Pterosins from Pteris multifida

Abstract

A new C₁₄ pterosin sesquiterpenoid, named (2R)-pterosin P (1), and a new natural product, named dehydropterosin B (3), were isolated from the aerial parts of Pteris multifida Poir., along with nine known compounds (2, 4–11). By chiral HPLC, compounds 1 and 2 were isolated as a pair of enantiomeric pterosin sesquiterpenoids. The planar structure of 1 was elucidated on the basis of NMR spectroscopy analysis, and the absolute configuration was established by the CD spectrum. In addition, the absolute structure of 1 was further confirmed by single-crystal X-ray diffraction (CuKα). Compounds 3, 5, and 6 showed potent cytotoxicity against PANC-1 (human pancreatic cancer) and NCI-H446 (human small-cell lung cancer) cell lines, with IC₅₀ values in the range of 4.27–14.63 µM.

Key words

Pteris multifida Poir. - Pteridaceae - (2R/S)‐pterosin P - sesquiterpenoids - absolute configuration

References

• 1 Editorial Committee of the Administration Bureau of Traditional Chinese Medicine .Zhong Hua Ben Cao, Vol. 2. Shanghai; Shanghai Science & Technology Press 1999: 122-124
• 2 Hong L, Jun H, Zhang L X, Tan R X. Bioactive constituents from Pteris multifida.  Planta Med. 1999;  65 586-587
• 3 Yoshihira K, Fukuoka M, Kuroyanagi M, Natori S, Umeda M, Morohoshi T, Enomoto M, Saito M. Chemical and toxicological studies on braken fern, Pteridium aquilinum var. latiusculum. I. Introduction, extraction and fractionation of constituents, and toxicological studies including carcinogenicity tests.  Chem Pharm Bull. 1978;  26 2346-2364
• 4 Fukuoka M, Kuroyanagi M, Yoshishira K, Natori S. Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. II. Structures of pterosins, sesquiterpenes having 1-indanone skeleton.  Chem Pharm Bull. 1978;  26 2365-2385
• 5 Murakami T, Maehashi H, Tanaka N, Satake T, Kuraishi T, Komazawa Y, Saiki Y, Chen C M. Chemical and chemotaxonomical studies on filices. LV. Studies on the constituents of several species of Pteris.  Yakugaku Zasshi. 1985;  105 640-648
• 6 Ge X, Ye G, Li P, Tang W J, Gao J L, Zhao W M. Cytotoxic diterpenoids and sesquiterpenoids from Pteris multifida.  J Nat Prod. 2008;  71 227-231
• 7 Kuraishi T, Murakami T, Taniguchi T, Kobuki Y, Maehashi H, Tanaka N, Saiki Y, Chen C M. Chemical and chemotaxonomical studies of ferns. LIV. Pterosin derivatives of the genus Microlepia (Pteridaceae).  Chem Pharm Bull. 1985;  33 2305-2312
• 8 Kuroyanagi M, Fukuoka M, Yoshihira K, Natori S. Circular dichroism and conformations of pterosins, 1-indanone derivatives from bracken.  Chem Pharm Bull. 1979;  27 731-741
• 9 Chen X M, Cai J W. Principles and practice of single crystal structure analysis, 2nd edition. Beijing; Science Press 2007: 177-178
• 10 Hooft R W W, Straver L H, Spek A L. Determination of absolute structure using Bayesian statistics on Bijvoet differences.  J Appl Crystallogr. 2008;  41 96-103
• 11 Tanaka N, Satake T, Takahashi A, Mochizuki M, Murakami T, Saiki Y, Yang J Z, Chen C M. Chemical and chemotaxonomical studies of ferns. XXXIX. Chemical studies on the constituents of Pteris bella Tagawa and Pteridium aquilinum subsp. wightianum (Wall) Shich.  Chem Pharm Bull. 1982;  30 3640-3646
• 12 Chen Y H, Chang F R, Lu M C, Hsieh P W, Wu M J, Du Y C, Wu Y C. New benzoyl glucosides and cytotoxic pterosin sesquiterpenes from Pteris ensiformis Burm.  Molecules. 2008;  13 255-266
• 13 Murakami T, Taguchi S, Nomura Y, Tanaka N, Satake T, Saiki Y, Chen C M. Weitere Indan-1-on Derivate der Gattung Pteris.  Chem Pharm Bull. 1976;  24 1961-1964