LC-MS Identification, Isolation, and Structural Elucidation of Anti-HIV Tigliane Diterpenoids from Wikstroemia lamatsoensis

Abstract

Structurally diverse tigliane diterpenoids have drawn significant research interest for drug discovery over many decades. Using LC-MS-guided fractionation and separation, the first phytochemical investigation on Wikstroemia lamatsoensis led to the isolation of eight tiglianes (1–8), including two new compounds, wikstrocin D (1) and wikstrocin E (2). The new structures were elucidated based on extensive physicochemical and spectroscopic analyses. The characteristic ESIMS/MS fragmentations of tiglianes 1–8 were also summarized. Among the isolated tiglianes, three compounds (8, 5, and 7) showed the most potent anti-HIV activity, with IC50 values of 0.18, 3.8, and 12.8 nM, respectively.

Study on Components with Neuroinflammation Inhibitory Activities from Croton tiglium L. var. xiaopadou

“…Especially the diterpenes, reported from Croton genus, have been widely concerned because of their significant anti-HIV and proinflammatory activity. [10,11,49] Combining the current research and our results, lignans are the main active material basis of C. tiglium L. var. xiaopadou responsible for the antiinflammatory effect (Table 1 and Figure 5).…”

“…xiaopadou stems was suggested to be lignans and terpenoids ( Figure 5). Especially the diterpenes, reported from Croton genus, have been widely concerned because of their significant anti‐HIV and proinflammatory activity [10,11,49] . Combining the current research and our results, lignans are the main active material basis of C. tiglium L. var.…”

Anti-HIV Tigliane-Type Diterpenoids from the Aerial Parts of Wikstroemia lichiangensis

“…As a result, tiglianes 1 – 5 showed potent anti-HIV activity with IC 50 values of 1.1–65.4 nM (Table ). A comparison between the tiglianes 3 (IC 50 = 65.4 nM) and 5 (IC 50 = 3.0 nM) with the same fatty acid substituents but different B-ring structures suggested that OH-5 was shown to reduce the anti-HIV activity, which was in accordance with our previous study . However, this phenomenon could not have been observed between 2 (IC 50 = 1.5 nM) and 4 (IC 50 = 1.1 nM).…”

“…In the ECD spectrum of 1 , the observed positive Cotton effect at 220–240 nm and negative Cotton effect at 240–260 nm were similar to previously reported tiglianes; thus the absolute configuration of 1 was assigned as being the same as stelleracin C (Figure ). Based on these data, the structure of 1 was determined as 12- O -benzoyl-13- O -decanoyl-5β-hydroxyphorbol. …”

“…However, this phenomenon could not have been observed between 2 (IC 50 = 1.5 nM) and 4 (IC 50 = 1.1 nM). On the other hand, the anti-HIV activities of tiglianes have been known to be largely dependent on the nature of fatty acid substituents. ,, Structurally, tiglianes 1 – 3 differ only in the degree of unsaturation of the fatty acid ester at C-13, with a decanoate in 1 , a 3 E -decenoate in 2 , and a 3 E ,5 E -decadienoate in 3 . Tiglianes 1 and 2 (IC 50 = 1.5 nM each) showed much higher anti-HIV potency than 3 , suggesting that the fatty acid ester substituent with a low degree of unsaturation was shown to enhance the anti-HIV activity.…”