Abstract
One atypical thiolane-type sulfide, garlicnin I2 (1), two 3,4-dimethylthiolane-type sulfides, garlicnins M (2) and N (3), and one thiabicyclic-type sulfide, garlicnin O (4), were isolated from the acetone extracts of Chinese garlic bulbs, Allium sativum and their structures were characterized. Hypothetical pathways for the production of the respective sulfides were discussed.
References
Theisen C (2001) What ever happened to…? Looking back 10 years. J Natl Cancer Inst 93:1049–1050
Dewick PM (2002) Medicinal natural products. A biosynthetic approach, 2nd edn. Wiley, Chichester
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 22:351–368
Amagase H (2006) Clarifying the real bioactive constituents of garlic. J Nut 136(Suppl):716S–725S
Corzo-Martinerz M, Corzo N, Villamiel M (2007) Diological properties of onion and garlic. Trends Food Sci Technol 18:609–625
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
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 42:717–727
Lewis CE, Pollard JW (2006) Distinct role of macrophages in different tumor microenvironments. Cancer Res 66:605–612
Hagemann T, Biswas SK, Lawrence T, Sica A, Lewis CE (2009) Regulation of macrophage function in tumors: the multifaceted role of NF-KB. Blood 113:3139–3146
Gordon S (2003) Alternative activation of macrophages. Nat Rev Immunol 3:23–35
Joyce JA, Pollard JW (2009) Microenvironmental regulation of metastasis. Nat Rev Cancer 9:239–252
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 18:349–355
Komohara Y, Ohnishi K, Kuratsu J, Takeya M (2008) Possible involvement of the M2 anti-inflammatory macrophage phenotype in growth of human gliomas. J Pathol 216:15–24
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 60:747–751
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 62:477–482
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 59:1340–1343
Nohara T, Fuiiwara 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 61:695–699
Ono M, Fujiwara Y, Ikeda T, Pan C, El-Aasr M, Lee JH, Nakano D, Kinjo J, Nohara T (2017) Atypical cyclic sulfides, Garlicnins G, I, and J, extracted from Allium sativum. Chem Pharm Bull 65:102–106
El-Aasr M, Fujiwara Y, Takeya M, Ikeda T, Tsukamoto S, Ono M, Nakano D, Okawa M, Kinjo J, Yoshimitsu H, Nohara T (2010) Onionin A from Allium cepa inhibits macrophage activation. J Nat Prod 73:1306–1308
Fujiwara Y, Horlad H, Shiraishi D, Tsuboki J, Kudo R, Ikeda T, Nohara T, Takeya M, Komohara Y (2016) Onionin A, a sulfur-containing compound isolated from onion, impairs tumor development and lung metastasis by inhibiting the protumoral and immunosuppressive functions of myeloid cells. Mol Nutr Food Res 60:2467–2480
Tsuboki J, Fujiwara Y, Horlad H, Shiraishi D, Nohara T, Tayama S, Motohara T, Saito Y, Ikeda T, Takaishi K, Tashiro H, Yonemoto Y, Katabuchi H, Takeya M, Komohara Y (2016) Onionin A inhibits ovarian cancer progression by suppressing cancer cell proliferation and the protumour function of macrophages. Sci Rep 6:29588
Nohara T, Fujiwara Y, Ikeda T, Murakami K, Ono M, El-Aasr M, Nakano D, Kinjo J (2016) Two new bicyclic sulfoxides from Welsh onion. J Nat Med 70:260–265
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Nohara, T., Ono, M., Nishioka, N. et al. New cyclic sulfides, garlicnins I2, M, N, and O, from Allium sativum . J Nat Med 72, 326–331 (2018). https://doi.org/10.1007/s11418-017-1133-2
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DOI: https://doi.org/10.1007/s11418-017-1133-2