Fragranol A: A new class of spiro-triflavanoid hybrid with an unprecedented carbon skeleton from Anneslea fragrans

Ashraf M. Omar; Sijia Sun; Min Jo Kim; Ahmed M. Tawila; Dya Fita Dibwe; Ampai Phrutivorapongkul; Naoki Toyooka; Suresh Awale

doi:10.1016/j.tetlet.2020.152099

Fragranol A: A new class of spiro-triflavanoid hybrid with an unprecedented carbon skeleton from Anneslea fragrans

Ashraf M. Omar, Sijia Sun, Min Jo Kim, Ahmed M. Tawila, Dya Fita Dibwe, Ampai Phrutivorapongkul, Naoki Toyooka, Suresh Awale^*

^*Corresponding author for this work

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

8 Scopus citations

Abstract

Phytochemical investigation of Anneslea fragrans twigs resulted in the discovery of fragranol A (1), a new class of structurally challenging and sterically hindered “spiro-triflavanoid” type compound possessing an unprecedented carbon skeleton. Fragranol A (1) consists of 45 carbons having six chiral carbons, including two spiro-chiral centers. Structural elucidation of 1 was achieved by HRFABMS, 1D and 2D NMR, analysis of spatial anisotropic effects, and quantum ECD calculations. A plausible biogenetic pathway of 1 is also proposed.

Original language	English
Article number	152099
Journal	Tetrahedron Letters
Volume	61
Issue number	29
DOIs	https://doi.org/10.1016/j.tetlet.2020.152099
State	Published - 2020/07/16

Keywords

Absolute configuration
Anisotropic shielding
Anneslea fragrans
Spiro-flavanoid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Fragranol A: A new class of spiro-triflavanoid hybrid with an unprecedented carbon skeleton from Anneslea fragrans",

abstract = "Phytochemical investigation of Anneslea fragrans twigs resulted in the discovery of fragranol A (1), a new class of structurally challenging and sterically hindered “spiro-triflavanoid” type compound possessing an unprecedented carbon skeleton. Fragranol A (1) consists of 45 carbons having six chiral carbons, including two spiro-chiral centers. Structural elucidation of 1 was achieved by HRFABMS, 1D and 2D NMR, analysis of spatial anisotropic effects, and quantum ECD calculations. A plausible biogenetic pathway of 1 is also proposed.",

keywords = "Absolute configuration, Anisotropic shielding, Anneslea fragrans, Spiro-flavanoid",

author = "Omar, {Ashraf M.} and Sijia Sun and Kim, {Min Jo} and Tawila, {Ahmed M.} and Dibwe, {Dya Fita} and Ampai Phrutivorapongkul and Naoki Toyooka and Suresh Awale",

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year = "2020",

month = jul,

day = "16",

doi = "10.1016/j.tetlet.2020.152099",

language = "英語",

volume = "61",

journal = "Tetrahedron Letters",

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T2 - A new class of spiro-triflavanoid hybrid with an unprecedented carbon skeleton from Anneslea fragrans

AU - Omar, Ashraf M.

AU - Sun, Sijia

AU - Kim, Min Jo

AU - Tawila, Ahmed M.

AU - Dibwe, Dya Fita

AU - Phrutivorapongkul, Ampai

AU - Toyooka, Naoki

AU - Awale, Suresh

PY - 2020/7/16

Y1 - 2020/7/16

N2 - Phytochemical investigation of Anneslea fragrans twigs resulted in the discovery of fragranol A (1), a new class of structurally challenging and sterically hindered “spiro-triflavanoid” type compound possessing an unprecedented carbon skeleton. Fragranol A (1) consists of 45 carbons having six chiral carbons, including two spiro-chiral centers. Structural elucidation of 1 was achieved by HRFABMS, 1D and 2D NMR, analysis of spatial anisotropic effects, and quantum ECD calculations. A plausible biogenetic pathway of 1 is also proposed.

AB - Phytochemical investigation of Anneslea fragrans twigs resulted in the discovery of fragranol A (1), a new class of structurally challenging and sterically hindered “spiro-triflavanoid” type compound possessing an unprecedented carbon skeleton. Fragranol A (1) consists of 45 carbons having six chiral carbons, including two spiro-chiral centers. Structural elucidation of 1 was achieved by HRFABMS, 1D and 2D NMR, analysis of spatial anisotropic effects, and quantum ECD calculations. A plausible biogenetic pathway of 1 is also proposed.

KW - Absolute configuration

KW - Anisotropic shielding

KW - Anneslea fragrans

KW - Spiro-flavanoid

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U2 - 10.1016/j.tetlet.2020.152099

DO - 10.1016/j.tetlet.2020.152099

M3 - 学術論文

AN - SCOPUS:85086176895

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

M1 - 152099

ER -

Fragranol A: A new class of spiro-triflavanoid hybrid with an unprecedented carbon skeleton from Anneslea fragrans

Abstract

Keywords

ASJC Scopus subject areas

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