Skip to main content
Log in

Glyceollin, a soybean phytoalexin with medicinal properties

  • Mini-Review
  • Published:
Applied Microbiology and Biotechnology Aims and scope Submit manuscript

Abstract

This review covers the biosynthesis of glyceollin and its biological activities including antiproliferative/antitumor action (toward B16 melanoma cells, LNCaP prostate cancer cells, and BG-1 ovarian cancer cells), anti-estrogenic action (through estrogen receptors α- and β-), antibacterial action (toward Erwinia carotovora, Escherichia coli, Bradyrhizobium japonicum, Sinorhizobium fredii ), antinematode activity, and antifungal activity (toward Fusarium solani, Phakospora pachyrhizi, Diaporthe phaseolorum, Macrophomina phaseolina, Sclerotina sclerotiorum, Phytophthora sojae, Cercospora sojina, Phialophora gregata, and Rhizoctonia solani). Other activities include insulinotropic action and attenuation of vascular contractions in rat aorta.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1

Similar content being viewed by others

References

  • Akashi T, Sasaki K, Aoki T, Ayabe S, Yazaki K (2009) Molecular cloning and characterization of a cDNA for pterocarpan 4-dimethylallyltransferase catalyzing the key prenylation step in the biosynthesis of glyceollin, a soybean phytoalexin. Plant Physiol 149:683–693

    Article  CAS  Google Scholar 

  • Boué SM, Raina AK (2003) Effects of plant flavonoids on fecundity, survival, and feeding of the Formosan subterranean termite. J Chem Ecol 29:2575–2584

    Article  Google Scholar 

  • Boué SM, Tilghman SL, Elliott S, Zimmerman MC, Williams KY, Payton-Stewart F, Miraflor AP, Howell MH, Shih BY, Carter-Wientjes CH, Segar C, Beckman BS, Wiese TE, Cleveland TE, McLachlan JA, Burow ME (2009) Identification of the potent phytoestrogen glycinol in elicited soybean (Glycine max). Endocrinology 150:2446–2453

    Article  Google Scholar 

  • Boydston R, Paxton JD, Koeppe DE (1983) Glyceollin: a site-specific inhibitor of electron transport in isolated soybean mitochondria. Plant Physiol 72:151–155

    Article  CAS  Google Scholar 

  • Burow ME, Boue SM, Collins-Burow BM, Melnik LI, Duong BN, Carter-Wientjes CH, Li S, Wiese TE, Cleveland TE, McLachlan JA (2001) Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor alpha and beta. J Clin Endocrinol Metab 86:1750–1758

    Article  CAS  Google Scholar 

  • Cline JM, Wood CE (2009) Estrogen/isoflavone interactions in cynomolgus macaques (Macaca fascicularis). Am J Primatol 71:722–731

    Article  CAS  Google Scholar 

  • Dann EK, Diers BW, Hammerschmidt R (1999) Suppression of sclerotinia stem rot of soybean by lactofen herbicide treatment. Phytopathology 89:598–602

    Article  CAS  Google Scholar 

  • Fliegmann J, Schüler G, Boland W, Ebel J, Mithöfer A (2003) The role of octadecanoids and functional mimics in soybean defense responses. Biol Chem 384:437–446

    Article  CAS  Google Scholar 

  • Giannini JL, Holt JS, Briskin DP (1988) Isolation of sealed plasma membrane vesicles from Phytophthora megasperma f. sp. glycinea: II. Partial characterization of Ca2+ transport and glyceollin effects. Arch Biochem Biophys 266:644–649

    Article  CAS  Google Scholar 

  • Graham MY (2005) The diphenylether herbicide lactofen induces cell death and expression of defense-related genes in soybean. Plant Physiol 139:1784–1794

    Article  CAS  Google Scholar 

  • Huang JS, Barker KR (1991) Glyceollin I in soybean-cyst nematode interactions: spatial and temporal distribution in roots of resistant and susceptible soybeans. Plant Physiol 96:1302–1307

    Article  CAS  Google Scholar 

  • Khupse RS, Erhardt PW (2008) Total syntheses of racemic, natural (−) and unnatural (+) glyceollin I. Org Lett 10:5007–5010

    Article  CAS  Google Scholar 

  • Kim HJ, Suh HJ, Lee CH, Kim JH, Kang SC, Park S, Kim JS (2010) Antifungal activity of glyceollins isolated from soybean elicited with Aspergillus sojae. J Agric Food Chem 58:9483–9487

    Article  CAS  Google Scholar 

  • Landini S, Graham MY, Graham TL (2003) Lactofen induces isoflavone accumulation and glyceollin elicitation competency in soybean. Phytochemistry 62:865–874

    Google Scholar 

  • Lee MR, Kim JY, Chun J, Park S, Kim HJ, Kim JS, Jeong JI, Kim JH (2010a) Induction of glyceollins by fungal infection in varieties of Korean soybean. J Microbiol Biotechnol 20:1226–1229

    Article  CAS  Google Scholar 

  • Lee YS, Kim HK, Lee KJ, Jeon HW, Cui S, Lee YM, Moon BJ, Kim YH, Lee YS (2010b) Inhibitory effect of glyceollin isolated from soybean against melanogensis in B16 melanoma cells. BMB Rep 43:461–467

    Article  CAS  Google Scholar 

  • Lozovaya VV, Lygin AV, Zernova OV, Li S, Hartman GL, Widholm JM (2004) Isoflavonoid accumulation in soybean hairy roots upon treatment with Fusarium solani. Plant Physiol Biochem 42:671–679

    Article  CAS  Google Scholar 

  • Lygin AV, Li S, Vittal R, Widholm JM, Hartman GL, Lozovaya VV (2009) The importance of phenolic metabolism to limit the growth of Phakopsora pachyrhizi. Phytopathology 99:1412–1420

    Article  CAS  Google Scholar 

  • Lygin AV, Hill CB, Zernova OV, Crull L, Widholm JM, Hartman GL, Lozovaya VV (2010) Response of soybean pathogens to glyceollin. Phytopathology 100:897–903

    Article  CAS  Google Scholar 

  • Mithöfer A, Fliegmann J, Daxberger A, Ebel C, Neuhaus-Url G, Bhagwat AA, Keister DL, Ebel J (2001) Induction of H(2)O(2) synthesis by beta-glucan elicitors in soybean is independent of cytosolic calcium transients. FEBS Lett 508:191–195

    Article  Google Scholar 

  • Park S, Ahn IS, Kim JH, Lee MR, Kim JS, Kim HJ (2010) Glyceollins, one of the phytoalexins derived from soybeans under fungal stress, enhance insulin sensitivity and exert insulinotropic actions. J Agric Food Chem 58:1551–1557

    Article  CAS  Google Scholar 

  • Parniske M, Ahlborn B, Werner D (1991) Isoflavonoid-inducible resistance to the phytoalexin glyceollin in soybean rhizobia. J Bacteriol 173:3432–3439

    CAS  Google Scholar 

  • Payton-Stewart F, Khupse RS, Boué SM, Elliott S, Zimmermann CM, Skripnikova EV, Ashe H, Tilghman SL, Beckman BS, Cleveland TE, McLachlan JA, Bhatnagar D, Wiese TE, Erhardt P, Burow ME (2010) Glyceollin I enantiomers distinctly regulate ER-mediated gene expression. Steroids 75(12):870–878

    Article  CAS  Google Scholar 

  • Qi Y, Moco S, Boeren S, De Vos CH, Bovy A (2005) Isolation and identification of glycinol from Glycine max L. Merri Article in Chinese Se Pu 23:353–357

    CAS  Google Scholar 

  • Salvo VA, Boué SM, Fonseca JP, Elliott S, Corbitt C, Collins-Burow BM, Curiel TJ, Srivastav SK, Shih BY, Carter-Wientjes C, Wood CE, Erhardt PW, Beckman BS, McLachlan JA, Cleveland TE, Burow ME (2006) Antiestrogenic glyceollins suppress human breast and ovarian carcinoma tumorigenesis. Clin Cancer Res 12:7159–7164

    Article  CAS  Google Scholar 

  • Song MJ, Baek I, Jeon SB, Seo M, Kim YH, Cui S, Jeong YS, Lee IJ, Shin DH, Hwang YH, Kim IK (2010) Effects of glyceollin I on vascular contraction in rat aorta. Naunyn Schmiedebergs Arch Pharmacol 381:517–528

    Article  CAS  Google Scholar 

  • Stäb MR, Ebel J (1987) Effects of Ca2+ on phytoalexin induction by fungal elicitor in soybean cells. Arch Biochem Biophys 257:416–423

    Article  Google Scholar 

  • Veech JA (1982) Phytoalexins and their role in the resistance of plants to nematodes. J Nematol 14:2–9

    CAS  Google Scholar 

  • Weinstein LI, Albersheim P (1983) Host-pathogen interactions: XXIII. The mechanism of the antibacterial action of glycinol, a pterocarpan phytoalexin synthesized by soybeans. Plant Physiol 72:557–563

    Article  CAS  Google Scholar 

  • Welle R, Schröder G, Schiltz E, Grisebach H, Schröder J (1991) Induced plant responses to pathogen attack. Analysis and heterologous expression of the key enzyme in the biosynthesis of phytoalexins in soybean (Glycine max L. Merr. cv. Harosoy 63). Eur J Biochem 196:423–430

    Article  CAS  Google Scholar 

  • Wood CE, Clarkson TB, Appt SE, Franke AA, Boue SM, Burow ME, McCoy T, Cline JM (2006) Effects of soybean glyceollins and estradiol in postmenopausal female monkeys. Nutr Cancer 56:74–81

    Article  CAS  Google Scholar 

  • Yazaki K, Sasaki K, Tsurumaru Y (2009) Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochemistry 70:1739–1745

    Article  CAS  Google Scholar 

  • Zimmermann MC, Tilghman SL, Boué SM, Salvo VA, Elliott S, Williams KY, Skripnikova EV, Ashe H, Payton-Stewart F, Vanhoy-Rhodes L, Fonseca JP, Corbitt C, Collins-Burow BM, Howell MH, Lacey M, Shih BY, Carter-Wientjes C, Cleveland TE, McLachlan JA, Wiese TE, Beckman BS, Burow ME (2010) Glyceollin I, a novel antiestrogenic phytoalexin isolated from activated soy. J Pharmacol Exp Ther 332:35–45

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The award of a direct grant by Medicine Panel, CUHK Research Committee is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Tzi Bun Ng or Xiu Yun Ye.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ng, T.B., Ye, X.J., Wong, J.H. et al. Glyceollin, a soybean phytoalexin with medicinal properties. Appl Microbiol Biotechnol 90, 59–68 (2011). https://doi.org/10.1007/s00253-011-3169-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00253-011-3169-7

Navigation