Liquidambar styraciflua: a renewable source of shikimic acid

Liza B. Enrich; Margaret L. Scheuermann; Ashley Mohadjer; Kathryn R. Matthias; Chrystal F. Eller; M. Scott Newman; Michael Fujinaka; Thomas Poon

doi:10.1016/j.tetlet.2008.02.140

Liquidambar styraciflua: a renewable source of shikimic acid

Liza B. Enrich, Margaret L. Scheuermann, Ashley Mohadjer, Kathryn R. Matthias, Chrystal F. Eller, M. Scott Newman, Michael Fujinaka, Thomas Poon

Pharmacy Practice and Science

Research output: Contribution to journal › Article › peer-review

60 Scopus citations

Abstract

An isolation procedure is presented that yields 2.4-3.7% w/w pure shikimic acid from the seeds of Liquidambar styraciflua (Sweetgum). Shikimic acid, the starting material in the commercial synthesis of the antiviral agent oseltamivir and an important intermediate in the biosynthesis of aromatic amino acids in plants, was found by HPLC to be abundant in the granular, aborted seeds (6.5% w/w) while present only in small amounts in the developed, fertile seeds (0.14% w/w). This extraction technique makes L. styraciflua, which is found in 40 states of the continental US, a potential renewable source of this important natural product.

Original language	English (US)
Pages (from-to)	2503-2505
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	16
DOIs	https://doi.org/10.1016/j.tetlet.2008.02.140
State	Published - Apr 14 2008

Keywords

Liquidambar styraciflua
Plant natural products
Shikimic acid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.02.140

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@article{59fd74dee9d54cc28a57b8977526c1eb,

title = "Liquidambar styraciflua: a renewable source of shikimic acid",

abstract = "An isolation procedure is presented that yields 2.4-3.7% w/w pure shikimic acid from the seeds of Liquidambar styraciflua (Sweetgum). Shikimic acid, the starting material in the commercial synthesis of the antiviral agent oseltamivir and an important intermediate in the biosynthesis of aromatic amino acids in plants, was found by HPLC to be abundant in the granular, aborted seeds (6.5% w/w) while present only in small amounts in the developed, fertile seeds (0.14% w/w). This extraction technique makes L. styraciflua, which is found in 40 states of the continental US, a potential renewable source of this important natural product.",

keywords = "Liquidambar styraciflua, Plant natural products, Shikimic acid",

author = "Enrich, {Liza B.} and Scheuermann, {Margaret L.} and Ashley Mohadjer and Matthias, {Kathryn R.} and Eller, {Chrystal F.} and Newman, {M. Scott} and Michael Fujinaka and Thomas Poon",

note = "Funding Information: Financial support was provided by the W. M. Keck Science Foundation. We thank Adam Johnson of Harvey Mudd College for assistance with optical rotation measurements and Dan Guthrie of the Joint Science Department and Sula Vanderplank of the Rancho Santa Ana Botanic Garden for assistance with herbarium samples. ",

year = "2008",

month = apr,

day = "14",

doi = "10.1016/j.tetlet.2008.02.140",

language = "English (US)",

volume = "49",

pages = "2503--2505",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Liquidambar styraciflua

T2 - a renewable source of shikimic acid

AU - Enrich, Liza B.

AU - Scheuermann, Margaret L.

AU - Mohadjer, Ashley

AU - Matthias, Kathryn R.

AU - Eller, Chrystal F.

AU - Newman, M. Scott

AU - Fujinaka, Michael

AU - Poon, Thomas

N1 - Funding Information: Financial support was provided by the W. M. Keck Science Foundation. We thank Adam Johnson of Harvey Mudd College for assistance with optical rotation measurements and Dan Guthrie of the Joint Science Department and Sula Vanderplank of the Rancho Santa Ana Botanic Garden for assistance with herbarium samples.

PY - 2008/4/14

Y1 - 2008/4/14

N2 - An isolation procedure is presented that yields 2.4-3.7% w/w pure shikimic acid from the seeds of Liquidambar styraciflua (Sweetgum). Shikimic acid, the starting material in the commercial synthesis of the antiviral agent oseltamivir and an important intermediate in the biosynthesis of aromatic amino acids in plants, was found by HPLC to be abundant in the granular, aborted seeds (6.5% w/w) while present only in small amounts in the developed, fertile seeds (0.14% w/w). This extraction technique makes L. styraciflua, which is found in 40 states of the continental US, a potential renewable source of this important natural product.

AB - An isolation procedure is presented that yields 2.4-3.7% w/w pure shikimic acid from the seeds of Liquidambar styraciflua (Sweetgum). Shikimic acid, the starting material in the commercial synthesis of the antiviral agent oseltamivir and an important intermediate in the biosynthesis of aromatic amino acids in plants, was found by HPLC to be abundant in the granular, aborted seeds (6.5% w/w) while present only in small amounts in the developed, fertile seeds (0.14% w/w). This extraction technique makes L. styraciflua, which is found in 40 states of the continental US, a potential renewable source of this important natural product.

KW - Liquidambar styraciflua

KW - Plant natural products

KW - Shikimic acid

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U2 - 10.1016/j.tetlet.2008.02.140

DO - 10.1016/j.tetlet.2008.02.140

M3 - Article

AN - SCOPUS:40849104789

SN - 0040-4039

VL - 49

SP - 2503

EP - 2505

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

Liquidambar styraciflua: a renewable source of shikimic acid

Abstract

Keywords

ASJC Scopus subject areas

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