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Three novel cadinane dimers, involucratusins A–C ( 1 – 3 ), five unique nor-cadinane-dimers, involucratusins D–H ( 4 – 8 ), together with a known compound ( 9 ) were isolated from the rhizomes of  Stahlianthus involucratus . Their challenging structures and absolute configurations were determined by spectroscopic data, CD experimentation, chemical conversions and single-crystal X-ray diffraction. Compounds  1 – 3  are unusual cadinane dimers with new connection and novel cores. Compound  4  is a unique nor-cadinane-dimer, and  5  and  6  are two pairs of hemiketal racemates with novel dinor-cadinane-dimer backbone. Compounds  7  and  8  represent unusual dodecanor-cadinane-dimer and tetradecanor-cadinane-dimer carbon skeletons, respectively. The possible biogenetic pathways of  1 – 8  were proposed, involving nucleophilic addition, S N 2 nucleophilic displacement, [3 + 3] benzannulation, oxidative cleavage, decarboxylation, and oxidative phenol coupling reactions. Multidrug resistance (MDR) reversal activity assay of the isolates were evaluated in doxorubicin-resistant human breast cancer cells (MCF-7/DOX). The combined use of these novel cadinane dimers at a concentration of 10  μ M increased the cytotoxicity of doxorubicin by 2.2–5.8-fold. It is the first report about the MDR reversal activity of cadinane dimers.

Involucratusins A–H: Unusual Cadinane Dimers from Stahlianthus involucratus with Multidrug Resistance Reversal Activity