Abietane Diterpenoids from Clerodendrum trichotomum and Correction of NMR Data of Villosin C and B

Abstract

Nine abietane diterpenoids (1–9) were isolated from the stems of Clerodendrum trichotomum Thunb. and identified by spectroscopic methods. Furthermore, corrected NMR data is provided for Villosin C (1) and B (2) whose absolute configurations were elucidated from circular dichroism (CD) data. All isolates were tested for cytotoxicity against four cancer cell lines (A549, HepG-2, MCF-7 and 4T1). Compounds 1, 2, 3, 4 and 8 were found to have remarkable cytotoxic effects with IC50 values ranging from 8.79 to 35.46 μM.

Biologically Active Diterpenoids in the Clerodendrum Genus—A Review

“…Eleven compounds were identified, including seven abietane diterpenes: sugiol (18) , teuvincenone A (48) , teuvincenone B (89) , teuvincenone F (10) , teuvincenone H (88) , uncinatone (9) and cyrtophyllone B (21) [ 94 ]. In further studies on C. trichotomum stems, the same authors also identified the diterpenoids villosin B (90) and villosin C (85) ; these demonstrate remarkable cytotoxic activities against tumour cell lines A549, HepG-2, MCF-7 and 4T1 with IC 50 values ranging from 14.93 to 29.74 µM [ 95 ].…”

“…The combined extracts were filtered and the solvent was removed under vacum to obtain a crude extract. Villosin B (90) Villosin C (85) Cyrtophyllone B (21) Uncinatone (9) Teuvincenone B (89) Sugiol (18) Teuvincenone F (10) Teuvincenone A (48) Teuvincenone H (88) [ 95 ] C. trichotomum Roots Cut and air-dried roots were extracted under reflux with 95% EtOH Extract was filtered and organic solvents evaporated to receive the crude residue 15,16-dehydroteuvincenone G (91) 3-dihydroteuvincenone G (92) 17-hydroxymandarone B (93) Trichotomin A (94) 15,16-dihydroformidiol (95) 18-hydroxyteuvincenone E (96) 2α-hydrocaryopincaolide F (97) 15α-hydroxyuncinatone (98) 15α-hydroxyteuvincenone E (99) Trichotomin B (100) Trichotomside A (101) Trichotomside B (102) [ 96 ] …”

Clerodenoids A—F: C‐ring Aromatized and/or Rearranged Abietane Diterpenoids from Clerodendrum chinense var. simplex

“…[ 1 ] Previous chemical studies on this genus resulted in the characterization of several diterpenoids exhibiting diverse biological activities including antibacterial, antioxidant, antiinflammatory, antidiabetic, antihypertensive, cytotoxic, and anti‐asthmatic properties. [ 2‐11 ] Clerodendrum chinense var . simplex , an ethnomedicinal plant of the Dai minority in China, has been used for the treatment of rheumatic arthritis, hypertension, erysipelas, and chronic osteomyelitis.…”

Two New Abietane Diterpenes From the Stems of Clerodendrum trichotomum Thunb

“…3 The major constituents reported include phenylpropanoids, terpenoids, flavonoids and steroids. [4][5][6][7] In earlier work, 5,7 the chemical constituents of the ethyl acetate fraction from the stems of C trichotomum have been studied systematically. However, relatively few papers have been devoted to the n-butanol extract so far.…”

“…Abietane diterpenoids are characteristic constituents of the genus Clerodendrum, which exhibit remarkable antitumor, 8 antiinflammatory, 9 and insecticidal activities. 10 This paper focused on the study of the chemical constituents from the n-butanol extract of C trichotomum stems, and 2 new abietane diterpenoids, (4S, 5S, 10S)-12-(β-D-glucopyranosyl)oxy-11-hydroxyabieta-8,11,13-triene-19-oic acid β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (1), and (3S, 5S, 10S, 15S)-3β-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]oxy-12-(β-D-glucopyranosyl)oxyabieta-8,11,13-triene-11,16-diol (2), along with 5 known terpene glycosides (3)(4)(5)(6)(7) were isolated and characterized (Figure 1, 1-7). Compounds 1-7 were evaluated for cytotoxicity against several cancer cell lines, and all of them were inactive.…”