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lanostane triterpenes

Kazumi Sagayama, Naonobu Tanaka, Takatoshi Fukumoto, Yoshiki Kashiwada
Chaga mushrooms, the sclerotium of Inonotus obliquus, have been used in Mongolia as a traditional hair shampoo to maintain healthy hair. Bioassay-guided fractionations of the extract of Chaga mushrooms using a proliferation assay on human follicle dermal papilla cells (HFDPCs) gave five lanostane-type triterpenes (1-5), whose structures were identified by spectroscopic evidence. Among these, lanosterol (1), inotodiol (3), lanost-8,24-diene-3β,21-diol (4), and trametenolic acid (5) demonstrated proproliferative effects on HFDPCs more potent than minoxidil, an anti-alopecia agent, used as the positive control...
January 31, 2019: Journal of Natural Medicines
Vladimir I Kalinin, Alexandra S Silchenko, Sergey A Avilov, Valentin A Stonik
Triterpene glycosides are known as characteristic metabolites of sea cucumbers (class Holothuroidea, phylum Echinodermata). The most of them have lanostane aglycones containing 18(20)-lactone, i.e. belongs to so-called holostane series. However non-holostane glycosides having no lactone (with the both normal and shortened side chains) or containing 18(16)-lactone function were also found in these invertebrates last a few decades. In addition, some very rare findings of the glycosides containing rearranged lanostane skeleton systems were reported...
November 22, 2018: Steroids
Yan Zheng, Shu Liu, Junpeng Xing, Zhong Zheng, Zifeng Pi, Fengrui Song, Zhiqiang Liu
Lanostane-type triterpene acids are one of the main active components in Poria cocos, which have strong anticancer, immune regulation, antiaging, and anti-inflammation effects. However, low abundance, structure similarity, poor ionization efficiency, and especially the lack of adequate standards has hampered their accurate quantification. In this work, we develop an equivalently quantitative ion strategy with quaternary ammonium cation derivatization and established only one calibration curve for highly sensitive quantification of lanostane-type triterpene acids by ultrahigh-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) in the absence of standards...
October 26, 2018: Analytical Chemistry
Gui-Fang Feng, Yan Zheng, Yufei Sun, Shu Liu, Zi-Feng Pi, Feng-Rui Song, Zhi-Qiang Liu
Rapid structural identification of natural compounds in the crude extract of traditional Chinese medicine by conventional liquid chromatography-mass spectrometry is complex and challenging. In particular, it is difficult to distinguish and identify structural isomers. In this work, we proposed a novel strategy that combines a typical ultrahigh-performance liquid chromatography-multidimensional mass spectrometry approach and the post-processing UNIFI scientific information system to rapidly identify lanostane analogs and isomers in Poria cocos...
November 29, 2018: Analytica Chimica Acta
Yi Sun, Liang-Liang Gao, Meng-Yue Tang, Bao-Min Feng, Yue-Hu Pei, Ken Yasukawa
Euphorbia maculata is a medicinal plant of the Euphorbiaceae family, which can produce anti-inflammatory and cancer chemopreventive agents of triterpenoids. The present study reports on the bioactive triterpenoids of this plant. Two new lanostane-type triterpenoids, named (3 S ,4 S ,7 S ,9 R )-4-methyl-3,7-dihydroxy-7(8→9) abeo -lanost-24(28)-en-8-one ( 1 ) and 24-hydroperoxylanost-7,25-dien-3β-ol ( 2 ), together with 15 known triterpene derivatives, were isolated from Euphorbia maculata . The structures of the new compounds were determined on the basis of extensive spectroscopic data (UV, MS, ¹H and 13 C-NMR, and 2D NMR) analysis...
August 22, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Ulrike Grienke, Julia Zwirchmayr, Ursula Peintner, Ernst Urban, Martin Zehl, Michaela Schmidtke, Judith M Rollinger
In an in vitro screening for anti-influenza agents from European polypores, the fruit body extract of Gloeophyllum odoratum dose-dependently inhibited the cytopathic effect of the H3N2 influenza virus A/Hong Kong/68 (HK/68) in Madin Darby canine kidney cells with a 50% inhibitory concentration (IC50 ) of 15 µg/mL, a noncytotoxic concentration. After a chromatographic work-up, eight lanostane triterpenes (1: -8: ) were isolated and their structures were elucidated based on high-resolution electrospray ionization mass spectrometry analyses, and one- and two-dimensional nuclear magnetic resonance experiments...
August 21, 2018: Planta Medica
Alexandra S Silchenko, Anatoly I Kalinovsky, Sergey A Avilov, Pelageya V Andryjaschenko, Pavel S Dmitrenok, Ekaterina A Yurchenko, Svetlana P Ermakova, Olesya S Malyarenko, Igor Yu Dolmatov, Vladimir I Kalinin
Eight new triterpene olygoglycosides, cladolosides C4 (1), D1 (2), D2 (3), M (4), M1 (5), M2 (6), N (7) and Q (8), were isolated from the tropical Indo-West Pacific sea cucumber Cladolabes schmeltzii (Sclerodactylidae, Dendrochirotida). Structures of these glycosides were elucidated by 2D NMR spectroscopy and HR ESI mass spectrometry. A novel hexasaccharide carbohydrate chain having xylose residues as the first, second and third sugars was found in the glycoside 7. Cladoloside C4 (1) contains an uncommon 20,21,22,23,24,25,26,27-octa-norlanostane aglycone...
October 2018: Carbohydrate Research
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
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
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
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
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
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
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
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
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
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
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
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
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
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