Synthesis and biological activities of flavolipids

Samiul M. Ahad; Alison L. Ange; Robert B. Bates; Bonnie L. Bell; Adria A. Bodour; Bryan R. Bourne; Cristina G. Contreras; Emily L. Goldberg; A. A.Leslie Gunatilaka; Sheryl King; Albert K. Lee; Rebecca L. Low; Raina M. Maier; Kathryn M. Marlor; Marilyn T. Marron; Ryan C. Scolnik; Matthew J. Streeter; Malgorzata Strelczuk; Long N. Trinh; Vu K. Truong; Sage P. Vissering; Megan C. Weick; Maria T. Williams

doi:10.1016/j.tet.2010.09.088

Synthesis and biological activities of flavolipids

Samiul M. Ahad, Alison L. Ange, Robert B. Bates, Bonnie L. Bell, Adria A. Bodour, Bryan R. Bourne, Cristina G. Contreras, Emily L. Goldberg, A. A.Leslie Gunatilaka, Sheryl King, Albert K. Lee, Rebecca L. Low, Raina M. Maier, Kathryn M. Marlor, Marilyn T. Marron, Ryan C. Scolnik, Matthew J. Streeter, Malgorzata Strelczuk, Long N. Trinh, Vu K. TruongSage P. Vissering, Megan C. Weick, Maria T. Williams

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2 Scopus citations

Abstract

Syntheses of the bacterial surfactants 6S,6S-, 9S,9S-, and 9U,9U-flavolipids confirmed the structures proposed for them from spectroscopic analysis of a flavolipid mixture and made pure flavolipids available for the first time. All three synthetic flavolipids and a straight chain analogue were found to be weakly cytotoxic and to inhibit metastatic cancer cell migration, with 9U,9U-flavolipid (the most abundant natural flavolipid) having the most activity. Biosynthetic routes to the branched side-chains of the flavolipids are suggested, and it is proposed that branched chains are employed to hinder biodegradation.

Original language	English (US)
Pages (from-to)	9107-9112
Number of pages	6
Journal	Tetrahedron
Volume	66
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2010.09.088
State	Published - Nov 20 2010

Keywords

Biosurfactant
Flavobacterium
Flavolipid
Siderophore

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2010.09.088

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Ahad, S. M., Ange, A. L., Bates, R. B., Bell, B. L., Bodour, A. A., Bourne, B. R., Contreras, C. G., Goldberg, E. L., Gunatilaka, A. A. L., King, S., Lee, A. K., Low, R. L., Maier, R. M., Marlor, K. M., Marron, M. T., Scolnik, R. C., Streeter, M. J., Strelczuk, M., Trinh, L. N., ... Williams, M. T. (2010). Synthesis and biological activities of flavolipids. Tetrahedron, 66(47), 9107-9112. https://doi.org/10.1016/j.tet.2010.09.088

Ahad, SM, Ange, AL, Bates, RB, Bell, BL, Bodour, AA, Bourne, BR, Contreras, CG, Goldberg, EL, Gunatilaka, AAL, King, S, Lee, AK, Low, RL, Maier, RM, Marlor, KM, Marron, MT, Scolnik, RC, Streeter, MJ, Strelczuk, M, Trinh, LN, Truong, VK, Vissering, SP, Weick, MC & Williams, MT 2010, 'Synthesis and biological activities of flavolipids', Tetrahedron, vol. 66, no. 47, pp. 9107-9112. https://doi.org/10.1016/j.tet.2010.09.088

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title = "Synthesis and biological activities of flavolipids",

abstract = "Syntheses of the bacterial surfactants 6S,6S-, 9S,9S-, and 9U,9U-flavolipids confirmed the structures proposed for them from spectroscopic analysis of a flavolipid mixture and made pure flavolipids available for the first time. All three synthetic flavolipids and a straight chain analogue were found to be weakly cytotoxic and to inhibit metastatic cancer cell migration, with 9U,9U-flavolipid (the most abundant natural flavolipid) having the most activity. Biosynthetic routes to the branched side-chains of the flavolipids are suggested, and it is proposed that branched chains are employed to hinder biodegradation.",

keywords = "Biosurfactant, Flavobacterium, Flavolipid, Siderophore",

author = "Ahad, {Samiul M.} and Ange, {Alison L.} and Bates, {Robert B.} and Bell, {Bonnie L.} and Bodour, {Adria A.} and Bourne, {Bryan R.} and Contreras, {Cristina G.} and Goldberg, {Emily L.} and Gunatilaka, {A. A.Leslie} and Sheryl King and Lee, {Albert K.} and Low, {Rebecca L.} and Maier, {Raina M.} and Marlor, {Kathryn M.} and Marron, {Marilyn T.} and Scolnik, {Ryan C.} and Streeter, {Matthew J.} and Malgorzata Strelczuk and Trinh, {Long N.} and Truong, {Vu K.} and Vissering, {Sage P.} and Weick, {Megan C.} and Williams, {Maria T.}",

note = "Funding Information: This work was supported by grant number 0714245 from the National Science Foundation and by a Camille and Henry Dreyfus Foundation Senior Scientist Mentor Initiative Award to R.B.B. ",

year = "2010",

month = nov,

day = "20",

doi = "10.1016/j.tet.2010.09.088",

language = "English (US)",

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T1 - Synthesis and biological activities of flavolipids

AU - Ahad, Samiul M.

AU - Ange, Alison L.

AU - Bates, Robert B.

AU - Bell, Bonnie L.

AU - Bodour, Adria A.

AU - Bourne, Bryan R.

AU - Contreras, Cristina G.

AU - Goldberg, Emily L.

AU - Gunatilaka, A. A.Leslie

AU - King, Sheryl

AU - Lee, Albert K.

AU - Low, Rebecca L.

AU - Maier, Raina M.

AU - Marlor, Kathryn M.

AU - Marron, Marilyn T.

AU - Scolnik, Ryan C.

AU - Streeter, Matthew J.

AU - Strelczuk, Malgorzata

AU - Trinh, Long N.

AU - Truong, Vu K.

AU - Vissering, Sage P.

AU - Weick, Megan C.

AU - Williams, Maria T.

N1 - Funding Information: This work was supported by grant number 0714245 from the National Science Foundation and by a Camille and Henry Dreyfus Foundation Senior Scientist Mentor Initiative Award to R.B.B.

PY - 2010/11/20

Y1 - 2010/11/20

N2 - Syntheses of the bacterial surfactants 6S,6S-, 9S,9S-, and 9U,9U-flavolipids confirmed the structures proposed for them from spectroscopic analysis of a flavolipid mixture and made pure flavolipids available for the first time. All three synthetic flavolipids and a straight chain analogue were found to be weakly cytotoxic and to inhibit metastatic cancer cell migration, with 9U,9U-flavolipid (the most abundant natural flavolipid) having the most activity. Biosynthetic routes to the branched side-chains of the flavolipids are suggested, and it is proposed that branched chains are employed to hinder biodegradation.

AB - Syntheses of the bacterial surfactants 6S,6S-, 9S,9S-, and 9U,9U-flavolipids confirmed the structures proposed for them from spectroscopic analysis of a flavolipid mixture and made pure flavolipids available for the first time. All three synthetic flavolipids and a straight chain analogue were found to be weakly cytotoxic and to inhibit metastatic cancer cell migration, with 9U,9U-flavolipid (the most abundant natural flavolipid) having the most activity. Biosynthetic routes to the branched side-chains of the flavolipids are suggested, and it is proposed that branched chains are employed to hinder biodegradation.

KW - Biosurfactant

KW - Flavobacterium

KW - Flavolipid

KW - Siderophore

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Synthesis and biological activities of flavolipids

Abstract

Keywords

ASJC Scopus subject areas

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