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Supplemental material, sj-docx-1-npx-10.1177_1934578X221094910 for Anti-skin Aging Activities of Sideritis scardica and 3 Flavonoids With an Uncommon 8-Hydroxyl Moiety by Fumiaki Sato, Chin Piow Wong, Kaito Furuya, Chikako Kuzu, Ryosuke Kimura, Tomoha Udo, Haruno Honda and Jinwei Yang in Natural Product Communications

Supplemental material, sj-docx-1-npx-10.1177_1934578X221094910 for Anti-skin Aging Activities of Sideritis scardica and 3 Flavonoids With an Uncommon 8-Hydroxyl Moiety by Fumiaki Sato, Chin Piow Wong, Kaito Furuya, Chikako Kuzu, Ryosuke Kimura, Tomoha Udo, Haruno Honda and Jinwei Yang in Natural Product Communications

Supplemental material, sj-docx-1-npx-10.1177_1934578X211053202 for A Novel Trimeric Triterpene From Chisocheton ceramicus Miq. by Alfarius Eko Nugroho, Marika Okabe, Yusuke Hirasawa and Chin Piow Wong, Toshio Kaneda, Takahiro Tougan, Toshihiro Horii, Hiroshi Morita in Natural Product Communications

A new alkylbenzoquinone named embeliquinone (1) together with five known compounds, lupeol (2), 3-O-[6′-O-palmitoyl-β-d-glucosyl]-spinasta-7,22(23)-diene (3), quercetin (4), (2S,3S,4R,8E)-2-[(2′R)-2′-hydroxy-heneicosanoylamino]-heneicosane-1,3,4-triol-8-ene (5), and β-sitosterol-3-O-β-d-glucopyranoside (6) were isolated from the MeOH leaf extract of Embelia rowlandii by using repeated open column chromatography techniques. The structure of the new compound was characterized by analyses of 1D- and 2D-NMR, and MS data. Embeliquinone (1) had moderate anti-cell proliferation activity against A549 cell line with the IC50 value of 21.8 μM. In addition, 1 exhibited weak antibacterial activities against Klebsiella pneumoniae and Staphylococcus aureus with an MIC value of 206.0 μM in both cases.

A new indole alkaloid, leucoridine A N-oxide (1), consisting of two units of a strychnan type of skeleton, was isolated from the leaves of Leuconotis griffithii. Its structure was elucidated by various spectroscopic means such as NMR and MS, and also by chemical means. Antiplasmodial activity against Plasmodium falciparum 3D7 of indole alkaloids isolated from L. griffithii was investigated.

A new acyclic diterpenoid (1) and a new erythroxan diterpenoid (2), together with 4 erythroxan diterpenoids and 3 triterpenoids, have been isolated from the aerial parts of Fagonia mollis. Their structures were elucidated on the basis of 1D and 2D NMR data. The cytotoxic activity of the isolated compounds was investigated against HL-60 cancer cells.

Two new 3,4- seco-apotirucallane triterpenoids, Apowalsogynes A and B (1 and 2), were isolated from the barks of Walsura chrysogyne, and their structures were determined on the basis of the NMR and CD spectra, and by using the modified Mosher's method. In addition, the cytotoxic activities of 1 and 2 against various cancer cell lines were evaluated.

Three new daphnane diterpenoids, altadaphnans A-C (1 – 3), have been isolated from the aerial parts of Daphne altaica, together with 7 known daphnane diterpenoids. Their structures were elucidated on the basis of 1D and 2D NMR data. Altadaphnans A-C (1 – 3) showed significant antiproliferative activity against human lung carcinoma cell line A549.

Pseuduvarines A (Ia) and B (Ib) show cytotoxicity against the human cancer cell lines MCF7, HepG2, and HL-60.

Pseuduvarines A (1) and B (2), two new dioxoaporphine alkaloids with an amino moiety, were isolated from the stem bark of Pseuduvaria rugosa and their structures were elucidated by combination of 2D-NMR spectroscopic analysis. Pseuduvarines A (1) and B (2) showed cytotoxicity against MCF7, HepG2, and HL-60 (1: IC₅₀, 0.9, 21.7, and >50.0 µM, respectively, 2: IC₅₀ >50.0, 15.7, and 12.4 µM, respectively).

Further analyses of the 1 H and 13 C NMR data of the aglycone moiety of 1 revealed their similarities to those of geranyllinalool [2g], except for those in the vicinity of C-3. Therefore, 1 was assumed to be geranyllinalool-3-O-glycoside. Further analyses of the 1D and 2D-NMR (HSQC, 1 H- 1 H COSY, HMBC and NOESY, Figure 2) data of 1, supported the structure of 1 to be geranyllinalool-3-O--glycopyranoside. The sugar moiety was suggested to be glucose based on the 13 C NMR chemical shifts; acid hydrolysis of 1 confirmed this identity as D-glucose. Unfortunately, we were unable to determine the configuration of C-3 since hydrolysis of 1 yielded a dehydration product of geranyllinalool. Thus, 1 was determined to be geranyllinalool-3-O--Dglucopyranoside.