Table of Naturally Occurring PPAPs

This web site attempts to catalog all of the polycyclic polyprenylated acylphloroglucinols (PPAPs) that scientists have reported isolating from natural sources.

Reviews of PPAP structures: Ciochina 2006, X.-W. Yang 2018

Go to the table now.

I have grouped structures according to the structure and stereochemistry of their polycyclic cores. The purpose of the groupings I have chosen is to make it easier to compare structures that are homologous or diastereomeric. I have grouped together homologous structures (e.g., one has a prenyl group where the next has a geranyl group), whereas I have put in separate groups those structures that are diastereomeric in their polycyclic core (e.g., one has an exo CMe2OH group where the next has an endo CMe2OH group). I treat β-hydroxy enone tautomers as interchangeable.

You can winnow down the displayed compounds by choosing to display only compounds that have any of or all certain characteristics.

In the drawings in these tables, I have arbitrarily chosen always to draw the bridging ketone (usually C(9)) pointing toward the reader to make it easier to compare structures, but no information about absolute configuration should be inferred therefrom. In cases where a structure's absolute configuration has been determined, I indicate with a footnote whether the configuration matches the drawing in the table or is opposite to it.

I have hyperlinked each structure to its MOL representation. You can copy the MOL code from the alert, paste it into your favorite drawing program (you may need to use a special paste function; in ChemDraw for Mac, use option-command-shift-P), and then 3D-minimize it to get a view of what the compound may really look like.

How to edit this table.


Hypericum perforatum

Hypericum monogynum

References are not exhaustive, but generally are restricted to works that described the isolation of a compound from a new species and works that established or corrected the structures and configurations of the different compounds. I have hyperlinked each reference to its original Web page as well as created a Web page that lists all the references in JACS style.

Corrections and suggestions are most welcome. Just email me at robert.grossman "at" uky.edu.

Thanks to the following people for their contributions to this project. Any errors in the tables are my responsibility, not theirs.

Dr. Shubhankar Dutta, University of Kentucky.
Barbara Grossman.
Dr. Helen Jacobs, University of West Indies at Mona.
Dr. Kong Ling-Yi, China Pharmaceutical University.
Dr. Xu Gang, Kunming Institute of Botany, Chinese Academy of Sciences.
Dr. Yang Xing-wei, Sun Yat-sen University.
Dr. Xue Yongbo and Dr. Zhang Yonghui, Huazhong University of Science & Technology.
Dr. Brian Myers, Ohio Northern University, and his team at the ACS Division of Organic Chemistry.
— Robert B. Grossman
University of Kentucky

Garcinia multiflora

Hypericum patulum

Documentation.