A Cytotoxic Butenolide, Two New Dolabellane Diterpenoids, a Chroman and a Benzoquinol Derivative Formosan Casearia membranacea

Abstract

Investigation of a cytotoxic chloroform-soluble fraction of the stem of Casearia membranacea (Flacourtiaceae) led to the isolation of five new compounds, including one butenolide, casealactone (1), one chroman, caseamemin (2), two dolabellane diterpenoids, casearimene A (3) and casearimene B (4), one benzoquinol ether, casearinone (5), together with fifteen known compounds, including two amides, N-trans-feruloyltyramine (6) and N-cis-feruloyltyramine (7), six steroids, β-sitosterol (8), stigmast-5-ene-3β,7α-diol (9), stigmast-5-ene-3β,7β-diol (10), stigmastane-3β,5α,6β-triol (11), β-sitostenone (12), β-sitosterol 3-O-β-glucoside (13), two triterpenoids, squalene (14) and friedelin (15), one lignan, (±)-syringaresinol (16), two benzenoids, syringaldehyde (17) and vanillic acid (18), one ester, methyl hexadecanoate (19), and anthraquinone (20), respectively. Among these isolates, 1 showed cytotoxicity against P-388 and HT-29 cancer cell lines in vitro, and 6 and 7 showed cytotoxicity against the P-388 cancer cell line. The structures of these compounds were determined by means of spectroscopic techniques, and the structure of 3 was confirmed by X-ray crystallographic analysis.

Key words

Casearia membranacea - Flacourtiaceae - stems - butenolide - casealactone - chroman - caseamemin - dolabellane diterpenoid - casearimene A - casearimene B - benzoquinol ether - casearinone - cytotoxicity

References

• 1 Li H L, Lo H C. Flacourtiaceae in Flora of Taiwan. 2nd Edition Taipei, Taiwan; Editorial Committee of the Flora of Taiwan; Vol. III 1993: pp. 794-6
• 2 Carvalho P RF, Furlan M, Young M CM, Kingston D GI, Bolzani V S. Acetylated DNA-damaging clerodane diterpenes from Casearia sylvestris .  Phytochemistry. 1998;  49 1659-62
• 3 Shaari K, Waterman P G. Podophyllotoxin-type lignans as major constituents of the stems and leaves of Casearia clarkei .  J Nat Prod. 1994;  57 720-4
• 4 Chao S C, Ku Y C, Lin S J, Pan T T. Measurements of fiber dimensions and analysis of the chemical composition of Taiwan hardwoods.  Tai-Wan Sheng Lin Yeh Shih Yen So Lin Wu Chu Ho Tso Shin Yen Pao Kao 1971; 14 : 26 (Chem Abstr. 1972;  76 101396h)
• 5 Takada K, Sakurawi K, Ishii H. Components of the Lauraceae family - I. New lactonic compounds from Litsea japonica .  Tetrahedron. 1972;  28 3757-66
• 6 Chen I S, Lai-Yaun I L, Duh C Y, Tsai I L. Cytotoxic butanolides from Litsea akoensis .  Phytochemistry. 1998;  49 745-50
• 7 Xiong Q, Shi D, Yamamoto H, Mizuno M. Alkylamides from pericarps of Zanthoxylum bungeanum .  Phytochemistry. 1997;  46 1123-6
• 8 Huneck S, Baxter G A, Cameron A F, Connolly J D, Harrison L J, Phillips W R, Rycroft D S, Sim G A. Dolabellane diterpenoids from the liverworts Barbilophozia floerkei, B. lycopodioides, and B. attenuata: spectroscopic and X-ray studies of structure, stereochemistry, and conformation. X-ray molecular structure of 3S,4S,7S,8S-diepoxy-10R,18-dihydroxydolabellane, 18-acetoxy-3S,4S;7S,8S-diepoxydolabellane, and 10R,18-diacetoxy-3S,4S-epoxydolabell-7E-ene.  J Chem Soc Perkin Trans. 1986;  1 809-14
• 9 Fukuda N, Yonemitsu M, Kimura T. Studies on the constituents of the stems of Tinospora tuberculata Beumee. I. N-trans- and N-cis-feruloyltyramine, and a new phenolic glucoside, tinotuberids.  Chem Pharm Bull (Tokyo). 1983;  31 156-61
• 10 Tsai I L, Hsieh C F, Duh C Y, Chen I S. Further study on the chemical constituents and their cytotoxicity from the leaves of Persea obovatifolia .  Chin Pharm J. 1999;  51 335-45
• 11 Chaurasia N, Wichtl M. Sterols and steryl glycosides from Urtica dioica .  J Nat Prod. 1987;  50 881-5
• 12 Meyer W, Jungnickel H, Jandke M, Dettner K, Spiteller G. On the cytotoxicity of oxidized phytosterols isolated from photoautotrophic cell cultures of Chenopodium rubrum tested on meal-worms Tenebrio molitor .  Phytochemistry. 1998;  47 789-97
• 13 Gaspar E MM, Neves H JC. Steroidal constituents from mature wheat straw.  Phytochemistry. 1993;  34 523-7
• 14 Nishiyama Y, Moriyasu M, Ichimaru M, Tachibana Y, Kato A, Mathenge S G, Nganga J N, Juma F D. Acyclic triterpenoids from Ekebergia capensis.  Phytochemistry. 1996;  42 803-7
• 15 Miyamura M, Nohara T, Tomimatsu T, Nishioka I. Seven aromatic compounds from bark of Cinnamomum cassia .  Phytochemistry. 1983;  22 215-8
• 16 Gutierrez A, Herz W. Bisabolones and other constituents of Mikania shushunensis .  Phytochemistry. 1988;  27 3871-4
• 17 Nishibe S, Okabe K, Hisada S. Isolation of phenolic compounds and spectroscopic analysis of a new lignan from Trachelospermum asiaticum var. intermedium .  Chem Pharm Bull (Tokyo). 1981;  29 2078-82
• 18 Seki K, Tomihari T, Haga K, Kaneko R. Iristectorenes A and C-G, monocyclic triterpene esters from Iris tectorum .  Phytochemistry. 1994;  36 425-31
• 19 Anastasia M, Allevi P, Bettini C, Fiecchi A, Sanvito A M. Preparation of anthraquinones by selective oxidation of the corresponding anthracenes and 9,10-dimethoxyanthracenes with copper or zinc nitrate supported on silica gel. Synthesis 1990;: 1083-4
• 20 Tsai I L, Chen J H, Duh C Y, Chen I S. Cytotoxic neolignans from the stem wood of Machilus obovatifolia .  Planta Med. 2000;  66 403-7