Top

Published in:

01-01-2018 | Review

Biological activity of Entada phaseoloides and Entada rheedei

Authors: Sachiko Sugimoto, Katsuyoshi Matsunami, Hideaki Otsuka

Published in: Journal of Natural Medicines | Issue 1/2018

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.

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 CrossRefPubMedPubMedCentral

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 CrossRefPubMed

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

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 CrossRef

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 CrossRefPubMed

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 CrossRefPubMed

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 CrossRefPubMed

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 CrossRef

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 CrossRef

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 CrossRefPubMed

11.

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

12.

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

13.

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

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 CrossRef

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 CrossRef

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 CrossRef

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 CrossRef

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 CrossRef

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 CrossRef

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 CrossRef

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 CrossRef

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 CrossRef

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 CrossRef

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 CrossRefPubMedPubMedCentral

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 CrossRefPubMed

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 CrossRefPubMed

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 CrossRefPubMed

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 CrossRefPubMed

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 CrossRef

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 CrossRefPubMed

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 CrossRefPubMed

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 CrossRefPubMed

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 CrossRefPubMed

34.

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

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 CrossRefPubMedPubMedCentral

36.

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

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 CrossRefPubMedPubMedCentral

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 CrossRef

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 CrossRefPubMed

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 CrossRefPubMed

Title: Biological activity of Entada phaseoloides and Entada rheedei
Authors: Sachiko Sugimoto
Katsuyoshi Matsunami
Hideaki Otsuka
Publication date: 01-01-2018
Publisher: Springer Singapore
Published in: Journal of Natural Medicines / Issue 1/2018
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-017-1146-x

At a glance: The STEP trials

Springer Medicine

Biological activity of Entada phaseoloides and Entada rheedei

Abstract

At a glance: The STEP trials

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 1/2018

Effect of oleuropein on cognitive deficits and changes in hippocampal brain-derived neurotrophic factor and cytokine expression in a rat model of post-traumatic stress disorder

Evaluation of raw nepodin extraction from Rumex japonicus and R. obtusifolius and their DNA polymorphisms

Piperine-like alkamides from Piper nigrum induce BDNF promoter and promote neurite outgrowth in Neuro-2a cells

18β-glycyrrhetinic acid inhibits migration and invasion of human gastric cancer cells via the ROS/PKC-α/ERK pathway

A novel mode of stimulating platelet formation activity in megakaryocytes with peanut skin extract

Oviposition inhibitor in umbelliferous medicinal plants for the common yellow swallowtail (Papilio machaon)