Eudesmane-Type Sesquiterpenoid and Guaianolides from Kandelia candel in a Screening Program for Compounds to Overcome TRAIL Resistance

Abstract

In a screening program for natural products that can overcome TRAIL resistance, a new eudesmane-type sesquiterpenoid (1), three new guaianolides, mehirugins A-C (2-4), and two known guaianolides (5 and 6) were isolated from a MeOH extract of Kandelia candel leaves. Compounds 1 and 3-6 in combination with TRAIL showed cytotoxic activity in sensitizing TRAIL-resistant human gastric adenocarcinoma cells.

Highly Oxidized Guaianolide Sesquiterpenoids with Potential Anti-inflammatory Activity from Chrysanthemum indicum

“…Analysis of their NMR spectroscopic data suggests that both 2 and 3 share the same guaiane-type sesquiterpene skeleton as 1 , except for a difference in their respective side chain moiety. Their respective 1 H NMR spectra exhibited resonances for a tigloyloxy moiety (Table ) in 2 and a senecioyloxy unit (Table ) in 3 . The HMBC (H-9/C-1′) and ROESY (H-6/H-8β, H-9/H-8β and H-14) correlations enabled the determination of the α-orientation of the C-9 substituent in both 2 and 3 .…”

Bio-active Natural Products with TRAIL-Resistance Overcoming Activity

“…10). Co-treatment with compounds 23 and 25-28 with TRAIL showed TRAILresistance overcoming activity in AGS cells 36) (Fig. 11).…”

“…Eudesmane-Type Sesquiterpenoid and Guaianolides from Kandelia candel Leaves Kandelia candel (Rhizophoraceae) is a mangrove found in coastal areas of South and Southeast Asia. From K. candel leaves, a new eudesmane sesquiterpenoid (23), 36) three new guaiane sesquiterpene lactones, mehirugins A-C (24, 25, 27), 36) notoserolide B 37) (26), and matricarin 38) (28) were isolated (Fig. 10).…”

“…Its sprouts and fruit are traditionally used for the treatment of cancer. 45) Bioassay-guided separation of P. pinnata fruit collected from Bangladesh led to the isolation of a new compound (35) 46) together with six known compounds (36)(37)(38)(39)(40)(41), which were identified as 5-methoxy-(3″,4″-dihydro-3″,4″-diacetoxy)-2″,2″-dimethylpyrano- ( [2″,3″:7,8] furanoflavone 50) (40), and isopongaflavone 51) (41), respectively (Fig. 14).…”

New Flavanol Dimers from the Bark of Celtis tetrandra and Their TRAIL Resistance-Overcoming Activity

“…Tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) is considered to be one the most promising alternative anticancer treatments recently since it promoted apoptosis in a variety of cancer cells but has no effect in many of normal cell [8]. Unfortunately, many of the cancer cells are resistant to TRAILinduced apoptosis, therefore searching for bioactive natural products which have potential TRAIL resistance-overcoming activity are important and it is our aim of research [9][10][11][12][13].…”