Moscatilin, a bibenzyl derivative from the orchid Dendrobium moscatum

doi:10.1016/S0031-9422(00)81777-X

Phytochemistry

Volume 26, Issue 7, 1987, Pages 2121-2124

https://doi.org/10.1016/S0031-9422(00)81777-X Get rights and content

Abstract

Moscatilin, a new bibenzyl derivative isolated from the orchid Dendrobium moscatum, was shown to have the structure 4,4′-dihydroxy-3,3′,5-trimethoxybibenzyl.

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Chemical constituents from Dendrobium chrysanthum and their chemotaxonomic significance
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Nineteen known compounds were isolated from the 75% alcohol extract of the stems of Dendrobium chrysanthum, including four phenols (1–4), three alkaloids (5–7), six phenanthrenes (8–13), three monoterpenes (14–16), and three lignans (17–19). This is the first report on compounds 3 (trans-3,4,5-trimethoxylcinnamyl alcohol), 5 (1-(6-hydroxy-[3]pyridyl)-propan-1-one), 16 ((+)-(1S,5R)-verbenon-10-oic acid) and 18 (cinnacassin F) isolated from the family Orchidaceae, compounds 2 (3-hydroxy-4,5-dimethoxypropiophenone) and 7 (1H-Indole-3-carbaldehyde) from the genus Dendrobium, and compounds 1 (syringaldehyde), 4 (apocynin), 8 (confusarin), 9 (nudol), 10 (orchinol), 11 (ephemeranthol-A), 12 (5,7-dimethoxyphenanthrene-2,6-diol), 13 (moscatilin), 15 (loliolide), 17 (3,3′-bis(3,4-dihydro-4-hydroxy-6-methoxy-2H-1-benzopyran) and 19 ((+)-syringaresinol) from D. chrysanthum. It is worth mentioning that compounds 6 (carbofuran) and 14 ((6R,7aR)-7a-hydroxy-3,6-dimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one) have not been previously reported from any plant. Their structures were elucidated on the basis of NMR spectroscopic data. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.
Phytochemical and chemotaxonomic study on Dendrobium lindleyi Stendel
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Citation Excerpt :
Dendrobium nobile is a source of compounds (3, 4, 5 and 6) (Yang et al., 2017; Zhou et al., 2016), and compounds 4 and 6 were also isolated from Dendrobium aphyllum (Yang et al., 2015; Zhang et al., 2009). Compounds 7 and 8 from Dendrobium chrysotoxum (Hu et al., 2012; Ma et al., 1996), as well as compound 9 from Dendrobium moscatum (Majumder and Sen, 1987). Compounds (10–15) are phenanthrenes.
Phytochemical investigation of Dendrobium lindleyi Stendel led to the isolation of one undescribed naphthalene, dendrolene A (1), together with eight known bibenzyls (2-9), six known phenanthrenes (10–15), one sterol (16), one p-hydroxyphenylpropionic methyl ester (17) and one dihydroconiferyl dihydro-p-cumarate (18). Structure elucidation of these isolates was performed based on MS, 1D and 2D NMR data. This is the first report of isolation of compounds (1–6), (10–14) and (17–18) from D. lindleyi. The chemotaxonomic significance of these compounds was also discussed, which demonstrated the relationships between D. lindleyi and some other species of the genus Dendrobium.
Phenanthrenes from Dendrobium senile and their pancreatic lipase inhibitory activity
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From the whole plant of Dendrobium senile, a new phenanthrene namely 2,5,7-trihydroxy-4-methoxyphenanthrene (1) was isolated, together with seven known compounds including moscatin (2), 2,5-dihydroxy-4,9-dimethoxyphenanthrene (3), moscatilin (4), aloifol I (5), 4,4′,8,8′-tetramethoxy[1,1′-biphenanthrene]-2,2′,7,7′-tetrol (6), 2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthrene (7) and bleformin G (8). The structure of the new compound was elucidated by analysis of its spectroscopic data. Moscatin (2) and 2,5-dihydroxy-4,9-dimethoxyphenanthrene (3) showed appreciable pancreatic lipase inhibitory effects when compared with the positive control orlistat.
Dendrocrepidamine, a novel octahydroindolizine alkaloid from the roots of Dendrobium crepidatum
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A novel octahydroindolizine alkaloid, named dendrocrepidamine (1) with an unusual 18,19,19′-cyclopropanone-dendrocrepine skeleton, was isolated from the ethanol extract of the roots of Dendrobium crepidatum, along with six known compounds (2–7). The structure of 1 was elucidated through HR-ESIMS, NMR spectroscopic data and computational calculations. All compounds were examined for their inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in RAW264.7 cells with IC₅₀ values in the range of 3.04–54.89 µM. In vivo, crepidatin (6) (80, 40 and 10 mg/kg) showed a significant protective effect against LPS-induced acute lung injury (ALI) in mice.
Molecular genetic homogeneity assessment of micropropagated Dendrobium moschatum Sw. - A rare medicinal orchid, using RAPD and ISSR markers
2019, Plant Gene
Generation of true-to-type plant is one of the most important aspects in germplasm conservation through micropropagation. In this study, reliable in vitro protocols were established for the generation of genetically stable plants of Dendrobium moschatum using seed explants via protocorm formation. Thidiazuron (TDZ) and 6-benzyl aminopurine (BAP) induced effective shooting when incorporated individually or in combination with auxins in the medium. High shooting response was observed in Mitra medium either with 2.4 mgL⁻¹BAP or 1.2 mgL⁻¹TDZ and 1.2 mgL⁻¹1-naphthyl acetic acid (NAA). Indole-3-butyric acid (IBA) or NAA produced better root multiplication in the culture than indole -3- acetic acid (IAA). Medium with 1.2 mg L⁻¹ TDZ + 1.2 mgL⁻¹ IBA or 1.2 mg L⁻¹ TDZ + 1.2 mg L⁻¹ NAA generated a good rooting response. Random Amplified Polymorphic DNA (RAPD) and Inter Simple Sequence Repeats (ISSR) markers analysis showed 95.2% and 98% genetic monomorphism respectively among in vitro regenerants and the mother plant. Nei’s genetic distance ranged from 0.00 to 0.044 disclosing high genetic similarity among the regenerants. The Unweighted Pair Group Method with Arithmetic Mean (UPGMA) based dendrograms generated from RAPD and ISSR marker analysis also revealed high genetic proximity between mother and micropropagated plants. Principal Coordinate Analysis (PCoA) further confirmed the grouping of plants in accordance with UPGMA dendrograms. Correlation analysis between the matrices of markers revealed higher efficiency of ISSR over RAPD markers. This is the first report of genetic homogeneity testing of in vitro propagated Dendrobium moschatum using molecular markers.
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A new phenanthrene dimer, namely dendropalpebrone (1), was isolated from the whole plant of Dendrobium palpebre, along with nine known compounds (2–10). All of the isolates were evaluated for their hydroxyl radical scavenging effects using a deoxyribose assay. Dendroflorin (10) showed an appreciable activity, and therefore was selected for further studied in RAW264.7 cells. Compound 10 significantly decreased ROS in H₂O₂-stimulated RAW264.7 cells in a dose-dependent manner, and improved activity of SOD, GPx, and CAT enzymes.

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Moscatilin, a bibenzyl derivative from the orchid Dendrobium moscatum

Abstract

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

Tetrahedron

Phytochemistry

Indian J. Chem.

J. Chem. Soc.