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Tripetalins A (1) and B (2), two new biphenyl-type neolignans were obtained from the fruits of Magnolia tripetala, along with four known analogues. The structures of the new compounds were characterized by comprehensive spectroscopic analyses including 1H, 13C, and 2D NMR, IR, and HRESIMS data. Tripetalin A (1) was the first magnolol-honokiol-type neolignan dimer linked through C-5′‒C5′′ carbon bond. Magnoquinone (5) and magnotriol B (6) displayed remarkable NO inhibitory activity with IC50 values of 4.52 ± 0.07 and 2.02 ± 0.03 μM, respectively.

Cunlanceloic acid A (1), a symmetric terpenoid peroxide bearing an unprecedented dimeric labdane backbone linked through C-16/C-16′ bonds, and cunlanceloic acids B–D (2–4), three asymmetric diterpenoid dimers with a new carbon skeleton linked through C12/C-13′ and C-15/C-16′ bonds between two labdane units, were isolated from the cones of Cunninghamia lanceolata. Their structures including absolute configurations were determined by extensive NMR spectroscopy, X-ray diffraction analysis, and chemical transformations. Compound 1 exhibited potent AChE inhibitory activity with an IC50 value of 6.14 ± 0.66 μM and compounds 2 and 3 showed remarkable cytotoxic activities against A-549 and SMMC-7721 cell lines with IC50 values of 5.90–9.21 μM.

Huperserratines A (1) and B (2), two Lycopodium alkaloids with an unprecedented 5-aza-bicyclo[10.4.0]hexadecane skeleton and an oxime function, were isolated from Huperzia serrata. Their structures including absolute configurations were determined by extensive NMR spectroscopic and X-ray diffraction analysis. Compounds 1 and 2 were the first examples of macrocyclic Lycopodium alkaloids with an aza-12-membered ring. A plausible biogenetic pathway of these compounds was also proposed. Compound 1 exhibited moderate anti-HIV-1 activity with an EC50 of 52.91 μg/mL and a therapy index greater than 3.78.

Two new seco- prezizaane-type sesquiterpenes, 2 β -hydroxy-6-deoxyneoanisatin ( 1 ) and 3,4-anhydro-2-oxo-1 α -hydroxy-6-deoxyneoanisatin ( 2 ), and two new prenylated C 6 -C 3 compounds, illilanceofunones A ( 3 ) and B ( 4 ), were obtained from the fruits of Illicium lanceolatum , along with four known prenylated C 6 -C 3 compounds ( 5-8 ). Their structures were proposed through HRESIMS, 1 H, 13 C, and 2D NMR data interpretation. Moreover, the absolute configuration of 1 and 2 were further assigned by single-crystal X-ray diffraction analysis and electronic circular dichroism (ECD) calculations, respectively . Illihenryipyranol A ( 6 ) exhibited neuroprotective activity against MPP + -induced PC12 cell damage in a dose-dependent manner .

Ten previously undescribed cassane diterpenoids, cassabonducins A–J, and eleven known compounds were isolated from the seeds of Caesalpinia bonduc. The structures of the undescribed compounds were elucidated by extensive analysis of spectroscopic data (IR, HRESIMS, and 1H, 13C and 2D NMR) and their absolute configurations were determined by the ECD data and single-crystal X-ray diffraction analysis. e-Caesalpin-Ⅶ was obtained from natural resources for the first time. Cassabonducin A possessed noteworthy inhibitory activity against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages with IC50 value of 6.12 μM. Cassabonducin D and neocaesalpin N showed moderate α-glucosidase inhibition at the concentration of 50 μM with inhibitory capacities of 47.17% and 43.83%, respectively.

Phlegmadine A (1), a Lycopodium alkaloid with a unique cyclobutane ring and featuring a complex tetracyclo[4.2.2.03,8.03,10]decane-bridged system, together with three biogenetically related known compounds, was isolated from the Phlegmariurus phlegmaria. The structures and absolute configurations of 1 and 2 were determined by NMR and single-crystal X-ray analysis. Among them, compound 2 exhibited noticeable protective effects for long-term potentiation impairment by corticosterone induced in mice. Moreover, we succeeded in the efficient synthesis of 1 from 3 by a biomimetic synthesis method.

Four new elemane sesquiterpenoids, magnograndins J-M (1-4), and one known sesquiterpenoid, 12,13-diacetoxyelema-1,3-dien-6α,11-diol (5), were obtained from 70% acetone extract of the leaves of Magnolia grandiflora. Their structures were determined with extensive spectroscopic (HRMS, IR, 1D and 2D NMR) analyses. Compound 1 represented the first example of elemane sesquiterpenoid with an orthoacetate unit. Compound 4 inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells with IC50 value of 17.83 μM.

A phytochemical study on the stem bark of Metasequoia glyptostroboides led to the isolation of sixty-one diterpenoids and sesquiterpenoids, including seventeen previously undescribed compounds, metaglyptins A-Q. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, and 1H, 13C and 2D NMR). The absolute configurations of metaglyptins I, J, and O were determined by the ECD data and single-crystal X-ray diffraction analysis. The undescribed compounds were evaluated for their cytotoxicity against HeLa, AGS, and MDA-MB-231 cancer cell lines. The results revealed that metaglyptin A exhibited moderate cytotoxicity against MDA-MB-231 cell line with IC50 value of 20.02 μM.

Isoselagintamarlin A (1), a selaginellin analogue featured a rare benzofuran unit, was isolated from Selaginella tamariscina. Its complete structural assignment was established through a combination of high-field NMR technique and biomimetic synthesis. Notably, isoselagintamarlin A (1) was successfully synthesized via sequential oxidations and intramolecular cyclization. Graphical Abstract Electronic supplementary material The online version of this article (10.1007/s13659-018-0195-5) contains supplementary material, which is available to authorized users.

Two unprecedented tetranorlanostane triterpenoids, poricolides A ( 1 ) and B ( 2 ), and two new lanostane triterpenoids, 3 β -acetoxy-24-methyllanosta-8,16,24(31)-trien-21-oic acid ( 3 ) and 3 β -acetoxylanosta-7,9(11),16,23-tetraen-21-oic acid ( 4 ), were isolated from the epidermis of Poria cocos . The structures of 1 - 4 were determined via analysis of 1 H-, 13 C-, and 2D-NMR, and HR-ESI-MS data, and the absolute configurations of 1 and 3 were established by single-crystal X-ray diffraction analysis. Compounds 1 and 2 were the first report of tetranorlanostane triterpenoid having a δ- lactone ring at C(17). Compounds 3 and 4 were rare lanostane triterpenoids having a double bond between C(16) and C(17). Compounds 1 - 4 exhibited potent antiproliferative effects against A549, SMMC-7721, MCF-7, and SW480 cancer cell lines with IC 50 values between 16.19 ± 0.38 to 27.74 ±1.12 μ M.

Six new rearranged neoclerodane diterpenoids (1–6), as well as three known ones, were obtained from the aerial part of Salvia hispanica L. Their structures were elucidated by extensive analysis of spectroscopic data (1D, 2D NMR, and HRESIMS) and Mosher's method. The absolute configurations of 1, 2, and 4 were determined by single-crystal X-ray diffraction analysis. All isolated compounds were evaluated for their cardioprotective effects against H2O2-induced cardiomyocytes injury, and compound 5 showed statistically significant cardioprotective effect in vitro assays.

Three dimeric cassane diterpenoids, caesalpanins A-C, were isolated from the seeds of Caesalpinia sappan L., as well as three known compounds. Their structures were determined via analysis of 1D-, 2D-NMR, and HR-ESI-MS data. Caesalpanins A and B were the second and third compounds that presented a nitrogen-containing cassane diterpenoid dimer linked through one ether bond between C-19 and C-20'. Caesalpanin B exhibited moderate cytotoxic activity against MCF-7 cell lines with IC50 value of 29.98 μm. Caesalpanins A and B had weak inhibitory effects against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages at 50 μm with inhibitory rate of 36.01 % and 32.93 %, respectively.

Salvifarinin A (1), a rearrangement product of Languidulane-type clerodane diterpenoids with a 6/5/7 tricyclic ring skeleton fused with gamma-lactone ring and furan ring, and two new biogenetically related diterpernoids, salvifarinins B (2) and C (3), were isolated from the aerial parts of Salvia farinacea. The absolute configuration of 1 was elucidated by extensive spectroscopic methods, and confirmed by single crystal X-ray diffraction and bio-inspired semisynthesis. The plausible biogenetic pathway was also proposed. Compound 2 displayed a potent effect on reducing hepatic steatosis. (C) 2018 Published by Elsevier Ltd.

A novel C17N Lycopodium alkaloid (LA), lycoplanine B (1), containing an unusual formyl group, along with two new LAs, lycoplanines C (2) and D (3), were isolated from the whole plant of Lycopodium complanatum. Their structures were elucidated by extensive NMR techniques, including 1D- and 2D-NMR experiments, as well as comparing their spectral data with those of the known analogues. A possible biogenetic pathway for 1 was also proposed. Graphical Abstract Electronic supplementary material The online version of this article (10.1007/s13659-018-0161-2) contains supplementary material, which is available to authorized users.

Five new fawcettimine-type alkaloids (1–5) and three new natural products (6–8), along with four known analogues, fawcettimine (9), fewcettidine (10), lycopoclavamine B (11), and lycopladine B (12), were isolated from the whole plant of Lycopodium complanatum var. glaucum Ching. The structures of lycogladines A-H (1–8) were determined based on HRESIMS, 1D and 2D NMR spectroscopic analysis, as well as single-crystal X-ray diffraction. Compound 1 possesses a new ring system that is formed through the linkage of C-13-O C-2, which is rarely present in Lycopodium alkaloids (LAs). Compounds 1–8 were tested for their β-site amyloid precursor protein (APP)-cleaving enzyme 1 (BACE1) and acetylcholinesterase (AChE) inhibitory activities.

A neo-clerodane diterpenoid, salvihispin A (1), as well as its glycoside, salvihispin A-2-O-beta-D-3-keto-glucopyranoside (2) were isolated from the aerial parts of Salvia hispanica. Compound 2 possessed an unusual 3-keto-glucopyranoside moiety. Their structures and absolute configurations were elucidated by extensive spectroscopic methods and confirmed by single crystal X-ray diffraction. Salvihispin A (1) and its glycoside (2) enhanced the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 mu M. (C) 2017 Elsevier Ltd. All rights reserved.

Catharanthus roseus is a well-known traditional herbal medicine for the treatment of cancer, hypertension, scald, and sore in China. Phytochemical investigation on the twigs and leaves of this species led to the isolation of two new monoterpene indole alkaloids, catharanosines A (1) and B (2), and six known analogues (3–8). Structures of 1 and 2 were established by 1H-, 13C- and 2D-NMR, and HREIMS data. The absolute configuration of 1 was confirmed by single-crystal X-ray diffraction analysis. Compound 2 represented an unprecedented aspidosperma-type alkaloid with a 2-piperidinyl moiety at C-10. Compounds 6–8 exhibited remarkable Cav3.1 low voltage-gated calcium channel (LVGCC) inhibitory activity with IC50 values of 11.83 ± 1.02, 14.3 ± 1.20, and 14.54 ± 0.99 μM, respectively.

A unique seco-prezizaane sesquiterpenoid with 5/5/6 tricyclic skeleton, illilanceolide A (1), and two rare 10,14-cycloseco-prezizaane sesquiterpenoids, 2-oxo-6-dehydroxyneoanisatinic acid (2) and 3,4-anhydro-2-oxo-6-dehydroxyneoanisatinic acid (3), together with two known sesquiterpenoids, were isolated from the fruits of Illicium lanceolatum. Their structures and absolute configurations were elucidated on the basis of extensive 1H, 13C, and 2D NMR, and HRESIMS data, as well as single-crystal X-ray diffraction analysis. Compounds 2–4 enhanced the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 μM with differentiation rates of 13.33%, 10.90%, and 11.76%, respectively. Moreover, compounds 2–4 were found to exhibit moderate neuroprotective effect against MPP+-induced PC12 cell damage.

Lycoplanine A (1), a Lycopodium alkaloid with a 6/9/5 tricyclic ring skeleton fused with the γ-lactone ring and featuring an unusual 1-oxa-6-azaspiro[4.4]nonane moiety and an unprecedented 3-azabicyclo[6.3.1]dodecane unit, was isolated from the club moss Lycopodium complanatum. The structure and absolute configuration of 1 were identified by a combination of NMR spectroscopic analysis and single-crystal X-ray diffraction. Biological studies showed that 1 is a potent Cav3.1 T-type calcium channel (TTCC) inhibitor with an IC50 value of 6.06 μM.

Sauruchinenols A (1) and B (2), two novel monocyclic diterpenes with unique carbon skeleton, as well as two new structurally related diterpenes, sauruchinenols C (3) and D (4), were isolated from the aerial part of Saururus chinensis. Their structures were elucidated based on the analysis of spectroscopic data. A hypothetical biogenetic pathway for sauruchinenols A and B was proposed.

A rare carotane-type sesquiterpenoid, forkienin A (1), a new eudesmane-type sesquiterpenoid, forkienin B (2), and a new natural eudesmane-type sesquiterpenoid, forkienin C (3), were isolated from the twigs and leaves of Fokienia hodginsii, along with eight known sesquiterpenoids. The structures of the new compounds were elucidated on the basis of their spectroscopic analysis, including 1D and 2D NMR methods. All compounds were evaluated for cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines.

(±)-Evodiakine (1a and 1b), a pair of rearranged rutaecarpine-type alkaloids with an unprecedented 6/5/5/7/6 ring system, were isolated from the nearly ripe fruits of Evodia rutaecarpa. Separation of the enantiomers have been achieved by chiral HPLC column. The structures of (±)-evodiakine were unambiguously elucidated by 1D and 2D NMR spectra, mass spectrometry, and single-crystal X-ray diffraction. Their absolute configurations were determined by comparison of experimental and calculated electronic circular dichroism spectra. A hypothetical biogenetic pathway for (±)-evodiakine was also proposed. Compounds 1a, 1b, and the racemate (1) were tested for their cytotoxic and anti-inflammatory activities. Graphical Abstract Electronic supplementary material The online version of this article (doi:10.1007/s13659-016-0113-7) contains supplementary material, which is available to authorized users.

Two rare lyconadin-type Lycopodium alkaloids, lyconadins G (1) and H (2), together with four known ones (3–6), were isolated from Lycopodium complanatum. The structures were determined on the basis of their spectroscopic analyses, and the absolute configuration of 1 was established by an X-ray crystallographic analysis. It is the first time to establish the absolute configuration of lyconadin-type Lycopodium alkaloid by an X-ray diffraction experiment. In addition, these findings may provide more information for the biosynthesis of lyconadins. Graphical Abstract Electronic supplementary material The online version of this article (doi:10.1007/s13659-016-0111-9) contains supplementary material, which is available to authorized users.

Phytochemical investigation of the flowers of Inula japonica led to isolation of nine sesquiterpenoids, inujaponins A-I, as well as eighteen known ones. These sesquiterpenoids belong to six skeletal-types, including eudesmane, 1,10-seco-eudesmane, germacrane, guaiane, 4,5-seco-guaiane, and pseudoguaiane sesquiterpenoids. Their structures were established by extensive spectroscopic analysis. The absolute configurations of inujaponin A, eupatolide, and deacetylovatifolin were determined by Cu-Kα X-ray crystallographic analysis. Most of the isolated compounds exhibited potent cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cancer cell lines, with IC50 values ranging from 1.57 to 22.58 μM. Some selected compounds also possessed significant inhibitory activity against LPS-induced NO production in RAW264.7 macrophages with IC50 values ranging from 1.42 to 8.99 μM.

Ten new neo-clerodane derivatives (1–10) and 10 known diterpenoids were identified from the aerial parts of Salvia leucantha. The structures of 1–10 were established by 1D and 2D NMR spectroscopic data analysis. The absolute configurations of 1, 3, 6, and 7 were determined by X-ray diffraction data. Compound 16 exhibited cytotoxicity against HCT116, BT474, and HepG2 cancer cell lines and was identified as a heat shock protein 90 inhibitor. Compounds 8, 15, and 16 exhibited moderate acetyl cholinesterase inhibitory activity.

Seven new fawcettimine-type (1-7) and two new lycopodine-type (8 and 9) Lycopodium alkaloids, as well as 10 known compounds, were isolated from the club moss, Lycopodium obscurum L. The structures of obscurumines H-P (1-9) were determined based on high-resolution MS and 1D and 2D NMR data. Compounds 1 and 2 include a new skeleton that is formed via the linkage of C-9-N-2', which is rarely present in Lycopodium alkaloids. The in vitro acetylcholinesterase (AChE) inhibitory activity assay showed that 5 exhibited weak anti-AChE activity with an IC50 value of 81.0 μM. Compound 8 exhibited inhibition of the secretion of IL-2 in phytohemagglutinin (PHA) and phorbol myristate acetate (PMA) stimulated Jurkat cells, and the IC50 value was 17.2 μM.

Three new monoterpenoid indole alkaloids, vinmajorines C-E (1-3), along with 18 known analogues (4-21), were isolated from the whole plants of Vinca major. The new structures were elucidated as (5,15,16R,17,19,20,21)-10,17-dimethoxy-21-methyl-18-oxa-5,16-cycloyohimban-19-ol (1), (5,15,16R,17,20,21)-10-methoxy-21-methyl-18-oxa-5,16-cycloyohimban-17-ol (2), and (5,15,16R,17,20,21)-10-methoxy-21-methyl-18-oxa-5,16-cycloyohimban-17-yl acetate (3), respectively, by extensive NMR and MS analysis and comparison with known compounds. Compounds 1-3 were evaluated for their cytotoxic activities against five human cancer cell lines, compounds 1 and 3 showing moderate cytotoxic activities.

Artemilavanolides A (1) and B (2), two unprecedented sesquiterpenoids with 6-oxabicyclo[3.2.1]octane scaffold, as well as one known biogenetically related sesquiterpenoid, 11β,13-dihydrosantamarin (3), were isolated from the aerial parts of Artemisia lavandulaefolia. The structures and absolute configurations of 1 and 2 were characterized by analysis of HRESIMS, NMR spectroscopic, single crystal X-ray diffraction, and electronic circular dichroism (ECD) data. The plausible biogenetic pathway for 1 and 2 was also proposed. Compound 1 was found to enhance the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 μM.

Two Lycopodium alkaloids named phlegmadines B (1) and C (2), along with biogenetically related known compounds 3–6, were obtained from Phlegmariurus phlegmaria. Their structures were elucidated based on NMR spectroscopic analysis, and the absolute configuration of 1 was determined by single-crystal X-ray diffraction. Compounds 1 and 2 represent the first pentacyclic (6/5/5/5/7) C16N2 Lycopodium alkaloid skeleton. In addition, a possible biosynthetic pathway for 1 and 2 was proposed. Moreover, compound 1 exhibited moderate neurotrophic effects on PC12 cells.

Ten undescribed neo-clerodane diterpenoids, named hispanins A-J, together with six known ones, were isolated from the aerial parts of Salvia hispanica L. Their structures were established by extensive spectroscopic analysis. The absolute configurations of the undescribed compounds were determined by the ECD data and single crystal X-ray diffraction analysis. Hispanins B and C represented the first neo-clerodane diterpenoids with a unique oxygen bridge between C-19 and C-20. All isolated compounds were evaluated for their protective effects against H2O2-induced cardiomyocyte injury. Five of these compounds showed significant cardioprotective effects.

Four new neoclerodane diterpenoids, leucansalvialins F I (1–4), and one rare 18(4 → 3)-abeo-abietane diterpenoid, leucansalvialin J (5), were isolated from the aerial part of Salvia leucantha Cav., along with 14 known analogues. Leucansalvialin F (1) represents the first rearranged salvigenane type clerodane-17,12:18,6-diolide. Their structures were elucidated by 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of 1, 2, 3, and 5 were determinded by X-ray diffraction crystal analysis and the ECD technique. All of the isolated components were evaluated for their neurotrophic activities on PC12 cells and all new compounds were evaluated for their cytotoxicity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW480). Compounds 2 and 5 showed moderate neuroprotective effects in an in vitro assay.

Four new fawcettimine-related alkaloids (1-4), together with 17 known ones, were isolated from club moss Phlegmariurus squarrosus. Notably, compound 1 was the derivative of lycoflexine with an unprecedented additional methyl group at C-17. Their structures were determined by extensive spectroscopic analysis, including 1D and 2D NMR, and HR-MS, as well as by comparison with the literature data. All new compounds were tested for their β-site amyloid precursor protein (APP)-cleaving enzyme 1 (BACE1) and acetylcholinesterase (AChE) inhibitory activities.

Three new nor-clerodane diterpenoids, crotoeurins A-C (1-3), together with four known ones were isolated from the twigs and leaves of Croton euryphyllus. Among them, crotoeurin A (1) is a new nor-clerodane diterpenoid dimer with a unique cyclobutane ring via a [2+2] cycloaddition. Their structures were elucidated by spectroscopic analyses and the stereochemistry of 1 was confirmed by single-crystal X-ray diffraction analysis. Compounds 1-3 exhibited neurite outgrowth-promoting activity on NGF-mediated PC12 cells at concentration of 10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

Geissoschizine methyl ether N-oxide, a new oxindole alkaloid, along with 14 known alkaloids, was isolated from the aerial part of Uncaria rhynchophylla. Their structures were identified by comprehensive spectral methods, including 2D NMR experiments, and confirmed by comparing with the literature data. In vitro acetylcholinesterase (AChE) inhibitory activity assay showed that the new compound exhibited anti-AChE activity with IC₅₀ value of 23.4 μM.

A phytochemical study on Huperzia serrata led to the isolation of four new 5-deoxyfawcettimine-related Lycopodium alkaloids, huperserines A-D (1-4), and one new lycodine-type alkaloid, huperserine E (5). Their structures were elucidated based on spectroscopic data, including 1D and 2D NMR techniques. 5-Carbonyl or 5-hydroxyl group is a typical characteristic of lycopodine- and fawcettimine-type alkaloids. This is the first report of the 5-deoxyfawcettimine type Lycopodium alkaloids. In vitro acetylcholinesterase (AChE) inhibitory activity assay showed that huperserine E exhibited moderate anti-AChE activity with an IC50 value of 6.71 mu M. (C) 2014 Elsevier B.V. All rights reserved.

Two new monoterpenoid indole alkaloids, vincamajorines A (1) and B (2), were isolated from Vinca major. Their structures were elucidated by means of 1D and 2D NMR, and HREIMS spectroscopic data. The relative and absolute configurations were deduced by comparing the experimental C-13 NMR, ECD spectra, and OR data with those theoretically calculated. Vincamajorine A (1) represents a new C-20 carbon skeleton arranged compactly in seven rings, and vincamajorine B(2) is an alkaloid with an unprecedented 6/5/7/5/6 pentacyclic ring system. A possible biosynthetic pathway was also proposed for the formation of 1 and 2. (C) 2014 Elsevier Ltd. All rights reserved.

A phytochemical study of the CHCl3 extract of the dried unripe fruits of Evodia rutaecarpa (Juss.) Benth. (Rutaceae) resulted in the isolation of three new alkaloids, evollionines A-C (1-3, resp.), together with two known compounds, evodianinine and wuzhuyumide I. The structures of the new compounds were elucidated on the basis of detailed spectroscopic evidence and confirmed in the case of compound 1 by single-crystal X-ray analysis.

Phytochemical investigation on the rhizomes of Sinomenium acutum led to the isolation of new alkaloids sinomacutines A E (1-5), and cephalonine-2-O-beta-n-glucopyranoside (6), along with known tetrahydroisoquinoline alkaloids (7-9). Among them, sinomacutines A C were new bistetrahydroisoquinoline alkaloids with morphinane-proaporphine and morphinane-benzyltetrahydroisoquinoline types, and coupled with unique C-CH2-N unit. Their structures with absolute configuration were elucidated on the basis of 1D and 2D NMR, and ECD spectra analysis. The new compounds were evaluated for their anti-inflammatory and cytotoxic activities, and sallisonine B (2) showed moderate ability to inhibit NO production of LPS-stimulated RAW264.7 macrophages, as well as sallisonine A (1) showed weak inhibitory effects against five cancer cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

Twenty-eight protostane triterpenoids, including a new degraded one (1), nine new ones (2 - 10), and two new natural ones (11 and 12), have been isolated from the dried rhizomes of Alisma orientale. Alisol R (1) was the first 20,21,22,23,24,25,26,27-octanorprotostane triterpenoid. The absolute configurations of 25-methoxyalisol F (2) and 16β-hydroperoxyalisol B 23-acetate (3) were determined by X-ray diffraction analysis. In addition, alismaketone-B 23-acetate (28) showed potent vasorelaxant activity on endothelium-intact thoracic aorta rings precontracted with KCl.

Three new lycodine-type Lycopodium alkaloids, namely 1-methyllycodine (1), 8α-hydroxy-15,16-dehydro-des-N-methyl-α-obscurine (2), N-methyl-16-hydroxyhuperzine B (3), and one new natural lycodine-type Lycopodium alkaloid, N-methylhuperzine A (4), along with 11 known analogues (5–15), were isolated from the whole plants of club moss Huperzia serrata. The structures of 1–4 were elucidated on the basis of NMR spectroscopic and mass spectrometry data. Among them, compound 1 was the first lycodine-type alkaloid possessing a methyl group at C-1. In addition, the structure of 5 was confirmed by the single-crystal X-ray crystallography data and its 13C NMR was reported for the first time in current study. Compounds 1–5 were tested their BACE1 inhibitory activity. Graphical Abstract Electronic supplementary material The online version of this article (doi:10.1007/s13659-017-0140-z) contains supplementary material, which is available to authorized users.

Three new lycopodine-type alkaloids, 4α-hydroxyanhydrolycodoline (1), 4α,6α-dihydroxyanhydrolycodoline (2), and 6-epi-8β-acetoxylycoclavine (3), and an artifact, lycoposerramine G nitrate (4), along with seventeen related known compounds, were isolated from the club moss Lycopodiumjaponicum Thunb. ex Murray (Lycopodiaceae). Their structures were elucidated by extensive spectroscopic methods as well as X-ray analysis. Compounds 1–4 were evaluated for their acetylcholine esterase inhibitory activity. Electronic supplementary material The online version of this article (doi:10.1007/s13659-014-0027-1) contains supplementary material, which is available to authorized users.

Vibsatins A (1) and B (2), a pair of 14,15,16,17-tetranorvibsane-type diterpenoids that feature a bicyclo[4.2.1]nonane moiety formed by a new C-13/C-2 bond, were isolated from the twigs and leaves of Viburnum tinus cv. variegatus. The structures and absolute configurations were elucidated by a combination of NMR spectra, optical rotation, and X-ray diffraction experiments. A possible biogenetic pathway is also proposed. Moreover, vibsatin A (1) enhanced the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 μM.

Three rearranged labdane-type diterpenoids, hypophyllins A–C (1–3), and a caged labdane diterpenoid possessing a 8,9-dioxatricyclic[4.2.1.13,7]decane moiety, hypophyllin D (4), as well as two new biogenetically related diterpernoids, hypophyllins E (5) and F (6), were isolated from the aerial parts of Hypoestes phyllostachya “Rosea”. The absolute configurations of 1–4 were determined by X-ray diffraction analysis. The plausible biogenetic pathway for 1–4 was also proposed. Compounds 4 and 5 showed potent vasorelaxant activity on endothelium-intact thoracic aorta rings precontracted with KCl.

Two new indole alkaloids, 5-oxodolichantoside (1) and deglycocadambine (2), were isolated from the twigs and leaves of Emmenopterys henryi, together with four known indole alkaloids and five known iridoids. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses, including 1D- and 2D-NMR experiments, and confirmed by single-crystal X-ray diffraction studies. This is the first report on the isolation of indole alkaloids from this species. The indole alkaloids were evaluated for their cytotoxic activities against five human cancer lines.

(+)-Salviaprione and (-)-salviaprione, a pair of unprecedented abietane-type diterpeniods having an unprecedented 5/6/6 tricyclic ring system with a unique five membered ring A formed by a new C-2/C-11 bond, were isolated from the whole plant of Salvia prionitis. The enantiomeric separation was achieved by HPLC on a chiral column. Their structures and absolute configurations were determined on the basis of 1D and 2D NMR spectra, X-ray diffraction, and electronic circular dichroism (ECD). The possible biogenesis for (+/-)-salviaprione was also postulated. (C) 2015 Elsevier Ltd. All rights reserved.

Three new abietane diterpenoids, fleuryinols A-C (1-3), together with fourteen known compounds, were isolated from the twigs and leaves of Podocarpus fleuryi. Their structures were established by spectroscopic analysis, including 1D- and 2D-NMR spectroscopic techniques. Compounds 1-8 were tested cytotoxic activity against five human cancer cell lines, HL-60, SMMC-772, A-549, MCF-7, and SW480, of which fleuryinol B (2) and 19-hydroxyferruginol (4) exhibited moderate cytotoxic activity against some cell lines. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

Three new Lycopodium alkaloids, obscurumines C-E (1–3), along with nine known compounds, were isolated from the club moss Lycopodium obscurum L. Structures of the new compounds were determined on the basis of their spectroscopic analysis and the relative configurations of 1 were established by X-ray crystallographic analysis. All the new isolates were tested for the acetylcholinesterase (AChE) inhibitory activity. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-013-0015-x and is accessible for authorized users.

A new eremophilane sesquiterpene, (2 beta)-2-deoxo-2-methoxytessaric acid (1), and two new eudesmane sesquiterpenes, (3 beta,10 alpha)-3-methoxyleudesma-4,11(13)-dien-12-oic acid (2) and (3 alpha,4 beta,8 alpha)-4-(acetyloxy)-3-(2,3-dihydroxy)-2-methyl-1-oxobutoxy-8-hydroxyeudesm-7(11)-eno-12,8-lactone (3), along with the ten known compounds 4-13 were isolated from the aerial parts of Laggera pterodonta. The structures of the new compounds were elucidated by spectroscopic analyses, including 2D-NMR data.

Three new labdane diterpenoids, calomacrins A-C (1-3), and a new diaryl butyrolactone-type lignan, calomacrol A (8), as well as four known labdane diterpenoids and six known lignans, were isolated from the twigs and leaves of Calocedrus macrolepis. Structures of the new compounds were elucidated on the basis of their spectroscopic methods, including 1D and 2D NMR techniques. Compounds 3-14 were evaluated for cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines. (C) 2013 Elsevier B.V. All rights reserved.

Five new Lycopodium alkaloids, phleghenrines A–D (1–4) and neophleghenrine A (5), were isolated from Phlegmariurus henryi (Baker) Ching. The structures and absolute configurations of 1–5 were determined using extensive spectroscopic data coupled with computational calculations and revealed 1–4 possess a bicyclo[3.2.2]nonane core, whereas 5 possesses an unprecedented 9-azaprotoadamantane core. Compounds 1 and 4 showed potent acetylcholinesterase (AChE) inhibitory activities, and 4 is a good lead natural product for the treatment of Alzheimer’s disease.