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1.
Nat Prod Res ; : 1-7, 2024 Jun 04.
Article in English | MEDLINE | ID: mdl-38832674

ABSTRACT

Five new sesquiterpenoids, (4S, 5S, 6S, 7S, 8 R)-5,6-dihydroxy-1-acetoxy-10(14)-en-britannilactone (1), (4S, 5 R, 6S, 7S, 8 R)-5,6-dihydroxy-1-acetoxy-10(14)-en-britannilactone (2), 6-O-propionyl-britannilactone (3), 1ß-hydroxy-3α-acetoxyeudesma-11(13)-en-12,8ß-olide (4) and 1ß,5ß-dihydroxyeudesma-11(13)-en-12,8ß-olide (5), along with twelve known ones were isolated from the flowers of Pentanema britannicum (L.) D.Gut.Larr. Among them, compounds 1 and 2 were stereoisomers which belong to 1,10-seco-eudesmane sesquiterpenoid with rare double bond between C-10 and C-14. The structures of the isolated compounds were elucidated by various spectroscopic methods, including 1D and 2D NMR experiments.

2.
Nat Prod Res ; 36(19): 5001-5008, 2022 Oct.
Article in English | MEDLINE | ID: mdl-33970718

ABSTRACT

Six new compounds, xylomexicanins K-N (1-4), granasteroid (5) and 5-methoxy-2-pentylbenzofuran-7-ol (6), along with nine known compounds were isolated from the leaves and twigs of Xylocarpus granatum. Among them, 1 was a biogenetic precursor of 1,8,9-phragmalin limonoid, and 4 represent the first example of degraded A-ring limonoid. The structures of them were elucidated on the basis of one- and two-dimensional NMR spectroscopic data (including 1H, 13C-NMR, DEPT, 1H-1H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry.[Formula: see text].


Subject(s)
Limonins , Meliaceae , Limonins/chemistry , Magnetic Resonance Spectroscopy , Meliaceae/chemistry , Molecular Structure , Plant Leaves
3.
J Nat Prod ; 80(9): 2547-2550, 2017 09 22.
Article in English | MEDLINE | ID: mdl-28829608

ABSTRACT

Two tetranortriterpenoids with new skeletons, xylomexicanins I and J (1 and 2), were isolated during the investigation of chemical constituents from seeds of the Chinese mangrove, Xylocarpus granatum. Xylomexicanin I (1) is an unprecedented limonoid with bridged B- and C-rings. A biosynthesis pathway for 1 from xylomexicanin F is proposed.


Subject(s)
Limonins/isolation & purification , Meliaceae/chemistry , Seeds/chemistry , Limonins/chemistry , Molecular Structure
4.
International Eye Science ; (12): 2055-2059, 2017.
Article in Chinese | WPRIM (Western Pacific) | ID: wpr-669226

ABSTRACT

Retinalvein occlusion (RVO) is the most common retinal vascular disease.The main causes of visual impairment and blindness are macular edema and retinal neovascularization.Drug therapies are the effective and safe method in the treatment of RVO currently.The main drugs conclude corticosteroid drugs,anti-vascular endothelial growth factor drugs,thrombolytic drugs and traditional drugs.This article reviews the recent progress in RVO in order to provide some valuable references for clinical treatment.

5.
Zhong Yao Cai ; 37(2): 243-51, 2014 Feb.
Article in Chinese | MEDLINE | ID: mdl-25095344

ABSTRACT

OBJECTIVE: To study the chemical constituents in the bark of Taxus chinensis var. mairei collected from southeast of China. METHODS: Chemical constituents were isolated and purified by column chromatography, Prep-TLC, and preparative HPLC. The structures were identified on the basis of 1D-and 2D-NMR spectral analysis. RESULTS: Twelve taxane diterpenoids were isolated from the bark of Taxus chinensis var. mairei grown in southeast of China. They were identified as: taxagifine (1), decinnamoyltaxagifine (2), 19-debenzoyl-19-acetyltaxinine M(3), 9-dihydro-13-acetyl-baccatin III (4), 7, 9-dideacetylbaccatin IV (5), 1,3-dihydro-taxinine (6), taxumairol C (7), taxezopidine J (8), 7-xylosyl-10-deacetyl-taxol A (9),10-deacetyltaxol (10), taxicin II (11), and 2alpha, 7beta, 10beta-triacetoxy-5alpha, 13alpha-dihydroxy-2 (3 --> 20) abeotaxa-4 (20), 11-dien-9-one (12). CONCLUSION: Compounds 1, 2, 4 - 6, 8, 9, 11 and 12 are obtained from this plant for the first time. Compound 7 is obtained from the bark of Taxus chinensis var. mairei for the first time.


Subject(s)
Diterpenes/chemistry , Plant Bark/chemistry , Plants, Medicinal/chemistry , Taxus/chemistry , China , Chromatography, High Pressure Liquid , Diterpenes/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Structure , Taxoids/chemistry , Taxoids/isolation & purification
6.
Nat Prod Commun ; 9(2): 149-50, 2014 Feb.
Article in English | MEDLINE | ID: mdl-24689275

ABSTRACT

A new sesquiterpene, eudesm-11-ene-4alpha,7beta,9beta-triol, was isolated from the EtOH extract of aerial parts of Dichrocephala integrifolia. Its structure was determined on the basis of spectral analysis of 1D and 2D NMR data.


Subject(s)
Asteraceae/chemistry , Sesquiterpenes, Eudesmane/isolation & purification , Magnetic Resonance Spectroscopy , Sesquiterpenes, Eudesmane/chemistry
7.
Biosci Biotechnol Biochem ; 77(4): 736-40, 2013.
Article in English | MEDLINE | ID: mdl-23563540

ABSTRACT

Two new limonoids, named xylomexicanins C and D, were isolated from a dichloromethane extract of the seeds of Xylocarpus granatum cultivated in Hainan, China, and their structures were elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C-NMR, DEPT, 1H-1H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry. Xylomexicanin C exhibited antiproliferative activity against human breast carcinoma cells (KT).


Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Limonins/chemistry , Limonins/pharmacology , Meliaceae/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Humans , Limonins/isolation & purification
8.
Zhong Yao Cai ; 36(8): 1267-70, 2013 Aug.
Article in Chinese | MEDLINE | ID: mdl-24558823

ABSTRACT

OBJECTIVE: To study the chemical constituents in the needles of Taxus cuspidata collected from Japan. METHODS: Chemical constituents were isolated by column chromatography, TLC and preparative HPLC. The structures were identified on the basis of NMR spectral analysis. RESULTS: Six non-taxoids were isolated and identified as: 4-[(1E)-3-hydroxy-1-buten-1-yl]-3,5,5-trimethyl-2-cyclohexen-1-one (1), megastigm-5-ene-3, 9-diol (2), 6alpha-epoxy-7-megastigmen-9-one (3), 4-(4-hydroxyphenyl)-2-butanone (4), 12-hydroxy-alpha-cyperone (5), scutellarein-7-O-alpha-L-rhamnoside (6). CONCLUSION: Compounds 2 - 6 are isolated from Taxus genus for the first time. Compound 1 is obtained from Taxus cuspidata for the first time.


Subject(s)
Taxus/chemistry , Chromatography, High Pressure Liquid , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , Taxoids
10.
Biosci Biotechnol Biochem ; 75(9): 1698-701, 2011.
Article in English | MEDLINE | ID: mdl-21897043

ABSTRACT

A novel 6/8/6-membered taxane with a rare C-12(13)-double bond and rare 2(3→20)abeotaxane were isolated from the needles of Taxus canadensis. Their structures were characterized as 7ß,9α,10ß-triacetoxytaxa-4(20),12-diene-2α,5α,11ß-triol (1) and 2α,7ß,10ß-triacetoxy-5α-hydroxy-2(3→20)abeotaxa-4(20),11-diene-9,13-dione (2) on the basis of 1D and 2D spectroscopic data. 1 is the first example of a natural taxane without substitution at both C-13 and C-14.


Subject(s)
Antineoplastic Agents/analysis , Plant Extracts/analysis , Taxoids/analysis , Taxus/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Breast Neoplasms/drug therapy , Breast Neoplasms/pathology , Cell Line, Tumor , Female , Humans , Magnetic Resonance Spectroscopy , Male , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Leaves/chemistry , Prostatic Neoplasms/drug therapy , Prostatic Neoplasms/pathology , Taxoids/chemistry , Taxoids/isolation & purification , Taxoids/pharmacology , Treatment Failure , Uterine Cervical Neoplasms/drug therapy , Uterine Cervical Neoplasms/pathology
11.
Phytomedicine ; 16(2-3): 156-60, 2009 Mar.
Article in English | MEDLINE | ID: mdl-18926678

ABSTRACT

To determine the chemical constituents responsible for pharmacological effects of Inula britannica-F., three specific sesquiterpene lactones in Inula britannica were isolated from chloroform extract and identified, including britannilactone (BL), 1-O-acetylbritannilactone (ABLO), and 1,6-O,O-diacetylbritannilactone (ABLOO). Electrophoretic mobility shift assay (EMSA) was performed to detect the nuclear translocation of nuclear factor-kappaB (NF-kappaB) p65. The expressions of IkappaBalpha, pIkappaBalpha, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), IkappaB kinase alpha/beta (IKKalpha/beta) and NF-kappaB kinase (NIK) were detected by Western blot and RT-PCR. We found that acetyl side groups enhanced the inhibitory action of the agents on LPS/IFN-gamma-induced iNOS and COX-2 expression. Their inhibiting activity was positive correlation with the acetyl side group number. The effects of LPS/IFN-gamma were reversed by ABLOO, and BL without acetyl side groups showed only a weak inhibitory action. Further study indicated that ABLOO markedly inhibited the phosphorylation of IKKbeta down to based level, but not IKKalpha, corresponding with decreased in IkappaBalpha degradation and phosphorylation induced by LPS/IFN-gamma, resulting in the suppression of NF-kappaB nuclear translocation and activity. These results suggest that the acetyl moieties add to the lipophilicity, and consequently enhance cellular penetration, so that ABLOO possess the most anti-inflammatory effect and may be a potent lead structure for the development of therapeutic and cytokine-suppressing remedies valuable for the treatment of various inflammatory diseases.


Subject(s)
Cyclooxygenase 2/metabolism , I-kappa B Kinase/antagonists & inhibitors , Inula , Lactones/pharmacology , NF-kappa B/antagonists & inhibitors , Nitric Oxide Synthase Type II/antagonists & inhibitors , Sesquiterpenes/pharmacology , Acetylation , Animals , Anti-Inflammatory Agents/pharmacology , Cell Line , Gene Expression Regulation , I-kappa B Kinase/genetics , Interferon-gamma/metabolism , Lipopolysaccharides/metabolism , Macrophages/metabolism , Mice , Phosphorylation/drug effects , Plant Extracts/pharmacology , RNA, Messenger/metabolism
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