X‐ray Study of Cembranoids with Flexible Rings from Boswellia papyrifera Resins Allowing Structural Revision of Misleading Structures from the Past 70 Years

Thirty new, highly oxygenated and stereogenic 14‐membered macrocyclic diterpenoids, papyrifuranols A‐Z (1–26) and AA‐AD (27–30), and eight known analogs have been isolated from Boswellia papyrifera resins. All the structures were characterized by detailed spectral analyses, quantum calculations, X‐r...

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Bibliographic Details
Published in:Chemistry : a European journal 2023-06, Vol.29 (33), p.e202300559-n/a
Main Authors: Sura, Madhu Babu, Zhu, Yan‐Xia, Cheng, Yong‐Xian
Format: Article
Language:English
Subjects:
Bioassays
Boswellia papyrifera
Boswellia papyrifera resins
Cell proliferation
cembranoids
Chemistry
Diterpenes
Mesenchymal stem cells
Resins
skeletal representations
Stem cells
Structural analysis
structural revisions
Umbilical cord
Wound healing
wound healing activity
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Summary:Thirty new, highly oxygenated and stereogenic 14‐membered macrocyclic diterpenoids, papyrifuranols A‐Z (1–26) and AA‐AD (27–30), and eight known analogs have been isolated from Boswellia papyrifera resins. All the structures were characterized by detailed spectral analyses, quantum calculations, X‐ray diffraction, and modified Mosher's methods. Notably, six previously reported structures were revised. Our study points out misleading factors of macrocyclic cembranoid (CB) representation in the past seven decades by analyzing of 25 X‐ray structures, lending a hand for the innately challenging structure identification of such flexible macrocyclic CBs and avoiding following the tracks of an overturned cart during future structure characterization and total synthesis. Biosynthetic conversions of all the isolates are proposed, and wound healing bioassays reveal that papyrifuranols N−P could significantly stimulate the proliferation and differentiation of umbilical cord mesenchymal stem cells. Over the past seven decades several cembranoids have been reported, but uncertainty still exists about their structures. In this study, we isolated 38 macrocyclic cembranoids from B. papyrifera. Our 25 single‐crystal analysis uncovered misleading factors in the previously determined stereochemistries, and this led to six structures being revised. In addition, we propose a biosynthetic pathway and briefly discuss SARs.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202300559