Top

Published in:

01-04-2016 | Note

Two new bicyclic sulfoxides from Welsh onion

Authors: Toshihiro Nohara, Yukio Fujiwara, Tsuyoshi Ikeda, Kotaro Murakami, Masateru Ono, Mona El-Aasr, Daisuke Nakano, Junei Kinjo

Published in: Journal of Natural Medicines | Issue 2/2016

Abstract

Newly identified bicyclic sulfoxides, welsonins A₁ (1) and A₂ (2), were isolated from acetone extracts of the bulbs of the Welsh onion (Allium fistulosum). In this study, the structures of 1 and 2, which are tetrahydrothiophene-S-oxide derivatives, were characterized by spectroscopic analysis. These compounds appeared to be derived from the coupling of 1-propenyl sulfenic acid and uronic acid. Welsonin A₁ (1) showed the potential to suppress tumor-cell proliferation by inhibiting the polarization of alternatively activated M2 macrophages.

Theisen C (2001) What ever happened to…? Looking back 10 years. J Natl Cancer Inst 93:1049–1050CrossRefPubMed

Rose P, Whiteman M, Moore PK, Zhu YZ (2005) Bioactive S-alk(en)yl cysteine sulfoxide metabolites in the genus Allium: the chemistry of potential therapeutic agents. Nat Prod Rep 22:351–368CrossRefPubMed

Amagase H (2006) Clarifying the real bioactivie constituents of garlic. J Nut 136(Suppl):716S–725S

Block E (2010) Garlic and other alliums: the lore and science. The Royal Society of Chemistry, Cambridge, UK

Dewick PM (2002) Medicinal natural products. A biosynthetic approach, 2nd edn. Wiley, Chichester, UK

El-Aasr M, Fujiwara Y, Takeya M, Ono M, Nakano D, Okawa M, Kinjo J, Ikeda T, Miyashita H, Yoshimitsu H, Nohara T (2011) Garlicnin A from the fraction regulating macrophage activation of Allium sativum. Chem Pharm Bull 59:1340–1343CrossRefPubMed

Nohara T, Kiyota Y, Sakamoto T, Manabe H, Ono M, Ikeda T, Fujiwara Y, Nakano D, Kinjo J (2012) Garlicnins B₁, C₁, and D, from the fraction regulating macrophage activation of Allium sativum. Chem Pharm Bull 60:747–751CrossRefPubMed

Nohara T, Fujiwara Y, Ikeda T, Murakami K, Ono M, Nakano D, Kinjo J (2013) Cyclic sulfoxides garlicnins B₂, B₃, B₄, C₂, and C₃ from Allium sativum. Chem Pharm Bull 61:695–699CrossRefPubMed

Nohara T, Fuiiwara Y, Ikeda T, Yamaguchi K, Manabe H, Murakami K, Ono M, Nakano D, Kinjo J (2014) Acyclic sulfides, garlicnins L-1-L-4, E, and F, from Allium sativum. Chem Pharm Bull 62:477–482CrossRefPubMed

10.

Nohara T, Fujiwara Y, Komota Y, Kondo Y, Saku T, Yamaguchi K, Komohara Y, Takeya M (2015) Cyclic sulfoxides-garlicnins K₁, K₂, and H₁-extracted from Allium sativum. Chem Pharm Bull 63:117–121CrossRefPubMed

11.

El-Aasr M, Fujiwara Y, Takeya M, Ikeda T, Tsukamoto S, Ono M, Nakano D, Okawa M, Kinjo J, Yoshimitsu H, Nohara T (2010) J Nat Prod 73:1306–1308CrossRefPubMed

12.

Nohara T, Fuiiwara Y, Kudo R, Yamaguchi K, Ikeda T, Murakami K, Ono M, Kajimoto T, Takeya M (2014) Isolation and characterization of new onionins A₂ and A₃ from Allium cepa, and onionins A₁, A₂, and A₃ from Allium fistulosum. Chem Pharm Bull 62:1142–1145

13.

Mantovani A, Schioppa T, Biswas SK, Marchesi F, Allavena P, Sica A (2003) Tumor associated macrophages and dendritic cells as prototypic type II polarized myeloid populations. Tumor 89:459–468

14.

Sica A, Schioppa T, Mantovani A, Allavena P (2006) Tumor-associated macrophages are a distinct M2 polarised population promoting tumour progression: potential targets of anti-cancer therapy. Eur J Cancer 42:717–727CrossRefPubMed

15.

Lewis CE, Pollard JW (2006) Distinct role of macrophages in different tumor microenvironments. Cancer Res 66:605–612CrossRefPubMed

16.

Hagemann T, Biswas SK, Lawrence T, Sica A, Lewis CE (2009) Regulation of macrophage function in tumors: the multifaceted role of NF-_KB. Blood 113:3139–3146PubMedCentralCrossRefPubMed

17.

Gordon S (2003) Alternative activation of macrophages. Nat Rev Immunol 3:23–35CrossRefPubMed

18.

Joyce JA, Pollard JW (2009) Microenvironmental regulation of metastasis. Nat Rev Cancer 9:239–252PubMedCentralCrossRefPubMed

19.

Sica A, Larghi P, Mancino A, Rubino L, Porta C, Totaro MG, Rimoldi M, Biswas SK, Allavena P, Mantovani A (2008) Macrophage polarization in tumour progression. Semin Cancer Biol 18:349–355CrossRefPubMed

20.

Juaristi E, Cruz-Sanchez JS, Petson A, Glass RS (1988) Conformational preference of the S=O group. 3. Continued evidence for a very strong S–S=O anomeric interaction from the NMR spectroscopic study 4,4,5,5-tetramethyl-1,2- dithiane-1-oxide. Tetrahedron 44:5653–5660CrossRef

21.

Ronayne J, Williams DH (1967) The mechanism of solvent shifts of proton resonances induced by benzene. J Chem Soc B 540–546

22.

Johnson CR, McCants D (1964) Equilibration of 4-substituted thiane 1-oxides. J Am Chem Soc 86:2935–2936CrossRef

23.

Martin JC, Uebel JJ (1964) Conformational equilibria and solvolyses of six-membered ring sulfoxide derivatives. J Am Chem Soc 86:2936–2937CrossRef

24.

Lambert JB, Keske RG (1966) Equilibrium conformations of thiane 1-oxide (pentamethylene sulfoxide). J Org Chem 31:3429–3431CrossRef

25.

Fujiwara Y, Komohara Y, Ikeda T, Takeya M (2011) Corosolic acid inhibits glioblastoma cell proliferation by suppressing the activation of STAT3 and NF-κB in tumor cells and tumor-associated macrophages. Cancer Sci 102:206–211CrossRefPubMed

Title: Two new bicyclic sulfoxides from Welsh onion
Authors: Toshihiro Nohara
Yukio Fujiwara
Tsuyoshi Ikeda
Kotaro Murakami
Masateru Ono
Mona El-Aasr
Daisuke Nakano
Junei Kinjo
Publication date: 01-04-2016
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 2/2016
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-015-0947-z

At a glance: The STEP trials

Springer Medicine

Two new bicyclic sulfoxides from Welsh onion

Abstract

At a glance: The STEP trials

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 2/2016

Composition of the endophytic filamentous fungi associated with Cinchona ledgeriana seeds and production of Cinchona alkaloids

Anti-osteoporotic effects of Pueraria candollei var. mirifica on bone mineral density and histomorphometry in estrogen-deficient rats

Optimization of combinations of ginsenoside-Rg1, ginsenoside-Rb1, evodiamine and rutaecarpine for effective therapy of mouse migraine

The renoprotective effect of shichimotsukokato on hypertension-induced renal dysfunction in spontaneously hypertensive rats

Chemical composition, aroma evaluation, and inhibitory activity towards acetylcholinesterase of essential oils from Gynura bicolor DC.

Comparative analysis of the constituents in Saposhnikoviae Radix and Glehniae Radix cum Rhizoma by monitoring inhibitory activity of nitric oxide production