Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

Zalihe Hakki; Benjamin Cao; Allison M. Heskes; Jason Q.D. Goodger; Ian E. Woodrow; Spencer J. Williams

doi:10.1016/j.carres.2010.07.029

Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

Zalihe Hakki
, Benjamin Cao
, Allison M. Heskes
, Jason Q.D. Goodger
, Ian E. Woodrow
, Spencer J. Williams

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

26 Citations (Scopus)

Abstract

Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K₁ and K ₂. Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena.

Original language	English
Pages (from-to)	2079-2084
Number of pages	6
Journal	Carbohydrate Research
Volume	345
Issue number	14
DOIs	https://doi.org/10.1016/j.carres.2010.07.029
Publication status	Published - 23 Sept 2010
Externally published	Yes

Keywords

Essential oils
Eucalyptus
Monoterpenoids
Noreugenin
Oleuropeic acid
Total synthesis

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10.1016/j.carres.2010.07.029

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title = "Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus",

abstract = "Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K1 and K 2. Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena.",

keywords = "Essential oils, Eucalyptus, Monoterpenoids, Noreugenin, Oleuropeic acid, Total synthesis",

author = "Zalihe Hakki and Benjamin Cao and Heskes, \{Allison M.\} and Goodger, \{Jason Q.D.\} and Woodrow, \{Ian E.\} and Williams, \{Spencer J.\}",

note = "Funding Information: This work was supported by grants from the Australian Research Council and the Holsworth Wildlife Research Fund ( Victorian Community Foundation , ANZ Charitable Trusts ). J.Q.D.G. is the recipient of an ARC Australian Research Fellowship. J. Karas is thanked for HPLC support. ",

year = "2010",

month = sep,

day = "23",

doi = "10.1016/j.carres.2010.07.029",

language = "English",

volume = "345",

pages = "2079--2084",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

number = "14",

}

TY - JOUR

T1 - Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

AU - Hakki, Zalihe

AU - Cao, Benjamin

AU - Heskes, Allison M.

AU - Goodger, Jason Q.D.

AU - Woodrow, Ian E.

AU - Williams, Spencer J.

N1 - Funding Information: This work was supported by grants from the Australian Research Council and the Holsworth Wildlife Research Fund ( Victorian Community Foundation , ANZ Charitable Trusts ). J.Q.D.G. is the recipient of an ARC Australian Research Fellowship. J. Karas is thanked for HPLC support.

PY - 2010/9/23

Y1 - 2010/9/23

N2 - Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K1 and K 2. Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena.

AB - Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K1 and K 2. Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena.

KW - Essential oils

KW - Eucalyptus

KW - Monoterpenoids

KW - Noreugenin

KW - Oleuropeic acid

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/77956410110

U2 - 10.1016/j.carres.2010.07.029

DO - 10.1016/j.carres.2010.07.029

M3 - Article

C2 - 20708173

AN - SCOPUS:77956410110

SN - 0008-6215

VL - 345

SP - 2079

EP - 2084

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 14

ER -

Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

Abstract

Keywords

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