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Isolation and structure elucidation of dichotomin, a furostanol saponin implicated in hepatogenous photosensitization of sheep grazing Panicum dichotomiflorum

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    Isolation and structure elucidation of dichotomin, a furostanol saponin implicated in hepatogenous photosensitization of sheep grazing Panicum dichotomiflorum
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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 1993, 41, 2, 267–271
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    https://doi.org/10.1021/jf00026a025
    Published February 1, 1993
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    This article is cited by 34 publications.

    1. Stephen T. Lee, Robert B. Mitchell, Zhirui Wang, Christian Heiss, Dale R. Gardner and Parastoo Azadi. Isolation, Characterization, and Quantification of Steroidal Saponins in Switchgrass (Panicum virgatum L.). Journal of Agricultural and Food Chemistry 2009, 57 (6) , 2599-2604. https://doi.org/10.1021/jf803907y
    2. Elizabeth Wina,, Stefan Muetzel, and, Klaus Becker. The Impact of Saponins or Saponin-Containing Plant Materials on Ruminant ProductionA Review. Journal of Agricultural and Food Chemistry 2005, 53 (21) , 8093-8105. https://doi.org/10.1021/jf048053d
    3. Wesley G. Taylor,, M. Shahid Zaman,, Zahir Mir,, Priya S. Mir,, Surya N. Acharya,, Gerald J. Mears, and, James L. Elder. Analysis of Steroidal Sapogenins from Amber Fenugreek (Trigonella foenum-graecum) by Capillary Gas Chromatography and Combined Gas Chromatography/Mass Spectrometry. Journal of Agricultural and Food Chemistry 1997, 45 (3) , 753-759. https://doi.org/10.1021/jf960200n
    4. Jian-Ke Jia, Jun Yang, Xing-Zhi Yang, Ji-Feng Luo, Xiao-Yan Duan, Ying-Li Yang, Jin-Fu Wan, Yue-Hu Wang. Cytotoxic steroidal glycosides from Paris rugosa rhizomes. Phytochemistry Letters 2024, 63 , 1-7. https://doi.org/10.1016/j.phytol.2024.07.011
    5. Jian‐Ke Jia, Jun Yang, Xing‐Zhi Yang, Ji‐Feng Luo, Xiao‐Yan Duan, Ying‐Li Yang, Jin‐Fu Wan, Yue‐Hu Wang. Polyhydroxylated Spirostanol Saponins from the Rhizomes of Paris dulongensis. Chemistry & Biodiversity 2024, 21 (7) https://doi.org/10.1002/cbdv.202400980
    6. Hien Bich Thi Le, Duc Viet Ho, Hien Minh Nguyen, Van Anh Thi Tran, Hoai Thi Nguyen. Aspidiatas C and D, two new spirostanol saponins from Aspidistra triradiata and their cytotoxic activities. Natural Product Research 2024, 38 (5) , 829-837. https://doi.org/10.1080/14786419.2023.2204432
    7. Yan Liu, Yu Bi, Jin-Ting Bai, Si-Yi Wang, Jia-Tong Wu, Yi-Kai Jiang, Peng Jiang, Juan Pan, Wei Guan, Hai-Xue Kuang, Bing-You Yang. Steroidal saponins from the roots of Paris verticillata and their anti-proliferative and anti-inflammatory activities. Phytochemistry 2024, 218 , 113941. https://doi.org/10.1016/j.phytochem.2023.113941
    8. Yang Liu, Na Tang, Qian Zhang, Peng-Cheng Qiu, Hai-Feng Tang, Yun-Yang Lu, Bang-Le Zhang. Cytotoxic steroidal glycosides from the roots of Paris verticillata M.Bieb. Phytochemistry Letters 2023, 53 , 231-238. https://doi.org/10.1016/j.phytol.2023.01.006
    9. Xiu-Xiang Yan, Yan-Qiang Zhao, Yun He, Terd Disayathanoowat, Hataichanok Pandith, Angkhana Inta, Li-Xin Yang. Cytotoxic and pro-apoptotic effects of botanical drugs derived from the indigenous cultivated medicinal plant Paris polyphylla var. yunnanensis. Frontiers in Pharmacology 2023, 14 https://doi.org/10.3389/fphar.2023.1100825
    10. Ling-Ling Yu, Shan Wang, Jie Wang, Huan Yan, Wei Ni, Hai-Yang Liu. Steroidal saponin components and their cancer cell cytotoxicity from Paris rugosa. Phytochemistry 2022, 204 , 113452. https://doi.org/10.1016/j.phytochem.2022.113452
    11. Song-Tao Liu, Huan Yu, A-Jiao Hou, Wen-Jing Man, Jia-Xu Zhang, Song Wang, Xue-Jiao Wang, Sen-Wang Zheng, Xiao-Lin Su, Liu Yang. A Review of the Pharmacology, Application, Ethnopharmacology, Phytochemistry, Quality Control, Processing, Toxicology, and Pharmacokinetics of Paridis Rhizoma. World Journal of Traditional Chinese Medicine 2022, 8 (1) , 21-49. https://doi.org/10.4103/wjtcm.wjtcm_4_21
    12. Kalai Vaani Muniandy, Eric Lim Teik Chung, Mimi Syazwani Jaapar, Muhammad Hazziq Mohd Hamdan, Annas Salleh, Faez Firdaus Abdullah Jesse. Filling the gap of Brachiaria decumbens (signal grass) research on clinico-pathology and haemato-biochemistry in small ruminants: A review. Toxicon 2020, 174 , 26-31. https://doi.org/10.1016/j.toxicon.2019.12.158
    13. Sarah J. Sillman, Stephen T. Lee, Jeff Claborn, Jennifer Boruch, Seth P. Harris. Fall panicum ( Panicum dichotomiflorum ) toxicosis in three juvenile goats. Journal of Veterinary Diagnostic Investigation 2019, 31 (1) , 90-93. https://doi.org/10.1177/1040638718820083
    14. Vittoria Graziani, Monica Scognamiglio, Valentina Belli, Assunta Esposito, Brigida D’Abrosca, Angela Chambery, Rosita Russo, Marta Panella, Aniello Russo, Fortunato Ciardiello, Teresa Troiani, Nicoletta Potenza, Antonio Fiorentino. Metabolomic approach for a rapid identification of natural products with cytotoxic activity against human colorectal cancer cells. Scientific Reports 2018, 8 (1) https://doi.org/10.1038/s41598-018-23704-9
    15. Bui Huu Tai, Nguyen Xuan Nhiem, Vu Van Doan, Pham Hai Yen, Tran Hong Quang, Do Thi Trang, Duong Thi Hai Yen, Nguyen Thi Cuc, Phan Van Kiem. Isolation of spirostanol glycosides from Solanum nigrum. Vietnam Journal of Chemistry 2018, 56 (5) , 548-552. https://doi.org/10.1002/vjch.201800045
    16. Yue-Hu Wang, Min Shi, Hong-Mei Niu, Jun Yang, Meng-Yuan Xia, Ji-Feng Luo, Ying-Jie Chen, Yi-Ping Zhou, Heng Li. Substituting one Paris for another? In vitro cytotoxic and in vivo antitumor activities of Paris forrestii , a substitute of Paris polyphylla var. yunnanensis. Journal of Ethnopharmacology 2018, 218 , 45-50. https://doi.org/10.1016/j.jep.2018.02.022
    17. Hyoung Jae Lee, Bunta Watanabe, Masaru Nakayasu, Michio Onjo, Yukihiro Sugimoto, Masaharu Mizutani. Novel steroidal saponins from Dioscorea esculenta (Togedokoro). Bioscience, Biotechnology, and Biochemistry 2017, 81 (12) , 2253-2260. https://doi.org/10.1080/09168451.2017.1381016
    18. Ahmed A. Zaki, Zulfiqar Ali, Yan-Hong Wang, Yasser A. El-Amier, Shabana I. Khan, Ikhlas A. Khan. Cytotoxic steroidal saponins from Panicum turgidum Forssk. Steroids 2017, 125 , 14-19. https://doi.org/10.1016/j.steroids.2017.06.003
    19. Susan Low. Signal Grass (Brachiaria decumbens) Toxicity in Grazing Ruminants. Agriculture 2015, 5 (4) , 971-990. https://doi.org/10.3390/agriculture5040971
    20. Yan-Shi Wen, Wei Ni, Xu-Jie Qin, Huan Yan, Chang-Xiang Chen, Yan Hua, Yung-Chi Cheng, Li He, Hai-Yang Liu. Steroidal saponins with cytotoxic activity from the rhizomes of Paris polyphylla var. yunnanensis. Phytochemistry Letters 2015, 12 , 31-34. https://doi.org/10.1016/j.phytol.2015.02.011
    21. Chang-Li Sun, Wei Ni, Huan Yan, Zhen-Hua Liu, Lian Yang, Yong-Ai Si, Yan Hua, Chang-Xiang Chen, Li He, Jin-Hua Zhao, Hai-Yang Liu. Steroidal saponins with induced platelet aggregation activity from the aerial parts of Paris verticillata. Steroids 2014, 92 , 90-95. https://doi.org/10.1016/j.steroids.2014.09.008
    22. Ying-Hsin Wang, Hsien-Wei Yeh, Hsiao-Wen Wang, Chia-Chun Yu, Jih-Hwa Guh, Der-Zen Liu, Pi-Hui Liang. Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy. Carbohydrate Research 2013, 375 , 118-135. https://doi.org/10.1016/j.carres.2013.04.022
    23. . Poaceae Barnhart. 2012, 888-997. https://doi.org/10.1002/9781118413425.ch58
    24. Zu-Yin Yu, Lin Guo, Bo Wang, Li-Ping Kang, Zhen-Hu Zhao, Ya-Jun Shan, He Xiao, Jia-Pei Chen, Bai-Ping Ma, Yu-Wen Cong. Structural requirement of spirostanol glycosides for rat uterine contractility and mode of their synergism. Journal of Pharmacy and Pharmacology 2010, 62 (4) , 521-529. https://doi.org/10.1211/jpp.62.04.0016
    25. K. Badiei, K. Mostaghni, S. Nazifi, A. Khodakaram Tafti, M. Ghane, S.A. Momeni. Experimental Panicum miliaceum poisoning in sheep. Small Ruminant Research 2009, 82 (2-3) , 99-104. https://doi.org/10.1016/j.smallrumres.2009.02.002
    26. Franklin Riet-Correa, Mitsue Haraguchi, Antônio F. M. Dantas, Rodrigo G. Burakovas, Akihito Yokosuka, Yoshihiro Mimaki, Rosane M.T. Medeiros, Polyanna F. de Matos. Sheep poisoning by Panicum dichotomiflorum in northeastern Brazil. Pesquisa Veterinária Brasileira 2009, 29 (1) , 94-98. https://doi.org/10.1590/S0100-736X2009000100015
    27. Li‐Ping Kang, Zhi‐Jun Liu, Lei Zhang, Da‐Wei Tan, Yang Zhao, Yu Zhao, He‐Bing Chen, Bai‐Ping Ma. New furostanol saponins from Allium ascalonicum L.. Magnetic Resonance in Chemistry 2007, 45 (9) , 725-733. https://doi.org/10.1002/mrc.2037
    28. A.L. Johnson, TJ. Divers, M.L. Freckleton, H.C. McKenzie, E. Mitchell, J.M. Cullen, S.P. McDonough. Fall Panicum ( Panicum dichotomiflorum ) Hepatotoxicosis in Horses and Sheep. Journal of Veterinary Internal Medicine 2006, 20 (6) , 1414-1421. https://doi.org/10.1111/j.1939-1676.2006.tb00760.x
    29. . Dichotomin, Proto-Pb. 2006, 1028-1029. https://doi.org/10.1007/978-0-387-39572-2_321
    30. Pawan K. Agrawal. Dependence of 1 H NMR chemical shifts of geminal protons of glycosyloxy methylene (H 2 ‐26) on the orientation of the 27‐methyl group of furostane‐type steroidal saponins. Magnetic Resonance in Chemistry 2004, 42 (11) , 990-993. https://doi.org/10.1002/mrc.1474
    31. A.A. Odenyo, P.O. Osuji, O. Karanfil, K. Adinew. Microbiological evaluation of Acacia angustissima as a protein supplement for sheep. Animal Feed Science and Technology 1997, 65 (1-4) , 99-112. https://doi.org/10.1016/S0377-8401(96)01087-5
    32. P. R. Cheeke. Biological Effects of Feed and Forage Saponins and Their Impacts on Animal Production. 1996, 377-385. https://doi.org/10.1007/978-1-4613-0413-5_32
    33. Jan St. Pyrek, Suresht K. Aggarval, Perry Barboza, Jack P. Goodman, Pei-Ying Yang. Metabolites of Nuatigenin ((22S,25S)22,25-Epoxy-3β,26-Dihydroxy-Furost-5-Ene) Accumulate in the Bile of Rabbits Fed Oats. 1996, 443-458. https://doi.org/10.1007/978-1-4899-1367-8_35
    34. A. Flåøyen, B.L. Smith, C.O. Miles. An attempt to reproduce crystal-associated cholangitis in lambs by the experimental dosing of sarsasapogenin or diosgenin alone and in combination with sporidesmin. New Zealand Veterinary Journal 1993, 41 (4) , 171-174. https://doi.org/10.1080/00480169.1993.35764
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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 1993, 41, 2, 267–271
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jf00026a025
    Published February 1, 1993
    Request reuse permissions

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