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lanostane triterpenes

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https://www.readbyqxmd.com/read/29953348/lanostane-type-triterpenes-and-abietane-type-diterpene-from-the-sclerotia-of-chaga-medicinal-mushroom-inonotus-obliquus-agaricomycetes-and-their-biological-activities
#1
Kutaiba Ibrahin Alzand, Sabri Ünal, Mansor S Mostafa Boufaris
Three new lanostane-type triterpenes (compounds 1-3), 1 new abietane-type diterpene (compound 4), and 10 known compounds (5-14) were isolated from sclerotia of Inonotus obliquus. Their structures were elucidated through a combination of spectrometric techniques, including infrared, 1-dimensional, and 2-dimensional nuclear magnetic resonance and high-resolution electrospray mass spectrometry. In in vitro assays, compounds 2 and 4-12 showed hepatoprotective effects against D-galactosamine-induced damage in WB-F344 cells, with inhibitory effects from 35...
2018: International Journal of Medicinal Mushrooms
https://www.readbyqxmd.com/read/29660562/hebecarposides-a-k-antiproliferative-lanostane-type-triterpene-glycosides-from-the-leaves-of-lyonia-ovalifolia-var-hebecarpa
#2
Yang Teng, Hanqi Zhang, Junfei Zhou, Guanqun Zhan, Guangmin Yao
Eleven previously undescribed lanostane-type triterpene glycosides, hebecarposides A-K, were isolated from the leaves of Lyonia ovalifolia var. hebecarpa (Ericaceae), along with two known analogues, lyonifolosides L and O. The structures of hebecarposides A-K were established by extensive spectroscopic analysis and chemical methods, and the absolute configuration of C-24 in hebecarposides A and E was determined to be S and R, respectively, by a Mo2 (OAc)4 -induced electronic circular dichroism method. This is the first report of the presence of lanostane-type triterpene glycosides in L...
July 2018: Phytochemistry
https://www.readbyqxmd.com/read/29603608/triterpenes-and-meroterpenes-with-neuroprotective-effects-from-ganoderma-leucocontextum
#3
Hongyu Chen, Jinjin Zhang, Jinwei Ren, Wenzhao Wang, Weiping Xiong, Yaodong Zhang, Li Bao, Hongwei Liu
Ganoderma leucocontextum is a well-known medicinal mushroom cultivated in the Tibet Plateau of China. Chemistry investigation on the fruiting bodies of this mushroom resulted in the isolation of sixteen secondary metabolites including three new lanostane triterpenes, ganoleucoins Q - S (1 - 3), as well as thirteen known compounds (4 - 16). The structures of compounds 1 - 3 were determined by NMR, MS, CD spectral analysis, and chemical derivation method. The neuroprotective effects of compounds 1 - 16 were tested on PC12 cells...
May 2018: Chemistry & Biodiversity
https://www.readbyqxmd.com/read/29490285/lanostane-triterpenes-from-the-mushroom-ganoderma-resinaceum-and-their-inhibitory-activities-against-%C3%AE-glucosidase
#4
Xian-Qiang Chen, Jing Zhao, Ling-Xiao Chen, Shen-Fei Wang, Ying Wang, Shao-Ping Li
Eighteen previously undescribed lanostane triterpenes and thirty known analogues were obtained from the fruiting bodies of Ganoderma resinaceum. Resinacein C was isolated from a natural source for the first time. The structures of all the above compounds were elucidated by extensive spectroscopic analysis and comparisons of their spectroscopic data with those reported in the literature. Furthermore, in an in vitro assay, Resinacein C, ganoderic acid Y, lucialdehyde C, 7-oxo-ganoderic acid Z3 , 7-oxo-ganoderic acid Z, and lucidadiol showed strong inhibitory effects against α-glucosidase compared with the positive control drug acarbose...
May 2018: Phytochemistry
https://www.readbyqxmd.com/read/29457741/lucidumol-d-a-new-lanostane-type-triterpene-from-fruiting-bodies-of-reishi-ganoderma-lingzhi
#5
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/29437000/extraction-identification-and-biological-activities-of-saponins-in-sea-cucumber-pearsonothuria-graeffei
#6
Rafat Afifi Khattab, Mohamed Elbandy, Andrew Lawrence, Tim Paget, Jung Rae-Rho, Yaser S Binnaser, Imran Ali
AIMS AND OBJECTIVES: Secondary metabolism in marine organisms produces a diversity of biologically important natural compounds that are not present 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 (antibacterial, antifungal, antileishmanial and anticancer properties) of saponins produced by the holothurian Pearsonothuria graeffei from the Red Sea, Egypt...
2018: Combinatorial Chemistry & High Throughput Screening
https://www.readbyqxmd.com/read/29247893/polycyclic-polyprenylated-acylphloroglucinols-and-biphenyl-derivatives-from-the-roots-of-garcinia-nuntasaenii-ngerns-suddee
#7
Suppisak Chaturonrutsamee, Chutima Kuhakarn, Panida Surawatanawong, Samran Prabpai, Palangpon Kongsaeree, Thaworn Jaipetch, Pawinee Piyachaturawat, Surawat Jariyawat, Radeekorn Akkarawongsapat, Kanoknetr Suksen, Jitra Limthongkul, Chanita Napaswad, Narong Nuntasaen, Vichai Reutrakul
Seven previously undescribed compounds, including three polycyclic polyprenylated acylphloroglucinols (garcinuntins A-C), three biphenyl derivatives (garcinuntabiphenyls A-C) and a lanostane triterpene (garcinuntine), along with thirteen known compounds were isolated from the root of Garcinia nuntasaenii Ngerns. & Suddee. Their structures were elucidated on the basis of spectroscopic techniques. For garcinuntins A-C, the absolute configurations were confirmed by the combination of single X-ray crystallography and ECD calculations...
February 2018: Phytochemistry
https://www.readbyqxmd.com/read/29130336/antiproliferative-and-cytotoxic-secondary-metabolites-from-fruits-of-leplaea-mayombensis
#8
Sidjui Sidjui Lazare, Soh Désiré, Dameue Tegang Joel Ebenezer, Happi Tchakounté Brice, Toghueo Kouipou Rufin Marie, Wembe Ngouonpe Alain, Shaiq Ali Muhammad, Folefoc Ngosong Gabriel
Two new seco-lanostane-type triterpenes, named mayomlactones A (1) and B (2) were isolated from the fruits of Leplaea mayombensis together with 10 known compounds (3-12). Structures of the new compounds were elucidated by extensive spectroscopic studies. Except compounds 11 and 12, all the other chemical compounds are newly reported from Leplaea genus. From the results of this investigation, compounds 1-10 were examined for antiproliferative activity against HeLa cells as well as cytotoxicity against 3T3 cell line...
November 13, 2017: Natural Product Research
https://www.readbyqxmd.com/read/28994535/-antitumor-activity-and-structure-activity-relationship-of-seven-lanostane-type-triterpenes-from-fomitopsis-pinicola-and-f-officinalis
#9
Zhen-Ting Shi, Hai-Ying Bao, Shuang Feng
Seven lanostane-type triterpenes including fomitopsin C(1),3-keto-dehydrosulfurenic acid(2),dehydroeburiconic acid(3),3-acetyloxylanosta-8, 24-dien-21-oic acid(4),pinicolic acid A(5),trametenolic acid B(6),and eburicoic acid(7),were isolated from the fruitbodies of Fomitopsis pinicola and F. officinalis. In vitro assay, all compounds were evaluated against MCF-7, HeLa, HepG2 and A549 cells lines using the MTT assay and the structure-activity relationship of antitumor activity was discussed. The results showed that the seven compounds were more sensitive to MCF-7 cells...
March 2017: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/28931319/lanostane-triterpenoids-from-cultivated-fruiting-bodies-of-the-basidiomycete-ganoderma-australe
#10
Masahiko Isaka, Panida Chinthanom, Sermsiri Mayteeworakoon, Kobkul Laoteng, Wilunda Choowong, Rattaket Choeyklin
A new lanostane triterpene (1), together with three known compounds (2-4), were isolated from cultivated fruiting bodies of the basidiomycete Ganoderma australe. The structure was elucidated on the basis of NMR spectroscopic and mass spectrometry data. The olefinic geometry of methyl australate (2) was revised from 20(22)Z to 20(22)E. These compounds (1-4) were different from the lanostanes isolated from mycelial cultures of the same strain source.
May 2018: Natural Product Research
https://www.readbyqxmd.com/read/28813020/nine-new-triterpene-glycosides-magnumosides-a%C3%A2-a%C3%A2-b%C3%A2-b%C3%A2-c%C3%A2-c%C3%A2-and-c%C3%A2-from-the-vietnamese-sea-cucumber-neothyonidium-massinium-magnum-structures-and-activities-against-tumor-cells-independently-and-in-synergy-with-radioactive-irradiation
#11
Alexandra S Silchenko, Anatoly I Kalinovsky, Sergey A Avilov, Vladimir I Kalinin, Pelageya V Andrijaschenko, Pavel S Dmitrenok, Ekaterina A Chingizova, Svetlana P Ermakova, Olesya S Malyarenko, Tatyana N Dautova
Nine new sulfated triterpene glycosides, magnumosides A₁ ( 1 ), A₂ ( 2 ), A₃ ( 3 ), A₄ ( 4 ), B₁ ( 5 ), B₂ ( 6 ), C₁ ( 7 ), C₂ ( 8 ) and C₄ ( 9 ) as well as a known colochiroside B₂ ( 10 ) have been isolated from the tropical Indo-West Pacific sea cucumber Neothynidium (= Massinium ) magnum (Phyllophoridae, Dendrochirotida) collected in the Vietnamese shallow waters. The structures of new glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. All the isolated new glycosides were characterized by the non-holostane type lanostane aglycones having 18(16)-lactone and 7(8)-double bond and differed from each other by the side chains and carbohydrate moieties structures...
August 16, 2017: Marine Drugs
https://www.readbyqxmd.com/read/28800422/cytotoxic-lanostane-triterpenoids-from-the-fruiting-bodies-of-piptoporus-betulinus
#12
Zeynep Tohtahon, Jingjing Xue, Jianxin Han, Yushuang Liu, Huiming Hua, Tao Yuan
Chemical investigation of a bioactive methanolic extract of the fruiting bodies of Piptoporus betulinus led to the isolation of five previously undescribed lanostane triterpenoids named piptolinic acids A-E, as well as five known lanostane triterpenoids. Their structures were elucidated on the basis of 1D and 2D NMR spectroscopic and HRESIMS analysis. Piptolinic acid A with an unusual moiety (3-hydroxy-4-methoxycarbonyl-3-methylbutyryloxy) at C-3 exhibited comparable cytotoxic activity against human promyelocytic leukemia cell line HL-60 (IC50 = 1...
November 2017: Phytochemistry
https://www.readbyqxmd.com/read/28800421/lanostane-type-triterpenoids-from-the-fruiting-body-of-ganoderma-calidophilum
#13
Sheng-Zhuo Huang, Qing-Yun Ma, Fan-Dong Kong, Zhi-Kai Guo, Cai-Hong Cai, Li-Li Hu, Li-Man Zhou, Qi Wang, Hao-Fu Dai, Wen-Li Mei, You-Xing Zhao
To search for active anti-cancer constituents in the fruiting body of Ganoderma calidophilum, we have successfully isolated four previously undescribed spiro-lactone lanostane triterpenoids (spiroganocalitones A-D), two previously undescribed lanostanoids (ganodecalones A and B) together with twenty-three known ones. The structures of the six previously undescribed compounds were elucidated based on 1D, 2D-NMR, and HRMS analyses. Ganoderone A showed moderate cytotoxic activity against K562, BEL7402, and SGC790 cell lines with IC50 values of 7...
November 2017: Phytochemistry
https://www.readbyqxmd.com/read/28783356/chemical-constituents-of-propolis-from-vietnamese-trigona-minor-and-their-antiausterity-activity-against-the-panc-1-human-pancreatic-cancer-cell-line
#14
Hai X Nguyen, Mai T T Nguyen, Nhan T Nguyen, Suresh Awale
The ethanol extract of propolis from the Vietnamese stingless bee Trigona minor possessed potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells in nutrient-deprived medium, with a PC50 value of 14.0 μg/mL. Chemical investigation of this extract led to the isolation of 15 cycloartane-type triterpenoids, including five new compounds (1-5), and a lanostane-type triterpenoid. The structures of the new compounds were elucidated on the basis of NMR spectroscopic analysis. Among the isolated compounds, 23-hydroxyisomangiferolic acid B (5) and 27-hydroxyisomangiferolic acid (13) exhibited the most potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under nutrition-deprived conditions, with PC50 values of 4...
August 25, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/28527898/triterpenes-and-meroterpenes-from-ganoderma-lucidum-with-inhibitory-activity-against-hmgs-reductase-aldose-reductase-and-%C3%AE-glucosidase
#15
Baosong Chen, Jin Tian, Jinjin Zhang, Kai Wang, Li Liu, Bo Yang, Li Bao, Hongwei Liu
Seven new compounds including four lanostane triterpenoids, lucidenic acids Q-S (1-3) and methyl ganoderate P (4), and three triterpene-farnesyl hydroquinone conjugates, ganolucinins A-C (5-7), one new natural product ganomycin J (8), and 73 known compounds (9-81) were isolated from fruiting bodies of Ganoderma lucidum. The structures of the compounds 1-8 were determined by spectroscopic methods. Bioactivities of compounds isolated were assayed against HMG-CoA reductase, aldose reductase, α-glucosidase, and PTP1B...
July 2017: Fitoterapia
https://www.readbyqxmd.com/read/28487074/protective-effect-of-lanostane-triterpenoids-from-the-sclerotia-of-poria-cocos-wolf-against-cisplatin-induced-apoptosis-in-llc-pk1-cells
#16
Dahae Lee, Seulah Lee, Sang Hee Shim, Hae-Jeung Lee, Youkyung Choi, Tae Su Jang, Ki Hyun Kim, Ki Sung Kang
Cisplatin-induced nephrotoxicity is a serious adverse effect that limits the use of cisplatin in cancer patients. In the present study, we investigated the protective effect of lanostane triterpenoids (1-10) isolated from the ethanolic extract of Poria cocos Wolf against cisplatin-induced cell death in LLC-PK1 kidney tubular epithelial cells. Treatment of cisplatin induced significant cell death, which was suppressed by treatment with dehydroeburicoic acid monoacetate (1) and 3β-acetoxylanosta-7,9(11),24-trien-21-oic acid (9)...
July 1, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28300703/highly-oxygenated-lanostane-type-triterpenoids-and-their-bioactivity-from-the-fruiting-body-of-ganoderma-gibbosum
#17
De-Bing Pu, Xi Zheng, Jun-Bo Gao, Xing-Jie Zhang, Yan Qi, Xiao-Si Li, Yong-Mei Wang, Xiao-Nian Li, Xiao-Li Li, Chun-Ping Wan, Wei-Lie Xiao
Eight new highly oxygenated lanostane triterpenes, gibbosic acids A-H (1-8), along with three known ones (9-11), were isolated from the fruiting body of Ganoderma gibbosum. The structures of new isolates were assigned by NMR and HRESIMS experiments. The absolute configurations of 1 were further confirmed by single crystal X-ray diffraction data and computational ECD methods. Immunoregulatory effect and anti-inflammatory activities of these compounds were screened in murine lymphocyte proliferation assay and in lipopolysaccharide (LPS)-stimulated RAW-264...
June 2017: Fitoterapia
https://www.readbyqxmd.com/read/28078535/tubulin-polymerization-stimulating-activity-of-ganoderma-triterpenoids
#18
Toshitaka Kohno, Tran Hai-Bang, Qinchang Zhu, Yhiya Amen, Seiichi Sakamoto, Hiroyuki Tanaka, Satoshi Morimoto, Kuniyoshi Shimizu
Tubulin polymerization is an important target for anticancer therapies. Even though the potential of Ganoderma triterpenoids against various cancer targets had been well documented, studies on their tubulin polymerization-stimulating activity are scarce. This study was conducted to evaluate the effect of Ganoderma triterpenoids on tubulin polymerization. A total of twenty-four compounds were investigated using an in vitro tubulin polymerization assay. Results showed that most of the studied triterpenoids exhibited microtuble-stabilizing activity to different degrees...
April 2017: Journal of Natural Medicines
https://www.readbyqxmd.com/read/28074433/partial-contribution-of-rho-kinase-inhibition-to-the-bioactivity-of-ganoderma-lingzhi-and-its-isolated-compounds-insights-on-discovery-of-natural-rho-kinase-inhibitors
#19
Yhiya Amen, Qinchang Zhu, Hai-Bang Tran, Mohamed S Afifi, Ahmed F Halim, Ahmed Ashour, Kuniyoshi Shimizu
Recent studies identified Rho-kinase enzymes (ROCK-I and ROCK-II) as important targets that are involved in a variety of diseases. Synthetic Rho-kinase inhibitors have emerged as potential therapeutic agents to treat disorders such as hypertension, stroke, cancer, diabetes, glaucoma, etc. Our study is the first to screen the total ethanol extract of the medicinal mushroom Ganoderma lingzhi with thirty-five compounds for Rho-kinase inhibitory activity. Moreover, a molecular binding experiment was designed to investigate the binding affinity of the compounds at the active sites of Rho-kinase enzymes...
April 2017: Journal of Natural Medicines
https://www.readbyqxmd.com/read/27792321/antiviral-triterpenes-from-the-twigs-and-leaves-of-lyonia-ovalifolia
#20
Xiao-Jing Lv, Yong Li, Shuang-Gang Ma, Jing Qu, Yun-Bao Liu, Yu-Huan Li, Dan Zhang, Li Li, Shi-Shan Yu
Eleven new 9,10-seco-cycloartan triterpene glycosides (1-11), seven new lanostane triterpene glycosides (12-18), and two new ursane triterpenoids (19-20) were isolated from the twigs and leaves of Lyonia ovalifolia. The structures of these compounds were elucidated by extensive MS and NMR spectroscopic analysis. The absolute configuration of compound 1a (the aglycone of 1) was established by X-ray crystallography, and that of C-24 in compounds 2, 7, and 12 was established by Mo2 (OAc)4 -induced electronic circular dichroism experiments...
November 23, 2016: Journal of Natural Products
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