Rotundatin, a new 9,10-didydrophenanthrene derivative from Dendrobium rotundatum

doi:10.1016/0031-9422(92)83480-M

Phytochemistry

Volume 31, Issue 9, September 1992, Pages 3225-3228

https://doi.org/10.1016/0031-9422(92)83480-M Get rights and content

Abstract

Rotundatin, a new 9,10-dihydrophenanthrene derivative was isolated from the orchid, Dendrobium rotundatum, which also afforded the known stilbenoids 2,7-dihydroxy-3,4,6-trimethoxyphenanthrene, 2,7-dihydroxy-3,4,6-trimethoxy-9,10-dihydrophenanthrene, nudol, moscatin and batatasin-III. Rotundatin was shown to be 2,5,9-trihydroxy-4-methoxy-9,10-dihydrophenanthrene from spectral and chemical evidence.

References (12)

P.L. Majumder et al.
Phytochemistry
(1991)
S.R. Bhandari et al.
Phytochemistry
(1985)
T. Hashimoto et al.
Phytochemistry
(1974)
P.L. Majumder et al.
Phytochemistry
(1985)
R.M. Letcher et al.
J. Chem. Soc. Perkin I
(1972)
P.L. Majumder et al.
J. Indian Chem. Soc.
(1981)

There are more references available in the full text version of this article.

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In previous studies, compound 10 was obtained from D. officinale (Zhao et al., 2018b). D. nobile is a source of compounds 8, 9, 11, and 12 (Zhou et al., 2016; Hwang et al., 2010), and compound 13 is extensively reported in the genus Dendrobium, including D. plicatile (Honda and Yamaki, 2000), D. loddigesii (Chen et al., 1994), D. densiflorum (Fan et al., 2001), D. trigonopus (Hu et al., 2008), D. rotundatum (Majumder and Pal, 1992), and D. polyanthum (Hu et al., 2009). The occurrence of compounds 8, 9, 11, and 12 supported that these compounds may have chemotaxonomic significance for verifying the close phylogenetic relationship between D. chrysanthum and D. nobile.
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The IR spectrum exhibited the presence of hydroxyl groups (3398 cm−1) and aromatic rings (1600 and 768 cm−1). Compound 1 shared the same molecular formula with a known biphenantherene rigidanthrin (12),10 which was also obtained from this plant in our research (NMR data shown in Table 1S). The 13C NMR spectrum of 1 showed 32 carbon signals, among which 16 carbon signals were in accordance with those of rigidanthrin (Table 1).
A phytochemical investigation of the whole plant of Liparis regnieri Finet led to the isolation of one new biphenantherene (1) and ten new nervogenic acid derivatives (2–11), together with nine known compounds. Their structures were elucidated mainly by extensive analyses of 1D and 2D NMR spectroscopic data and chemical reactions. Additionally, for the first time a previously unreported biphenantherene was discovered to effectively suppress TNF-α induced expression of NF-κB-Luc in Hela cells with the IC₅₀ value of 1.80 μM and the structure-activity relationshipwas also discussed.
Isolation of novel stilbenoids from the roots of Cyrtopodium paniculatum (Orchidaceae)
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for C18H21O6, 333.1333) accounting for nine degrees of unsaturation. The UV maximal absorption at 218, 281 and 311 nm were indicative of a 9,10-dihydrophenanthrene skeleton [46,47]. The IR spectrum exhibited absorption bands at 3365 cm− 1 for hydroxyl group and 1584, 1454, 1089 and 843 cm− 1 due to aromatic ring.
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Two new phenanthrene glycosides from Liparis regnieri Finet and their antibacterial activities
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Furthermore, thirty previously reported compounds were also obtained. Their structures were identified by spectroscopic data comparison with literature values and were assigned as {1-O-[6-acetyl-O-β-d-glucopyranosyl]}-4-hydroxy-3,5-bis(3-methyl-2-butenyl) benzoate (3) (Huang et al., 2013a), 4-hydroxy-3,5-bis(3′-methyl- 2-butenyl)benzoic acid O-β-d-glucopyranoside (4) (Jiang et al., 2013), 4-(O-β-d-glucopyranosyl)-3,5-bis(3-methyl-2-butenyl) benzoic acid (5), 4-(O-β-d-glucopyranosyl)-3-prenylbenzoic acid methyl ester (6), aloifol I (7) (Zhao et al., 2016), liparisglycoside F (8) (Xie et al., 2015), liparacid A–C (9–11) (Kuo et al., 2007), 8-(3-hydroxyisoamyl)-2,2-dimethylchromane-6-carboxylic acid (12) (Zhao et al., 2013), flavanthrinin (13), 4-methoxy- 9,10-dihydro-phenanthrene-2,5-diol (14), tristin (15) (Xu et al., 2014), gymnopusin (16) (Majumder et al., 2008), rotundatin (17) (Majumder and Pal, 1992), 4-methoxy-2,5,7,9S-tetrahydroxy-9,10-dihydrophenanthrene (18), 1,2,5,9R-tetrahydroxy-9,10-dihydrophenanthrene-5-O-β-d-glucopyranoside (19) (Lin et al., 2013), vanillin (20) (Kikuzaki et al., 1999), actinidiolide (21) (Joshi et al., 2011), vanillic acid (22) (Sakushima et al., 1995), denneanoside A and F (23–24), 3,5,4′-trihydroxy-bibenzyl-3-O-β-d-glucoside (25) (Feng et al., 2005), polydotin peceid (26) (Ali et al., 2004), bletilol A–C (27–29) (Yamaki et al., 1993), β-sitosterol (30), dancosterol (31) (Guan et al., 2014) and pyromeconic acid (32) (Thorson et al., 2014). Phenanthrenes and their derivatives were previously reported to possess significant antibacterial activities (Husseini and Stretton, 1981; Yoshikawa et al., 2012).
Two new phenanthrene glycosides, nudolglycosides A and B (1 and 2) and thirty known compounds (3–32) were isolated from the whole plant of Liparis regnieri Finet. Their structures were assigned by detailed analysis of MS and NMR spectroscopic data. All the isolates were evaluated for their antibacterial activities against Bacillus subtilis, Enterococcus faecalis, Riemerella anatipestifer, Salmonella gallinarum, Staphylococcus aureus, Streptococcus agalactiae and Vibrio Parahemolyticus. Six known phenanthrene derivatives (33–38) exhibited significant antibacterial activity against S. agalactiae and B. subtilis with MIC values ranging from 48.0 to 54.4 μg/mL.
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Rotundatin, a new 9,10-didydrophenanthrene derivative from Dendrobium rotundatum

Abstract

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

J. Chem. Soc. Perkin I

J. Indian Chem. Soc.