A New Nortriterpene from the Root of Celastrus hypoleucus

Abstract

A new nortriterpene, 2-hydroxy-3-methyl-21-oxo-12,24-dinor-D : B-friedooleana-1,3,5(10),7-tetraen-29-oic acid (1), was isolated from the root of Celastrus hypoleucus, together with the two known compounds, celastorol (2) and pristimerine (3). Their structures were elucidated on the basis of spectroscopic analyses. Compounds 1 -3 exhibited in vitro significant antioxidant (against lipid peroxidation; by the TBARS method) and antitumor activities (against cancer cell lines P-388, A-549, HL-60, and BEL-7402).Introduction. -Celastrus hypoleucus (Oliv. ) Warb. is a species of the Celastraceae family and commonly named as Nan She Teng (Chinese trade name). It is widely distributed in China and has been used for the treatment of inflammation and detumescence. As part of our continuing investigation of bioactive components from the Celastraceae family [1 -7], many new antioxidant and antitumor-active metabolites have been isolated and characterized from C. hypoleucus [1] [6] [7]. In this article, we report a new nortriterpene, 2-hydroxy-3-methyl-21-oxo-12,24-dinor-D : B-friedooleana-1,3,5(10),7-tetraen-29-oic acid 1 ) (1), and two known triterpenes, i.e., celastorol (2) [8] and pristimerine (3) [9], from the root of C. hypoleucus (Fig. 1). In addition, their antioxidant and antitumor activities were investigated.

Triterpenoids

“…268 Stems of Momordica charantia are the source of 3b-hydroxymultiflor-8-en-28-oic acid 458 87 and the feruloyl ester 459. 270 2,3-Secofriedel-1-en-3-oic acid 462, 3b-hydroxyfriedelan-23oic acid 463 and 1b-hydroxyfriedelan-3-one 464 have been isolated from Garcia parviflora. 269 A glutinane derivative 461, with C-ring contraction and a methyl migration to C-3, has been found in the roots of Celastrus hypoleucus.…”

“…269 A glutinane derivative 461, with C-ring contraction and a methyl migration to C-3, has been found in the roots of Celastrus hypoleucus. 270 2,3-Secofriedel-1-en-3-oic acid 462, 3b-hydroxyfriedelan-23oic acid 463 and 1b-hydroxyfriedelan-3-one 464 have been isolated from Garcia parviflora. 271 The structure of 464 was confirmed by X-ray analysis.…”

Bigelovii A induces apoptosis of HL-60 human acute promyelocytic leukaemia cells

“…Nortriterpene saponin is an important triterpene saponin and numerous studies have reported the anti-inflammatory (5), anticancer (6), anticomplement (7), anti-HIV (8,9), insecticidal (10), melanogenesis inhibitory (11), gastroprotective, platelet aggregative (12), antioxidant (13), antiviral (14) and protein tyrosine phosphatase inhibitory (15) activities of nortriterpenoids. Although various bioactivity studies of nortriterpenoids have been performed, the molecular mechanism by which nortriterpene saponin acts on cancer cells remains unclear.…”