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
Prof. Jun Zhou You-Xing Zhao
State Key Laboratory of Phytochemistry and Plant Resource in West China
Kunming Institute of Botany
The Chinese Academy of Sciences
Kunming 650204
People’s Republic of China
Telefon: +86-871-522-3264
Fax: +86-871-522-3261
eMail: jzhou@mail.kib.ac
eMail: cnyxzhao@mail.kib.ac.cn