3α, 11α-Dihydroxy-23-oxo-lup-20(29)-en-28-oic acid from Acanthopanax trifoliatus

Ty,; Lischewski, M.; Phiet, H.V.; Preiß, A.; Nguyen, Ph.V.; Adam, G.

doi:10.1016/s0031-9422(00)84914-6

Cited by 16 publications

(2 citation statements)

References 6 publications

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“…The chemical shifts of C-1 (δ 35.7), C-3 (δ 73.7) C-5 (δ 44.4), and C-24 (δ 15.1) further confirmed the α configuration of the hydroxyl group at C-3 by comparing with the corresponding signals of the 3β-hydroxy-lup-20(29)-en-23-al-28-oic acid (Liu et al, 2002) [δ values for 38.9 (C-1), 71.7 (C-3), 47.9 (C-5), and 9.4 (C-24)]. Also within 13 C NMR data of 1, close agreement was found with 3α,11α-dihydroxy-23-oxolup-20(29)-en-28-oic acid (Ty et al, 1985;Chang et al, 1999;Kiem et al, 2003) for the sequence C-1 to C-17 (rings A, B, C and partly D suggesting that the two α-hydroxyl groups were at C-3 and C-11, and the aldehydic group was at C-4). Furthermore, in the HMBC spectrum, the aldehydic proton signal at δ 9.48 (1H, s, H-23) correlated with carbons C-3 (δ 73.7), C-4 (δ 53.5), and with C-5 (δ 44.4), the proton signal at δ 0.99 (3H, s, H-24) correlated with carbons C-3 (δ 73.7), C-4 (δ 53.5), and C-23 (δ 210.9) (See Fig.…”

Section: Resultsmentioning

confidence: 56%

A new norlupane triterpene from the leaves of Acanthopanax koreanum increases the differentiation of osteoblastic MC3T3-e1 cells

et al. 2010

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A new norlupane-triterpene, 3alpha,11alpha-dihydroxy-20,23-dioxo-30-norlupane-28-oic acid (1), and four known compounds; 3alpha,11alpha-dihydroxy-23-oxo-lup-20(29)-en-28-oic acid (2), 3alpha,11alpha-dihydroxylup-20(29)-en-28-oic acid (3), ent-kaur-16-en-19-oic acid (4), and betulabuside B (5) were isolated from the methanolic extract of the leaves of Acanthopanax koreanum. Their chemical structures were elucidated by mass, 1D- and 2D-NMR spectroscopy. To investigate the bioactivities of these compounds, their effects on the differentiation of osteoblastic MC3T3-E1 cells were tested. Compounds 3 and 4 significantly increased osteoblastic cell growth and differentiation as assessed by the MTT assay and collagen content, respectively (p < 0.05). Compounds 1 and 5 significantly increased the growth of MC3T3-E1 cells and caused a significant elevation of osteoblastic cell differentiation as assessed by the alkaline phosphatase activity. These results suggest that the compounds isolated from A. koreanum leaves have a direct stimulatory effect on bone formation in vitro and may contribute to the prevention for osteoporosis.

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Section: Resultsmentioning

confidence: 56%

A new norlupane triterpene from the leaves of Acanthopanax koreanum increases the differentiation of osteoblastic MC3T3-e1 cells

et al. 2010

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“…Because of its fragrance, more and more studies focused on its terpenoids (Phuong et al 2006) and triterpenes (Ty et al 1984;Lischewski et al 1985;Ty et al 1985;Yook et al 1999;Kiem et al 2003). In the present study, one sesquiterpene synthase gene in E. trifoliatus was identified and characterized.…”

Section: Introductionmentioning

confidence: 99%

Identification and functional characterization of a sesquiterpene synthase gene from Eleutherococcus trifoliatus

Wen

Tseng

Chu

2011

HFSG

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In the present study, one sesquiterpene synthase gene in Eleutherococcus trifoliatus was identified and characterized. Full-length cDNA was obtained from stems. It contained an open reading frame of 1671 bp (EtCop) with a predicted molecular mass of 64.5 kDa. The amino acid sequence of EtCop contained the common terpene synthase family motifs RR(x)(8)W, RxR and DDxxD. The recombinant protein from Escherichia coli was incubated with farnesyl diphosphate in order to identify the function of EtCop. The product of EtCop could be identified as an alpha-copaene by means of gas chromatography-mass spectrometry analysis and comparison with an authentic standard

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Composition of the essential oil ofAcanthopanax trifoliatus (L.) Merr. (Araliacaea) from Vietnam

Muselli

Hoi²,

Cu³

et al. 1999

Flavour Fragr. J.

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3α, 11α-Dihydroxy-23-oxo-lup-20(29)-en-28-oic acid from Acanthopanax trifoliatus

Cited by 16 publications

References 6 publications

A new norlupane triterpene from the leaves of Acanthopanax koreanum increases the differentiation of osteoblastic MC3T3-e1 cells

A new norlupane triterpene from the leaves of Acanthopanax koreanum increases the differentiation of osteoblastic MC3T3-e1 cells

Identification and functional characterization of a sesquiterpene synthase gene from Eleutherococcus trifoliatus

Composition of the essential oil ofAcanthopanax trifoliatus (L.) Merr. (Araliacaea) from Vietnam

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