radiation indicated that eleven derivatives were new compounds. The results will provide reference for chemistry study on natural product derivatives of dihydro-β-agarofuran sesquiterpenoids.
Biological Products
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Euonymus
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Molecular Structure
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Sesquiterpenes
5.Study on chemical constituents of Wedelia trilobata.
Quan-Yu LIU ; Hong-Fang YANG ; Shan FENG ; Yan HU
China Journal of Chinese Materia Medica 2021;46(3):630-634
A new taraxer-based triterpenoid ester, taraxer-14-en-30-al-3β-O-palmitate(1), was isolated from the whole plant of Wedelia trilobata, along with six known compounds, ent-kaur-16-en-19-oic acid(2), 16α-hydroxy-ent-kauran-19-oic acid(3), tara-xerol(4), β-amyrin(5), 1β-acetoxy-4α, 9α-dihydroxy-6β-isobutyroxyprostatolide(6), and stigmasterol(7). Their structures were elucidated with use of a combination of spectroscopic techniques(IR, HR-ESI-MS, 1 D, 2 D NMR data) and chemical methods.
Magnetic Resonance Spectroscopy
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Molecular Structure
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Triterpenes
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Wedelia
6.Two new sucrose cinnamates from Polygonum lapathifolium var. salicifolium.
Zhi-Hua CHEN ; Guo-En WANG ; Ren-Wang JIANG
China Journal of Chinese Materia Medica 2021;46(4):944-950
Two new sucrose cinnamates(1 and 2) along with nine known compounds(3-11) were isolated from ethanol extract of Polygonum lapathifolium var. salicifolium by silica gel column chromatography, ODS column chromatography and semi-preparative HPLC. Their structures were elucidated by extensive spectroscopic methods including 1 D-and 2 D-NMR experiments, as well as HR-ESI-MS analysis. Eleven compounds(7 sucrose cinnamates, 3 phenylpropanoids and 1 lactone) were obtained and their structures were identified as(1,3-O-di-p-coumaroyl)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside(1),(1,3-O-di-p-coumaroyl)-β-D-fructofuranosyl-(2→1)-(6-O-acetyl)-α-D-glucopyranoside(2),(3-O-feruloyl)-β-D-fructofuranosyl-(2→1)-(6-O-p-coumaroyl)-α-D-glucopyranoside(3), hydropiperoside(4), vanicoside C(5),(1,3-O-di-p-coumaroyl)-β-D-fructofuranosyl-(2→1)-(6-O-feruloyl)-α-D-glucopyranoside(6), vanicoside B(7),trans-p-hydroxycinnamic acid methyl ester(8), trans-p-hydroxycinnamic acid ethyl ester(9), methyl ferulate(10) and dimethoxydimethylphthalide(11), respectively. Compounds 1 and 2 were two new sucrose cinnamates, and compounds 1-11 were isolated from this plant for the first time. The antioxidant activities of the isolated compounds 1-9 were investigated by an oxygen radical absorbance capacity(ORAC) assay, and all nine compounds were found to show strong antioxidant activities. Among them, compound 6(10 μmol·L~(-1)) was the supreme one in antioxidant activities, with its ORAC value equivalent to(1.60±0.05) times of 50 μmol·L~(-1) Trolox.
Antioxidants
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Cinnamates
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Esters
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Molecular Structure
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Polygonum
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Sucrose
7.A new sesquiterpene from Chloranthus henryi.
Yu-Ting BIAN ; Fang-You CHEN ; Wei-Ming HUANG ; Zhi-Chao CHEN ; Peng-Cheng SHUANG ; Yong-Ming LUO
China Journal of Chinese Materia Medica 2021;46(8):2067-2071
Eight sesquiterpenes were isolated and purified from the ethanol extract of Chloranthus henryi by column chromatographies over silica gel, ODS and Sephadex LH-20,and preparative HPLC. Their chemical structures were established by spectral data and physiochemical properties as(1S,6S,8S,10R)-8-ethoxy-10-methoxychlomultin C(1),tianmushanol(2),multistalide A(3),myrrhterpenoid N(4),1α,9α-dihydroxy-8,12-expoxy-eudesma-4,7,11-trien-6-one(5),4β,10α-aromadendranediol(6),oplopanone(7),10α-hydroxycadinan-4-en-3-one(8). Among them, compound(1) was a new compound, and compounds 2-8 were isolated from Chloranthus henryi for the first time.
Chromatography, High Pressure Liquid
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Molecular Structure
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Sesquiterpenes
8.Chemical constituents of Allophylus longipes.
Xiang-Yun ZHANG ; Xiang-Hai CAI ; Xiao-Dong LUO
Chinese Journal of Natural Medicines (English Ed.) 2012;10(1):36-39
AIM:
To investigate the chemical constituents of Allophylus longipes.
METHODS:
Compounds were isolated and purified by various chromatographic techniques and their structures were elucidated by physicochemical characteristics and spectral data.
RESULTS:
Twenty-five compounds were isolated and identified as cycloart-24-en-3β, 26-diol (1), 3-oxotrirucalla-7, 24-dien-21-oic acid (2), zizyberenalic acid (3), colubrinic acid (4), ent-4(15)-eudesmene-1β, 6α-diol (5), 4(15)-eudesmene-1β, 8α-diol (6), 4(15)-eudesmene-1β, 5α-diol (7), methyl asterrate (8), betulin (9), betulinic aldehyde (10), betulinic acid (11), 3β-hydroxy-5α, 8α-epidioxyergosta-6, 22-dien (12), 3-oxo-19α-hydroxyurs-12-en-28-oic acid (13), ursolic acid (14), scopoletin (15), fraxidin (16), cleomiscosin A (17), 4-hydroxy-3-methoxybenzaldehyde (18), 4-hydroxy-3-methoxycinnamaldehyde (19), 2',6'-dihydroxy-4'-methoxyacetophenone (20), p-(aminoalkyl)-benzoic acid (21), 4-hydroxy-3-methoxybenzoic acid (22), 1-O-p-coumaroylglucose (23), β-sitosterol (24), and poriferast-5-ene-3β, 4β-diol (25).
CONCLUSION
All the compounds were isolated from Allophylus longipes for the first time.
Molecular Structure
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Plant Extracts
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chemistry
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Sapindaceae
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chemistry
9.C_(19)-diterpenoid alkaloids from Aconitum austroyunnanense.
Jiang HU ; Tao LYU ; Jian CAI ; Xiu GAO ; Li-Fang ZHANG ; Nian-Hua JING ; Tian-Feng PENG ; Jun-You SHI ; Shan-Hu HAO
China Journal of Chinese Materia Medica 2019;44(4):717-722
Eight C_(19)-diterpenoid alkaloids( 1-8) were isolated from the ethyl acetate soluble fraction of 95% ethanol extract of the ground roots of Aconitum austroyunnanense through various column chromatographies on silica gel,ODS,Sephadex LH-20 and MCI gel.Their structures were elucidated as 14α-benzoyloxy-13β,15α-dihydroxy-1α,6α,8β,16β,18-pentamethoxy-19-oxoaconitan( 1),N-deethylaconitine( 2),spicatine B( 3),leucanthumsine A( 4),acofamine B( 5),macrorhynine B( 6),aconitilearine( 7),and ambiguine( 8) based on their chemical and physicochemical properties and spectroscopic data. Compound 1 was a new compound and alkaloids 2-8 were isolated from this plant for the first time. Some isolated alkaloids were tested in vitro for cytotoxic potential by employing the MTT method. As a result,alkaloid 1 exhibited weak cytotoxic activity against three tested tumor cell lines( A-549,He La,and Hep G2) with IC_(50) values less than 20 μmol·L~(-1).
Aconitum
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Alkaloids
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Diterpenes
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Molecular Structure
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Plant Roots
10.Advances in studies on structure and pharmacological activities of natural tirucallane-type triterpenoids.
Jun XIE ; Chang-Kang LI ; Jia FU ; Hong-Qing WANG ; Bao-Ming LI ; Ruo-Yun CHEN ; Jie KANG
China Journal of Chinese Materia Medica 2020;45(15):3617-3630
The tirucallane-type triterpenoids, composed of six isoprene units, belong to a group of tetracyclic triterpenoids. Although the naturally-derived tirucallane-type triterpenoids were found in a small amount, the kind of compounds showed various structures, which consist of apo-type, linear said-chain-type and cyclolike said-chain-type and broad bioactivities, such as cytotoxicity, anti-inflammation, antioxidation and anti-plasmin, etc. This paper summarized origins, structures and bioactivities of tirucallane-type triterpenoids in recent ten years. The future research and exploration of tirucallane-type triterpenoids were discussed and prospected.
Antineoplastic Agents, Phytogenic
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Molecular Structure
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Triterpenes