Inhibitory Effects of Cucurbitane Glycosides and Other Triterpenoids from the Fruit of Momordica grosvenori on Epstein−Barr Virus Early Antigen Induced by Tumor Promoter 12-O-Tetradecanoylphorbol-13-acetate
Two new triterpene benzoates, 5-dehydrokarounidiol dibenzoate (1) and karounidiol dibenzoate (2), and two new triterpene glycosides, 5α,6α-epoxymogroside IE1 (8) and 11-oxomogroside A1 (9), along with 15 known triterpenoids (one triterpene benzoate, 3; three triterpene mono-ols, 4−6; one triterpene...
Gespeichert in:
| Veröffentlicht in: | Journal of agricultural and food chemistry 2002-11, Vol.50 (23), p.6710-6715 |
|---|---|
| Hauptverfasser: | , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 6715 |
|---|---|
| container_issue | 23 |
| container_start_page | 6710 |
| container_title | Journal of agricultural and food chemistry |
| container_volume | 50 |
| creator | Ukiya, Motohiko Akihisa, Toshihiro Tokuda, Harukuni Toriumi, Masakazu Mukainaka, Teruo Banno, Norihiro Kimura, Yumiko Hasegawa, Jun-ichi Nishino, Hoyoku |
| description | Two new triterpene benzoates, 5-dehydrokarounidiol dibenzoate (1) and karounidiol dibenzoate (2), and two new triterpene glycosides, 5α,6α-epoxymogroside IE1 (8) and 11-oxomogroside A1 (9), along with 15 known triterpenoids (one triterpene benzoate, 3; three triterpene mono-ols, 4−6; one triterpene aglycon, 7; and 10 triterpene glycosides, 10−19), were isolated from the ethanol extract of the fruit of Momordica grosvenori. The structures of 1, 2, 8, and 9 were determined on the basis of spectroscopic and chemical methods. Among the known triterpene glycosides, mogroside I E1 (12) was a new naturally occurring compound. Eighteen triterpenoids (2−19) and 11-oxomogrol (20), a hydrolysis product of 9, were evaluated with respect to their inhibitory effects on the induction of Epstein−Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor promoters. All of the compounds tested showed potent inhibitory effects on EBV-EA induction (70−100% inhibition at 1 × 103 mol ratio/TPA). Keywords: Momordica grosvenori; fruit; Cucurbitaceae; sweet principle; triterpenoids; cucurbitane glycosides; antitumor promoter; Epstein−Barr virus early antigen |
| doi_str_mv | 10.1021/jf0206320 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_19188559</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>19188559</sourcerecordid><originalsourceid>FETCH-LOGICAL-a446t-439a0f77fe88cb0672ab6f33358a45091b5d25d0c78e9226bb303a0f200dadac3</originalsourceid><addsrcrecordid>eNptkc1u1DAURiMEokNhwQsgb0BiEfBPnGSW7XQ6jCiaiga2lmM7HQ8ZO712EHkD1jwZz8CT4GpGZcPK0r3H50rfl2UvCX5HMCXvdx2muGQUP8pmhFOcc0Lqx9kMp2Ve85KcZM9C2GGMa17hp9kJoQXmVVnOst9rt7WtjR4mtOw6o2JAvkOLUY2QxtIZtOon5YPVJiDpNNrErQHUgI0GBuO81QF14PcozdEljDbeCz75vQdtlUS34MP3xIFF3qHlEKKx7s_PX-cSAH21MAa0lNBP6MxFe2scWjs9KqNRO6FmTBZ0new-XUOE5pu8MRGkNko6P_XD1kPr-5ywXCoTZTTPsyed7IN5cXxPsy-Xy2bxIb_arNaLs6tcFkUZ84LNJe6qqjN1rVpcVlS2ZccY47UsOJ6TlmvKNVZVbeaUlm3LMEs_KMZaaqnYafbm4B3A340mRLG3QZm-T5H5MQgyJ3XN-TyBbw-gSkEEMJ0YwO4lTIJgcV-feKgvsa-O0rHdG_2PPPaVgPwA2BTjj4e9hG-irFjFRXN9I25WF6vPH8-ZuEj86wMvVRA7P4JLmfzn8F-2IbTB</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>19188559</pqid></control><display><type>article</type><title>Inhibitory Effects of Cucurbitane Glycosides and Other Triterpenoids from the Fruit of Momordica grosvenori on Epstein−Barr Virus Early Antigen Induced by Tumor Promoter 12-O-Tetradecanoylphorbol-13-acetate</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Ukiya, Motohiko ; Akihisa, Toshihiro ; Tokuda, Harukuni ; Toriumi, Masakazu ; Mukainaka, Teruo ; Banno, Norihiro ; Kimura, Yumiko ; Hasegawa, Jun-ichi ; Nishino, Hoyoku</creator><creatorcontrib>Ukiya, Motohiko ; Akihisa, Toshihiro ; Tokuda, Harukuni ; Toriumi, Masakazu ; Mukainaka, Teruo ; Banno, Norihiro ; Kimura, Yumiko ; Hasegawa, Jun-ichi ; Nishino, Hoyoku</creatorcontrib><description>Two new triterpene benzoates, 5-dehydrokarounidiol dibenzoate (1) and karounidiol dibenzoate (2), and two new triterpene glycosides, 5α,6α-epoxymogroside IE1 (8) and 11-oxomogroside A1 (9), along with 15 known triterpenoids (one triterpene benzoate, 3; three triterpene mono-ols, 4−6; one triterpene aglycon, 7; and 10 triterpene glycosides, 10−19), were isolated from the ethanol extract of the fruit of Momordica grosvenori. The structures of 1, 2, 8, and 9 were determined on the basis of spectroscopic and chemical methods. Among the known triterpene glycosides, mogroside I E1 (12) was a new naturally occurring compound. Eighteen triterpenoids (2−19) and 11-oxomogrol (20), a hydrolysis product of 9, were evaluated with respect to their inhibitory effects on the induction of Epstein−Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor promoters. All of the compounds tested showed potent inhibitory effects on EBV-EA induction (70−100% inhibition at 1 × 103 mol ratio/TPA). Keywords: Momordica grosvenori; fruit; Cucurbitaceae; sweet principle; triterpenoids; cucurbitane glycosides; antitumor promoter; Epstein−Barr virus early antigen</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf0206320</identifier><identifier>PMID: 12405766</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>11-Oxomogroside A1 ; 5-dehydrokarounidiol dibenzoate ; 5^a,6^a-Epoxymogroside IE1 ; Antigens, Viral - biosynthesis ; Antigens, Viral - drug effects ; Chromatography, Gas ; Chromatography, High Pressure Liquid ; Epstein-Barr virus ; Fruit - chemistry ; Glycosides - isolation & purification ; Glycosides - pharmacology ; karounidiol dibenzoate ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Momordica - chemistry ; Momordica grosvenori ; Tetradecanoylphorbol Acetate - pharmacology ; Triterpenes - chemistry ; Triterpenes - isolation & purification ; Triterpenes - pharmacology ; triterpenoids</subject><ispartof>Journal of agricultural and food chemistry, 2002-11, Vol.50 (23), p.6710-6715</ispartof><rights>Copyright © 2002 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a446t-439a0f77fe88cb0672ab6f33358a45091b5d25d0c78e9226bb303a0f200dadac3</citedby><cites>FETCH-LOGICAL-a446t-439a0f77fe88cb0672ab6f33358a45091b5d25d0c78e9226bb303a0f200dadac3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf0206320$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf0206320$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12405766$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ukiya, Motohiko</creatorcontrib><creatorcontrib>Akihisa, Toshihiro</creatorcontrib><creatorcontrib>Tokuda, Harukuni</creatorcontrib><creatorcontrib>Toriumi, Masakazu</creatorcontrib><creatorcontrib>Mukainaka, Teruo</creatorcontrib><creatorcontrib>Banno, Norihiro</creatorcontrib><creatorcontrib>Kimura, Yumiko</creatorcontrib><creatorcontrib>Hasegawa, Jun-ichi</creatorcontrib><creatorcontrib>Nishino, Hoyoku</creatorcontrib><title>Inhibitory Effects of Cucurbitane Glycosides and Other Triterpenoids from the Fruit of Momordica grosvenori on Epstein−Barr Virus Early Antigen Induced by Tumor Promoter 12-O-Tetradecanoylphorbol-13-acetate</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Two new triterpene benzoates, 5-dehydrokarounidiol dibenzoate (1) and karounidiol dibenzoate (2), and two new triterpene glycosides, 5α,6α-epoxymogroside IE1 (8) and 11-oxomogroside A1 (9), along with 15 known triterpenoids (one triterpene benzoate, 3; three triterpene mono-ols, 4−6; one triterpene aglycon, 7; and 10 triterpene glycosides, 10−19), were isolated from the ethanol extract of the fruit of Momordica grosvenori. The structures of 1, 2, 8, and 9 were determined on the basis of spectroscopic and chemical methods. Among the known triterpene glycosides, mogroside I E1 (12) was a new naturally occurring compound. Eighteen triterpenoids (2−19) and 11-oxomogrol (20), a hydrolysis product of 9, were evaluated with respect to their inhibitory effects on the induction of Epstein−Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor promoters. All of the compounds tested showed potent inhibitory effects on EBV-EA induction (70−100% inhibition at 1 × 103 mol ratio/TPA). Keywords: Momordica grosvenori; fruit; Cucurbitaceae; sweet principle; triterpenoids; cucurbitane glycosides; antitumor promoter; Epstein−Barr virus early antigen</description><subject>11-Oxomogroside A1</subject><subject>5-dehydrokarounidiol dibenzoate</subject><subject>5^a,6^a-Epoxymogroside IE1</subject><subject>Antigens, Viral - biosynthesis</subject><subject>Antigens, Viral - drug effects</subject><subject>Chromatography, Gas</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Epstein-Barr virus</subject><subject>Fruit - chemistry</subject><subject>Glycosides - isolation & purification</subject><subject>Glycosides - pharmacology</subject><subject>karounidiol dibenzoate</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Momordica - chemistry</subject><subject>Momordica grosvenori</subject><subject>Tetradecanoylphorbol Acetate - pharmacology</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - isolation & purification</subject><subject>Triterpenes - pharmacology</subject><subject>triterpenoids</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1u1DAURiMEokNhwQsgb0BiEfBPnGSW7XQ6jCiaiga2lmM7HQ8ZO712EHkD1jwZz8CT4GpGZcPK0r3H50rfl2UvCX5HMCXvdx2muGQUP8pmhFOcc0Lqx9kMp2Ve85KcZM9C2GGMa17hp9kJoQXmVVnOst9rt7WtjR4mtOw6o2JAvkOLUY2QxtIZtOon5YPVJiDpNNrErQHUgI0GBuO81QF14PcozdEljDbeCz75vQdtlUS34MP3xIFF3qHlEKKx7s_PX-cSAH21MAa0lNBP6MxFe2scWjs9KqNRO6FmTBZ0new-XUOE5pu8MRGkNko6P_XD1kPr-5ywXCoTZTTPsyed7IN5cXxPsy-Xy2bxIb_arNaLs6tcFkUZ84LNJe6qqjN1rVpcVlS2ZccY47UsOJ6TlmvKNVZVbeaUlm3LMEs_KMZaaqnYafbm4B3A340mRLG3QZm-T5H5MQgyJ3XN-TyBbw-gSkEEMJ0YwO4lTIJgcV-feKgvsa-O0rHdG_2PPPaVgPwA2BTjj4e9hG-irFjFRXN9I25WF6vPH8-ZuEj86wMvVRA7P4JLmfzn8F-2IbTB</recordid><startdate>20021106</startdate><enddate>20021106</enddate><creator>Ukiya, Motohiko</creator><creator>Akihisa, Toshihiro</creator><creator>Tokuda, Harukuni</creator><creator>Toriumi, Masakazu</creator><creator>Mukainaka, Teruo</creator><creator>Banno, Norihiro</creator><creator>Kimura, Yumiko</creator><creator>Hasegawa, Jun-ichi</creator><creator>Nishino, Hoyoku</creator><general>American Chemical Society</general><scope>BSCLL</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>7U9</scope><scope>H94</scope></search><sort><creationdate>20021106</creationdate><title>Inhibitory Effects of Cucurbitane Glycosides and Other Triterpenoids from the Fruit of Momordica grosvenori on Epstein−Barr Virus Early Antigen Induced by Tumor Promoter 12-O-Tetradecanoylphorbol-13-acetate</title><author>Ukiya, Motohiko ; Akihisa, Toshihiro ; Tokuda, Harukuni ; Toriumi, Masakazu ; Mukainaka, Teruo ; Banno, Norihiro ; Kimura, Yumiko ; Hasegawa, Jun-ichi ; Nishino, Hoyoku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a446t-439a0f77fe88cb0672ab6f33358a45091b5d25d0c78e9226bb303a0f200dadac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>11-Oxomogroside A1</topic><topic>5-dehydrokarounidiol dibenzoate</topic><topic>5^a,6^a-Epoxymogroside IE1</topic><topic>Antigens, Viral - biosynthesis</topic><topic>Antigens, Viral - drug effects</topic><topic>Chromatography, Gas</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Epstein-Barr virus</topic><topic>Fruit - chemistry</topic><topic>Glycosides - isolation & purification</topic><topic>Glycosides - pharmacology</topic><topic>karounidiol dibenzoate</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Momordica - chemistry</topic><topic>Momordica grosvenori</topic><topic>Tetradecanoylphorbol Acetate - pharmacology</topic><topic>Triterpenes - chemistry</topic><topic>Triterpenes - isolation & purification</topic><topic>Triterpenes - pharmacology</topic><topic>triterpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ukiya, Motohiko</creatorcontrib><creatorcontrib>Akihisa, Toshihiro</creatorcontrib><creatorcontrib>Tokuda, Harukuni</creatorcontrib><creatorcontrib>Toriumi, Masakazu</creatorcontrib><creatorcontrib>Mukainaka, Teruo</creatorcontrib><creatorcontrib>Banno, Norihiro</creatorcontrib><creatorcontrib>Kimura, Yumiko</creatorcontrib><creatorcontrib>Hasegawa, Jun-ichi</creatorcontrib><creatorcontrib>Nishino, Hoyoku</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ukiya, Motohiko</au><au>Akihisa, Toshihiro</au><au>Tokuda, Harukuni</au><au>Toriumi, Masakazu</au><au>Mukainaka, Teruo</au><au>Banno, Norihiro</au><au>Kimura, Yumiko</au><au>Hasegawa, Jun-ichi</au><au>Nishino, Hoyoku</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibitory Effects of Cucurbitane Glycosides and Other Triterpenoids from the Fruit of Momordica grosvenori on Epstein−Barr Virus Early Antigen Induced by Tumor Promoter 12-O-Tetradecanoylphorbol-13-acetate</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2002-11-06</date><risdate>2002</risdate><volume>50</volume><issue>23</issue><spage>6710</spage><epage>6715</epage><pages>6710-6715</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>Two new triterpene benzoates, 5-dehydrokarounidiol dibenzoate (1) and karounidiol dibenzoate (2), and two new triterpene glycosides, 5α,6α-epoxymogroside IE1 (8) and 11-oxomogroside A1 (9), along with 15 known triterpenoids (one triterpene benzoate, 3; three triterpene mono-ols, 4−6; one triterpene aglycon, 7; and 10 triterpene glycosides, 10−19), were isolated from the ethanol extract of the fruit of Momordica grosvenori. The structures of 1, 2, 8, and 9 were determined on the basis of spectroscopic and chemical methods. Among the known triterpene glycosides, mogroside I E1 (12) was a new naturally occurring compound. Eighteen triterpenoids (2−19) and 11-oxomogrol (20), a hydrolysis product of 9, were evaluated with respect to their inhibitory effects on the induction of Epstein−Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor promoters. All of the compounds tested showed potent inhibitory effects on EBV-EA induction (70−100% inhibition at 1 × 103 mol ratio/TPA). Keywords: Momordica grosvenori; fruit; Cucurbitaceae; sweet principle; triterpenoids; cucurbitane glycosides; antitumor promoter; Epstein−Barr virus early antigen</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>12405766</pmid><doi>10.1021/jf0206320</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8561 |
| ispartof | Journal of agricultural and food chemistry, 2002-11, Vol.50 (23), p.6710-6715 |
| issn | 0021-8561 1520-5118 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_19188559 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | 11-Oxomogroside A1 5-dehydrokarounidiol dibenzoate 5^a,6^a-Epoxymogroside IE1 Antigens, Viral - biosynthesis Antigens, Viral - drug effects Chromatography, Gas Chromatography, High Pressure Liquid Epstein-Barr virus Fruit - chemistry Glycosides - isolation & purification Glycosides - pharmacology karounidiol dibenzoate Magnetic Resonance Spectroscopy Mass Spectrometry Momordica - chemistry Momordica grosvenori Tetradecanoylphorbol Acetate - pharmacology Triterpenes - chemistry Triterpenes - isolation & purification Triterpenes - pharmacology triterpenoids |
| title | Inhibitory Effects of Cucurbitane Glycosides and Other Triterpenoids from the Fruit of Momordica grosvenori on Epstein−Barr Virus Early Antigen Induced by Tumor Promoter 12-O-Tetradecanoylphorbol-13-acetate |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T06%3A50%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Inhibitory%20Effects%20of%20Cucurbitane%20Glycosides%20and%20Other%20Triterpenoids%20from%20the%20Fruit%20of%20Momordica%20grosvenori%20on%20Epstein%E2%88%92Barr%20Virus%20Early%20Antigen%20Induced%20by%20Tumor%20Promoter%2012-O-Tetradecanoylphorbol-13-acetate&rft.jtitle=Journal%20of%20agricultural%20and%20food%20chemistry&rft.au=Ukiya,%20Motohiko&rft.date=2002-11-06&rft.volume=50&rft.issue=23&rft.spage=6710&rft.epage=6715&rft.pages=6710-6715&rft.issn=0021-8561&rft.eissn=1520-5118&rft_id=info:doi/10.1021/jf0206320&rft_dat=%3Cproquest_cross%3E19188559%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=19188559&rft_id=info:pmid/12405766&rfr_iscdi=true |