- Original Article
- Published:
The polar neutral and basic taxoids isolated from needles and twigs of Taxus cuspidata and their biological activity
Journal of Wood Science volume 54, pages 390–401 (2008)
Abstract
Twelve basic taxoids and 22 neutral taxoids were isolated from basic and polar neutral fractions of the extracts of needles and twigs of Taxus cuspidata. Among them, taxine NA-13, 3,11-cyclotaxinine NN-1, taxinine NN-6, 11(15→1)abeo-taxinine NN-1, taxine NA-8, and taxine NA-4 were isolated first from natural sources by us. The cytotoxic activity of isolated compounds was evaluated against three human cell lines: normal human fibroblast cells (WI-38), malignant tumor cells induced from WI-38 (VA-13), and human liver tumor cells (HepG2). 7-Epitaxol, 7-epicephalomannine, taxinine NN-6, taxine NA-2, taxuspine H, and taxagifine were active toward VA-13 cells and 7-epitaxol, 7-epicephalomannine, taxinine NN-1, 9,10-deacetyltaxinine, and taxagifine were active toward HepG2 cells. The multidrug-resistant (MDR) cancer reversal activity of isolated compounds was evaluated on the basis of the amount of vincristine (VCR) accumulated in MDR human ovarian cancer 2780 AD. Taxine NA-8, taxine NA-2, 5-cinnamoyl-10-acetyltaxicin II, and taxinine NN-1 indicated stronger MDR cancer reversal activity than verapamil. The result of primary screening based on 39 human cancer cell lines suggests that taxinine NN-1 belongs to a new mechanistic class and is a new anticancer agents. 7-Epicephalomannine was found to be an effective anticancer agent with tubulin as its molecular target, which is the same as paclitaxel.
References
Kingston DGI, Molinero AA, Rimoldi JM (1993) The taxane diterpenoids. Prog Chem Org Nat Prod 61:1–192
Baloglu E, Kingston DGI (1999) The taxane diterpenoids. J Nat Prod 62:1448–1472
Kobayashi J, Ogiwara A, Hosoyama H, Sigemori H, Yoshida N, Sasaki T, Li Y, Iwasaki S, Naito M, Tsuruo T (1994) Taxuspines A∼C, new taxoids from Japanese yew Taxus cuspidata inhibiting drug transport activity of p-glycoprotein in multidrug-resistant cells. Tetrahedron 50:7401–7416
Kobayashi J, Hosoyama H, Sigemori H, Koiso Y, Iwasaki S (1995) Taxuspine D, a new taxane diterpene from Taxus cuspidata with potent inhibitory activity against Ca2+-induced depolymerization of microtubules. Experimentia 51:592–595
Kobayashi J, Inubushi A, Hosoyama H, Yoshida N, Sasaki T, Shigemori H (1995) Taxuspines E∼H and J, new taxoids from the Japanese yew Taxus cuspidata. Tetrahedron 51:5971–5978
Ando M, Sakai J, Zhang S, Watanabe Y, Kosugi K, Suzuki T, Hagiwara H (1997) A new basic taxoid from Taxus cupidata. J Nat Prod 60:499–501
Kosugi K, Sakai J, Zhang S, Watanabe Y, Sasaki H, Suzuki T, Hagiwara H, Hirose K, Ando M, Tomida A, Turuo T (2000) Neutral taxoids from Taxus cuspidata as modulators of multidrugresistant tumor cells. Phytochemistry 54:839–845
Sakai J, Sasaki H, Kosugi K, Zhang S, Hirata N, Hirose K, Tomida A, Turuo T (2001) Two taxoids from Taxus cuspidata as modulations of multidrug-resistant tumor cells. Heterocycles 54:999–1009
Tachibana S, Ishikawa H, Itoh K (2005) Antifungal activities of compounds isolated from the leaves of Taxus cuspidata va. nana against pathogenic fungi. J Wood Sci 51:181–184
Shiro M, Sato T, Koyama H, Maki Y, Nakanishi K, Uyeo S (1966) The stereochemistry of taxinine: X-ray analysis of 2,5,9,10-tetra-O-acetyl-14-bromotaxinol. J Chem Soc Chem Commun 97–98
Dukes M, Eyre DH, Harrison JW, Lythgoe B (1965) The stereochemistry of taxicin-I and taxicin-II. Tetrahedron Lett 6:4765–4773
Eyre DH, Harrison JW, Lythgoe B (1967) Taxine. Part VI. The stereochemistry of taxicin-I and taxicin-II. J Chem Soc C 452–462
Yoshizaki F, Madarame M, Takahashi C, Hisamichi S (1986) Principal constituents of the seeds of Japanese yew (Taxus cuspidate). Shoyakugaku Zashi 40:429–432
Ando M (2000) Jpn. Appl JP 2000044523 A, 15 February 2000. JP 19980214507, 29 July 1998. Priority: JP 19980214507, 29 July 1998. Isolation of taxane diterpenoids from needle leaves of Taxus cuspidata. Chem Abstr 132:156816
Ando M (2001) PCT Int Appl WO 2001007040 A1, 1 February 2001. Appl WO 2000-JP 5036, 27 July 2000. Priority: JP 1999-214273, 28 July 1999; JP 1999-224652, 6 August 1999; JP 2000-76404, 14 March 2000. Multidrug-resistant cancer overcoming agents and process for producing the same. Chem Abstr 2001, 134:136666
Huang CHO, Kingston DGI, Magri NF, Samaranayake G (1986) New taxanes from taxus brevifolia. J Nat Prod 49:665–669
Chmurny GN, Hilton BD, Brobst S, Look SA, Witherup KM, Beutler JA (1992) 1H-and 13C-NMR assignments for taxol, 7-epi-taxol, and cephalomannine. J Nat Prod 55:414–423
Wani MC, Taylor HL, Wall ME (1972) Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc19: 2325–2326
Bellis PD, Lovati M, Pace R, Pererlongo F, Zini GF (1995) Isolation of 7-epi-cephalomannine from Taxus × media cv. “Hicksii” needles. Fitoterapia 66:521–524
Shi Q, Wang HK, Bastow KF, Tachibana Y, Chen K, Lee FY, Lee KH (2001) Antitumor agents 210, synthesis and evaluation of taxoid-epipodophyllotoxin conjugates as novel cytotoxic agents. Bioorg Med Chem 9:2999–3004
Daniewski WM, Gumulka M, Anczwski W, Masnyk M, Bloszyk E, Gupta KK (1998) Why the yew tree (Taxus baccata) is not attacked by insects. Phytochemsitry 49:1279–1282
Zhang H, Tadeda Y, Sun H (1995) Taxanes from Taxus yunnanesis. Phytochemistry 39:1147–1151
Ettouati L, Ahond A, Convert O, Laurent D, Poupat C, Potier P (1988) Plantes de nouvelle-caledonie. 114. Taxanes isoles des feuilles d’Austrotaxus spicata Compton (taxacees). Bull Soc Chim Fr 4:749–755
Shi QW, Oritani T, Zhao D, Murakami R, Oritani T (2000) Three new taxoids from the seeds of Japanese yew, Taxus cuspidata. Planta Med 66:294–299
Zhang JZ, Fang QC, Liang XT, He CH, Kong M, He WY, Jin XL (1995) Taxoids from the barks of Taxus wallichiana. Phytochemistry 40:881–884
Chen YJ, Chen CY, Shen YC (1999) New taxoids from the seeds of Taxus chinesis. J Nat Prod 62:149–151
Shigemori H, Wang XX, Yoshida N, Kobayashi J (1997) Taxuspines X-Z, new taxoids from Japanese yew Taxus cuspidate. Chem Pharm Bull 45:1205–1208
Appendino G, Gariboldi P, Pisetta A, Bombardelli E, Gabetta B (1992) Taxanes from Taxus baccata. Phytochemistry 31:4253–4257
Jenniskens LHD, van Rozendaal ELM, van Beek TA (1996) Identification of six taxine alkaloids from Taxus baccata needles. J Nat Prod 59:117–123
Yue Q, Fang QC, Liang XT (1996) A taxane-11,12-oxide from Taxus yunnanensis. Phytochemistry 43:639–642
Yang SJ, Fang JM, Cheng YA (1996) Taxanes from Taxus mairei. Phytochemistry 43:839–842
Wang XX, Shigemori H, Kobayashi J (1998) Taxezopidines B-H, new taxoids from Japanese yew Taxus cuspidata. J Nat Prod 61:474–479
Appendino G, Lusso P, Gariboldi P, Bombardelli E, Gabetta B (1992) A 3,11-cyclotaxane from Taxus baccata. Phytochemistry 31:4259–4262
Kobayashi T, Kurono M, Sato H, Nakanishi K (1972) Nature of photochemically induced transannular hydrogen abstraction of taxinines. J Am Chem Soc 19:2863–2865
Yoshizaki F, Fukuda M, Hisamichi S, Ishida T, In Y (1988) Structures of taxane diterpenoids from the seeds of Japanese yew, Taxus cuspidata. Chem Pharm Bull 36:2098–2102
Zhang Z, Jia Z, Zhu Z, Cui Y, Cheng J, Wang Q (1990) New taxanes from Taxus chinensis. Planta Med 56:293–294
Chauviere G, Guenard D, Pascard C, Picot F, Potier P, Prange T (1982) Taxagifine: new taxane derivative from Taxus baccata L. (Taxaceae). J Chem Soc Chem Commun 495–496
Chattopadhyay SK, Sharma RP (1995) A taxane from the Himalayan yew, Taxus wallichiana. Phytochemistry 39:935–936
Kobayashi J, Hosoyama H, Wang XX, Shigemori H, Sudo Y, Tsuruo T (1998) Modulation of multidrug resistance by taxuspine C and other taxoids from Japanese yew. Bioorg Med Chem Lett 8:1555–1558
Chiang HC, Woods MC, Nakadaira Y, Nakanishi K (1967) The structures of four new taxinine congeners, and a photochemical transannular reaction. J Chem Soc Chem Commun 1201–1202
Hosoyama H, Shigemori H, In Y, Ishida T, Kobayashi J (1998) Occurrence of a new dimeric compound of 5-oxotaxinine A through Diels-Alder cycloaddition. Tetrahedron Lett 39:2159–2162
Kingston DGI, Hawkins DR, Ovington L (1982) New taxanes from Taxus brevifolia. J Nat Prod 45:466–470
Schneider B, Zhao Y, Blitzke T, Schmitt B, Nookandeh A, Sun X, Stockigt J (1998) Taxane analysis by high performance liquid chromatography-nuclear magnetic resonance spectroscopy of Taxus species. Phytochem Anal 9:237–244
Shi QW, Oritani T, Kiyota H, Zhao D (2000) Taxane diterpenoids from Taxus yunnanensis and Taxus cuspidata. Phytochemistry 54:829–834
Suzuki H, Sako M, Hirota K (1998) Thermolysis of taxinine and taxinine H. Allylic rearrangement of the ester moiety in the C-ring. Chem Pharm Bull 46:1314–1316
Bai J, Kitabatake M, Toyoizumi K, Fu L, Zhang S, Dai J, Sakai J, Hirose K, Yamori T, Tomida A, Tsuruo T, Ando M (2004) Production of biologically active taxoids by a callus culture of Taxus cuspidata. J Nat Prod 67:58–63
Ueda K, Cardarelli C, Gottesman MM, Pastan I (1987) Expression of a full-length cDNA for the human “MDR1” gene confers resistance to colchicine, doxorubicin, and vinblastine. Proc Natl Acad Sci USA 84:3004–3008
Ueda K, Komano T (1988) The multidrug-resistance gene MDR1. Gan To Kagaku Ryoho 15:2858–2862
Tsuruo T, Iida-Saito H, Kawabata H, Oh-hara T, Hamada H, Utakoji T (1986) Characteristics of resistance to adriamycin in human myelogenous leukemia K562 resistant to adriamycin and in isolated clones. Jpn J Cancer Res 77:682–692
Shigemori H, Kobayashi J (2004) Biological activity and chemistry of taxoids from the Japanese yew, Taxus cuspidata. J Nat Prod 67:245–256
Author information
Authors and Affiliations
Corresponding author
Additional information
Part of this work was presented at the 74th Annual Meeting of the Chemical Society of Japan, Tanabe, March 1998, and the 41st Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics, Gifu, December 1998. The results of this work were also presented as patent documents at PCT Int: Appl WO 2001007040 A1, February 2001; Appl WO 2000-Jp 5036, 27 July 2000. Priority: JP 1999-214273, 28 July 1999; JP 1999-224652, 6 August 1999; JP 2000-76404, 14 March 2000
Rights and permissions
About this article
Cite this article
Wang, L., Bai, L., Tokunaga, D. et al. The polar neutral and basic taxoids isolated from needles and twigs of Taxus cuspidata and their biological activity. J Wood Sci 54, 390–401 (2008). https://doi.org/10.1007/s10086-008-0964-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10086-008-0964-6