Five New Diarylpropan-1-ols from Combretum yunnanense

Abstract

Five new 1,3-diarylpropan-1-ols, combretol A–E (1–5), together with one known coumarin (6) and ten known triterpenes (7–16), were isolated from Combretum yunnanense. Their structures were determined by spectroscopic investigation, including ¹H and ¹³C NMR, NOESY, HSQC, HMBC, and HRESIMS analyses. This is the first report on the occurrence of 1,3-diarylpropan-1-ols and coumarin in the Combretum genus including C. yunnanense. Also, to the best of our knowledge, 1,3-diarylpropan-1-ols are rare in nature.

Key words

Combretum yunnanense - Combretaceae - 1,3-diarylpropan-1-ol - combretols A–E

References

• 1 Wu M M, Wang L Q, Hua Y, Chen Y G, Wang Y Y, Li X Y, Li Y, Li T, Yang X Y, Tang Z R. New chalcone and dimeric chalcones with 1,4-p-benzoquinone residue from Combretum yunnanense.  Plant Med. 2011;  77 481-484
• 2 Wu Q, Zou L, Yang X W, Fu D X. Novel sesquiterpene and coumarin constituents from the whole herbs of Crossostephium chinense.  J Asian Nat Prod Res. 2009;  11 85-90
• 3 Kitajima J, Shindo M, Tanaka Y. Two new triterpenoid sulfates from the leaves of Schefflera octophylla.  Chem Pharm Bull. 1990;  38 714-716
• 4 Liu P, Duan H Q, Pan Q, Zhang Y W, Yao Z. Triterpenes from herb of Potentilla chinesis.  China J Chin Mater Med. 2006;  31 1875-1879
• 5 Li X C, Joshi A S, ElSohly H N, Khan S I, Jacob M R, Zhang Z Z, Khan I A, Ferreira D, Walker L A, Broedel S E, Raulli R E, Cihlar R L. Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.  J Nat Prod. 2002;  65 1909-1914
• 6 Jossang A, Seuleiman M, Maidou E, Bodo B. Pentacyclic triterpenes from Combretum nigricans.  Phytochemistry. 1996;  41 591-594
• 7 Yang Z G, Li H R, Wang L Y, Li Y H, Lu S G, Wen X F, Wang J, Daikonya A, Kitanaka S. Triterpenoids from Hippophae rhamnoides L. and their nitric oxide production-inhibitory and DPPH radical-scavenging activities.  Chem Pharm Bull. 2007;  55 15-18
• 8 Anjaneyulu A S R, Rama Prasad A V. Chemical examination of the roots of Terminalia arjuna–the structures of arjunoside III and arjunoside IV, two new triterpenoid glycosides.  Phytochemistry. 1982;  21 2057-2060
• 9 Braca A, Sortino C, Mendez J, Morelli I. Triterpenes from Licania licaniaeflora.  Fitoterapia. 2001;  72 585-587
• 10 Hambley T W, Rideout J A, Taylor W C. The chemical constituents of Australian Flindersia species, XXIV. 1,3-diphenylpropanes from the wood of Flindersia brassii.  Aust J Chem. 1990;  43 1327-1334
• 11 Getahun Z, Jurd L, Chu P S, Lin C M, Hamel E. Synthesis of alkoxy-substituted diaryl compounds and correlation of ring separation with inhibition of tubulin polymerization: differential enhancement of inhibitory effects under suboptimal polymerization reaction conditions.  J Med Chem. 1992;  35 1058-1067