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Triterpenoids

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https://www.readbyqxmd.com/read/29457748/structural-determination-of-two-new-acacic-acid-type-saponins-from-the-stem-barks-of-albizia-zygia-dc-j-f-macbr
#1
Olivier Placide Noté, Line Made Simo, Joséphine Ngo Mbing, Dominique Guillaume, Christian Dominique Muller, Dieudonné Emmanuel Pegnyemb, Annelise Lobstein
As a continuation of our interest in the study of triterpenoid saponins from Albizia zygia, phytochemical investigation of its stem barks led to the isolation of two new oleanane-type saponins, named zygiaosides C-D (1-2). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as, 3-O-[ β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→6)]-β-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester (1) and 3- O-[β-d-glucopyranosyl-(1→2) -[ β-d-fucopyranosyl-(1→6)]-β-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester (2)...
February 19, 2018: Natural Product Research
https://www.readbyqxmd.com/read/29457747/lebbeckoside-c-a-new-triterpenoid-saponin-from-the-stem-barks-of-albizia-lebbeck-inhibits-the-growth-of-human-glioblastoma-cells
#2
Olivier Placide Noté, Joséphine Ngo Mbing, Marie-Claude Kilhoffer, Dieudonné Emmanuel Pegnyemb, Annelise Lobstein
One new acacic acid-type saponin, named lebbeckoside C (1), was isolated from the stem barks of Albizia lebbeck. Its structure was established on the basis of extensive analysis of 1D and 2D NMR (1 H,13 C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as 3-O-[β-d-xylopyranosyl-(l→2)-β-d-fucopyranosyl-(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl]-21-O-{(2E,6S)-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-β-d-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28 O-[β-d-quinovopyranosyl-(l→3)-[α-l-arabinofuranosyl-(l→4)]-α-l-rhamnopyranosyl-(l→2)-β-d-glucopyranosyl] ester...
February 19, 2018: Natural Product Research
https://www.readbyqxmd.com/read/29457741/lucidumol-d-a-new-lanostane-type-triterpene-from-fruiting-bodies-of-reishi-ganoderma-lingzhi
#3
Dedi Satria, Yhiya Amen, Yasuharu Niwa, Ahmed Ashour, Ahmed E Allam, Kuniyoshi Shimizu
A new lanostane-type triterpenoid, lucidumol D (1) was isolated from the fruiting bodies of Ganoderma lingzhi. Its structure was elucidated on the basis of extensive 1D- and 2D-NMR studies as well as mass spectrometry. The cytotoxicity of lucidumol D against proliferation of several cancer cells were assayed by using MTT method and the obtained result suggested selective anti-proliferative and cytotoxic effects against MCF-7, HepG2, HeLa, Caco-2, and HCT-116. In comparison to lucidumol C (2) isolated previously by our group, the structure-activity relationship indicated that carbonyl function at C-11 is necessary to enhance the cytotoxicity...
February 19, 2018: Natural Product Research
https://www.readbyqxmd.com/read/29456668/fpoa-induces-the-apoptosis-of-hepg2-cells
#4
Mingjie Song, Haiying Bao, Tolgor Bau
The triterpenoid 3-acetoxylanosta-8,24-dien-21-oic acid (FPOA) is isolated from the fruiting body of Fomitopsis pinicola . The present study reports that FPOA exerts cytotoxic activity and describes the molecular mechanism of FPOA-induced apoptosis on human HepG2 hepatoma cells. FPOA exhibited significant cytotoxic effects against HepG2, MCF-7 and HeLa cells. However, FPOA was particularly cytotoxic towards HepG2 cells, with a half maximal inhibitory concentration value of 42.10 µM, thus these cells were taken forward for further analysis...
March 2018: Experimental and Therapeutic Medicine
https://www.readbyqxmd.com/read/29454829/bioactive-triterpenoids-from-twigs-of-betula-schmidtii
#5
Kyoung Jin Park, Lalita Subedi, Sun Yeou Kim, Sang Un Choi, Kang Ro Lee
Investigation of the MeOH extract of Betula schmidtii twigs resulted in the isolation and identification of three new triterpenoids (1-3), along with ten known ones (4-13). The structures of new compounds (1-3) were elucidated by spectroscopic methods, including 1D, 2D NMR (1 H and13 C NMR, COSY, HSQC, HMBC, and NOESY), HR-MS, and chemical methods. All the isolated compounds were evaluated for their cytotoxicity against A549, SK-OV-3, SK-MEL-2, and HCT-15 cell lines. Compound 11 exhibited potent cytotoxic activities against four cell lines, and compounds 5 and 13 significantly induced nerve growth factor secretion in a C6 rat glioma cell line...
February 10, 2018: Bioorganic Chemistry
https://www.readbyqxmd.com/read/29453649/reinereins-a-and-b-new-onocerane-triterpenoids-from-reinwardtiodendron-cinereum
#6
Alfarius Eko Nugroho, Daisuke Inoue, Chin Piow Wong, Yusuke Hirasawa, Toshio Kaneda, Osamu Shirota, A Hamid A Hadi, Hiroshi Morita
Bioactivity guided separation of Reinwardtiodendron cinereum barks methanol extract led to the isolation of two new onocerane triterpenoids, reinereins A and B (1 and 2), together with three known onocerane triterpenoids. Their structures were elucidated on the basis of NMR spectroscopic data. In vitro cytotoxic activities of the isolated compounds against several type of cancer cells were evaluated.
February 16, 2018: Journal of Natural Medicines
https://www.readbyqxmd.com/read/29453016/metabolic-profiling-of-gegenqinlian-decoction-in-rat-plasma-urine-bile-and-feces-after-oral-administration-by-ultra-high-performance-liquid-chromatography-coupled-with-fourier-transform-ion-cyclotron-resonance-mass-spectrometry
#7
Ting Liu, Xiumin Tian, Zhaoqin Li, Fei Han, Bin Ji, Yunli Zhao, Zhiguo Yu
Gegenqinlian decoction (GQLD) as a traditional Chinese medical (TCM) prescription is made from four Chinese herbs and has been used for centuries to treat pyrexia and diarrhea. In this work, an ultra-high performance liquid chromatography coupled with Fourier transform ion cyclotron resonance mass spectrometry (UHPLC-FT-ICR-MS) method was established to profile the metabolic fate of GQLD in rat plasma, urine, bile and feces. The analysis was performed on a Waters Acquity UPLC HSS T3 column (2.1 mm × 100 mm, 1...
February 6, 2018: Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences
https://www.readbyqxmd.com/read/29451710/salvisertin-a-a-new-hexacyclic-triterpenoid-and-other-bioactive-terpenes-from-salvia-deserta-root
#8
Yin-Ru Wang, Yun Yu, Shu-Ming Li, Wei Liu, Wei Li, Susan L Morris-Natschke, Masuo Goto, Kuo-Hsiung Lee, Xue-Feng Huang
Using various chromatographic methods, a new hexacyclic triterpenoid, 2β, 3β, 24β-trihydroxy-12, 13-cyclo-taraxer-l4-en-28oic acid (1), together with ten known compounds, 2α, 3α, 23- trihydroxyurs-12, 20(30)-dien-28oic acid (2), 6, 7-dehydroroyleanone (3), horminone (4), 7-O-methylhorminone (5), sugiol (6), demethylcryptojaponol (7), 14-deoxycoleon U (8), 5, 6-didehydro-7-hydroxy-taxodone (9), ferruginol (10) and dichroanone (11), were isolated from the roots of Salvia deserta. Their structures were identified on the basis of spectroscopic analysis and comparison with the reported data...
February 16, 2018: Chemistry & Biodiversity
https://www.readbyqxmd.com/read/29448823/chemical-constituents-of-genista-numidica-spach-aerial-parts-and-their-antimicrobial-antioxidant-and-antityrosinase-activities
#9
Naima Boutaghane, Abdulmagid Alabdul Magid, Amin Abedini, Anaïs Cafolla, Hanène Djeghim, Sophie C Gangloff, Laurence Voutquenne-Nazabadioko, Zahia Kabouche
A previously undescribed triterpenoid saponin, 3-O-[α-l-rhamnopyranosyl-(1→2)-{β-d-glucopyranosyl-(1→6)-}β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl]-sophoradiol (1), in addition to twenty-nine known constituents (2-30) were isolated from the aerial parts of Genista numidica Spach. Structures elucidation was performed by comprehensive 1D- and 2D-NMR analyses and HRESIMS. The extracts, fractions and isolated compounds were evaluated for their antibacterial, antioxidant and tyrosinase inhibitory activities...
February 15, 2018: Natural Product Research
https://www.readbyqxmd.com/read/29447977/serratene-type-triterpenoids-from-palhinhaea-cernua
#10
Jiao-Jiao Wei, Wen-Qiong Wang, Wei-Bin Song, Li-Jiang Xuan
Phytochemical investigation of the 95% ethanol extract of the whole plant of Palhinhaea cernua afforded five new serratene-type triterpenoids (1-5) together with four known analogues (6-9). The structures of the new compounds were elucidated by extensive spectroscopic analysis and X-ray crystallographic data. Compounds 1-3 triggered apoptosis of Hela -/- cell with EC 50 values of 3.49 ± 0.05, 0.28 ± 0.13 and 7.98 ± 0.03 μM, respectively.
February 12, 2018: Fitoterapia
https://www.readbyqxmd.com/read/29445224/lup-20-29-en-3%C3%AE-28-di-yl-nitrooxy-acetate-affects-mcf-7-proliferation-through-the-crosstalk-between-apoptosis-and-autophagy-in-mitochondria
#11
Xiaoning Yan, Lei Yang, Gaili Feng, Zhuli Yu, Minjie Xiao, Weibin Cai, Yanmei Xing, Shasha Bai, Junqia Guo, Zhiyu Wang, Tao Wang, Rong Zhang
Betulin (BT), a pentacyclic lupine-type triterpenoid natural product, possesses antitumor activity in various types of cancers. However, its clinical development was discouraged due to its low biological activities and poor solubility. We prepared lup-20(29)-en-3β,28-di-yl-nitrooxy acetate (NBT), a derivative of BT, that was chemically modified at position 3 of ring A and C-28 by introducing a NO-releasing moiety. This study mainly explored the mechanism of NBT in treating breast cancer through the crosstalk between apoptosis and autophagy in mitochondria...
February 14, 2018: Cell Death & Disease
https://www.readbyqxmd.com/read/29439445/two-new-triterpenoids-from-the-roots-of-codonopsis-pilosula
#12
Tao Zheng, Li-Zhi Cheng, Yong-Ming Yan, Bao-Hua Liu, Fu-Ying Qin, Fu-Rong Xu, Yong-Xian Cheng
Pseudolarolides U and V, two new triterpenoids, and four biogenetically related compounds, pseudolarolides E, F, K, and P were isolated from the roots of Codonopsis pilosula (Campanulaceae). Their structures were determined by spectroscopic data. The regulation of Sirtuin 1 (SIRT1) activity by all the isolated compounds was evaluated.
February 11, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
https://www.readbyqxmd.com/read/29438895/piriformospora-indica-cell-wall-extract-as-the-best-elicitor-for-asiaticoside-production-in-centella-asiatica-l-urban-evidenced-by-morphological-physiological-and-molecular-analyses
#13
S Jisha, P R Gouri, K N Anith, K K Sabu
Vascular plants synthesise a multitude of organic molecules or phytochemicals, referred to as "secondary metabolites". These molecules are involved in a variety of roles in the life span of plants, ranging from structural ones to protection. Centella asiatica (L.) Urban has probably been used since prehistoric times and has been reported to have been used for various medicinal and cosmetic purposes. The plant contains several active constituents, of which the most important is asiaticoside, a triterpenoid. Asiaticoside content in C...
February 7, 2018: Plant Physiology and Biochemistry: PPB
https://www.readbyqxmd.com/read/29437000/extraction-identification-and-biological-activities-of-saponins-in-sea-cucumber-pearsonothuria-graeffei
#14
Rafat Afifi Khattab, Mohamed Elbandy, Andrew Lawrence, Tim Paget, Jung Rae-Rho, Yaser S Binnaser, Imran Ali
AIM AND OBJECTIVE: Secondary metabolism in marine organisms produced a diversity of biological important natural compounds which are unpresented in terrestrial species. Sea cucumbers belong to the invertebrate Echinodermata and are famous for their nutraceutical, medical and food values. They are known for possession triterpenoid glycosides (saponins) with various ecological roles. The current work aimed to separate, identify and test various biological activities (anti-bacterial, antifungal, antileishmanial and anticancer properties) of saponins produced by the holothurian Pearsonothuria graeffei from the Red Sea, Egypt...
February 12, 2018: Combinatorial Chemistry & High Throughput Screening
https://www.readbyqxmd.com/read/29434869/a-hederagenin-saponin-isolated-from-clematis-ganpiniana-induces-apoptosis-in-breast-cancer-cells-via-the-mitochondrial-pathway
#15
Lin Cheng, Liang Shi, Jing Wu, Xujie Zhou, Xiaoxia Li, Xi Sun, Lei Zhu, Tian-Song Xia, Qiang Ding
Natural plants offer a treasure trove of resources for anticancer drug development. Clematis are widely used in Traditional Chinese Medicine. However, studies on the active substances in Clematis are scarce. In the present study, four monomer compounds were successfully extracted from this species and their inhibitory effects on the growth of breast cancer cells were investigated using bioactivity tests. Among them, Clematis hederagenin saponin (CHS) belongs to the class of triterpenoid saponins. CHS showed cytotoxic effects on breast cancer cells in a dose- and time-dependent manner...
February 2018: Oncology Letters
https://www.readbyqxmd.com/read/29433672/protective-role-of-%C3%AE-patchoulene-from-pogostemon-cablin-against-indomethacin-induced-gastric-ulcer-in-rats-involvement-of-anti-inflammation-and-angiogenesis
#16
Jia-Zhen Wu, Yu-Hong Liu, Jia-Li Liang, Qiong-Hui Huang, Yao-Xing Dou, Juan Nie, Jian-Yi Zhuo, Xue Wu, Jian-Nan Chen, Zi-Ren Su, Qi-Duan Wu
BACKGROUND: Non-steroidal anti-inflammatory drugs (NSAIDs) are most widely used as effective anti-inflammatory agents. However, their clinical application brings about inevasible gastrointestinal side effects. Pogostemon cablin is a traditional herbal medicine used for the treatment of gastrointestinal diseases in China. One of its representative components, the tricyclic triterpenoid β-patchoulone (β-PAE) has demonstrated great anti-inflammatory activity and gastroprotective effect against ethanol-induced gastric injury, but its protective effect against gastric ulcer induced by indomethacin is still unknown...
January 15, 2018: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
https://www.readbyqxmd.com/read/29433389/phytotherapeutic-activities-of-sanguisorba-officinalis-and-its-chemical-constituents-a-review
#17
Eungyeong Jang, Kyung-Soo Inn, Young Pyo Jang, Kyung-Tae Lee, Jang-Hoon Lee
Sanguisorba officinalis Linne (S. officinalis, Rosaceae) has been used as a medicinal plant for the treatment of burns, hematemesis, melena, intestinal infections, and dermatitis for a long time in China, Korea, and Japan. The therapeutic efficacy of this herb is intimately associated with its anti-oxidant, anti-inflammatory, antiviral, antifungal, hemostatic, and anticancer activities. Its root contains triterpenoid saponins (zigyuglycoside I: C[Formula: see text]H[Formula: see text]O[Formula: see text] and ziyuglycoside II: C[Formula: see text]H[Formula: see text]O8) and tannins (sanguiin H-6: C[Formula: see text]H[Formula: see text]O[Formula: see text])...
February 12, 2018: American Journal of Chinese Medicine
https://www.readbyqxmd.com/read/29425646/immunomodulatory-hemolytic-and-cytotoxic-activity-potentials-of-triterpenoid-saponins-from-eight-cephalaria-species
#18
Nazli Boke Sarikahya, Ayse Nalbantsoy, Hilal Top, Ramazan Suleyman Gokturk, Huseyin Sumbul, Suheyla Kirmizigul
BACKGROUND: Saponins isolated from a number of plants possess a broad spectrum of biological and pharmacological activities by using in vitro and in vivo bioassays. The recent investigations and findings in biological activity studies of saponins have mostly focused on immunomodulatory, hemolytic and cytotoxic properties. HYPOTHESIS/PURPOSE: Considering the great potential of saponins as bioactive agents, we investigated the cytotoxic, hemolytic and immunomodulatory activities of nineteen triterpenoid saponins from the aerial parts of eight Cephalaria species from Turkey...
January 1, 2018: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
https://www.readbyqxmd.com/read/29425586/cucurbitacin-b-suppresses-metastasis-mediated-by-reactive-oxygen-species-ros-via-focal-adhesion-kinase-fak-in-breast-cancer-mda-mb-231-cells
#19
Wei-Wei Luo, Wen-Wen Zhao, Jin-Jian Lu, Yi-Tao Wang, Xiu-Ping Chen
Metastasis is responsible for the majority of cancer-related deaths and prevention of metastasis remains a big challenge for cancer therapy. Cucurbitacin B (Cuc B) is a natural triterpenoid with potent anticancer activities while its effect on metastasis remains unclear. In the present study, the inhibitory effect and mechanisms of Cuc B on metastasis were investigated in MDA-MB-231 breast cancer cells. The cells were treated with or without Cuc B, and the cytotoxicity was determined by MTT assay. The effect of Cuc B on metastasis was evaluated with wound healing, transwell, and adhesion assays...
January 2018: Chinese Journal of Natural Medicines
https://www.readbyqxmd.com/read/29423083/betulinic-acid-impairs-metastasis-and-reduces-immunosuppressive-cells-in-breast-cancer-models
#20
An-Qi Zeng, Yan Yu, Yu-Qin Yao, Fang-Fang Yang, Mengya Liao, Lin-Jiang Song, Ya-Li Li, Yang Yu, Yu-Jue Li, Yuan-Le Deng, Shu-Ping Yang, Chen-Juan Zeng, Ping Liu, Yong-Mei Xie, Jin-Liang Yang, Yi-Wen Zhang, Ting-Hong Ye, Yu-Quan Wei
Breast cancer is the most common female cancer with considerable metastatic potential, explaining the need for new candidates that inhibit tumor metastasis. In our study, betulinic acid (BA), a kind of pentacyclic triterpenoid compound derived from birch trees, was evaluated for its anti-metastasis activity in vitro and in vivo. BA decreased the viability of three breast cancer cell lines and markedly impaired cell migration and invasion. In addition, BA could inhibit the activation of stat3 and FAK which resulted in a reduction of matrix metalloproteinases (MMPs), and increase of the MMPs inhibitor (TIMP-2) expression...
January 9, 2018: Oncotarget
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