Xylomolones A-D from the Thai Mangrove Xylocarpus moluccensis: Assignment of Absolute Stereostructures and Unveiling a Convergent Strategy for Limonoid Biosynthesis

Wan Shan Li, Attila Mándi, Jun Jun Liu, Li Shen, T. Kurtán, Jun Wu

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Two new 9,10-seco limonoids with a central 3,4-dihydro-2H-pyran motif, named xylomolones A and B (1 and 2, respectively), possessing identical absolute configurations but reversed alignments of ring A, compared to the tricyclic core of rings B-D, were obtained from seeds of the Thai mangrove Xylocarpus moluccensis, together with a highly modified 1,2-seco limonoid, named xylomolone C (3), containing a novel 3-oxabicyclo[3.2.1]octane-2,7-dione motif, and a new C 11 -terpenic acid methyl ester (4). The relative and absolute configurations of 1-4 were evidenced by extensive nuclear magnetic resonance (NMR) investigations combined with density functional theory and time-dependent density functional theory calculations of electronic circular dichroism, specific optical rotation, and 13 C NMR data. The co-isolation of 1-4 allowed us to propose a novel convergent strategy for limonoid biosynthesis for the first time. This study demonstrates that mangroves of the genus Xylocarpus harbor new limonoid biosynthetic routes.

Original languageEnglish
Pages (from-to)2596-2606
Number of pages11
JournalJournal of Organic Chemistry
Volume84
Issue number5
DOIs
Publication statusPublished - Mar 1 2019

Fingerprint

Limonins
Biosynthesis
Density functional theory
Nuclear magnetic resonance
Optical rotation
Dichroism
Ports and harbors
Seed
Esters
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Xylomolones A-D from the Thai Mangrove Xylocarpus moluccensis : Assignment of Absolute Stereostructures and Unveiling a Convergent Strategy for Limonoid Biosynthesis. / Li, Wan Shan; Mándi, Attila; Liu, Jun Jun; Shen, Li; Kurtán, T.; Wu, Jun.

In: Journal of Organic Chemistry, Vol. 84, No. 5, 01.03.2019, p. 2596-2606.

Research output: Contribution to journalArticle

@article{598a669c9ca849858b53d1eff7c7e297,
title = "Xylomolones A-D from the Thai Mangrove Xylocarpus moluccensis: Assignment of Absolute Stereostructures and Unveiling a Convergent Strategy for Limonoid Biosynthesis",
abstract = "Two new 9,10-seco limonoids with a central 3,4-dihydro-2H-pyran motif, named xylomolones A and B (1 and 2, respectively), possessing identical absolute configurations but reversed alignments of ring A, compared to the tricyclic core of rings B-D, were obtained from seeds of the Thai mangrove Xylocarpus moluccensis, together with a highly modified 1,2-seco limonoid, named xylomolone C (3), containing a novel 3-oxabicyclo[3.2.1]octane-2,7-dione motif, and a new C 11 -terpenic acid methyl ester (4). The relative and absolute configurations of 1-4 were evidenced by extensive nuclear magnetic resonance (NMR) investigations combined with density functional theory and time-dependent density functional theory calculations of electronic circular dichroism, specific optical rotation, and 13 C NMR data. The co-isolation of 1-4 allowed us to propose a novel convergent strategy for limonoid biosynthesis for the first time. This study demonstrates that mangroves of the genus Xylocarpus harbor new limonoid biosynthetic routes.",
author = "Li, {Wan Shan} and Attila M{\'a}ndi and Liu, {Jun Jun} and Li Shen and T. Kurt{\'a}n and Jun Wu",
year = "2019",
month = "3",
day = "1",
doi = "10.1021/acs.joc.8b03037",
language = "English",
volume = "84",
pages = "2596--2606",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "5",

}

TY - JOUR

T1 - Xylomolones A-D from the Thai Mangrove Xylocarpus moluccensis

T2 - Assignment of Absolute Stereostructures and Unveiling a Convergent Strategy for Limonoid Biosynthesis

AU - Li, Wan Shan

AU - Mándi, Attila

AU - Liu, Jun Jun

AU - Shen, Li

AU - Kurtán, T.

AU - Wu, Jun

PY - 2019/3/1

Y1 - 2019/3/1

N2 - Two new 9,10-seco limonoids with a central 3,4-dihydro-2H-pyran motif, named xylomolones A and B (1 and 2, respectively), possessing identical absolute configurations but reversed alignments of ring A, compared to the tricyclic core of rings B-D, were obtained from seeds of the Thai mangrove Xylocarpus moluccensis, together with a highly modified 1,2-seco limonoid, named xylomolone C (3), containing a novel 3-oxabicyclo[3.2.1]octane-2,7-dione motif, and a new C 11 -terpenic acid methyl ester (4). The relative and absolute configurations of 1-4 were evidenced by extensive nuclear magnetic resonance (NMR) investigations combined with density functional theory and time-dependent density functional theory calculations of electronic circular dichroism, specific optical rotation, and 13 C NMR data. The co-isolation of 1-4 allowed us to propose a novel convergent strategy for limonoid biosynthesis for the first time. This study demonstrates that mangroves of the genus Xylocarpus harbor new limonoid biosynthetic routes.

AB - Two new 9,10-seco limonoids with a central 3,4-dihydro-2H-pyran motif, named xylomolones A and B (1 and 2, respectively), possessing identical absolute configurations but reversed alignments of ring A, compared to the tricyclic core of rings B-D, were obtained from seeds of the Thai mangrove Xylocarpus moluccensis, together with a highly modified 1,2-seco limonoid, named xylomolone C (3), containing a novel 3-oxabicyclo[3.2.1]octane-2,7-dione motif, and a new C 11 -terpenic acid methyl ester (4). The relative and absolute configurations of 1-4 were evidenced by extensive nuclear magnetic resonance (NMR) investigations combined with density functional theory and time-dependent density functional theory calculations of electronic circular dichroism, specific optical rotation, and 13 C NMR data. The co-isolation of 1-4 allowed us to propose a novel convergent strategy for limonoid biosynthesis for the first time. This study demonstrates that mangroves of the genus Xylocarpus harbor new limonoid biosynthetic routes.

UR - http://www.scopus.com/inward/record.url?scp=85061925862&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85061925862&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b03037

DO - 10.1021/acs.joc.8b03037

M3 - Article

C2 - 30719915

AN - SCOPUS:85061925862

VL - 84

SP - 2596

EP - 2606

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 5

ER -