Biotransformation of Patchouli Alcohol by Cladosporium cladosporioides and the Anti-Influenza Virus Activities of Biotransformation Products.

The biotransformation of patchouli alcohol by Cladosporium cladosporioides afforded 31 products, including 21 new ones (1-3, 5, 6, 8-14, and 17-25). Their structures were determined by extensive spectroscopic data analysis (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, ROESY, and HRESIMS), and the absolute configuration of compounds 1, 2, 8, 9, and 17 was determined by single-crystal X-ray diffraction using Cu Kα radiation. Structurally, compounds 21-24 were patchoulol-type norsesquiterpenoids without Me-12. Among them, a Δ3(4) double bond existed in compounds 21 and 22; a three-membered ring was formed between C-4, C-5, and C-6 in compound 23; an epoxy moiety appeared between C-3 and C-4 in compound 24. Furthermore, the biotransformation products 9, 10, 12, and 25 showed potent anti-influenza virus activity with EC50 values of 2.11, 7.94, 20.87, and 3.45 µM, respectively.

Triterpenoids, steroids and other constituents from Euphorbia kansui and their anti-inflammatory and anti-tumor properties.

Six undescribed triterpenoids (euphokanols A-F), two undescribed C21-steroidal glycosides (euphokanosides A and B), together with fifty-four known compounds were isolated from the roots of Euphorbia kansui. Their structures were demonstrated by extensive spectroscopic data (1D, 2D NMR and HR-ESI-MS), and the absolute configuration of euphokanol A was elucidated based on electronic circular dichroism (ECD) calculation. Among them, euphokanol A was a tetracyclic triterpenoid with a 5,10-epoxy moiety and concurrent rearrangement of Me-19(10 â†’ 9) and Me-30 (14 â†’ 8), while euphokanols B and C were rare 19(10 â†’ 9) abeo-tirucallane-type triterpenoids with Δ5(10) double bonds and 7,8-epoxy moieties. In addition, ten C21-steroidal glycosides were isolated from Euphorbia plants for the first time. Moreover, cynotophylloside B, caudatin, 5α,8α-epidioxy-22E-ergosta-6,22-diene-3ß-ol, 6ß,7ß-epoxy-3ß,4ß,5ß-trihydroxyl-20-deoxyingenol, 13-hydroxyingenol-3-(2,3- dimethylbutanoate)-13-dodecanoate, ingenol, 3-O-benzoyl-13-O-dodecanoateingenol, 3-O-(2'E,4'Z-decadienoyl)-20-O-acetylingenol, 20-O-acetylingenol and 20- deoxyingenol exhibited significant inhibition on NO production with IC50 values of 9.10, 17.38, 1.71, 0.55, 0.57, 12.22, 0.56, 0.30, 11.21 and 2.98 µM, respectively. Furthermore, wilfoside KIN, cynsaccatol L, kanesulone A, and 3ß,7ß,15ß-triacetyloxy-5α-benzoyloxy-2α,8α-dihydroxyjatropha-6(17),11E-diene-9, 14-dione showed cytotoxicity against HepG2 cell line, with IC50 values of 12.55, 12.61, 18.24 and 18.26 µM, respectively. 13-Hydroxyingenol-3-(2,3-dimethylbutanoate)-13- dodecanoate exhibited anti-proliferation activity on MCF-7 cell line with an IC50 value of 17.12 µM. Specifically, euphol selectively inhibited the growth of human glioma stem cells (GSC-3# and GSC-12#), with IC50 values of 8.89 and 13.00 µM, respectively.

Jatavaleridoids A-H, eight new iridoids from the roots and rhizomes of Valeriana jatamansi Jones.

Eight new iridoids, jatavaleridoids A-H (1-8), were isolated from the roots and rhizomes of Valeriana jatamansi. Their structures and absolute configurations were elucidated based on NMR and HRESIMS spectroscopic data, as well as quantum chemical calculation. Structurally, compounds 1-5 and 8 were rare iridoids with long-chain fatty acid esters at C-10. In addition, compound 7 showed cytotoxicity, while compounds 1 and 2 exhibited inhibition on NO production.

Valeridoids G - Q, Eleven seco-Iridoids from Valeriana jatamansi and Their Bioactivites.

Eleven new seco-iridoids, valeridoids G-Q (1-6 and 8-12), along with four known products, 9-epi-valtral C (7), desacylbaldrinal (13), 11-methoxyviburtinal (14) and baldrinal (15), were obtained from Valeriana jatamansi. Among them, the new compounds were identified by their NMR, HR-ESI-MS spectroscopic data and ECD calculation. Moreover, valeridoid N and O were a pair of C3 epimers, whose ether bonds between C-1 and C-3 opened, and new ether bonds formed between C-3 and C-6. Valeridoid Q belonged to the C-1 degradation of seco-iridoids. As a result, 9-epi-valtral C displayed significant inhibition on Streptococcus agalactiae, Staphylococcus aureus, Staphylococcus argenteus, Shigella flexneri and Klebsiella pneumoniae, and valeridoid Q exhibited the most significant inhibition against Salmonella enteritidis. 9-Epi-valtral C and baldrinal selectively inhibited the growth of human glioma stem cells. Valeridoid Q exhibited significant anti-influenza activity, while valeridoid O inhibited nitric oxide production.