Chemical constituents from the fruits of Vitex trifolia L. (Verbenaceae) and their chemotaxonomic significance
Graphical abstract
Section snippets
Subject and source
The genus Vitex belongs to the family Verbenaceae and comprises about 250 species distributed in tropical and subtropical areas around the world (Rani and Sharma, 2013). Only fourteen of them are widely distributed in China. Vitex trifolia L. is a small deciduous shrub, and the fruits of this plant are used in folk medicine for the treatment of headache, eye pain, migraine, cold, and cancer (Wu et al., 2009). In this present study, the fruits of V. trifolia were purchased from Anguo, Hebei
Previous work
Previous phytochemical studies on V. trifolia have reported the isolation of diverse second metabolites such as sesquiterpenoids (Suksamrarn et al., 1991), diterpenoids (Ono et al., 2000; Zheng et al., 2013; Luo et al. 2017a, 2017b; Tiwari et al., 2013), triterpenoids (Jangwan et al., 2013), flavonoids (Li et al., 2005), and iridoids (Bao et al., 2018).
Present study
The air-dried and powdered fruits of V. trifolia (30 kg) were extracted with 95% ethanol (100 L) at room temperature once a week during three weeks successively. After removing the organic solvent under reduced pressure, the residue (941 g) was suspended in H2O and partitioned with EtOAc. The EtOAc extract (450 g) was subjected to silica gel column chromatography (CC) using petroleum ether-acetone mixtures (40:1, 20:1, 10:1, 5:1, 2:1, 1:1, V/V) to afford fractions A-F. Monitored by thin-layer
Chemotaxonomic significance
Terpenoids are the characteristic constituents of the genus Vitex, and diterpenoids are the most dominants. In the present study, fifteen diterpenoids (1–15) were isolated from the fruits of V. trifolia, which included eight labdane-type (1–8), two norlabdane-type (9 and 10), two halimane-type (11 and 12), two abietane-type (13 and 14) and one cyclophytane-type (15) diterpenoids.
Viterotulin D (1), a new labdane-type diterpenoid, was isolated and reported from the family Verbenaceae for the
CRediT authorship contribution statement
Komi Djimabi: Investigation, Methodology, Data curation, Formal analysis, Writing – original draft, Writing – review & editing. Bing Li: Investigation, Methodology, Formal analysis. Xiao-Han Chen: Methodology, Formal analysis, Data curation. Pan-Jie Su: Methodology, Formal analysis, Data curation. Xu Liu: Methodology, Formal analysis, Data curation. Ru-Yue Wang: Investigation, Formal analysis, Data curation. Feng-Ming Qi: Data curation, Formal analysis. Mei-Jie Wang: Formal analysis, Data
Declaration of competing interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Acknowledgment
This work was financially supported by the National Natural Science Foundation of China (No. 31870324 and No. 31670350).
References (50)
- et al.
New icetexane diterpenes with intestinal α-glucosidase inhibitory and free-radical scavenging activity isolated from Premna tomentosa roots
Fitoterapia
(2012) - et al.
Diterpenoids from Calceolaria thyrsiflora
Phytochemistry
(1991) - et al.
Labdane diterpenoids from Aframomum sceptrum: NMR study and antiparasitic activities
Phytochem. Lett.
(2011) - et al.
Abietane diterpenoids from Cephalotaxus lanceolata
Nat. Prod. Res.
(2017) - et al.
Anti-inflammatory diterpenes from the fruits of Vitex trifolia L. var. simplicifolia Cham
J. Asian Nat. Prod. Res.
(2019) - et al.
Diversified abietane family diterpenoids from the leaves of Leucosceptrum canum and their cytotoxic activity
Phytochemistry
(2019) - et al.
Bioactivity-guided isolation of cytotoxic constituents from stem-bark of Premna tomentosa
Bioorg. Med. Chem. Lett
(2009) - et al.
Triterpenes and other minor chemical constituents of Boophone haemanthoides F.M. Leight (Amaryllidaceae)
South Afr. J. Bot.
(2021) - et al.
Antimalarial diterpenoids from Vitex rotundifolia: isolation, structure elucidation, and in vitro antiplasmodial activity
Bioorg. Chem.
(2020) - et al.
Diterpenoids with diverse scaffolds from Vitex trifolia as potential topoisomerase I inhibitor
Fitoterapia
(2017)