Related Experiment Video
Updated: Oct 9, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Rearranged abietane diterpenoids from Clerodendrum mandarinorum
1Department of Natural Pharmaceutical Chemistry, China Pharmaceutical University, Nanjing.
Abstract:
Five new abietane derivatives which have a commonly rearranged abietane skeleton contained a 17(15-->16),18(4-->3)-diabeo-abietane framework, mandarones D-H, were isolated from the stem of Clerodendrum nmantarinorum Diels (Verbenaceae). The structures were characterized as (16S)-12,16-epoxy-11-hydroxy-17(15-->16), 18(4-->3)-diabeo-abieta-3,5,8,11,13-pentaene-7-one (mandarone D, 1), 12,16-epoxy-11,14-dihydroxy-17(15-->16),18(4-->3)-diabeo-abieta-3,5,8,11, 13,15-hexaene-7-one (mandarone E, 2), 12,16-epoxy-6,11,14-trihydroxy-17(15-->16),18(4-->3)-diabeo-abieta-3,5,8,11,13,15-hexaene-7-one (mandarone F, 3),12,16-epoxy-11,14-dihydroxy-6-methoxy-17(15-->16),18(4-->3)-diabeo-abieta-3,5,8,11,13,15-hexaene-2,7-dione (mandarone G, 4) and 12,16-epoxy-11,14-dihydroxy-17(15-->16),18(4-->3)-diabeo-abieta-3,5,8,11,13,15-hexaene-1,7-dione (mandarone H, 5) respectively, mainly based on the spectral analysis and by comparison with those of closely related compounds.
Related Concept Videos
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Prochirality
Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
