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.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
4.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
5.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
6.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
7.Two new sesquiterpenes in Qi-nan Aquilariae Lignum Resinatum.
De-Li CHEN ; Guo-Xu MA ; Hui-Mei LIU ; Can-Hong WANG ; Yang-Yang LIU ; Yun YANG ; Jian-He WEI
China Journal of Chinese Materia Medica 2023;48(23):6403-6407
This study aimed to investigate the chemical constituents of supercritical extract from Qi-nan Aquilariae Lignum Resinatum by silica gel column chromatography, thin-layer chromatography, and semi-preparative high-performance liquid chromatography. One new elemane-type and one new eudesmane-type sesquiterpene compounds were isolated from the extract, and their structures were identified by MS, UV, IR, NMR, and ECD spectroscopic techniques, and named aquqinanol C(1) and aquqinanol D(2). Both compounds are novel compounds. The neuroprotective effect of the compounds on CORT-induced PC12 cell damage was determined in vitro. The results showed that compounds 1 and 2 exhibited a certain protective effect against CORT-induced damage in PC12 cells.
Rats
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Animals
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Qi
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Sesquiterpenes/pharmacology*
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Molecular Structure
8.Geranylated or prenylated flavonoids from Cajanus volubilis.
Li RAO ; Yu SU ; Qian HE ; Jia YE ; Yu LIU ; Yue FAN ; Feng HU ; Zhen ZHOU ; Lishe GAN ; Yonghui ZHANG ; Chuanrui ZHANG
Chinese Journal of Natural Medicines (English Ed.) 2023;21(4):292-297
Five new flavonoid derivatives, cajavolubones A-E (1-5), along with six known analogues (6-11) were isolated from Cajanus volubilis, and their structures were elucidated by spectroscopic analysis and quantum chemical calculations. Cajavolubones A and B (1 and 2) were identified as two geranylated chalcones. Cajavolubone C (3) was a prenylated flavone, while cajavolubones D and E (4 and 5) were two prenylated isoflavanones. Compounds 3, 8, 9 and 11 displayed cytotoxicity against HCT-116 cancer cell line.
Flavonoids/chemistry*
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Cajanus
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Molecular Structure
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Chalcones/chemistry*
9.Polycyclic polyprenylated acylphloroglucinols from Hypericum species and their biological activities.
Ping SONG ; Ji HAO ; Yan WANG ; Xin-Zhou YANG
China Journal of Chinese Materia Medica 2021;46(19):4881-4890
Hypericum species are distributed widely in China, especially in the southwest. This genus is rich in species types in China, including 55 species and 8 subspecies. The main chemical constituents of Hypericum species are flavonoids, xanthones and polycyclic polyprenylated acylphloroglucinols(PPAPs). PPAPs are characterized by polycyclic and branched-chain substitutions in their structures, which make their structure types diverse. Moreover, they have been found to have antitumor, antiviral, antibacterial, anti-inflammatory and other biological activities. This research classified and summarized 344 polycyclic polyprenylated acylphloroglucinols from Hypericum plants in order to provide a scientific basis for further development and utilization of PPAPs from the genus.
Flavonoids
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Hypericum
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Molecular Structure
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Phloroglucinol/pharmacology*
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Xanthones
10.Three new carabrane sesquiterpenoid derivatives from the whole plant of Carpesium abrotanoides L.
Jie-Wei WU ; Chun-Ping TANG ; Sheng YAO ; Chang-Qiang KE ; Yang YE
Chinese Journal of Natural Medicines (English Ed.) 2021;19(11):868-873
Dicarabrols B and C (1 and 2), two new carabrane sesquiterpenoid dimers, along with one new carabrane sesquiterpenoid (3) were isolated from the whole plant of Carpesium abrotanoides L. Their full structures were established by extensive analysis of HR-ESI-MS and NMR spectroscopic data, and time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. Dicarabrol B possesses a novel C
Asteraceae
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Circular Dichroism
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Humans
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Molecular Structure
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Sesquiterpenes