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Статті в журналах з теми "Guaiane sesquiterpenoids"

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Автор: Grafiati

Опубліковано: 10 грудня 2022

Оновлено: 28 січня 2023

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1

Huang, Sheng, Qing Ma, Qi Wang, Hao Dai, Yu Liu, Jun Zhou, and You Zhao. "Daphnauranins C–E, Three New Antifeedants from Daphne aurantiaca Roots." Molecules 23, no. 10 (September 21, 2018): 2429. http://dx.doi.org/10.3390/molecules23102429.

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Анотація:

Daphnauranins C–E (compounds 1–3), two sesquiterpenoids and one monoterpenoid were isolated from the roots of Daphne aurantiaca Diels. Daphnauranin C is a 9-O-13 etherified and hydroperoxy-substituted guaiane sesquiterpenoid, daphnauranin D is a guaiane sesquiterpenoid ketal, and daphnauranin E is a monoterpenoid lactone. Their structures were elucidated by comprehensive analyses of MS, 1D NMR, and 2D NMR spectroscopic data. In an anti-feeding activities test, daphnauranins C–E showed activity against male fruit fly with anti-feeding indexes (AI) up to 39.1, 39.2, and 27.8% respectively, at 1 mM.

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2

Wang, Xia-Chang, Shi-Ping Ma, Jing-Han Liu, and Li-Hong Hu. "Guaiane Sesquiterpenoids from Jatropha curcas." Natural Product Communications 3, no. 10 (October 2008): 1934578X0800301. http://dx.doi.org/10.1177/1934578x0800301012.

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Two new guaiane sesquiterpenoids named jatrophaols A and B (1, 2), along with three known analogues, were isolated from the roots of Jatropha curcas. Their structures were determined by spectroscopic methods, including 1D and 2D NMR spectroscopy, HR-EI-MS, HR-ESI-MS, and X-ray diffraction, as well as by comparison of their spectral data with those of related compounds.

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3

Labbé, Cecilia, Francesca Faini, Josep Coll, and Pere Carbonell. "Guaiane sesquiterpenoids from Haplopappus foliosus." Phytochemistry 49, no. 3 (October 1998): 793–95. http://dx.doi.org/10.1016/s0031-9422(97)00871-6.

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4

Xie, Zhi-Yong, Ting-Ting Lin, Mei-Cun Yao, Jin-Zhi Wan, and Sheng Yin. "Unusual Guaiane Sesquiterpenoids fromArtemisia rupestris." Helvetica Chimica Acta 96, no. 6 (June 2013): 1182–87. http://dx.doi.org/10.1002/hlca.201200408.

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5

Lyakhova, Ekaterina G., Chau Ngoc Diep, Dmitrii V. Berdyshev, Sophia A. Kolesnikova, Anatoly L. Kalinovsky, Pavel S. Dmitrenok, Vu Anh Tu, et al. "Guaiane Sesquiterpenoids from the Gorgonian Menella woodin." Natural Product Communications 11, no. 7 (July 2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100712.

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Анотація:

Two new guaiane derivatives (1 and 2) along with six known sesquiterpenoids (3-8) were isolated from the gorgonian Menella woodin. Their structures were elucidated by ID and 2D NMR and HRESIMS data as well as by comparison of their spectra with those in the literature. Relative configurations of asymmetric centers in 1 and 2 were suggested on the basis of NOESY and ID NOE correlations, absolute stereochemistry of these compounds was proposed in result of comparison of calculated (for both enatiomers) and experimental ECD. Some suggestions were made regarding a biosynthesis of guaiane sesquiterpenoids in this species. All the compounds were firstly isolated from M woodin.

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6

Peng, Guo-Ping, Gang Tian, Xian-Feng Huang, and Feng-Chang Lou. "Guaiane-type sesquiterpenoids from Alisma orientalis." Phytochemistry 63, no. 8 (August 2003): 877–81. http://dx.doi.org/10.1016/s0031-9422(03)00222-x.

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7

Zhang, Beibei, Mengnan Zeng, Meng Li, Wenjing Chen, Benke Li, Yuxuan Kan, Weisheng Feng, and Xiaoke Zheng. "Guaiane-Type Sesquiterpenoids From Dendranthema morifolium (Ramat.) S. Kitam Flowers Protect H9c2 Cardiomyocyte From LPS-Induced Injury." Natural Product Communications 14, no. 7 (July 2019): 1934578X1986417. http://dx.doi.org/10.1177/1934578x19864179.

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This study investigated the protective effects of guaiane-type sesquiterpenoids isolated from Dendranthema morifolium (Ramat.) S. Kitam ﬂowers on lipopolysaccharide (LPS)-induced injury in H9c2 cardiomyocyte. Cell viability was determined by thiazolyl blue tetrazolium bromide (MTT). The content of released tumor necrosis factor alpha (TNF- α) and interleukin 6 (IL-6) was evaluated by enzyme-linked immunosorbent assay. The levels of lactate dehydrogenase (LDH) and creatine phosphate kinase (CK) were measured by using commercial available kits. The protein expression levels of pelF2 α, GRP78, Bax, caspase-3, caspase-9, Bcl-2, LC3-II, and p62 were measured by in-cell Western. Flow cytometry was used to detect H9c2 cardiomyocyte apoptosis. Compounds 5, 7, 1, 8, and 2 exhibited the effects of cardioprotection and activity sequence enhancement. The levels of IL-6, TNF- α, LDH, CK, pelF2 α, GRP78, Bax, caspase-3, caspase-9, p62, and H9c2 cardiomyocyte apoptosis were increased in LPS-treated H9c2 cardiomyocyte, while those of Bcl-2 and LC3-II were decreased. These effects could be effectively reversed by compounds 5, 7, 1, 8, and 2. Results demonstrated that the guaiane-type sesquiterpenoids could prevent LPS-induced injury in cardiomyocyte by decreasing endoplasmic reticulum (ER) stress, apoptosis, and autophagy as well as downregulating the inflammatory mediators. In addition, the active groups of guaiane-type sesquiterpenoids might be the angelate at C-8 and the exocyclic double bond at C-11.

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8

Ma, Qing-Yun, Yi-Chun Chen, Sheng-Zhuo Huang, Zhi-Kai Guo, Hao-Fu Dai, Yan Hua, and You-Xing Zhao. "Two New Guaiane Sesquiterpenoids from Daphne holosericea (Diels) Hamaya." Molecules 19, no. 9 (September 11, 2014): 14266–72. http://dx.doi.org/10.3390/molecules190914266.

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9

Takaya, Yoshiaki, Ken-ichi Kurumada, Yoshie Takeuji, Hye-Sook Kim, Yasuharu Shibata, Naomi Ikemoto, Yusuke Wataya, and Yoshiteru Oshima. "Novel antimalarial guaiane-type sesquiterpenoids from Nardostachys chinensis roots." Tetrahedron Letters 39, no. 11 (March 1998): 1361–64. http://dx.doi.org/10.1016/s0040-4039(97)10844-9.

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10

Tanitsu, Masa-aki, Yoshiaki Takaya, Megumi Akasaka, Masatake Niwa, and Yoshiteru Oshima. "Guaiane- and aristolane-type sesquiterpenoids of Nardostachys chinensis roots." Phytochemistry 59, no. 8 (April 2002): 845–49. http://dx.doi.org/10.1016/s0031-9422(01)00469-1.

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11

Raharivelomanana, Phila, Jean-Pierre Bianchini, Robert Faure, Aimé Cambon, and Marcel Azzaro. "Two guaiane and eudesmane-type sesquiterpenoids from Neocallitropsis pancheri." Phytochemistry 41, no. 1 (January 1996): 243–46. http://dx.doi.org/10.1016/0031-9422(95)00079-8.

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12

Mi, Cheng-Neng, Wen-Li Mei, Hao Wang, Li Yang, Wen-Hua Dong, Cui-Juan Gai, Jing-Zhe Yuan, Wen-Xing Long, and Hao-Fu Dai. "Four new guaiane sesquiterpenoids from agarwood of Aquilaria filaria." Fitoterapia 135 (June 2019): 79–84. http://dx.doi.org/10.1016/j.fitote.2019.04.007.

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13

Peng, Li-Yan, Gang Xu, Juan He, Xing-De Wu, Liao-Bin Dong, Xiu Gao, Xiao Cheng, et al. "Nor-lupane triterpenoid and guaiane sesquiterpenoids from Schefflera venulosa." Fitoterapia 103 (June 2015): 294–98. http://dx.doi.org/10.1016/j.fitote.2015.05.005.

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14

Yun, Young Sook, Tomomi Nakano, Haruhiko Fukaya, Yukio Hitotsuyanagi, Miho Nakamura, Megumi Umetsu, Nobuko Matsushita, et al. "Retusone A, a Guaiane-Type Sesquiterpene Dimer from Wikstroemia retusa and Its Inhibitory Effects on Histone Acetyltransferase HBO1 Expression." Molecules 27, no. 9 (May 3, 2022): 2909. http://dx.doi.org/10.3390/molecules27092909.

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Анотація:

Retusone A (1), a new sesquiterpene dimer consisting of two guaiane-type sesquiterpenoids, and oleodaphnal (2) were isolated from heartwood of Wikstroemia retusa (Thymelaeaceae). The planar structure of 1 was elucidated on the basis of HRESIMS and NMR spectroscopic data, and the relative stereochemistry was established by X-ray diffraction analysis. The absolute configuration of 1 was determined by electronic circular dichroism. Compound 1 suppressed luciferase reporter gene expression driven by the HBO1 (histone acetyltransferase binding to ORC1) gene promoter in human breast cancer MCF7 cells. Compound 1 also decreased the expression of endogenous HBO1 mRNA and protein, and inhibited proliferation of the cells. These results suggest that retusone A (1), which has a unique dimeric sesquiterpenoid structure with inhibitory activity against HBO1 expression, may contribute to the development of a novel therapeutic candidate for the treatment of breast cancer.

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15

Li, Hong-Mei, Min Fan, Yong Xue, Li-Yan Peng, Xing-De Wu, Dan Liu, Rong-Tao Li, and Qin-Shi Zhao. "Guaiane-Type Sesquiterpenoids from Alismatis Rhizoma and Their Anti-inflammatory Activity." Chemical and Pharmaceutical Bulletin 65, no. 4 (2017): 403–7. http://dx.doi.org/10.1248/cpb.c16-00798.

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16

Zhou, Xue-Ming, Cai-Juan Zheng, Yu-Qin Zhang, Xiao-Peng Zhang, Xiao-Ping Song, Wei Xu, and Guang-Ying Chen. "Guaiane-Type Sesquiterpenoids from Fissistigma oldhamii Inhibit the Proliferation of Synoviocytes." Planta Medica 83, no. 03/04 (July 12, 2016): 217–23. http://dx.doi.org/10.1055/s-0042-111440.

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17

Zhuzbaev, B. T., Sergazy M. Adekenov, and Vladimir V. Veselovsky. "Approaches to the total synthesis of sesquiterpenoids of the guaiane series." Russian Chemical Reviews 64, no. 2 (February 28, 1995): 187–200. http://dx.doi.org/10.1070/rc1995v064n02abeh000144.

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18

Wang, Man-Yuan, Yong-Song Zhai, and Chun-Hui Liang. "Two new guaiane-type sesquiterpenoids from Valeriana hardwickii and their cytotoxicity." Journal of Asian Natural Products Research 19, no. 10 (June 25, 2017): 987–92. http://dx.doi.org/10.1080/10286020.2017.1339350.

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19

Brocksom, Timothy John, Ursula Brocksom, and Daniel Frederico. "Synthesis of guaiane sesquiterpenoids by a ring-closing metathesis annulation sequence." Tetrahedron Letters 45, no. 50 (December 2004): 9289–91. http://dx.doi.org/10.1016/j.tetlet.2004.10.053.

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20

Kim, Dong Chun, Jeong Ah Kim, Byung Sun Min, Tae-Su Jang, MinKyun Na, and Seung Ho Lee. "Guaiane Sesquiterpenoids Isolated from the Fruits ofTorilis japonicaand Their Cytotoxic Activity." Helvetica Chimica Acta 93, no. 4 (April 2010): 692–97. http://dx.doi.org/10.1002/hlca.200900278.

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21

Tanitsu, Masa-aki, Toshiaki Takaya, Megumi Akasaka, Masatake Niwa, and Yoshiteru Oshima. "ChemInform Abstract: Guaiane- and Aristolane-Type Sesquiterpenoids of Nardostachys chinensis Roots." ChemInform 33, no. 34 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200234208.

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22

Raharivelomanana, P., J. P. Bianchini, A. R. P. Ramanoelina, J. R. E. Rasoharahona, F. Chatel, and R. Faure. "Structures of cadinane- and guaiane-type sesquiterpenoids fromEnterospermum madagascariensis (Baill.) Homolle." Magnetic Resonance in Chemistry 43, no. 12 (2005): 1049–52. http://dx.doi.org/10.1002/mrc.1705.

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23

Perveen, Shagufta, Jawaher Alqahtani, Raha Orfali, Hanan Y. Aati, Areej M. Al-Taweel, Taghreed A. Ibrahim, Afsar Khan, Hasan S. Yusufoglu, Maged S. Abdel-Kader, and Orazio Taglialatela-Scafati. "Antibacterial and Antifungal Sesquiterpenoids from Aerial Parts of Anvillea garcinii." Molecules 25, no. 7 (April 9, 2020): 1730. http://dx.doi.org/10.3390/molecules25071730.

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Анотація:

Two new sesquiterpenoids belonging to the guaiane, 4α,9α,10α-trihydroxyguaia-11(13)en-12,6α-olide (1), and germacrane, 9β-hydroxyparthenolide-9-O-β-D-glucopyranoside (2), classes have been isolated from the leaves of the Saudi medicinal plant Anvillea garcinii along with seven known compounds (3–9). The structures of the new metabolites were elucidated by spectroscopic analysis, including one-dimensional (1D) and two-dimensional (2D) Nuclear Magnetic Resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESIMS). The antimicrobial properties of 1–9 were screened against seven different pathogenic microbes, and compounds 1–3 showed a potent antifungal activity.

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24

Zhou, Qin-Mei, Ming-Hua Chen, Xiao-Hong Li, Cheng Peng, Da-Sheng Lin, Xiao-Nian Li, Yang He, and Liang Xiong. "Absolute Configurations and Bioactivities of Guaiane-Type Sesquiterpenoids Isolated from Pogostemon cablin." Journal of Natural Products 81, no. 9 (September 6, 2018): 1919–27. http://dx.doi.org/10.1021/acs.jnatprod.7b00690.

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25

Diep, Chau Ngoc, Ekaterina G. Lyakhova, Dmitrii V. Berdyshev, Anatoly I. Kalinovsky, Vu Anh Tu, Nguyen Xuan Cuong, Nguyen Hoai Nam, Chau Van Minh, and Valentin A. Stonik. "Structures and absolute stereochemistry of guaiane sesquiterpenoids from the gorgonian Menella woodin." Tetrahedron Letters 56, no. 50 (December 2015): 7001–4. http://dx.doi.org/10.1016/j.tetlet.2015.10.102.

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26

Fu, Hong-wei, Lin Zhang, Tao Yi, Yu-lin Feng, and Jing-kui Tian. "Two new guaiane-type sesquiterpenoids from the fruits of Daucus carota L." Fitoterapia 81, no. 5 (July 2010): 443–46. http://dx.doi.org/10.1016/j.fitote.2009.12.008.

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27

Chen, Wenliang, Qunfang Liu, Jian Wang, Jian Zou, Dahai Meng, Jianping Zuo, Xingzu Zhu, and Weimin Zhao. "New guaiane, megastigmane and eudesmane-type sesquiterpenoids and anti-inflammatory constituents fromYoungia japonica." Planta Medica 72, no. 6 (May 2006): 578. http://dx.doi.org/10.1055/s-2006-947171.

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28

Park, Hye Won, Sang-Un Choi, Nam-In Baek, Sung-Hoon Kim, Jae Soon Eun, Jae Heon Yang, and Dae Keun Kim. "Guaiane sesquiterpenoids fromTorilis japonica and their cytotoxic effects on human cancer cell lines." Archives of Pharmacal Research 29, no. 2 (February 2006): 131–34. http://dx.doi.org/10.1007/bf02974273.

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29

Chen, Wenliang, Qunfang Liu, Jian Wang, Jian Zou, Dahai Meng, Jianping Zuo, Xingzu Zhu, and Weimin Zhao. "New Guaiane, Megastigmane and Eudesmane-Type Sesquiterpenoids and Anti-Inflammatory Constituents fromYoungia japonica." Planta Medica 72, no. 02 (December 2006): 143–50. http://dx.doi.org/10.1055/s-2005-916182.

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30

Muhammad, Ishaq, Wei Luo, Rana Muhammad Shoaib, Guang-li Li, Syed Shams ul Hassan, Zhi-hua Yang, Xue Xiao, et al. "Guaiane-type sesquiterpenoids from Cinnamomum migao H. W. Li: And their anti-inflammatory activities." Phytochemistry 190 (October 2021): 112850. http://dx.doi.org/10.1016/j.phytochem.2021.112850.

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31

Cheng, Zhuo-Yang, Zi-Lin Hou, Jing-Xian Ren, Ding-Ding Zhang, Bin Lin, Xiao-Xiao Huang, and Shao-Jiang Song. "Guaiane-type sesquiterpenoids from the roots of Stellera chamaejasme L. and their neuroprotective activities." Phytochemistry 183 (March 2021): 112628. http://dx.doi.org/10.1016/j.phytochem.2020.112628.

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32

Wang, Jie, Qing-Bo Liu, Zi-Lin Hou, Shao-Chun Shi, Hui Ren, Guo-Dong Yao, Bin Lin, Xiao-Xiao Huang, and Shao-Jiang Song. "Discovery of guaiane-type sesquiterpenoids from the roots of Daphne genkwa with neuroprotective effects." Bioorganic Chemistry 95 (January 2020): 103545. http://dx.doi.org/10.1016/j.bioorg.2019.103545.

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33

Moiseenkov, A. M., B. T. Zhuzbaev, V. V. Veselovsky, K. M. Turdybekov, A. V. Buevich, S. M. Adekenov, and Yu T. Struchkov. "A novel synthesis of guaiane sesquiterpenoids based ontrans-3-isoprenyl-2-(2-methoxycarbonylethyl)cyclopentanone." Russian Chemical Bulletin 42, no. 1 (January 1993): 113–18. http://dx.doi.org/10.1007/bf00699989.

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34

Diep, Chau Ngoc, Ekaterina G. Lyakhova, Dmitrii V. Berdyshev, Anatoly I. Kalinovsky, Vu Anh Tu, Nguyen Xuan Cuong, Nguyen Hoai Nam, Chau Van Minh, and Valentin A. Stonik. "ChemInform Abstract: Structures and Absolute Stereochemistry of Guaiane Sesquiterpenoids from the Gorgonian Menella woodin." ChemInform 47, no. 15 (March 2016): no. http://dx.doi.org/10.1002/chin.201615189.

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35

Chen, Lili, Yunyun Liu, Yifei Li, Wu Yin, and Yongxian Cheng. "Anti-Cancer Effect of Sesquiterpene and Triterpenoids from Agarwood of Aquilaria sinensis." Molecules 27, no. 16 (August 22, 2022): 5350. http://dx.doi.org/10.3390/molecules27165350.

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Анотація:

Two new guaiane sesquiterpenes, aquisinenoids A and B (1 and 2), two new eudesmane-type sesquiterpenoids, aquisinenoids C and D (3 and 4), one new cucurbitacin, aquisinenoid E (5), and five known cucurbitacins (6–10) were isolated from agarwood of Aquilaria sinensis. The structures of these new compounds, including their absolute configurations, were characterized by spectroscopic and computational methods. The biological evaluation showed that compounds 3 and 9 had an anti-cancer effect on most of the cancer cells at 5 μM, especially in human breast cancer cells. Interestingly, the new compound 3 exhibited more sensitivity on cancer cells than normal cells, highlighting its potential as a novel anti-cancer agent. Mechanically, compound 3 treatment increased the ROS generation and triggered apoptosis of human breast cancer cells.

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36

Ren, Qiang, Wen-Yu Zhao, Shao-Chun Shi, Feng-Ying Han, Ying-Ying Zhang, Qing-Bo Liu, Guo-Dong Yao, Bin Lin, Xiao-Xiao Huang, and Shao-Jiang Song. "Guaiane-Type Sesquiterpenoids from the Roots of Daphne genkwa and Evaluation of Their Neuroprotective Effects." Journal of Natural Products 82, no. 6 (May 31, 2019): 1510–17. http://dx.doi.org/10.1021/acs.jnatprod.8b01049.

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37

Su, Li-Hua, Yun-Bao Ma, Chang-An Geng, Tian-Ze Li, Xiao-Yan Huang, Jing Hu, Xin Zhang, et al. "Artematrovirenins A–P, guaiane-type sesquiterpenoids with cytotoxicities against two hepatoma cell lines from Artemisia atrovirens." Bioorganic Chemistry 114 (September 2021): 105072. http://dx.doi.org/10.1016/j.bioorg.2021.105072.

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38

Shu, Zhiheng, Jiang Pu, Ling Chen, Yuanbin Zhang, Khalid Rahman, Luping Qin, and Chengjian Zheng. "Alisma orientale: Ethnopharmacology, Phytochemistry and Pharmacology of an Important Traditional Chinese Medicine." American Journal of Chinese Medicine 44, no. 02 (January 2016): 227–51. http://dx.doi.org/10.1142/s0192415x16500142.

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Анотація:

Alisma orientale (Sam.) Juzep. (Alismataceae) is a traditional and famous Chinese medicinal herb. Its rhizomes, which possess versatile bioactivities, are commonly used to treat oliguria, edema, gonorrhea with turbid urine, leukorrhea, diarrhea and dizziness. Approximately 120 compounds have been isolated from A. orientale. Terpenoids have been identified as A. orientale’s characteristic constituents, which include protostane triterpenoids and guaiane sesquiterpenoids. The traditional medical uses of A. orientale in TCM have been evaluated in modern pharmacological studies, which have shown that A. orientale and its active constituents exhibit a wide range of bioactivities, such as diuretic, anti-urolithiatic, antinephritic, anti-atherosclerotic, immunomodulatory, and hepatoprotective activities. The medicinal potential of A. orientale makes it an ideal candidate for new drug development. Further studies are still required to identify its bioactive constituents, and elucidate the structure–activity relationship and detailed mechanisms of action. Additionally, the use of the other medicinal parts of A. orientale may reduce resource waste and afford novel secondary metabolites.

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39

Anke, H., O. Bergendorff, and O. Sterner. "Assays of the biological activities of guaiane sesquiterpenoids isolated from the fruit bodies of edible lactarius species." Food and Chemical Toxicology 27, no. 6 (January 1989): 393–97. http://dx.doi.org/10.1016/0278-6915(89)90145-2.

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40

Pan, Jun, Jun-Cheng Su, Yi-Hui Liu, Bin Deng, Zhuo-Fan Hu, Jia-Le Wu, Ru-Feng Xia, et al. "Stelleranoids A–M, guaiane-type sesquiterpenoids based on [5,7] bicyclic system from Stellera chamaejasme and their cytotoxic activity." Bioorganic Chemistry 115 (October 2021): 105251. http://dx.doi.org/10.1016/j.bioorg.2021.105251.

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41

Dong, Shu-Hui, Zhi-Kang Duan, Yun-Fei Ai, Xiao-Fang Zhou, Xin Zhang, Mei-Ya Lian, Xiao-Xiao Huang, Ming Bai, and Shao-Jiang Song. "Guaiane-type sesquiterpenoids with various ring skeletons from Daphne bholua uncovered by molecular networking and structural revisions of previously reported analogues." Bioorganic Chemistry 129 (December 2022): 106208. http://dx.doi.org/10.1016/j.bioorg.2022.106208.

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42

Azevedo, Luíse, Larissa Faqueti, Marina Kritsanida, Antonia Efstathiou, Despina Smirlis, Gilberto C. Franchi, Grégory Genta-Jouve, et al. "Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography." Beilstein Journal of Organic Chemistry 12 (April 12, 2016): 674–83. http://dx.doi.org/10.3762/bjoc.12.68.

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Анотація:

Jungia sellowii (Asteraceae) is a shrub that grows in Southern Brazil and polar extract of its leaves presents anti-inflammatory properties. Cyperane, guaiane, nortrixane, and trixane sesquiterpene types were reported as the main metabolites in Jungia species. This work aims to describe the isolation and identification of sesquiterpenes in the leaves of J. sellowii using liquid–liquid partition and centrifugal partition chromatography. Thus, the crude extract of fresh leaves of J. sellowii was partitioned with hexane, dichloromethane, ethyl acetate and butanol, respectively. The butanol fraction was then subjected to a selected ternary system optimized for the CPC (centrifugal partition chromatography): ethyl acetate–ethanol–water (9:2:10, v/v/v). The separation was carried out isocratically at a flow rate of 25 mL/min at 1200 rpm, affording seven fractions A to G. TLC of fractions B, C and F displayed a single spot corresponding to three new glycosylated sesquiterpenoids. Their structures were established by using spectroscopic data in comparison to those reported in the literature. Furthermore, the isolates were evaluated for their leishmanicidal and cytotoxic effects. No cytotoxic effect was observed against the three cancer cell lines (HL60, JURKAT and REH), but compound 1 showed a weak antiprotozoal activity. Liquid–liquid partition and CPC turned to be a versatile technique of glycoside purification which is environmentally friendly and requires a limited amount of organic solvents.

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Huang, An-Cheng, Christopher J. Sumby, Edward R. T. Tiekink, and Dennis K. Taylor. "Synthesis of Guaia-4(5)-en-11-ol, Guaia-5(6)-en-11-ol, Aciphyllene, 1-epi-Melicodenones C and E, and Other Guaiane-Type Sesquiterpenoids via the Diastereoselective Epoxidation of Guaiol." Journal of Natural Products 77, no. 11 (October 20, 2014): 2522–36. http://dx.doi.org/10.1021/np500611z.

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44

Anjaneyulu, A. S. R., and P. Mangala Gowri. "ChemInform Abstract: Two New Guaiane Sesquiterpenoids from the Soft Coral Sarcophyton buitendijki of the Andaman and Nicobar Island of the Indian Ocean." ChemInform 32, no. 17 (April 24, 2001): no. http://dx.doi.org/10.1002/chin.200117184.

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45

Phan, Chin-Soon, Takashi Kamada, Takahiro Ishii, Toshiyuki Hamada, and Charles Santhanaraju Vairappan. "A New Guaiane-type Sesquiterpenoid from a Bornean Soft Coral, Xenia stellifera." Natural Product Communications 13, no. 1 (January 2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300105.

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A new guaiane-type sesquiterpenoid, 10β- O-methyl-1αH,5αH-guaia-6-en-4β-ol (1) along with two known compounds, 10- O -methyl alismoxide (2) and alismoxide (3) were isolated from a population of Bornean soft coral Xenia stellifera. The structure of this metabolite was elucidated based on spectroscopic data such as NMR and HRESIMS. These compounds were evaluated for their biological activity against adult T-cell leukemia cell line.

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46

Choi, Ji, MinKyun Na, In Hyun Hwang, Seung Ho Lee, Eun Young Bae, Bo Yeon Kim, and Jong Seog Ahn. "Isolation of Betulinic Acid, its Methyl Ester and Guaiane Sesquiterpenoids with Protein Tyrosine Phosphatase 1B Inhibitory Activity from the Roots of Saussurea lappa C.B.Clarke." Molecules 14, no. 1 (January 8, 2009): 266–72. http://dx.doi.org/10.3390/molecules14010266.

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47

Cui, Y., F. Zhao, J. Liu, D. Shi, K. Chen, X. Wang, J. Du, and M. Guo. "PM130 Time Course of Vascular Healing and Potential Mechanisms for Guaiane-Type Sesquiterpenoids of Curcuma Zedoaria Eluting Stent in a Porcine Coronary Injury Model." Global Heart 11, no. 2 (June 2016): e93. http://dx.doi.org/10.1016/j.gheart.2016.03.322.

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48

Liu, Lanying, Fuqin Guan, Yu Chen, Fan Wang, Pengxu Chen, Min Yin, Bi Wang, et al. "Two Novel Sesquiterpenoid Glycosides from the Rhizomes of Atractylodes lancea." Molecules 27, no. 18 (September 6, 2022): 5753. http://dx.doi.org/10.3390/molecules27185753.

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Анотація:

Secoatractylohexone A (1), an unprecedented secoguaiane lactone glycoside featuring 6/7 cores and dihydroxy-9-guaine-3-one 11-O-β-d-glucopyranoside (2), a 9,10-unsaturated guaiene-type glycoside possessing an uncommon scaffold, were isolated from the water-soluble portion of the ethanolic extract of Atractylodes lancea rhizomes together with five known compounds (3–7). The structures of 1 and 2 were elucidated on the basis of extensive spectroscopic data and application of the CD technique. The potential biological activities of secoatractylohexone A were predicted by network pharmacology in silico, the result of which indicated that secoatractylohexone A may be used to treat type II diabetes.

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Tan, Xiang‐Mei, Qi Li, Yan‐Duo Wang, Tie‐Lin Wang, Jian Yang, Bing‐Da Sun, Lan‐Ping Guo, and Gang Ding. "UPLC‐Q‐TOF‐MS/MS analysis of the guaiane sesquiterpenoids oxytropiols A–J and detection of undescribed analogues from the locoweed endophytic fungus Alternaria oxytropis (Pleosporaceae)." Phytochemical Analysis 33, no. 3 (November 9, 2021): 344–54. http://dx.doi.org/10.1002/pca.3092.

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Yu, Yang, Hao Gao, Yi Dai, Gao-Keng Xiao, Hua-Jie Zhu, and Xin-Sheng Yao. "Guaiane-type sesquiterpenoid glucosides from Gardenia jasminoides Ellis." Magnetic Resonance in Chemistry 49, no. 5 (March 29, 2011): 258–61. http://dx.doi.org/10.1002/mrc.2730.

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