Cassane‐Type Diterpenes from the Seeds of Caesalpinia crista

Abstract

A new dimer 1 and two new cassane-type diterpenes 2 and 3, designated taepeenin J -L, were isolated from the seeds of Caesalpinia crista L. Compound 1 possesses a dimeric vouacapane skeleton. Their structures were elucidated on the basis of spectroscopic analysis.Introduction. -Caesalpinia crista L., known locally as Taepee in Thai, is a climber distributed from India and Ceylon through most of Southeast Asia to the Ryu-Kyu Islands, Queensland, and Caledonia [1]. In the preceding paper, we isolated taepeenin A -I and nortaepeenin A and B from the stems and roots of C. crista [2]. As a continuation of our study on this plant, we now report the isolation of a new dimer 1 and of two new cassane-type diterpenes 2 and 3 along with three known compounds, (5a,8b)-vouacapane (4) [3], (5a,6b,8b)-vouacapan-6-ol (5) [4], and (5a)-vouacapa-8(14),9(11)-diene (6) [5] from the seeds of C. crista 1 ).

Cassane diterpenoids from the stem of Caesalpinia pulcherrima

“…The 1 H NMR spectroscopic data supported a cassane-type furanoditerpenoid framework (Cheenpracha et al, 2005(Cheenpracha et al, , 2006McPherson et al, 1986;Patil et al, 1997;Ragasa et al, 2002;Roach et al, 2003;Yodsaoue et al, 2008). Three tertiary methyl groups resonated at d 1.04 (Me-19), 1.39 (Me-20), and 1.47 (Me-18) and one secondary methyl group resonated at d 1.02 (d, J = 6.9 Hz, Me-17).…”

“…The basic skeleton of compounds 1-10 was identified to be that of a cassane diterpene on the basis of their IR and UV spectroscopic data and a positive Ehrlich test (Kuroda et al, 2004). The UV absorptions of 1-3 (k max 211-225 nm) were characteristic of a furano cassane-type diterpene (Cheenpracha et al, 2005(Cheenpracha et al, , 2006, whereas structures 4-6 showed absorption bands of an a,b-butenolide ring conjugated with an extra double bond (k max 279-280 nm) (Kinoshita, 2000;Kinoshita et al, 2005). In addition, the IR spectrum of all new compounds indicated the presence of a carbonyl ester functionality (1700-1777 cm À1 ).…”

“…The genus Caesalpinia is a rich source of cassane-type diterpenoids. In the previous studies, we isolated several cassane-type diterpenes from C. crista (Cheenpracha et al, 2005(Cheenpracha et al, , 2006. and C. sappan (Yodsaoue et al, 2008).…”

Phanginin A–K, diterpenoids from the seeds of Caesalpinia sappan Linn.

“…The heartwood of this plant has been used in folk medicine as a blood tonic, expectorant, emmenagogue, and has interesting biological activities such as antioxidation (Safitri et al, 2003;Badami et al, 2003), immunomodulation (Choi et al, 1997), antimicrobial (Lim et al, 2007), anticomplementary (Oh et al, 1998), sedative effect (Nagai et al, 1986) and vasorelaxation (Xie et al, 2000;Hu et al, 2003) properties. In the preceding papers, we isolated several cassane-type diterpenes from Caesalpinia crista (Cheenpracha et al, 2005(Cheenpracha et al, , 2006. As a continuation of our study on this genus, we now report the isolation and elucidation of 11 new cassane-type diterpenoids (1-11) from the seeds of C. sappan.…”

New Cassane Diterpenoids from <em>Caesalpinia sappan</em> and Their Antiplasmodial Activity

“…Previous phytochemical investigations indicated that this genus contains an abundant source of cassane diterpenes with different structure types, and most of them showed in vitro or in vivo pharmacological impacts such as antiproliferative [1][2][3], antiplasmodial [4][5], antibacterial [6], antihelmintic, and antineoplastic activity [7]. As a continuation of our project towards new bioactive diterpenes discovery from the genus Caesalpinia [2][3]8], we examined the chemical constituents of C. sappan and obtained two new cassane diterpenes, designated caesalsappanin R (1) and caesalsappanin S (2) (Figure 1).…”