Cytotoxic triterpenoids from Abies recurvata

Li, Yongli; Gao, Youguang; Yang, Xian‐Wen; Jin, Hui‐Zi; Ye, Ji; Simmons, Luke; Wang, Ning; Steinmetz, André; Zhang, Wei‐Dong

doi:10.1016/j.phytochem.2012.05.032

Cited by 26 publications

(31 citation statements)

References 38 publications

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“…However, the previously described compounds 7 , 9 , 10 and 11 have been shown to possess the usual configuration for triterpenes [8,10–11]. The structures of many other triterpenes isolated from the genus Abies were also reported with this absolute configuration according to their X-ray crystallographic data [20–22]. …”

Section: Resultsmentioning

confidence: 98%

Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin

Lavoie¹,

Gauthier²,

Legault³

et al. 2013

Beilstein J. Org. Chem.

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SummaryPhytochemical analysis of A. balsamea oleoresin led to the isolation of three new 3,4-seco-lanostane triterpenoids 1–3, one new cycloartane triterpenoid 4 along with fourteen known terpenoids. Structure determinations were based on extensive 1D/2D NMR, IR and MS spectroscopic analyses, and comparison with literature data. The isolated compounds were evaluated in vitro for their cytotoxicity against human cell lines (A549, DLD-1, WS1) and their antibacterial activity against E. coli and S. aureus. Abiesonic acid (6) exhibited weak cytotoxic activity against A549 (IC50 = 22 µM) while compounds 1 and 4 were weakly active against S. aureus (MIC = 25 µM).

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Section: Resultsmentioning

confidence: 98%

Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin

Lavoie¹,

Gauthier²,

Legault³

et al. 2013

Beilstein J. Org. Chem.

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“…Its relative configuration was established by analyses of proton‐proton coupling constants (Table S2) and the ROESY spectrum. The ROE correlations (Figure 3 b) of H 3 ‐19/H‐2 β , H‐2 β /H 3 ‐29, H 3 ‐28/H‐5, H‐5/H‐7 α , H‐7 β /H 3 ‐18, and H‐30b/H‐7 α ascertained the relative configuration of the triterpenoid moiety to be consistent with those of neoabiestrine F and analogs [12] . Meanwhile, the ROE correlation between H 3 ‐19′ and H 3 ‐20′, and those between the axial protons of H‐5′ ( δ H 1.69, br d, J= 12.0 Hz) with H‐1′ α and of H‐1′ α with H‐9′ established the relative configuration of the A/B rings in the diterpenoid moiety as those of usual abietanes [14] (Figure 3 b).…”

Section: Figurementioning

confidence: 68%

Forrestiacids A and B, Pentaterpene Inhibitors of ACL and Lipogenesis: Extending the Limits of Computational NMR Methods in the Structure Assignment of Complex Natural Products

et al. 2021

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Forrestiacids A (1) and B (2) are a novel class of [4+2] type pentaterpenoids derived from a rearranged lanostane moiety (dienophile) and an abietane unit (diene). These unprecedented molecules were isolated using guidance by molecular ion networking (MoIN) from Pseudotsuga forrestii, an endangered member of the Asian Douglas Fir Family. The intermolecular hetero‐Diels–Alder adducts feature an unusual bicyclo[2.2.2]octene ring system. Their structures were elucidated by spectroscopic analysis, GIAO NMR calculations and DP4+ probability analyses, electronic circular dichroism calculations, and X‐ray diffraction analysis. This unique addition to the pentaterpene family represents the largest and the most complex molecule successfully assigned using computational approaches to predict accurately chemical shift values. Compounds 1 and 2 exhibited potent inhibitory activities (IC50s <5 μM) of ATP‐citrate lyase (ACL), a new drug target for the treatment of glycolipid metabolic disorders including hyperlipidemia. Validating this activity 1 effectively attenuated the de novo lipogenesis in HepG2 cells. These findings provide a new chemical class for developing potential therapeutic agents for ACL‐related diseases with strong links to traditional medicines.

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“…Compound 5 1.04 (3H, s, Me-30); d C 18.4 (C-18), 18.0 (C-19), 16.2 (C-21), 17.1 (C-27), 25.8 (C-28), 20.9 (C-29), 20.9 (C-30)], six methylenes, six methines (three olefinic carbons), 11 quaternary carbons including three sp 2 carbons (d C 122.2, 155.3, and 139.8), one ester carbonyl (d C 176.2), and three ketone carbonyls (d C 214.7, 198.2, and 208.4) (Li et al, 2012a), 5 was regarded to have the same side-chain: (25R) methyl 23-oxo-26-oate. By further detailed analysis of its 2D NMR spectra and the literature data (Raldugin and Shevtsov, 1990;Raldugin et al, 1987), the structure of 5 was elucidated as methyl (25R)-3,7,23-trioxo-8,11,14-mariesiatrien-26-oate.…”

Section: Resultsmentioning

confidence: 99%