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Cyclic sulfur-containing compounds from Allium fistulosum ‘Kujou’

Journal of Natural Medicines volume 73, pages 397–403 (2019)Cite this article

Abstract

Sulfur-containing compounds, allicin and ajoene, etc., were isolated from Allium species. In a recent study, some sulfur-containing cyclic compounds were isolated from A. sativum, A. cepa, and A. fistulosum. Four new compounds with multiple rings with methyl disulfide or propyl disulfide at the side chain of the 7-position, kujounins A3 (1), B1 (2), B2 (3) and B3 (4), and two new thiolane type compounds with methoxy and methyl sulfoxide moiety at the 2- and 5-positions, and allium sulfoxides A2 (5) and A3 (6), were isolated from the acetone extract of the fresh white parts of Allium fistulosum ‘Kujou’ with three known compounds, kujounin A1 (7) and A2 (8), and allium sulfoxide A1 (9). The chemical structures of the new compounds were elucidated on the basis of physicochemical evidence. The kujounins had a rare molecular skeleton, which was tetrahydro-2H-difuro[3,2-b:2′,3′-c]furan-5(5aH)-one.

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References

  1. Kinjo J, Nakano D, Fujioka T, Okabe H (2016) Screening of promising chemotherapeutic candidates from plants extracts. J Nat Med 70:335–360

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Thomson JS, Rippon P, Butts C, Olsen S, Shaw M, Joyce IN, Eady CC (2013) Inhibition of platelet activation by lachrymatory factor synthase (LFS)-silenced (tearless) onion juice. J Agric Food Chem 61:10574–10581

    Article  CAS  PubMed  Google Scholar 

  3. Elosta A, Slevin M, Rahman K, Ahmed N (2017) Aged garlic has more potent antiglycation and antioxidant properties compared to fresh garlic extract in vitro. Sci Rep 7:39613

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  5. El-Aasr M, Fujiwara Y, Takeya M, Ikeda T, Tsukamoto S, Ono M, Nakano D, Okawa M, Kinjo J, Miyashita H, Yoshimitsu H, Nohara T (2010) Onionin A from Allium cepa inhibits macrophage activation. J Nat Prod 73:1306–1308

    Article  CAS  PubMed  Google Scholar 

  6. 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

    Article  PubMed  Google Scholar 

  7. 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

    Article  CAS  PubMed  Google Scholar 

  8. 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

    Article  CAS  PubMed  Google Scholar 

  9. Fukaya M, Nakamura S, Nakagawa R, Nakashima S, Yamashita M, Matsuda H (2018) Rare sulfur-containing compounds, kujounins A1 and A2 and allium sulfoxide A1, from Allium fistulosum ‘Kujou’. Org Lett 20:28–31

    Article  CAS  PubMed  Google Scholar 

  10. Foroutan-Rad M, Tappeh HK, Khademvatan S (2017) Antileishmanial and immunomodulatory activity of Allium sativum (garlic). J Evid Based Complement Altern Med 22:141–155

    Article  CAS  Google Scholar 

  11. 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

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. 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 onions, impairs tumor development and lung metastasis by inhibiting the protumoral and immunosuppressive functions of myeloid cells. Mol Nutr Food Res 60:2467–2480

    Article  CAS  PubMed  Google Scholar 

  13. Ito T, Tanaka T, Iinuma M, Nakaya K, Takahashi Y, Nakamura H, Hiroshi Naganawa, Riswan S (2003) A new dimeric stilbenoid with a five-membered lactone ring from Shorea hemsleyana. Helv Chim Acta 86:3394–3401

    Article  CAS  Google Scholar 

  14. Robertson PL, Duffy S, Wang Y, Wang D, Avery MV, Carroll RA (2017) Pimentelamines A–C, indole alkaloids isolated from the leaves of the australian tree Flindersia pimenteliana. J Nat Prod 80:3211–3217

    Article  CAS  PubMed  Google Scholar 

  15. Zhao JX, Yu YY, Wang SS, Huang SL, Shen Y, Gao XH, Cheng L, Li JY, Leng Y, Li J, Yue JM (2018) Structural elucidation and bioinspired total syntheses of ascorbylated diterpenoid hongkonoids A–D. J Am Chem Soc 140:2485–2492

    Article  CAS  PubMed  Google Scholar 

  16. Caraballo R, Rahm M, Vongviali P, Brinck T, Ramström O (2008) Phosphine-catalyzed disulfide metathesis. Chem Commun 48:6603–6605

    Article  CAS  Google Scholar 

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Acknowledgements

This research was supported in part by a Ministry of Education, Culture, Sports, Science and Technology (MEXT)-Supported Program for the Strategic Research Foundation at Private Universities 2015–2019 and hoansya. This work was supported by JSPS KAKENHI Grant number 17K08354 (S.N.). The authors thank KOTO KYOTO CO., LTD. for supplying materials.

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Authors and Affiliations

  1. Department of Pharmacognosy, Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, 607-8412, Japan

    Masashi Fukaya, Seikou Nakamura, Ryota Nakagawa, Manami Kinka, Souichi Nakashima & Hisashi Matsuda

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  1. Masashi Fukaya
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  2. Seikou Nakamura
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  3. Ryota Nakagawa
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  4. Manami Kinka
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  5. Souichi Nakashima
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  6. Hisashi Matsuda
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Correspondence to Hisashi Matsuda.

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Fukaya, M., Nakamura, S., Nakagawa, R. et al. Cyclic sulfur-containing compounds from Allium fistulosum ‘Kujou’. J Nat Med 73, 397–403 (2019). https://doi.org/10.1007/s11418-018-1272-0

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  • DOI: https://doi.org/10.1007/s11418-018-1272-0

Keywords

  • Allium fistulosum ‘Kujou’
  • Kujounin
  • Allium sulfoxide
  • Sulfur-containing compound