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Thiolane-type sulfides from garlic, onion, and Welsh onion
In this paper, we review our work in the last 10 years wherein we examined the sulfides in the acetone extracts of garlic ( Allium sativum ), onion ( A. cepa ), and Welsh onion ( A. fistulosum ), obtained and characterized the structures of new sulfides, three 3,4-dimethylthiolane-type sulfides from...
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| Published in: | Journal of natural medicines 2021-09, Vol.75 (4), p.741-751 |
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| Main Authors: | , , , , , , |
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| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c564t-e532d30ad32e601ffdbdd38c42067e6eb46b5497f4527e3059cc9aecf54af6fb3 |
| container_end_page | 751 |
| container_issue | 4 |
| container_start_page | 741 |
| container_title | Journal of natural medicines |
| container_volume | 75 |
| creator | Nohara, Toshihiro Fujiwara, Yukio El-Aasr, Mona Ikeda, Tsuyoshi Ono, Masateru Nakano, Daisuke Kinjo, Junei |
| description | In this paper, we review our work in the last 10 years wherein we examined the sulfides in the acetone extracts of garlic (
Allium sativum
), onion (
A. cepa
), and Welsh onion (
A. fistulosum
), obtained and characterized the structures of new sulfides, three 3,4-dimethylthiolane-type sulfides from onion and Welsh onion, respectively, and four acyclic-type, nine 3,4-dimethyl- thiolane-type, four 2-methylthiolane (and thiane)-type, two 1,2-dithiolane-type, and two 2-oxothiolane-type sulfides, together with (
E
)-ajoene and one kujounin-type sulfide from garlic. During this process, structural corrections were made in onionin A group, garlicnin A, and garlicnin B group in some 3,4-dimethylthiolane-type sulfides. Next, hypothetical pathways for the production of the aforementioned sulfides were proposed. Furthermore, it was revealed that a typical 3,4-dimethylthiolane-type sulfide, onionin A
1
obtained from onion, having the isomeric structure of garlicnin B
1
obtained from garlic, decreased tumor proliferation and controlled tumor metastasis. These results showed that onionin A
1
is an effective agent for controlling tumors, and that the antitumor effects observed in vivo are likely caused by reversing the antitumor immune system. Activation of the antitumor immune system by onionin A
1
might be an effective adjuvant therapy for patients with osteosarcoma, ovarian cancer and other malignant tumors. |
| doi_str_mv | 10.1007/s11418-021-01533-x |
| format | article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8397685</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2565483195</sourcerecordid><originalsourceid>FETCH-LOGICAL-c564t-e532d30ad32e601ffdbdd38c42067e6eb46b5497f4527e3059cc9aecf54af6fb3</originalsourceid><addsrcrecordid>eNp9kctO5DAQRS3EiPcPsECR2MyCDLbLdhIWSCPEYySk2TRiaTlOuTsoHTd2B8Hf455A81jMynbVqVu-uoQcMvqLUVqcRsYEK3PKWU6ZBMifN8gOK1V68go20x0EzUEI2Ca7MT5QKjgA2yLbqV4yXrAdcjaZtb4zPebLlwVmcehc22DMXPDzbGpC19qTzPet708y0zfZPXZxNhb2yQ9nuogHb-ceubu6nFzc5Ld_r_9c_L7NrVRimaME3gA1DXBUlDnX1E0DpRWcqgIV1kLVUlSFE5IXCFRW1lYGrZPCOOVq2CPno-5iqOfYWOyXwXR6Edq5CS_am1Z_7fTtTE_9ky6hKlQpk8DPN4HgHweMSz1vo8VuZdsPUXMJqqSMV1VCj7-hD34IfbKXKCVFCaxaCfKRssHHGNCtP8OoXkWjx2h0ikb_i0Y_p6GjzzbWI-9ZJABGIKZWP8Xwsfs_sq_mb5ot</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2565483195</pqid></control><display><type>article</type><title>Thiolane-type sulfides from garlic, onion, and Welsh onion</title><source>Springer Link</source><creator>Nohara, Toshihiro ; Fujiwara, Yukio ; El-Aasr, Mona ; Ikeda, Tsuyoshi ; Ono, Masateru ; Nakano, Daisuke ; Kinjo, Junei</creator><creatorcontrib>Nohara, Toshihiro ; Fujiwara, Yukio ; El-Aasr, Mona ; Ikeda, Tsuyoshi ; Ono, Masateru ; Nakano, Daisuke ; Kinjo, Junei</creatorcontrib><description>In this paper, we review our work in the last 10 years wherein we examined the sulfides in the acetone extracts of garlic (
Allium sativum
), onion (
A. cepa
), and Welsh onion (
A. fistulosum
), obtained and characterized the structures of new sulfides, three 3,4-dimethylthiolane-type sulfides from onion and Welsh onion, respectively, and four acyclic-type, nine 3,4-dimethyl- thiolane-type, four 2-methylthiolane (and thiane)-type, two 1,2-dithiolane-type, and two 2-oxothiolane-type sulfides, together with (
E
)-ajoene and one kujounin-type sulfide from garlic. During this process, structural corrections were made in onionin A group, garlicnin A, and garlicnin B group in some 3,4-dimethylthiolane-type sulfides. Next, hypothetical pathways for the production of the aforementioned sulfides were proposed. Furthermore, it was revealed that a typical 3,4-dimethylthiolane-type sulfide, onionin A
1
obtained from onion, having the isomeric structure of garlicnin B
1
obtained from garlic, decreased tumor proliferation and controlled tumor metastasis. These results showed that onionin A
1
is an effective agent for controlling tumors, and that the antitumor effects observed in vivo are likely caused by reversing the antitumor immune system. Activation of the antitumor immune system by onionin A
1
might be an effective adjuvant therapy for patients with osteosarcoma, ovarian cancer and other malignant tumors.</description><identifier>ISSN: 1340-3443</identifier><identifier>EISSN: 1861-0293</identifier><identifier>DOI: 10.1007/s11418-021-01533-x</identifier><identifier>PMID: 34081271</identifier><language>eng</language><publisher>Singapore: Springer Singapore</publisher><subject>Allium cepa ; Allium fistulosum ; Allium sativum ; Antioxidants ; Antitumor activity ; Biological Products ; Biomedical and Life Sciences ; Biomedicine ; Complementary & Alternative Medicine ; Garlic ; Humans ; Immune system ; Medicinal Chemistry ; Metastases ; Onions ; Osteosarcoma ; Ovarian cancer ; Pharmacology/Toxicology ; Pharmacy ; Plant Sciences ; Review ; Sulfides ; Thiolane ; Tumors</subject><ispartof>Journal of natural medicines, 2021-09, Vol.75 (4), p.741-751</ispartof><rights>The Author(s) 2021</rights><rights>2021. The Author(s).</rights><rights>The Author(s) 2021. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c564t-e532d30ad32e601ffdbdd38c42067e6eb46b5497f4527e3059cc9aecf54af6fb3</citedby><cites>FETCH-LOGICAL-c564t-e532d30ad32e601ffdbdd38c42067e6eb46b5497f4527e3059cc9aecf54af6fb3</cites><orcidid>0000-0001-6221-5128</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34081271$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nohara, Toshihiro</creatorcontrib><creatorcontrib>Fujiwara, Yukio</creatorcontrib><creatorcontrib>El-Aasr, Mona</creatorcontrib><creatorcontrib>Ikeda, Tsuyoshi</creatorcontrib><creatorcontrib>Ono, Masateru</creatorcontrib><creatorcontrib>Nakano, Daisuke</creatorcontrib><creatorcontrib>Kinjo, Junei</creatorcontrib><title>Thiolane-type sulfides from garlic, onion, and Welsh onion</title><title>Journal of natural medicines</title><addtitle>J Nat Med</addtitle><addtitle>J Nat Med</addtitle><description>In this paper, we review our work in the last 10 years wherein we examined the sulfides in the acetone extracts of garlic (
Allium sativum
), onion (
A. cepa
), and Welsh onion (
A. fistulosum
), obtained and characterized the structures of new sulfides, three 3,4-dimethylthiolane-type sulfides from onion and Welsh onion, respectively, and four acyclic-type, nine 3,4-dimethyl- thiolane-type, four 2-methylthiolane (and thiane)-type, two 1,2-dithiolane-type, and two 2-oxothiolane-type sulfides, together with (
E
)-ajoene and one kujounin-type sulfide from garlic. During this process, structural corrections were made in onionin A group, garlicnin A, and garlicnin B group in some 3,4-dimethylthiolane-type sulfides. Next, hypothetical pathways for the production of the aforementioned sulfides were proposed. Furthermore, it was revealed that a typical 3,4-dimethylthiolane-type sulfide, onionin A
1
obtained from onion, having the isomeric structure of garlicnin B
1
obtained from garlic, decreased tumor proliferation and controlled tumor metastasis. These results showed that onionin A
1
is an effective agent for controlling tumors, and that the antitumor effects observed in vivo are likely caused by reversing the antitumor immune system. Activation of the antitumor immune system by onionin A
1
might be an effective adjuvant therapy for patients with osteosarcoma, ovarian cancer and other malignant tumors.</description><subject>Allium cepa</subject><subject>Allium fistulosum</subject><subject>Allium sativum</subject><subject>Antioxidants</subject><subject>Antitumor activity</subject><subject>Biological Products</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Complementary & Alternative Medicine</subject><subject>Garlic</subject><subject>Humans</subject><subject>Immune system</subject><subject>Medicinal Chemistry</subject><subject>Metastases</subject><subject>Onions</subject><subject>Osteosarcoma</subject><subject>Ovarian cancer</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><subject>Plant Sciences</subject><subject>Review</subject><subject>Sulfides</subject><subject>Thiolane</subject><subject>Tumors</subject><issn>1340-3443</issn><issn>1861-0293</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kctO5DAQRS3EiPcPsECR2MyCDLbLdhIWSCPEYySk2TRiaTlOuTsoHTd2B8Hf455A81jMynbVqVu-uoQcMvqLUVqcRsYEK3PKWU6ZBMifN8gOK1V68go20x0EzUEI2Ca7MT5QKjgA2yLbqV4yXrAdcjaZtb4zPebLlwVmcehc22DMXPDzbGpC19qTzPet708y0zfZPXZxNhb2yQ9nuogHb-ceubu6nFzc5Ld_r_9c_L7NrVRimaME3gA1DXBUlDnX1E0DpRWcqgIV1kLVUlSFE5IXCFRW1lYGrZPCOOVq2CPno-5iqOfYWOyXwXR6Edq5CS_am1Z_7fTtTE_9ky6hKlQpk8DPN4HgHweMSz1vo8VuZdsPUXMJqqSMV1VCj7-hD34IfbKXKCVFCaxaCfKRssHHGNCtP8OoXkWjx2h0ikb_i0Y_p6GjzzbWI-9ZJABGIKZWP8Xwsfs_sq_mb5ot</recordid><startdate>20210901</startdate><enddate>20210901</enddate><creator>Nohara, Toshihiro</creator><creator>Fujiwara, Yukio</creator><creator>El-Aasr, Mona</creator><creator>Ikeda, Tsuyoshi</creator><creator>Ono, Masateru</creator><creator>Nakano, Daisuke</creator><creator>Kinjo, Junei</creator><general>Springer Singapore</general><general>Springer Nature B.V</general><scope>C6C</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-6221-5128</orcidid></search><sort><creationdate>20210901</creationdate><title>Thiolane-type sulfides from garlic, onion, and Welsh onion</title><author>Nohara, Toshihiro ; Fujiwara, Yukio ; El-Aasr, Mona ; Ikeda, Tsuyoshi ; Ono, Masateru ; Nakano, Daisuke ; Kinjo, Junei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c564t-e532d30ad32e601ffdbdd38c42067e6eb46b5497f4527e3059cc9aecf54af6fb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Allium cepa</topic><topic>Allium fistulosum</topic><topic>Allium sativum</topic><topic>Antioxidants</topic><topic>Antitumor activity</topic><topic>Biological Products</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Complementary & Alternative Medicine</topic><topic>Garlic</topic><topic>Humans</topic><topic>Immune system</topic><topic>Medicinal Chemistry</topic><topic>Metastases</topic><topic>Onions</topic><topic>Osteosarcoma</topic><topic>Ovarian cancer</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><topic>Plant Sciences</topic><topic>Review</topic><topic>Sulfides</topic><topic>Thiolane</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nohara, Toshihiro</creatorcontrib><creatorcontrib>Fujiwara, Yukio</creatorcontrib><creatorcontrib>El-Aasr, Mona</creatorcontrib><creatorcontrib>Ikeda, Tsuyoshi</creatorcontrib><creatorcontrib>Ono, Masateru</creatorcontrib><creatorcontrib>Nakano, Daisuke</creatorcontrib><creatorcontrib>Kinjo, Junei</creatorcontrib><collection>Springer Nature OA Free Journals</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of natural medicines</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nohara, Toshihiro</au><au>Fujiwara, Yukio</au><au>El-Aasr, Mona</au><au>Ikeda, Tsuyoshi</au><au>Ono, Masateru</au><au>Nakano, Daisuke</au><au>Kinjo, Junei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiolane-type sulfides from garlic, onion, and Welsh onion</atitle><jtitle>Journal of natural medicines</jtitle><stitle>J Nat Med</stitle><addtitle>J Nat Med</addtitle><date>2021-09-01</date><risdate>2021</risdate><volume>75</volume><issue>4</issue><spage>741</spage><epage>751</epage><pages>741-751</pages><issn>1340-3443</issn><eissn>1861-0293</eissn><abstract>In this paper, we review our work in the last 10 years wherein we examined the sulfides in the acetone extracts of garlic (
Allium sativum
), onion (
A. cepa
), and Welsh onion (
A. fistulosum
), obtained and characterized the structures of new sulfides, three 3,4-dimethylthiolane-type sulfides from onion and Welsh onion, respectively, and four acyclic-type, nine 3,4-dimethyl- thiolane-type, four 2-methylthiolane (and thiane)-type, two 1,2-dithiolane-type, and two 2-oxothiolane-type sulfides, together with (
E
)-ajoene and one kujounin-type sulfide from garlic. During this process, structural corrections were made in onionin A group, garlicnin A, and garlicnin B group in some 3,4-dimethylthiolane-type sulfides. Next, hypothetical pathways for the production of the aforementioned sulfides were proposed. Furthermore, it was revealed that a typical 3,4-dimethylthiolane-type sulfide, onionin A
1
obtained from onion, having the isomeric structure of garlicnin B
1
obtained from garlic, decreased tumor proliferation and controlled tumor metastasis. These results showed that onionin A
1
is an effective agent for controlling tumors, and that the antitumor effects observed in vivo are likely caused by reversing the antitumor immune system. Activation of the antitumor immune system by onionin A
1
might be an effective adjuvant therapy for patients with osteosarcoma, ovarian cancer and other malignant tumors.</abstract><cop>Singapore</cop><pub>Springer Singapore</pub><pmid>34081271</pmid><doi>10.1007/s11418-021-01533-x</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-6221-5128</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | Journal of natural medicines, 2021-09, Vol.75 (4), p.741-751 |
| issn | 1340-3443 1861-0293 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8397685 |
| source | Springer Link |
| subjects | Allium cepa Allium fistulosum Allium sativum Antioxidants Antitumor activity Biological Products Biomedical and Life Sciences Biomedicine Complementary & Alternative Medicine Garlic Humans Immune system Medicinal Chemistry Metastases Onions Osteosarcoma Ovarian cancer Pharmacology/Toxicology Pharmacy Plant Sciences Review Sulfides Thiolane Tumors |
| title | Thiolane-type sulfides from garlic, onion, and Welsh onion |
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