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Biological activity of Entada phaseoloides and Entada rheedei

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  • In memoriam to Professor Shoji Shibata: Pioneer in Modern Pharmacognosy
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Abstract

The aim of our study is to find functional compounds from natural resources. We focus on plants grown in tropical areas, especially Madagascar and Thailand, because they have unique flora and are expected to contain interesting compounds. We review the functional compounds of the seed kernels of Entada phaseoloides and E. rheedei and their biological activities such as anti-proliferation and melanogenesis inhibitory properties, etc.

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References

  1. Vorontsova MS, Besnard G, Forest F, Malakasi P, Moat J, Clayton WD, Ficinski P, Savva GM, Nanjarisoa OP, Razanatsoa J, Randriatsara FO, Kimeu JM, Luke WRQ, Kayombo C, Linder P (2016) Madagascar’s grasses and grasslands: anthropogenic or natural? Proc R Soc B 283:20152262. https://doi.org/10.1098/rspb.2015.2262

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Myers N, Mittermeier RA, Mittermeier CA, da Fonseca AB, Kent J (2000) Biodiversity hotspots for conservation priorities. Nature 403:853–858. https://doi.org/10.1038/35002501

    Article  CAS  PubMed  Google Scholar 

  3. Office of Natural Resources and Environmental Policy and Planning (2009) National report on the implementation of convention on biological diversity: 4th national report on 2009. Ministry of Natural Resources and Environment, Bangkok

    Google Scholar 

  4. Yamashita-Higuchi Y, Sugimoto S, Matsunami K, Otsuka H (2014) Grevillosides J-Q, arbutin derivatives from the leaves of Grevillea robusta and their melanogenesis inhibitory activity. Chem Pharm Bull 62:364–372. https://doi.org/10.1248/cpb.c13-00962

    Article  CAS  Google Scholar 

  5. Nomoto Y, Harinantenaina L, Sugimoto S, Matsunami K, Otsuka H (2014) 3,4-seco-24-homo-28-nor-Cycloartane and drimane-type sesquiterpenes and their lactams from the EtOAc-soluble fraction of a leaf extract of Cinnamosma fragrans and their biological activity. J Nat Med 68:513–521. https://doi.org/10.1007/s11418-014-0828-x

    Article  CAS  PubMed  Google Scholar 

  6. Nagashima J, Matsunami K, Otsuka H, Lhieochaiphant D, Lhieochaiphant S (2010) The unusual canangafruticosides A-E: five monoterpene glucosides, two monoterpenes and a monoterpene glucoside diester of the aryldihydronaphthalene lignan dicarboxylic acid from leaves of Cananga odorata var. fruticosa. Phytochemistry 71:1564–1572. https://doi.org/10.1016/j.phytochem.2010.06.009

    Article  CAS  PubMed  Google Scholar 

  7. Matsunami K, Nagashima J, Sugimoto S, Otsuka H, Takeda Y, Lhieochaiphant D, Lhieochaiphant S (2010) Megastigmane glucosides and an unusual monoterpene from the leaves of Cananga odorata var. odorata, and absolute structures of megastigmane glucosides isolated from C. odorata var. odorata and Breynia officinalis. J Nat Med 64:460–467. https://doi.org/10.1007/s11418-010-0434-5

    Article  CAS  PubMed  Google Scholar 

  8. Katsui H, Sugimoto S, Matsunami K, Otsuka H, Lhieochaiphant S (2017) Lignan diesters of canangafruticoside a from the leaves of Cananga odorata var. odorata. Chem Pharm Bull 65:97–101. https://doi.org/10.1248/cpb.c16-00611

    Article  CAS  Google Scholar 

  9. Widyowati R, Sugimoto S, Yamano Y, Harjotaruno S, Otsuka H, Matsunami K (2016) New isolinariins C, D and E, flavonoid glycosides from Linaria japonica. Chem Pharm Bull 64:517–521. https://doi.org/10.1248/cpb.c16-00073

    Article  CAS  Google Scholar 

  10. Samy MN, Fahim JR, Sugimoto S, Otsuka H, Matsunami K, Kamel MS (2017) Chodatiionosides A and B: two new megastigmane glycosides from Chorisia chodatii leaves. J Nat Med 71:321–328. https://doi.org/10.1007/s11418-016-1052-7

    Article  CAS  PubMed  Google Scholar 

  11. Kitamura S, Murata G (1971) Gensyokunihonsyokubutsuzukan. Hoikusha 1:362

    Google Scholar 

  12. Barua AK (1956) Triterpenoids. III. The constitution of entagenic acid. Naturwissenschaften 43:250. https://doi.org/10.1007/BF00617587

    Article  CAS  Google Scholar 

  13. Barua AK, Chakrabarti P, Pal SK, Das B (1983) The structure and stereochemistry of entagenic acid. J Indian Chem Soc 47:195–198

    Google Scholar 

  14. Okada Y, Shibata S, Kamo O, Okuyama T (1988) Carbon-13 NMR spectral studies of entagenic acid to establish its structure. Chem Pharm Bull 36:5028–5030. https://doi.org/10.1248/cpb.36.5028

    Article  CAS  Google Scholar 

  15. Ikegami F, Shibasaki I, Ohmiya S, Ruangrungsi N, Murakoshi I (1985) Entadamide A, a new sulfur-containing amide from Entada phaseoloides seeds. Chem Pharm Bull 33:5153–5154. https://doi.org/10.1248/cpb.33.5153

    Article  CAS  Google Scholar 

  16. Ikegami F, Ohmiya S, Ruangrungsi N, Sakai S, Murakoshi I (1987) Entadamide B, a second new sulfur-containing amide from Entada phaseoloides. Phytochemistry 26:1525–1526. https://doi.org/10.1016/S0031-9422(00)81850-6

    Article  CAS  Google Scholar 

  17. Ikegami F, Sekine T, Duangteraprecha S, Matsushita N, Matsuda N, Ruangrungsi N, Murakoshi I (1989) Entadamide C, a sulfur-containing amide from Entada phaseoloides. Phytochemistry 28:881–882. https://doi.org/10.1016/0031-9422(89)80135-9

    Article  CAS  Google Scholar 

  18. Murakoshi I, Kidoguchi E, Kubota M, Haginiwa J, Ohmiya S, Otomatsu H (1982) Lupine alkaloids from Echinosophora koreensis. Phytochemistry 21:2385–2388. https://doi.org/10.1016/0031-9422(82)85211-4

    Article  CAS  Google Scholar 

  19. Okada Y, Shibata S, Ikekawa T, Javellana AMJ, Kamo O (1987) Entada saponin III, a saponin isolated from the bark of Entada phaseoloides. Phytochemistry 26:2789–2796. https://doi.org/10.1016/S0031-9422(00)83592-X

    Article  CAS  Google Scholar 

  20. Bergsteinsson I, Noller CR (1934) Saponins and sapogenins. I. Echinocystic acid. J Am Chem Soc 56:1403–1405. https://doi.org/10.1021/ja01321a059

    Article  CAS  Google Scholar 

  21. Noller CR, Carson JF (1941) Saponins and sapogenins. XIX. The decarboxylation of echinocystic acid. J Am Chem Soc 63:2238–2239. https://doi.org/10.1021/ja01853a059

    Article  CAS  Google Scholar 

  22. Okada Y, Shibata S, Ikekawa T, Javellana AMJ, Kamo O (1988) Entada saponins (ES) II and IV from the bark of Entada phaseollides. Chem Pharm Bull 36:1264–1269. https://doi.org/10.1248/cpb.36.1264

    Article  CAS  Google Scholar 

  23. Dai J, Kardono LBS, Tsauri S, Padmawinata K, Pezzuto JM, Kinghorn AD (1991) Studies on Indonesian medicinal plants. Part 3. Phenylacetic acid derivatives and a thioamide glycoside from Entada phaseoloides. Phytochemistry 30:3749–3752. https://doi.org/10.1016/0031-9422(91)80102-7

    Article  CAS  Google Scholar 

  24. Chen L, Zhang Y, Ding G, Ba M, Guo Y, Zou Z (2013) Two new derivatives of 2,5-dihydroxyphenylacetic acid from the kernel of Entada phaseoloides. Molecules 18:1477–1482. https://doi.org/10.3390/molecules18021477

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Freiburghaus F, Steck A, Pfander H, Brun R (1998) Bioassay-guided isolation of a diastereoisomer of kolavenol from Entada abyssinica active on Trypanosoma brucei rhodesiense. J Ethnopharmacol 61:179–183. https://doi.org/10.1016/S0378-8741(98)00035-X

    Article  CAS  PubMed  Google Scholar 

  26. Zheng T, Hao X, Wang Q, Chen L, Jin S, Bian F (2016) Entada phaseoloides extract suppresses hepatic gluconeogenesis via activation of the AMPK signaling pathway. J Ethnopharmacol 193:691–699. https://doi.org/10.1016/j.jep.2016.10.039

    Article  CAS  PubMed  Google Scholar 

  27. Xiong H, Zheng Y, Yang G, Wang H, Mei Z (2015) Triterpene saponins with anti-inflammatory activity from the stems of Entada phaseoloides. Fitoterapia 103:33–45. https://doi.org/10.1016/j.fitote.2015.03.001

    Article  CAS  PubMed  Google Scholar 

  28. Xing S, Wang M, Peng Y, Dong Y, Li X (2015) Intestinal bacterial metabolism and anti-complement activities of three major components of the seeds of Entada phaseoloides. J Nat Med 69:171–177. https://doi.org/10.1007/s11418-014-0874-4

    Article  CAS  PubMed  Google Scholar 

  29. Xiong H, Mei Z, Yang G, Mo S, Yang X, Zhang P, Wu J (2013) Triterpene saponins from Entada phaseoloides. Helv Chim Acta 96:1579–1589. https://doi.org/10.1002/hlca.201200491

    Article  CAS  Google Scholar 

  30. Mo S, Xiong H, Shu G, Yang X, Wang J, Zheng C, Xiang W, Mei Z (2013) Phaseoloideside E, a novel natural triterpenoid saponin identified from Entada phaseoloides, induces apoptosis in Ec-109 esophageal cancer cells through reactive oxygen species generation. J Pharmacol Sci 122:163–175. https://doi.org/10.1254/jphs.12193FP

    Article  CAS  PubMed  Google Scholar 

  31. Dong Y, Shi H, Yang H, Peng Y, Wang M, Li X (2012) Antioxidant phenolic compounds from the stems of Entada phaseoloides. Chem Biodivers 9:68–79. https://doi.org/10.1002/cbdv.201100002

    Article  CAS  PubMed  Google Scholar 

  32. Nzowa LK, Barboni L, Teponno RB, Ricciutelli M, Lupidi G, Quassinti L, Bramucci M, Tapondjou LA (2010) Rheediinosides A and B, two antiproliferative and antioxidant triterpene saponins from Entada rheedii. Phytochemistry 71:254–261. https://doi.org/10.1016/j.2009.10.004

    Article  CAS  PubMed  Google Scholar 

  33. Iwamoto Y, Sugimoto S, Harinantenaina L, Matsunami K, Otsuka H (2012) Entadosides A-D, triterpene saponins and a glucoside of the sulphur-containing amide from the kernel nuts of Entada phaseoloides (L.) Merrill. J Nat Med 66:321–328. https://doi.org/10.1007/s11418-011-0591-1

    Article  CAS  PubMed  Google Scholar 

  34. Dash SK, Padhy S (2006) Review on ethnomedicines for diarrhoea diseases from Orissa: prevalence versus culture. J Hum Ecol 20:59–64

    Article  Google Scholar 

  35. Uprety Y, Asselin H, Boon EK, Yadav S, Shrestha KKJ (2010) Indigenous uses and bio-efficacy of medicinal plants in Rasuwa district, Central Nepal. J Ethnobiol Ethnomed 6:3. https://doi.org/10.1186/1746-4269-6-3

    Article  PubMed  PubMed Central  Google Scholar 

  36. Tunsaringkarn T, Rungsiyothin A, Ruangrungsi N (2008) α-Glucosidase inhibitory activity of Thai mimosaceous plant extracts. J Health Res 22:29–33

    CAS  Google Scholar 

  37. Nzowa LK, Teponno RB, Tapondjou LA, Verotta L, Liao Z, Graham D, Zink MC, Barboni L (2013) Two new tryptophan derivatives from the seed kernels of Entada rheedei: effects on cell viability and HIV infectivity. Fitoterapia 87:37–42. https://doi.org/10.1016/j.fitote.2013.03.017

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. Sugimoto S, Matsunami K, Otsuka H (2011) Medicinal plants of Thailand. I: structures of rheedeiosides A-D and cis-entadamide A β-D-glucopyranoside from the seed kernels of Entada rheedei. Chem Pharm Bull 59:466–471. https://doi.org/10.1248/cpb.59.466

    Article  CAS  Google Scholar 

  39. Sugimoto S, Matsunami K, Otsuka H (2012) Medicinal plants of Thailand. II: chemical studies on the seed kernels of Entada rheedei Sprengel. J Nat Med 66:552–557. https://doi.org/10.1007/s11418-011-0608-9

    Article  CAS  PubMed  Google Scholar 

  40. Newman DJ, Cragg GM (2016) Natural products as sources of new drugs from 1981 to 2014. J Nat Prod 79:629–661. https://doi.org/10.1021/acs.jnatprod.5b01055

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

The authors are grateful for access to the superconducting NMR instrument (JEOL JNM-LA500 and ECA-600K) and the Thermo Fisher Scientific LTQ Orbitrap XL mass spectrometer at the Natural Science Center for Basic Research and Development, Hiroshima University. This work was supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology of Japan, and the Japan Society for the Promotion of Science. Thanks are also due to the Takeda Science Foundation for financial support.

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Authors and Affiliations

  1. Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima, 734-8553, Japan

    Sachiko Sugimoto & Katsuyoshi Matsunami

  2. Faculty of Pharmacy, Yasuda Women’s University, 6-13-1 Yasuhigashi, Asaminami-ku, Hiroshima, 731-0153, Japan

    Hideaki Otsuka

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  1. Sachiko Sugimoto
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Correspondence to Hideaki Otsuka.

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Sugimoto, S., Matsunami, K. & Otsuka, H. Biological activity of Entada phaseoloides and Entada rheedei . J Nat Med 72, 12–19 (2018). https://doi.org/10.1007/s11418-017-1146-x

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