Five New Compounds from Dendrobium longicornu

Abstract

A novel bibenzyl, a new bibenzyl, two new phenanthrenes, and a new lignin glycoside, namely longicornuol A (1), 4-[2-(3-hdroxyphenol)-1-methoxyethyl]-2,6-dimethoxyphenol (2), 5-hydroxy-7-methoxy-9,10-dihydrophenanthrene-1,4-dione (3), 7-methoxy-9,10-dihydrophenanthrene-2,4,5-triol (4) and erythro-1-(4-O-β-D-glucopyranosyl-3-methoxyphenyl)-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]-1,3-propanediol (5), together with 14 known compounds, were isolated from the stems of Dendrobium longicornu. All structures were elucidated by spectroscopic methods (NMR, MS, UV and IR). Anti-platelet aggregation activities of compounds 1 - 5 were also tested.

Key words

Orchidaceae - Dendrobium longicornu - bibenzyl - phenanthrenes - lignin glycoside - anti-platelet aggregation activity

References

• 1 Dictionary of Chinese Medicines. Shanghai; Shanghai Science and Technology Press 1986: 586
• 2 Pharmacopoeia of China, Part I. Beijing; Chemistry and Industry Press 2005: 62
• 3 Juneja R K, Sharma S C, Tandon J S. Two substituted bibenzyls and a dihydrophenanthrene from Cymbidium aloifolium.  Phytochemistry. 1987;  26 1123-5
• 4 Letcher R M, Nhamo L RM. Chemical constituents of the Combretaceae part III. Substituted phenanthrenes, 9, 10-dihydrophenanthrenes and bibenzyls from the heartwood of Combretum psidioides.  J Chem Soc [Perkin I]. 1972;  23 2941-6
• 5 Li X C, Barnes D L, Khan I A. A new lignan glycoside from Eleutherococcus senticosus.  Planta Med. 2001;  67 776-8
• 6 Bhaskar M U, Rao L JM, Rao N SP, Rao P RM. Ochrone A, a novel 9,10-dihydro-1,4-phenanthraquinone from Coelogyne ochracea.  J Nat Prod. 1991;  54 386-9
• 7 Leong Y W, Kang C C, Harrison L J, Powell A D. Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum.  Phytochemistry. 1997;  44 157-65
• 8 Zhang Z Z, ElSohly H N, Li X C, Khan S I, Broedel Jr S E, Raulli R E. et al . Phenolic compounds from Nymphaea odorata.  J Nat Prod. 2003;  66 548-50
• 9 Yoshikawa K, Sugawara S, Arihara S. Phenylpropanoids and other secondary metabolites from fresh fruits of Picrasma quassioides.  Phytochemistry. 1995;  40 253-6
• 10 Miyase T, Ueno A, Takizawa N, Kobayashi H, Oguchi H. Studies on the glycosides of Epimedium grandiflorum Morr var. thunbergianum (Miq.) Nakai .  Chem Pharm Bull. 1987;  35 3713-9
• 11 Bai L, Masukawa N, Yamaki M, Takagi S. Two bibenzyl glucosides from Pleione bulbocodioides.  Phytochemistry. 1997;  44 1565-7
• 12 Leslie C, Jamieson S V. Dihydrostilbenes of cannabis, synthesis of canniprene.  J Chem Soc [Perkin I]. 1982;  7 1467-75
• 13 Majumder P L, Sen R C. Moscatilin, a bibenzyl derivative from the orchid Dendrobium moscatum.  Phytochemistry. 1987;  26 2121-4
• 14 Majumder P L, Pal S. Cumulantin and tristin, two bibenzyl derivatives from the orchids Dendrobium cumulatum and Bulbophyllum triste.  Phytochemistry. 1993;  32 1561-5
• 15 Anton H, Schoeneborn R, Mues R. Bibenzyls and bisbibenzyls from a neotropical Plagiochila species.  Phytochemistry. 1999;  52 1639-45
• 16 Geiger H, El-Dessouki S, Seeger T. (3S,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-carboxylic acid from Sequoiadendron giganteum.  Phytochemistry. 1995;  40 1705-7
• 17 Cioffi G, Escobar L M, Braca A, De Tommasi N. Antioxidant chalcone glycosides and flavanones from Maclura (Chlorophora) tinctoria.  J Nat Prod. 2003;  66 1061-4
• 18 Hylands P J, Ingolfsdottir K. The isolation of methyl β-orsellinate from Stereocaulon alpinum and comments on the isolation of 4, 6-dihydroxy-2-methoxy-3-methylacetophenone from Stereocaulon species.  Phytochemistry. 1985;  24 127-9
• 19 Chang F R, Chao Y C, Teng C M, Wu T C. Chemical constituents from Cassytha filiformis II.  J Nat Prod. 1998;  61 863-6
• 20 Cardona M L, Garcia B, Pedro J R, Sinisterra J F. Flavonoids, flavonolignans and a phenylpropanoid from Onopordon corymbosum.  Phytochemistry. 1990;  29 629-31
• 21 Ranganathan R. A novel purine nucleoside synthesis: 9-β-D-arabinofuranosyl-ademine.  Tetrahedron Lett. 1975;  13 1185-8
• 22 Takeda Y, Ooiso Y, Masuda T, Honda G, Otsuka H, Sezik E. et al . Iridoid and eugenol glycosides from Nepeta cadmea.  Phytochemistry. 1998;  49 787-91
• 23 Chen C C, Wu L G, Ko F N, Teng C M. Antiplatelet aggregation principles of Dendrobium loddigesii.  J Nat Med. 1994;  57 1271-4
• 24 Fan C Q, Wang W, Wang Y P, Qin G W, Zhao W M. Chemical constituents from Dendrobium densiflorum.  Phytochemistry. 2001;  57 1255-8