Cycloartane-type Triterpenoids Research Articles

Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells

A cycloartane-type triterpenoid ( 1), an aliphatic alcohol glycoside ( 2), an eudesmane-type sesquiterpenoid ( 3), and a guaiane-type sesquiterpenoid ( 4) were isolated from the resinous exudates of Commiphora opobalsamum along with six known sesquiterpenoids ( 5– 10). Their structures were established by extensive analysis of their 1D and 2D NMR spectroscopic data and chemical methods. The isolated compounds 1– 3 and 5– 9 were tested against human prostate cancer cell PC 3 and LNCaP. Among them, 1 and 2 showed moderate antiproliferative effects on human prostate cancer cell lines with IC 50 values ranging from 5.7 to 23.6 μM; they were also able to inhibit the expression of androgen receptor (AR) in LNCaP cells. The six sesquiterpenoids were inactive in the bioassays.

New Cycloartane-type Triterpenoids from Artocarpus nobilis

Recent phytochemical studies on the ethanolic extract of Artocarpus nobilis, collected from Sri Lanka, have resulted in the isolation of two new cycloartane-type triterpenoids, artocarpuate A (1) and artocarpuate B (2). Structures of these new compounds were established with the aid of extensive NMR spectroscopic studies. Compounds 1 and 2 were found to exhibit weak acetylcholinesterase inhibitory activity.

Cimicifugae Rhizoma: From Origins, Bioactive Constituents to Clinical Outcomes

Cimicifugae Rhizoma, mainly originated from C. acerina, C. dahurica, C. foetida, C. heracleifolia, C. racemosa and C. simplex, has long been used in traditional medicine system. During the past 45 years, a lot of efforts have been dedicated to the studies on their bioactive constituents, pharmacological effects and clinical uses, and a variety of biological activities including relief of hot flash, anti-osteoporosis, anti-human immunodeficiency virus (HIV), antiinflammatory, antidiabetes, antimalaria and vasoactive property have been discovered. Although C. racemosa is widely applied to relieve menopause symptoms in clinic for its hormonal-like action, meaningfully, no estrogenic effect was confirmed up to date. The purpose of this paper is to systematically highlight these achievements and the further therapeutic potential. The origins and distributions of the rhizome are simply listed and phytochemical aspects including over 200 compounds mainly belonging to cycloartane-type triterpenoids have been summarized. The pharmacological characterizations, especially, as a clinically effective phytomedicine, the effects of the rhizoma on menopause symptoms and the clinical applications including possible mechanism have been reviewed in detail. Various in vivo, in vitro studies on the anti-bone resorption effects of the triterpenoids, together with structure-activity relationships are also incorporated to explore the therapeutic potential on osteoporosis, a major public health threat for postmenopausal women.

Tyrosinase inhibitory cycloartane type triterpenoids from the methanol extract of the whole plant of Amberboa ramosa Jafri and their structure–activity relationship

New tyrosinase inhibitory cycloartane triterpenoids have been discovered from the methanol extract of the whole plant of Amberboa ramosa (Roxb.) Jafri, which is a member from the Compositae family. Utilizing the conventional spectroscopic techniques, including 1D and 2D NMR analysis, and also by comparing the experimental with literature data, the isolated compounds proved to be cycloartane type triterpenoids. These cycloartanes are: (22 R)-cycloart-20, 25-dien-2α3β22α triol ( 1), (22 R)-cycloart-23-ene-3β, 22α, 25-triol ( 2), cycloartenol ( 3), cycloart-23-ene-3β, 25-diol ( 4), cycloart-20-ene-3β, 25-diol ( 5), cycloart-25-ene-3β, (22 R) 22-diol ( 6), 3β, 21, 22, 23-tetrahydroxy-cycloart-24 (31), 25 (26)-diene ( 7), and (23 R)-5α-cycloart-24-ene-3β, 21, 23-triol ( 8). Out of these eight compounds, compound 3 did not show any activity against the enzyme tyrosinase. Among them compound 7 was found to be the most potent (1.32 μM) when compared with the standard tyrosinase inhibitors kojic acid (16.67 μM) and l-mimosine (3.68 μM). Finally in this paper, we have discussed the structure–activity relationships of these molecules.

Cycloartane type triterpenoids from the rhizomes of Polygonum bistorta

Two new compounds, 24( E)-ethylidenecycloartanone ( 1) and 24( E)-ethylidenecycloartan-3α-ol ( 2) were isolated from the rhizomes of Polygonum bistorta, together with seven known compounds viz., cycloartane-3,24-dione ( 3), 24-methylenecycloartanone ( 4), γ-sitosterol ( 5), β-sitosterol ( 6), β-sitosterone ( 7), friedelin ( 8) and 3β-friedelinol ( 9). All the cycloartane type triterpenoids, compounds 7 and 8 are reported for the first time from this plant. A combination of 1D and 2D NMR spectroscopy and MS were mainly used to elucidate the structures of the new compounds 1 and 2.

New Sterols and Triterpenoids of Ficus pumila Fruit.

From the methanolic extract of Ficus pumila L. fruit (Moraceae), two new sterols, (24S)-stigmast-5-ene-3β,24-diol, (24S)-24-hydroxystigmast-4-en-3-one, two new cycloartane-type triterpenoids, (24RS)-3β-acetoxyeycloart-25-en-24-ol, (23Z)-3β-acetoxycycloart-23-en-25-O and a new euphane-type triterpenoid, (23Z)-3β-acetoxyeupha-7,23-dien-25-ol were obtained along with known sterols, triterpenoids and a furocoumarin (psoralene). The structures of the new compounds were determined by spectral methods.

Cycloartane triterpenoids from Aglaia harmsiana

Two new and two known cycloartane-type triterpenoids were isolated from the leaves of Aglaia harmsiana. The structures were determined using 1H, 13C and 2D NMR techniques.

Pregnanes and triterpenoid hydroperoxides from the leaves of Aglaia grandis

Three pregnanes and two known cycloartane-type triterpenoid hydroperoxides were isolated from the leaves of Aglaia grandis. Their structures were determined using 1H, 13C and 2D NMR techniques. © 1997 Elsevier Science Ltd. All rights reserved

Four diterpene esters from Euphorbia myrsinites

The Turkish species Euphorbia myrsinites has yielded four new tetracyclic diterpene tetraesters from a cytotoxic acetone extract, in addition to the known cycloartane-type triterpenoids and betulin. The new compounds and their hydrolysis product have been extensively characterized by high field spectroscopic techniques, and were shown to be four new tetraesters of the parent alcohol, myrsinol.

Constituents of Cimicifugae Rhizoma. I. Isolation and Characterization of Ten New Cycloartenol Triterpenes from Cimicifuga heracleifolia Komarov.

Ten new highly oxidized cycloartane-type triterpenoids, 24-epi-7, 8-didehydrocimigenol, 7, 8-didehydrocimigenol, 25-O-acetyl-7, 8-didehydrocimigenol, 3-keto-24-epi-7, 8-didehydrocimigenol, 2', 4'-O-diacetyl-24-epi-7, 8-didehydrocimigenol-3-xyloside, 3'-O-acetyl-24-epi-7, 8-didehydrocimigenol-3-xyloside, 24-epi-7, 8-didehydrocimigenol-3-xyloside, 7, 8-didehydro-24-O-acetylhydroshengmanol-3-xyloside, 24-epi-acerinol and heracleifolinol, were isolated from the rhizome of Cimicifuga heracleifolia KOMAROV and their structures were determined by the use of two-dimensional nuclear magnetic resonance (2D NMR) techniques (1H-1H correlation spectroscopy (COSY), 1H-13C COSY, 1H-13C long-range COSY) and by X-ray diffraction analysis of the 3-keto compound.

A novel method for functionalization of C-4 methyl in triterpenoids. A synthesis of cycloeucalanone

Functionalization of 4α-methyl group in cycloartane-type triterpenoids has been accomplished utilizing, in the key step, photolytic decomposition of an hypoiodite derived from a 3β-hydroxymethyl-4,4-dimethyl precursor. The synthesis of cycloeucalanone from cyclolaudanone is reported.