Disesquiterpenoid and Sesquiterpenes from the Flos of <i>Chrysanthemum indicum</i>

Abstract

One new disesquiterpenoid (1), two new sesquiterpenoids (2, 3), were isolated from the dry flos of Chrysanthemum indicum. The structures were elucidated by spectroscopic analysis, the absolute configurations of 1 and 3, were determined by single X-ray diffraction study.

Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum

“…The downled oxygenated carbon at d C 86.0 indicated a hydroxyl location being part of the quarternary fused-ring system that was assigned to C-10. 21 The relative stereochemistry assignment for H-6 to an a-conguration was based on biogenetic precedent and was consistent with previously reported NMR chemical shi data for similar cadinane-type sesquiterpenes. 19 H-6 NOESY correlations with d H 1.50 (m, H-7a) and 2.33 (m, H-1a) as well as between H-1a and H-2 indicated these protons to be on the same face in an a-conguration (Fig.…”

“…The b-orientation of the hydroxyl group at C-10 was assigned based on carbon shi data. 20,21 Therefore 2 was assigned to 2b,10b-dihydroxycadin-3,9(14)-dien-12-oic acid (tanacetolide B).…”

Natural sesquiterpenoids

“…The iphionane sesquiterpene 489 has been obtained from Chrysanthemum indicum. 362 Two total syntheses of the eudesmane-derived sesquiterpenoid (+)-cyperolone have been reported. 363,364 17 Vetisperane and spiroaxane Argutalactone 490 is a novel sesquiterpene with a rigid skeleton, which has been obtained from the roots of Incarvillea arguta.…”

“…458 The sesquiterpene 702 has been isolated from Chrysanthemum indicum. 362 The rhizomes of Cyperus rotundus 282 and the stem of Syringa pinnatifolia 395 contain the sesquiterpenes 703 and 704, respectively, whilst calamusin A 705 and calamusin B 706 have been obtained from rhizomes of Acorus calamus. 163 Balsamiferine A 707 is another new sesquiterpenoid, which has been isolated from Blumea balsamifera.…”

Monomeric and Dimeric Cytotoxic Guaianolide-Type Sesquiterpenoids from the Aerial Parts of Chrysanthemum indicum

“…A number of studies have also reported that this plant has activities against viral − and bacterial infections, oxidation, osteoporosis, and immunomodulation . Previously, flavonoids , and various sesquiterpenoids ,− have been identified from this plant. In earlier studies, a new guaianolide-type sesquiterpenoid trimer (chrysanolide A), a dimer (chrysanolide C), and a monomer (chrysanolide B) were identified from an extract of the flowers of C. indicum .…”