Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata

Andrew M. White; Gregory K. Pierens; Tina Skinner-Adams; Katherine T. Andrews; Paul V. Bernhardt; Elizabeth H. Krenske; Ernesto Mollo; Mary J. Garson

doi:10.1021/acs.jnatprod.5b00354

Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata

Andrew M. White, Gregory K. Pierens, Tina Skinner-Adams, Katherine T. Andrews, Paul V. Bernhardt, Elizabeth H. Krenske, Ernesto Mollo, Mary J. Garson^*

^*Corresponding author for this work

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

33 Citations (Scopus)

Abstract

Five new isocyano/isothiocyanato sesquiterpenes (1-5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC₅₀ 0.26-0.30 μM), while isothiocyanate 3 and formamide 6 had IC₅₀ values of >10 μM.

Original language	English
Pages (from-to)	1422-1427
Number of pages	6
Journal	Journal of Natural Products
Volume	78
Issue number	6
DOIs	https://doi.org/10.1021/acs.jnatprod.5b00354
Publication status	Published - 26 Jun 2015
Externally published	Yes

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title = "Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata",

abstract = "Five new isocyano/isothiocyanato sesquiterpenes (1-5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC50 0.26-0.30 μM), while isothiocyanate 3 and formamide 6 had IC50 values of >10 μM.",

author = "White, \{Andrew M.\} and Pierens, \{Gregory K.\} and Tina Skinner-Adams and Andrews, \{Katherine T.\} and Bernhardt, \{Paul V.\} and Krenske, \{Elizabeth H.\} and Ernesto Mollo and Garson, \{Mary J.\}",

note = "Publisher Copyright: {\textcopyright} 2015 The American Chemical Society and American Society of Pharmacognosy.",

year = "2015",

month = jun,

day = "26",

doi = "10.1021/acs.jnatprod.5b00354",

language = "English",

volume = "78",

pages = "1422--1427",

journal = "Journal of Natural Products",

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T1 - Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata

AU - White, Andrew M.

AU - Pierens, Gregory K.

AU - Skinner-Adams, Tina

AU - Andrews, Katherine T.

AU - Bernhardt, Paul V.

AU - Krenske, Elizabeth H.

AU - Mollo, Ernesto

AU - Garson, Mary J.

PY - 2015/6/26

Y1 - 2015/6/26

N2 - Five new isocyano/isothiocyanato sesquiterpenes (1-5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC50 0.26-0.30 μM), while isothiocyanate 3 and formamide 6 had IC50 values of >10 μM.

AB - Five new isocyano/isothiocyanato sesquiterpenes (1-5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC50 0.26-0.30 μM), while isothiocyanate 3 and formamide 6 had IC50 values of >10 μM.

UR - https://www.scopus.com/pages/publications/84933055130

U2 - 10.1021/acs.jnatprod.5b00354

DO - 10.1021/acs.jnatprod.5b00354

M3 - Article

C2 - 26056748

AN - SCOPUS:84933055130

SN - 0163-3864

VL - 78

SP - 1422

EP - 1427

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 6

ER -

Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata

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