Diterpenoids from the Roots of Croton oblongifolius

Abstract

Two new clerodane diterpenes, methyl 15,16-epoxy-3,13(16),14-ent-clerodatrien-18,19-olide-17-carboxylate (1) and dimethyl 15,16-epoxy-12-oxo-3,13(16),14-ent-clerodatriene-17,18-dicarboxylate (2), together with seven known compounds (3 - 9), were isolated from the roots of Croton oblongifolius. The isolated compounds showed only mild cytotoxic activity against HuCCA-1, KB, HeLa, MDA-MB231, and T47D cell lines with IC₅₀ values ranging from 10 to 50 μg/mL.

References

• 1 Pudhom K, Vilaivan T, Ngamrojanavanich N, Dechangvipart S, Sommit D, Petsom A. et al . Furanocembranoids from the stem bark of Croton oblongifolius .  J Nat Prod. 2007;  70 659-61.
• 2 Roengsumran S, Pornpakakul S, Muangsin N, Sangvanich P, Nhujak T, Singtothong P. et al . New halimane diterpenoids from Croton oblongifolius .  Planta Med. 2004;  70 87-9.
• 3 Ngamrojnavanich N, Sirimongkon S, Roengsumran S, Petsom A, Kamimura H. Inhibition of Na⁺,K⁺-ATPase activity by (-)-ent-kaur-16-en-19-oic acid and its derivatives.  Planta Med. 2003;  69 555-6.
• 4 Sommit D, Petsom A, Ishikawa T, Roengsumran S. Cytotoxic activity of natural labdanes and their semi-synthetic modified derivatives from Croton oblongifolius .  Planta Med. 2003;  69 167-70.
• 5 Roengsumran S, Musikul K, Petsom A, Vilaivan T, Sangvanich P, Pornpakakul S. et al . Croblongifolin, a new anticancer clerodane from Croton oblongifolius .  Planta Med. 2002;  68 274-7.
• 6 Roengsumran S, Petsom A, Kuptiyanuwat N, Vilaivan T, Ngamrojnavanich N, Chaichantipyuth C. et al . Cytotoxic labdane diterpenoids from Croton oblongifolius .  Phytochemistry. 2001;  56 103-7.
• 7 Roengsumran S, Singtothong P, Pudhom K, Ngamrochanavanich N, Petsom A, Chaichantipyuth C. Neocrotocembranal from Croton oblongifolius .  J Nat Prod. 1999;  62 163-4.
• 8 Roengsumran S, Achayindee S, Petsom A, Pudhom K, Singtothong P, Surachetapan C. et al . Two new cembranoids from Croton oblongifolius .  J Nat. Prod1998;  61 652-4.
• 9 Chaichantipyuth C, Petsom A, Taweechotipatr P, Muangsin N, Chaichit N, Puthong S. et al . New labdane-type diterpenoids from Croton oblongifolius and their cytotoxic activity.  Heterocycles. 2005;  65 809-22.
• 10 Hasan C M, Khan S, Jabbar A, Rashid M A. Nasimaluns A and B: neo-clerodane diterpenoids from Barringtonia racemosa .  J Nat Prod. 2000;  63 410-1.
• 11 Moulis C, Fouraste I, Bon M. Levatin, an 18-norclerodane diterpene from Croton levatii .  J Nat Prod. 1992;  55 445-9.
• 12 Moulis C, Bon M, Jaud J, Fouraste I. Crovatin, a furanoid diterpene from Croton levatii .  Phytochemistry. 1992;  31 1421-3.
• 13 Pandey U C, Singhal A K, Barua N C, Sharma R P, Baruah J N, Watanabe K. et al . Stereochemistry of strictic acid and related furanoditerpenes from Conyza japonica and Grangea maderaspatana .  Phytochemistry. 1984;  23 391-7.
• 14 Blaes B, Zapp J, Becker H. ent-Clerodane diterpenes and other constituents from the liverwort Adelanthus lindenbergianus (Lehm.) Mitt.  Phytochemistry. 2004;  65 127-37.
• 15 Thebtaranonth C, Thebtaranonth Y, Wanauppathamkul S, Yuthavong Y. Antimalarial sesquiterpenes from tubers of Cyperus rotundus: structure of 10,12-peroxycalamenene, a sesquiterpene endoperoxide.  Phytochemistry. 1995;  40 125-8.
• 16 Komlaiad C. Chemical constituents of stem bark of Croton oblongifolius from Amphoe Phanat Nikhom, Chon Buri Province [dissertation]. Bangkok; Chulalongkorn University 2003.
• 17 Ohsaki A, Yan L T, Ito S, Edatsugi H, Iwata D, Komoda Y. The isolation and in vivo potent antitumor activity of clerodane diterpenoid from the oleoresin of the Brazilian medicinal plant, Copaifera langsdorfii Desfon.  Bioorg Med Chem Lett. 1994;  4 2889-92.
• 18 Tengchaisri T, Chawengkirttikul R, Rachaphaew N, Reutrakul V, Sangsuwan R, Sirisinha S. Antitumor activity of triptolide against cholangiocarcinoma growth in vitro and in hamsters.  Cancer Lett. 1998;  33 169-75.