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Journal articles on the topic 'Stemona alkaloid'

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Author: Grafiati

Published: 4 June 2021

Last updated: 19 February 2022

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1

Yi, Min, Xue Xia, Hoi-Yan Wu, Hai-Yan Tian, Chao Huang, Paul Pui-Hay But, Pang-Chui Shaw, and Ren-Wang Jiang. "Structures and Chemotaxonomic Significance of Stemona Alkaloids from Stemona japonica." Natural Product Communications 10, no. 12 (December 2015): 1934578X1501001. http://dx.doi.org/10.1177/1934578x1501001221.

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A pair of new alkaloid stereo-isomers, stemocochinin (1) and isostemocochinin (2), was obtained from the roots of Stemona japonica Miq., along with seven known alkaloids, stemonamine (3), isostemonamine (4), maistemonine (5), isomaistemonine (6), croomine (7), stemonine (8), and protostemonine (9). The complete structure and stereochemistry of the pair of isomers were established by extensive analysis of the spectral data. Furthermore, our results indicated that S. japonica is chemically closer to S. sessilifolia than S. tuberosa, which are consistent with our previous DNA study on Stemona species.

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2

Sastraruji, Thanapat, Araya Jatisatienr, Kritchaya Issakul, Stephen G. Pyne, Alison T. Ung, Wilford Lie, and Morwenna C. Williams. "Phytochemical Studies on Stemona Plants: Isolation of New Tuberostemonine and Stemofoline Alkaloids." Natural Product Communications 1, no. 10 (October 2006): 1934578X0600101. http://dx.doi.org/10.1177/1934578x0600101001.

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Two new tuberostemonine alkaloids, tuberostemonine L (3) and tuberostemonine M (4) and a new stemofoline alkaloid, (3′S)-hydroxystemofoline (5), along with two known alkaloids, (2′S)-hydroxystemofoline (1) and neotuberostemonine (2) have been isolated from a root extract of an unidentified Stemona species (Stemona sp.). The structure and relative configuration of these new alkaloids has been determined by spectral data interpretation, while the 3′S configuration of 5 was determined from NMR analysis of its (R)- and (S)-Mosher esters.

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3

Wang, Peng, Hai Lin Qin, Zhi Hong Li, Ai Lin Liu, and Guan Hua Du. "A new alkaloid from Stemona sessilifolia." Chinese Chemical Letters 18, no. 2 (February 2007): 152–54. http://dx.doi.org/10.1016/j.cclet.2006.12.007.

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4

Chotikadachanarong, K., S. Dheeranupattana, and A. Jatisatienr. "MICROPROPAGATION AND ALKALOID PRODUCTION IN STEMONA SP." Acta Horticulturae, no. 676 (February 2005): 67–72. http://dx.doi.org/10.17660/actahortic.2005.676.7.

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5

Takeya, Koichi, Yukio Hitotsuyanagi, Maho Hikita, Kazuhiro Nakada, and Haruhiko Fukaya. "Sessilifoliamide I, a New Alkaloid from Stemona sessilifolia." HETEROCYCLES 71, no. 9 (2007): 2035. http://dx.doi.org/10.3987/com-07-11051.

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6

Lin, Li-Gen, Chun-Ping Tang, Pham-Huu Dien, Ren-Sheng Xu, and Yang Ye. "Cochinchistemonine, a novel skeleton alkaloid from Stemona cochinchinensis." Tetrahedron Letters 48, no. 9 (February 2007): 1559–61. http://dx.doi.org/10.1016/j.tetlet.2007.01.013.

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7

Wipf, Peter, Yuntae Kim, and David M. Goldstein. "Asymmetric Total Synthesis of the Stemona Alkaloid (-)-Stenine." Journal of the American Chemical Society 117, no. 45 (November 1995): 11106–12. http://dx.doi.org/10.1021/ja00150a010.

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8

Ramli, Rosdayati Alino, Wilford Lie, and Stephen G. Pyne. "Alkaloids from the Roots and Leaves of Stichoneuron halabalensis and their Acetylcholinesterase Inhibitory Activities." Natural Product Communications 8, no. 6 (June 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800603.

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A study of the hitherto unreported Stichoneuron halabalensis Inthachub led to the characterization of the known compounds (+)-α-tocopherol and ( R)-(+)-goniothalamin; four known Stemona alkaloids, bisdehydoxystemoninine A (1), stemoninine (2), sessilistemonamine C (3) and sessilistemonamine A (4); and three new alkaloids, stichoneurine C (5), D (6) and E (7). The structures of these compounds were determined on the basis of their spectroscopic data. Alkaloid 7 showed significant inhibitory activity against electric eel acetylcholinesterase (AChE) (IC50 5.90±0.084 μM), while goniothalamin and compounds 1 and 2 showed significant inhibitory activities against human AChE (IC50 7.24±0.52, 5.52±0.13 and 3.74±0.09 μM, respectively).

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9

WIPF, P., Y. KIM, and D. M. GOLDSTEIN. "ChemInform Abstract: Asymmetric Total Synthesis of the Stemona Alkaloid (-)-Stenine." ChemInform 27, no. 13 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199613247.

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10

Morimoto, Yoshiki, Maki Iwahashi, Takamasa Kinoshita, and Koji Nishida. "ChemInform Abstract: Stereocontrolled Total Synthesis of the Stemona Alkaloid (-)-Stenine." ChemInform 33, no. 9 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200209221.

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11

Pyne, Stephen G., Christopher W. G. Au, Andrew S. Davis, Ian R. Morgan, Thunwadee Ritthiwigrom, and Arife Yazici. "Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis." Pure and Applied Chemistry 80, no. 4 (January 1, 2008): 751–62. http://dx.doi.org/10.1351/pac200880040751.

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We have demonstrated that the borono-Mannich reaction is a versatile and efficient reaction for the diastereoselective preparation of chiral 1,2-amino alcohols. These Mannich products are valuable starting materials as shown in this report by the synthesis of bioactive polyhydroxylated pyrrolizidine and indolizidine alkaloids. Initial studies, directed at the more complex Stemona alkaloids and using the borono-Mannich reaction on cyclic N-acyliminium ions, are encouraging, as demonstrated by the synthesis of the pyrido[1,2-a]azepine core structure of stemocurtisinol.

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12

Shengule, Sudhir R., Anthony C. Willis, and Stephen G. Pyne. "Model support studies toward the total synthesis of the stemona alkaloid stemocurtisine." Tetrahedron 69, no. 37 (September 2013): 8042–50. http://dx.doi.org/10.1016/j.tet.2013.06.099.

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13

Kongkiatpaiboon, Sumet, Vichien Keeratinijakal, and Wandee Gritsanapan. "TLC-Image Analysis of Non-Chromophoric Tuberostemonine Alkaloid Derivatives in Stemona Species." Natural Product Communications 8, no. 8 (August 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800807.

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A simple, selective, precise, and accurate thin-layer chromatographic (TLC) image analytical method was developed and validated for simultaneous quantification of the major components in the root extracts of Stemona. tuberosa (tuberostemonine, tuberostemonine N and neotuberostemonine)), and S. phyllantha (tuberostemonine and tuberostemonine A). The analysis was performed by TLC on silica gel 60 F254 aluminum plates using a mixture of dichloromethane: ethyl acetate: methanol: ammonium hydroxide (50:45:4:1) as mobile phase. Post-derivatization was employed by dipping the TLC plate into Dragendorff's reagent to visualize the spots. Image analysis of the scanned TLC plate was performed to detect the contents of tuberostemonine derivatives. The polynomial regression data for the calibration plots showed good linear relationships within the concentration range of 2–7 μg/spot. The method gave satisfactory precision, accuracy, selectivity and could simultaneously quantify tuberostemonine, tuberostemonine A, tuberostemonine N and neotuberostemonine. Dried powdered roots of S. tuberosa grown in Thailand contained 1.31 + 0.28, 1.63 + 0.18 and 1.24 + 0.27% tuberostemonine, tuberostemonine N, and neotuberostemonine (dry weight), respectively, while S. phyllantha roots contained 1.39 + 0.14% tuberostemonine and 0.39 + 0.08 % tuberostemonine A (dry weight). The proposed method was simple, inexpensive, and more accessible to apply for many local authorities and small laboratories.

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14

Kongkiatpaiboon, Sumet, and Wandee Gritsanapan. "Optimized extraction for high yield of insecticidal didehydrostemofoline alkaloid in Stemona collinsiae root extracts." Industrial Crops and Products 41 (January 2013): 371–74. http://dx.doi.org/10.1016/j.indcrop.2012.04.047.

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15

Wu, Yan, Liting Ou, Dong Han, Yongbin Tong, Mian Zhang, Xianghong Xu, and Chaofeng Zhang. "Pharmacokinetics, biodistribution and excretion studies of neotuberostemonine, a major bioactive alkaloid of Stemona tuberosa." Fitoterapia 112 (July 2016): 22–29. http://dx.doi.org/10.1016/j.fitote.2016.05.003.

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16

Dheeranupa, Srisulak, and Natthiya Chaichana. "Effects of Sodium Acetate and Sucrose on in vitro Alkaloid Production From Stemona Sp. Culture." Asian Journal of Plant Sciences 12, no. 2 (February 15, 2013): 92–96. http://dx.doi.org/10.3923/ajps.2013.92.96.

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17

Frankowski, K. J., V. Setola, J. M. Evans, B. Neuenswander, B. L. Roth, and J. Aube. "Synthesis and receptor profiling of Stemona alkaloid analogues reveal a potent class of sigma ligands." Proceedings of the National Academy of Sciences 108, no. 17 (February 28, 2011): 6727–32. http://dx.doi.org/10.1073/pnas.1016558108.

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18

G. Pyne, Stephen, and Nalivela Kumara Swamy. "Model Studies Towards the Total Synthesis of the Stemona Alkaloid 1-Hydroxyprotostemonine: Synthesis of ent-1-Hydroxystemoamide." HETEROCYCLES 84, no. 1 (2012): 473. http://dx.doi.org/10.3987/com-11-s(p)8.

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19

Swamy, Nalivela Kumara, and Stephen G. Pyne. "ChemInform Abstract: Model Studies Towards the Total Synthesis of the Stemona Alkaloid 1-Hydroxyprotostemonine: Synthesis of ent-1-Hydroxystemoamide." ChemInform 43, no. 19 (April 12, 2012): no. http://dx.doi.org/10.1002/chin.201219207.

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20

Wang, Feng-Peng, and Qiao-Hong Chen. "Stemona Alkaloids: Biosynthesis, Classification, and Biogenetic Relationships." Natural Product Communications 9, no. 12 (December 2014): 1934578X1400901. http://dx.doi.org/10.1177/1934578x1400901238.

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Stemona alkaloids form a unique class, which can be attributed to hemiterpenoid pyrrolidine- and monoterpenoid pyrrolidine-class alkaloids originated from L-ornithine and glutamic acid. By the end of 2013, approximately 183 Stemona alkaloids had been isolated from nature. The literature on Stemona alkaloids in the realms of chemical structure, synthesis, and bioactivities has been elegantly summarized and reviewed. We thus summarize in this review the biosynthesis, structural classification, and the intrinsic, biogenetic relationships of Stemona alkaloids. Based on the comprehensive consideration of biogenetic pathways and chemical features, the 183 Stemona alkaloids are classified into two classes (hemiterpenoid pyrrolidine- and monoterpenoid pyrrolidine) and fourteen types.

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21

Huang, Sheng-Zhuo, Fan-Dong Kong, Qing-Yun Ma, Zhi-Kai Guo, Li-Man Zhou, Qi Wang, Hao-Fu Dai, and You-Xing Zhao. "Nematicidal Stemona Alkaloids from Stemona parviflora." Journal of Natural Products 79, no. 10 (September 29, 2016): 2599–605. http://dx.doi.org/10.1021/acs.jnatprod.6b00528.

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22

Dong, Jian-Li, Zhong-Duo Yang, Shuang-Yan Zhou, Hai-Tao Yu, Xiao-Jun Yao, Hong-Yan Xue, and Zong-Mei Shu. "Two Stemona alkaloids from Stemona sessilifolia (Miq.) Miq." Phytochemistry Letters 19 (March 2017): 259–62. http://dx.doi.org/10.1016/j.phytol.2017.01.016.

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23

Ye, Yang, Guo-Wei Qin, and Ren-Sheng Xu. "Alkaloids of Stemona japonica." Journal of Natural Products 57, no. 5 (May 1994): 665–69. http://dx.doi.org/10.1021/np50107a019.

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24

Yang, Y. E., Qin Guo-Wei, and Xu Ren-Sheng. "Alkaloids from Stemona tuberosa." Phytochemistry 37, no. 4 (November 1994): 1201–3. http://dx.doi.org/10.1016/s0031-9422(00)89558-8.

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25

Yang, Ye, Qin Guo-Wei, and Xu Ren-Sheng. "Alkaloids of Stemona japonica." Phytochemistry 37, no. 4 (November 1994): 1205–8. http://dx.doi.org/10.1016/s0031-9422(00)89559-x.

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26

Cai, Xiang-Hai, and Xiao-Dong Luo. "Alkaloids from Stemona mairei." Planta Medica 73, no. 2 (February 2007): 170–73. http://dx.doi.org/10.1055/s-2006-957064.

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27

Pham, Huu-Dien, Bing-Wu Yu, Van-Minh Chau, Yang Ye, and Guo-Wei Qin. "Alkaloids from Stemona collinsae." Journal of Asian Natural Products Research 4, no. 2 (January 2002): 81–85. http://dx.doi.org/10.1080/10286020290027344.

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28

Liu, Xiao-Yu, and Feng-Peng Wang. "Recent Advances in the Synthesis of Stemona Alkaloids." Natural Product Communications 10, no. 6 (June 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000674.

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Stemona alkaloids, featuring polycyclic structures and interesting bioactivities, constitute a distinct class from the Stemonaceae family. In this review, recent advances in the synthesis of these unique alkaloids are briefly discussed, highlighting the application of novel synthetic strategies to access the core structures, as well as creative solutions to the installation of multiple stereogenic centers. The literature reviewed in this article covers the publications from 2010 to November 2014, a period that witnessed the prosperity of the synthesis of Stemona alkaloids.

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29

Hitotsuyanagi, Yukio, Genta Shigemori, Haruhiko Fukaya, Maho Hikita, Shu Zhu, Katsuko Komatsu, and Koichi Takeya. "Stemona-amines C–E, new alkaloids from Stemona tuberosa." Tetrahedron Letters 54, no. 51 (December 2013): 6995–98. http://dx.doi.org/10.1016/j.tetlet.2013.10.014.

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30

Yue, Yong, An-Jun Deng, Zhi-Hong Li, Ai-Lin Liu, Lin Ma, Zhi-Hui Zhang, Xiu-Li Wang, Gu-Hua Du, and Hai-Lin Qin. "New Stemona alkaloids from the roots of Stemona tuberosa." Magnetic Resonance in Chemistry 52, no. 11 (June 30, 2014): 719–28. http://dx.doi.org/10.1002/mrc.4099.

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31

Hitotsuyanagi, Yukio, Yoshiyuki Sekiya, Haruhiko Fukaya, Hyun Sun Park, Shu Zhu, and Katsuko Komatsu. "Stemona-amines F and G, new alkaloids from Stemona tuberosa." Tetrahedron Letters 57, no. 51 (December 2016): 5746–49. http://dx.doi.org/10.1016/j.tetlet.2016.10.096.

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32

Lin, Wen-Han, Yang Ye, and Ren-Sheng Xu. "Chemical Studies on New Stemona Alkaloids, IV. Studies on New Alkaloids from Stemona tuberosa." Journal of Natural Products 55, no. 5 (May 1992): 571–76. http://dx.doi.org/10.1021/np50083a003.

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33

Yue, Yong, An-Jun Deng, Dong-Sheng Xu, and Hai-Lin Qin. "Two new stemona alkaloids fromStemona tuberosaLour." Journal of Asian Natural Products Research 15, no. 2 (February 2013): 145–50. http://dx.doi.org/10.1080/10286020.2012.757595.

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34

Fukaya, Haruhiko, Yukio Hitotsuyanagi, Yutaka Aoyagi, Zhu Shu, Katsuko Komatsu, and Koichi Takeya. "Absolute Structures of Stemona-Lactam S and Tuberostemospiroline, Alkaloids from Stemona tuberosa." Chemical and Pharmaceutical Bulletin 61, no. 10 (2013): 1085–89. http://dx.doi.org/10.1248/cpb.c13-00454.

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35

Hitotsuyanagi, Yukio, Genta Shigemori, Haruhiko Fukaya, Maho Hikita, Shu Zhu, Katsuko Komatsu, and Koichi Takeya. "ChemInform Abstract: Stemona-Amines C (Ia) - E (II), New Alkaloids from Stemona tuberosa." ChemInform 45, no. 17 (April 10, 2014): no. http://dx.doi.org/10.1002/chin.201417220.

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36

Pilli, Ronaldo Aloise, Giovanni Bernardi Rosso, and Maria da Conceição Ferreira de Oliveira. "The chemistry of Stemona alkaloids: An update." Natural Product Reports 27, no. 12 (2010): 1908. http://dx.doi.org/10.1039/c005018k.

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37

Pyne, Stephen G., Araya Jatisatienr, Pitchaya Mungkornasawakul, Alison T. Ung, Pornngarm Limtrakul, Thanapat Sastraruji, Kwankamol Sastraruji, et al. "Phytochemical, Synthetic and Biological Studies on Stemona and Stichoneuron Plants and Alkaloids: A Personal Perspective." Natural Product Communications 12, no. 8 (August 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200848.

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38

Lin, Ligen, Han Bao, Anqi Wang, Chunping Tang, Pham-Huu Dien, and Yang Ye. "Two New N-Oxide Alkaloids from Stemona cochinchinensis." Molecules 19, no. 12 (December 3, 2014): 20257–65. http://dx.doi.org/10.3390/molecules191220257.

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39

Hitotsuyanagi, Yukio, Maho Hikita, Takahisa Oda, Daichi Kakuta, Haruhiko Fukaya, and Koichi Takeya. "Structures of four new alkaloids from Stemona sessilifolia." Tetrahedron 63, no. 4 (January 2007): 1008–13. http://dx.doi.org/10.1016/j.tet.2006.11.020.

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40

Williams, David R., David L. Brown, and John W. Benbow. "Studies of Stemona alkaloids. Total synthesis of (+)-croomine." Journal of the American Chemical Society 111, no. 5 (March 1989): 1923–25. http://dx.doi.org/10.1021/ja00187a081.

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41

Han Lin, Wen, Li Ma, Meng Shen Cai, and Roderick A. Barnes. "Two minor alkaloids from roots of Stemona tuberosa." Phytochemistry 36, no. 5 (August 1994): 1333–35. http://dx.doi.org/10.1016/s0031-9422(00)89662-4.

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42

Peng, Shuying, Jianhua Sheng, and Yang Ye. "Mass Spectrometric Behavior of Four Typical Stemona Alkaloids." Chinese Journal of Analytical Chemistry 34, no. 4 (April 2006): 497–503. http://dx.doi.org/10.1016/s1872-2040(06)60027-3.

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43

Zhong, Ying, Ying Gao, Qiu-Ping Guo, and Wei-Min Li. "ChemInform Abstract: Two New Alkaloids from Stemona tuberosa." ChemInform 41, no. 21 (May 25, 2010): no. http://dx.doi.org/10.1002/chin.201021197.

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44

Guo, Aobo, Li Jin, Zhiwei Deng, Shaoqing Cai, Shunxin Guo, and Wenhan Lin. "New Stemona Alkaloids from the Roots ofStemona sessilifolia." Chemistry & Biodiversity 5, no. 4 (April 2008): 598–605. http://dx.doi.org/10.1002/cbdv.200890056.

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45

Greger, Harald. "Structural classification and biological activities of Stemona alkaloids." Phytochemistry Reviews 18, no. 2 (March 19, 2019): 463–93. http://dx.doi.org/10.1007/s11101-019-09602-6.

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46

Shi, Ze-Hui, Zhong-Bo Zhou, Wan-Ning Qin, Jing-Jing Wei, Sai-Sai Xie, Jia-Meng Jiang, Dan Xia, and Ke Pan. "New Stemona alkaloids from the roots of Stemona tuberosa and structural revision of stemonatuberone B." Tetrahedron Letters 61, no. 22 (May 2020): 151925. http://dx.doi.org/10.1016/j.tetlet.2020.151925.

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47

Fukaya, Haruhiko, Yukio Hitotsuyanagi, Yutaka Aoyagi, Zhu Shu, Katsuko Komatsu, and Koichi Takeya. "ChemInform Abstract: Absolute Structures of Stemona-Lactam S (I) and Tuberostemospiroline (II), Alkaloids from Stemona tuberosa." ChemInform 45, no. 16 (April 3, 2014): no. http://dx.doi.org/10.1002/chin.201416224.

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48

Gao, Yu, Jun Wang, Chao-Feng Zhang, Xiang-Hong Xu, Mian Zhang, and Ling-Yi Kong. "Seven new alkaloids from the roots of Stemona tuberosa." Tetrahedron 70, no. 4 (January 2014): 967–74. http://dx.doi.org/10.1016/j.tet.2013.12.003.

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49

Hitotsuyanagi, Yukio, Maho Hikita, Gou Uemura, Haruhiko Fukaya, and Koichi Takeya. "Structures of stemoxazolidinones A–F, alkaloids from Stemona sessilifolia." Tetrahedron 67, no. 2 (January 2011): 455–61. http://dx.doi.org/10.1016/j.tet.2010.11.013.

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50

Hitotsuyanagi, Yukio, Gou Uemura, and Koichi Takeya. "Sessilifoliamides K and L: new alkaloids from Stemona sessilifolia." Tetrahedron Letters 51, no. 43 (October 2010): 5694–96. http://dx.doi.org/10.1016/j.tetlet.2010.08.059.

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