Structure elucidation of some highly unusual tricyclic cis-caryophyllane sesquiterpenes from Marasmiellus troyanus

Liam Evans; John Hedger; Gemma O'Donnell; Brian W. Skelton; Allan H. White; R. Thomas Williamson; Simon Gibbons

doi:10.1016/j.tetlet.2010.08.036

Structure elucidation of some highly unusual tricyclic cis-caryophyllane sesquiterpenes from Marasmiellus troyanus

Liam Evans, John Hedger, Gemma O'Donnell, Brian W. Skelton, Allan H. White, R. Thomas Williamson, Simon Gibbons

School of Pharmacy

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

6 Citations (Scopus)

Abstract

Three new unusual sesquiterpenes (1-3) were isolated from the tropical rainforest basidiomycete, Marasmiellus troyanus and their structure elucidation was achieved by NMR spectroscopy, single-crystal X-ray structural analysis and a modified Mosher's ester method to determine the absolute stereochemistry of compound 1. These unusual metabolites are probably derived from the caryophyllane class of sesquiterpenes and a possible biosynthetic route to these compounds is proposed. These small natural products represent the best possible features of chemical diversity, being chiral and exhibiting extensive functional group chemistry highlighting the value of natural products as a screening resource for therapeutics discovery programmes.

Original language	English
Pages (from-to)	5493-5496
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	41
Early online date	17 Aug 2010
DOIs	https://doi.org/10.1016/j.tetlet.2010.08.036
Publication status	Published - 13 Oct 2010

Keywords

Basidiomycetes
Caryophyllane
Marasmiellus troyanus
Sesquiterpene

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10.1016/j.tetlet.2010.08.036

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title = "Structure elucidation of some highly unusual tricyclic cis-caryophyllane sesquiterpenes from Marasmiellus troyanus",

abstract = "Three new unusual sesquiterpenes (1-3) were isolated from the tropical rainforest basidiomycete, Marasmiellus troyanus and their structure elucidation was achieved by NMR spectroscopy, single-crystal X-ray structural analysis and a modified Mosher's ester method to determine the absolute stereochemistry of compound 1. These unusual metabolites are probably derived from the caryophyllane class of sesquiterpenes and a possible biosynthetic route to these compounds is proposed. These small natural products represent the best possible features of chemical diversity, being chiral and exhibiting extensive functional group chemistry highlighting the value of natural products as a screening resource for therapeutics discovery programmes.",

keywords = "Basidiomycetes, Caryophyllane, Marasmiellus troyanus, Sesquiterpene",

author = "Liam Evans and John Hedger and Gemma O'Donnell and Skelton, {Brian W.} and White, {Allan H.} and Williamson, {R. Thomas} and Simon Gibbons",

year = "2010",

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doi = "10.1016/j.tetlet.2010.08.036",

language = "English",

volume = "51",

pages = "5493--5496",

journal = "Tetrahedron Letters",

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number = "41",

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Structure elucidation of some highly unusual tricyclic cis-caryophyllane sesquiterpenes from Marasmiellus troyanus. / Evans, Liam; Hedger, John; O'Donnell, Gemma; Skelton, Brian W.; White, Allan H.; Williamson, R. Thomas; Gibbons, Simon.

In: Tetrahedron Letters, Vol. 51, No. 41, 13.10.2010, p. 5493-5496.

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

TY - JOUR

T1 - Structure elucidation of some highly unusual tricyclic cis-caryophyllane sesquiterpenes from Marasmiellus troyanus

AU - Evans, Liam

AU - Hedger, John

AU - O'Donnell, Gemma

AU - Skelton, Brian W.

AU - White, Allan H.

AU - Williamson, R. Thomas

AU - Gibbons, Simon

PY - 2010/10/13

Y1 - 2010/10/13

N2 - Three new unusual sesquiterpenes (1-3) were isolated from the tropical rainforest basidiomycete, Marasmiellus troyanus and their structure elucidation was achieved by NMR spectroscopy, single-crystal X-ray structural analysis and a modified Mosher's ester method to determine the absolute stereochemistry of compound 1. These unusual metabolites are probably derived from the caryophyllane class of sesquiterpenes and a possible biosynthetic route to these compounds is proposed. These small natural products represent the best possible features of chemical diversity, being chiral and exhibiting extensive functional group chemistry highlighting the value of natural products as a screening resource for therapeutics discovery programmes.

AB - Three new unusual sesquiterpenes (1-3) were isolated from the tropical rainforest basidiomycete, Marasmiellus troyanus and their structure elucidation was achieved by NMR spectroscopy, single-crystal X-ray structural analysis and a modified Mosher's ester method to determine the absolute stereochemistry of compound 1. These unusual metabolites are probably derived from the caryophyllane class of sesquiterpenes and a possible biosynthetic route to these compounds is proposed. These small natural products represent the best possible features of chemical diversity, being chiral and exhibiting extensive functional group chemistry highlighting the value of natural products as a screening resource for therapeutics discovery programmes.

KW - Basidiomycetes

KW - Caryophyllane

KW - Marasmiellus troyanus

KW - Sesquiterpene

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DO - 10.1016/j.tetlet.2010.08.036

M3 - Article

AN - SCOPUS:80052083138

VL - 51

SP - 5493

EP - 5496

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 41

ER -

Structure elucidation of some highly unusual tricyclic cis-caryophyllane sesquiterpenes from Marasmiellus troyanus

Abstract

Keywords

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